Dwolla became the flag-bearer for the nascent startup community in 2009 through leaders who didn’t just build a new payments platform to disrupt the expensive credit card payment monopoly, but did it in the public view, sharing wins, losses, spirit and energy through community meetups. Ben Milne, the effervescent, present, and brutally honest CEO was more than the company’s leader, he became a community champion. The team of independent thinkers and builders he assembled has amplified their collective impact.

Although Dwolla’s product may have been just a hair too early, or perhaps free platforms such as Venmo were more palatable to America, Dwolla pivoted to B2B payments and, over time, became what is often referred to as payment rails, the underlying picks and shovels that make payment networks possible. Teams shrunk, experiments succeeded and failed, leadership changed, engineering shifted, and business customers replaced individual users. Dwolla persisted in downtown Des Moines despite attracting venture capital from both coasts from individual investors and storied VC firms such as Andreesen Horowitz and Union Square Ventures.

Dwolla also built more than a payments platform by inspiring a generation of Iowa founders, an outcome of successful startups I set out to uncover on this Substack. ’s post lists the remarkable impact on the community but I’d like to share a non-exhaustive list of diverse startups created by the diaspora.

• Workhound: Max Farrell and Andrew Kirpalani recognized a need in the trucking industry to better engage drivers for employment stability and built a Des Moines & Chattanooga company that was subsequently acquired. They both continue to invest in new, young companies.

• Hummingbirds: Recognizing an opportunity to enable creative micro-influencers to help grow and support small business communitie, this Des Moines company now boasts coast to coast coverage .

• Brale: Ben completed his tenure at Dwolla but didn’t stop with payment rails. He helped birth Basis Theory and is now CEO of Brale, another picks & shovels company providing the infrastructure for banks to issue and support tokenized assets such as stablecoins.

Dwolla was acquired last week after a 16-year run. Sixteen years is a lifetime in startup-land where companies attempt to find a successful business model quickly, pivot as necessary, and either disappear or find a strategic buyer in 7-10 years from birth. Several strategic acquisitions by huge corporates have disappeared over time, either absorbed masterfully into their corporate parents or euthanized in culture clashes.

Dwolla’s acquisition by a mid-size buyer gives me hope that the rails produced by the dozens of passionate engineers, builders, funders, and supporters will have an active life ahead. We may never see the Dwolla API on our apps or screens again but are certain to live on as parts of payment networks.

I hope you enjoy Diana’s lived personal experience in her ode below and subscribe to her two Substack publications to keep your finger on the pulse of Iowa startups.

Beyond moving money: Dwolla’s outsized impact

by Diana Wright

The darling startup of Des Moines, Dwolla, sold this week to payment platform, NMI (headquartered in Schaumburg, IL, valued at $2B).

L to R: Dwolla investor Ashton Kutcher with founder Ben Milne, DSM Register; Team outing at Seven Oaks in Boone; Community builder team outing in Kansas City; The Dwolla Koala and an orange 1-year anniversary Moleskine.

When most startups fail, Dwolla didn’t.

I was only there for a small fraction of the 18-year company journey (2012-2015), when the founding leadership was moving fast to hit ambitious goals and proving that meaningful startups could be built far away from the coasts, in an often-overlooked place like Des Moines, Iowa!

Both national and local media loved this story, which is why Dwolla became the darling of the Iowa and Midwest startup community in the early years. Most everyday Iowans, often outsiders to the startup community, started to share pride for what could be built right here. This ‘signal of support’ alone is critically impactful to the entrepreneurs following in Dwolla’s footsteps today.

Outside the news headlines, every day there was a group of super smart people quietly trying to dominate payments-by-phone (before Venmo was acquired by Braintree/PayPal), move money safely in real-time, and lessen the credit card fee burden on small business merchants.

The model and product have changed since, now enterprise-facing, account-to-account (A2A) payments, but you can still find familiar faces from the early days of the product team staying on for its next chapter with NMI.

One constant over the years: Dwolla’s value, “We are never done,” has remained on the wall and on its website right up to this week’s acquisition. This mindset has powered the Dwolla team through many product and business model iterations, even during times that felt like starting over.

One thing most people won’t see in the headlines

Dwolla’s outsized impact on the Iowa startup community comes from its alumni network, which has since gone on to start companies or work for the next breakout startup.

Some call this term “startup mafias”, popularized by the PayPal Mafia, or you can think of it as a startup’s diaspora.

Here’s my lens on the impact:

• New companies started in Iowa by Dwolla alumni:

  • Brale

  • Hummingbirds

  • Workhound

  • Trility Consulting

  • Basis Theory

• Companies and communities shaped by Dwolla alumni:

  • Agrisync

  • TractorZoom

  • BarnTools

  • Roboflow

  • Coviance

  • Fastpath Solutions

  • Carrot Fertility

  • Vertex

  • FarmlandFinder

  • ManchesterStory

  • Lean Techniques

  • HyVee

  • Clay & Milk

  • ISU Pappajohn Center for Entrepreneurship

  • Techstars Iowa

  • Monetery Conference

  • v-Sum

  • StartupCity Des Moines

  • Global Insurance Accelerator

  • ISU Pappajohn Center for Entrepreneurship

  • Greater Des Moines Partnership

  • Outside of Iowa, the list is much longer and not in any way exhaustive, including CloudFlare, Trello/Atlassian, Stripe, Amazon, Apple, IBM, Clipboard, Finex, Aeropay, gener8tor, and Mastercraft Ventures to name a few.

What did I miss? Share in the comments!

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The right ingredients for a generation of builders

If you go beyond simply defining startup mafias, there were several important ingredients at Dwolla that uniquely positioned many team members for future success:

1. An early-stage environment with an unusually high level of ownership among its team members

2. Deep exposure to risk dynamics and the fintech industry

Ben Milne, founder of Dwolla:

“For many of us, I imagine Dwolla was a risk apprenticeship in this context. It selected for people willing to work on hard, non-obvious infrastructure, then gave us all years of reps inside high-consequence systems.

A lot of startups take product risk: will users want this?

Dwolla took product risk, regulatory risk, bank-partnership risk, developer-platform risk, geographic risk, and investor-access risk simultaneously. It was what needed to happen to make it all work, and people who can pull things like that off can do just about anything they set their mind to.”

1. A culture that forged friendships and resilience—the phrase “building in the trenches” was well lived, teaching team members how to navigate ambiguity, solve problems but not alone, and evolve quickly as the company would change

Those conditions don’t just create employees with experience — they create operators who were prepared to go build, lead, and invest elsewhere afterward. Pair that with the

💡 How do you create longstanding entrepreneurial communities?

Bet on the people building startups and creating the space for the next outsized impact right now.

Dwolla became more than a startup-it became a proving ground that produced founders, community builders, investors, and operators who carried those lessons into the next generation of great companies and communities.

Hat’s off to everyone at Dwolla from both the early days to today who have built it and saw its success through to the next chapter at NMI. It was a defining part of my early career that made me who I am, and it’s why I choose to be around those who are “never done” and aren’t afraid of a good challenge.

If you want any reason to join a startup, I think Kate Lidgett Wagner’s article sums it up (p.s., she is hiring): Startups Will Break You. And That’s Why You Should Join One.

Please visit Diana’s Substack and subscribe here

Iowans generously donate to the endowments at our colleges. Endowments whose primary purpose is to honor donor intent (e.g. funding scholarships, buildings, programs) and to exist in perpetuity. Perpetuity, meaning forever, requires that endowments grow above the rate of inflation, maintain a diverse asset allocation, and spend no more than 4% each year. This endowment investment model includes investments in risk assets (e.g. real estate, commodities, venture capital) as well as risk free (e.g. bonds). It is the venture capital investment that flows out of our state into national venture funds requiring our entrepreneurs to seek those funds elsewhere.

The Senate File 2453 that has passed the two chambers and now sits on the Governor’s desk seeks to resolve that very item and is the subject of a wonderful guest post, an op-ed that appeared in the May 17 Des Moines Register. I hope you give Zach’s post a full study. Zach Veigulis is the co-founder and Chief AI Officer of Claimable Inc., an AI-powered health insurance appeals platform based in West Des Moines. He holds a B.A. in Health and Human Physiology and an M.S. in Business Analytics from the University of Iowa and is a graduate of Lincoln High School in Des Moines.

I am grateful to him for allowing me to share his thoughts on this Substack.

I grew up on the south side of Des Moines, graduated from Lincoln High School, and earned my bachelor’s and master’s degrees from the University of Iowa. Today, I’m the co-founder and Chief AI Officer of Claimable Inc., a venture-backed artificial intelligence startup based in West Des Moines that helps patients appeal denied health insurance claims. We’ve been covered by NBC News, Bloomberg, Forbes, and Fast Company’s World Changing Ideas list. Nearly 90 percent of our technical team are graduates of Iowa’s three regent universities.

I say all of that because I want the Board of Regents and Governor Reynolds to understand exactly who is asking them to sign Senate File 2453 into law, an Iowan who stayed, who built something here, and who is watching far too many of his colleagues make the decision to leave.

A startup is not a small business

There is a common misconception that a venture-backed startup is just a small business with a flashy pitch deck. It is not. A traditional small business generates revenue from day one and grows incrementally. A venture-backed startup is built to scale rapidly, often at a loss in the early years, with the expectation of creating significant economic value, jobs, and returns over a compressed timeline. To do that, startups raise capital from investors, typically venture capital funds, in exchange for equity. Without that capital pipeline, most of the companies that created Silicon Valley, Boston’s biotech corridor, and Austin’s tech scene would never have existed.

This model is not a coastal curiosity. It is the proven mechanism for turning university research, technical talent, and entrepreneurial ambition into high-growth companies. Iowa has all three ingredients. What it has historically lacked is a local venture ecosystem large enough to keep that energy from leaving the state.

Iowa educates them. The coasts hire them.

The numbers are not ambiguous. According to a 2026 report from the Common Sense Institute Iowa, the state has forfeited an estimated $96 billion in cumulative earnings over two decades due to the out-migration of public university graduates. Only about half of all graduates from Iowa’s three regent universities remain in the state ten years after receiving their degree. The University of Iowa’s ten-year retention rate sits at just 37.7 percent.

In 2023 alone, Iowa lost a net of 3,445 college-educated young adults between the ages of 25 and 29. The state ranks seventh nationally and first in the Midwest for net out-migration of young degree-holders. Iowa has invested roughly $255,000 in combined public and private resources to educate a single student from kindergarten through a regent university degree. When that student leaves for Chicago, NYC or San Francisco, that investment leaves with them.

I have watched this play out within my own team. Brilliant engineers, data scientists and technical leaders who grew up in Iowa, trained at Iowa schools, and genuinely wanted to stay here had to weigh a difficult reality: the opportunity they were looking for simply did not exist in Iowa. We were lucky enough to offer them something compelling. Most Iowa startups cannot say the same, because without a mature local venture ecosystem, most Iowa startups never get off the ground.

This is not a tax. The money is already going to venture capital.

Critics of SF 2453, including some legislators and the Board of Regents itself, have characterized this bill as a “tax” on university endowments, an act of government confiscation, or a violation of donor intent. That framing is wrong, and it obscures what the bill actually does.

Iowa’s regent university endowments already invest in venture capital. As Rep. Taylor Collins noted during House debate, those investments are currently directed primarily to coastal-based funds, including Commonfund Venture Partners on the East Coast. Those funds deploy capital into startups concentrated in California, Massachusetts, New York, and Texas. The endowment returns funded by Iowa donors and Iowa taxpayers are compounding the wealth of coastal economies.

SF 2453 asks Iowa’s public universities to redirect just one percent of their unrestricted endowment assets into Iowa-certified innovation funds, funds specifically designed to support the commercialization of university research and Iowa-based startups. The bill was carefully amended to apply only to unrestricted pooled assets, to allow foundation boards to grant one-year waivers when market conditions warrant, and to give each institution full discretion over timing and structure.

Twenty-eight states have created some form of state-sponsored venture capital program because they recognized a simple truth: ecosystems don’t build themselves. Iowa has tried to compete without one. The results speak for themselves. SF 2453 doesn’t force universities to do anything they aren’t already doing. It asks them to do one percent of it here.

Sign the bill. Keep the talent.

I did not move to the coasts. I built a company here, hired here, and am investing my own career in proving that Iowa can be a home for high-growth technology companies.

People have started calling it the Silicon Prairie. We’re working on it. But the talent is already here, and so is the will. What’s been missing is the capital infrastructure to keep both of them from leaving.

SF 2453 is a step toward fixing that. One percent of unrestricted endowment assets redirected toward Iowa innovation funds is not a risk. It is an investment in the students Iowa is already funding, training, and then watching drive away on I-80. If we want to keep the AI in Iowa, we have to give it somewhere to land.

Governor Reynolds has an opportunity to sign a bill that would begin building the infrastructure Iowa’s innovation economy needs. The Board of Regents’ registering against the bill is an institution protecting a status quo that hasn’t worked.

Iowa grows its own talent better than almost anyone. It is time we started growing our own opportunities for them, too (emphasis mine-Tej).

Business Record and Innovation Iowa

The Des Moines Business Record is a weekly newspaper covering businesses across the metro. An entrepreneurial venture at its core, it honors journalistic principles and rules throughout its coverage across varied mediums. Staff journalists such as Erin Crawford, Kyle Oppenhuizen, Sarah Diehn and Lisa Rossi have told numerous stories of small business owners and startups, individual innovators and major corporations, and government programs that affect statewide innovation.

Lisa Rossi, the subject of this story recently became one of the storytellers for a quartet of publications just as her predecessor, Sarah Diehn, was appointed editor of the Business Record newspaper. The quartet comprises the annual Innovation Iowa magazine, the weekly Innovation Iowa email newsletter, the annual Innovation summit, and support for the organization’s podcasts. She also contributes to the Business Record’s print publication. She covers innovation, entrepreneurship, insurance, healthcare and food insecurity.

Learning Foundations

Her recent journeys cover such varied topics as understanding the role of AI during an appointment with a physician. She needed to understand the changing landscape of medical interactions, privacy, information security, speech-to-text transcriptions, electronic health records, employee burnout, insurance and more. Understanding the diverse (and divergent) viewpoints, distilling them into a relatable story for her audience, and publishing the story for varied requirements by the quartet of publications required her to dig deep into more the widely divergent background matter.

Another story crisscrossed the changing role of a CIO which was once singularly a technology leadership position. As she reported on Sanjeev Satturu, CIO of Caseys in Ankeny, IA, she learned about the CIO’s shift from technology leadership. She learned how the technology role has shifted toward a critical executive with wide-ranging responsibilities covering human resources, policy, financial oversight, vendor management, innovation, digital transformation, marketing and communications.

Another example covered a topic on top of mind for many Iowans - data centers, water use, and energy. Here she needed to learn and understand data center operations, why and how water is utilized, its impact on aquifers and fragile ecosystems, hyperscalers, hosted data centers where multiple clients lease data center spaces, data center operators’ sustainability programs, energy generation, usage, and pricing, and renewable energy programs.

These required more than a cursory understand of the various technologies listed and required her to listen and learn from her readers’ perspective, a skill learned in school, honed at the Des Moines Register, and connected to an undiscovered interest later at Stanford University.

Early Career

Lisa grew up in rural Iowa, in the small town of Dike near Waterloo and Cedar Falls. A bachelor’s degree in political science with a minor in journalism and internships at various newspapers including the Des Moines Register, The (Cedar Rapids) Gazette, and the St. Louis Post-Dispatch ultimately brought her to the role of reporter at the Des Moines Register in 2003. She continued to hone her skill and move through storied magazines and journals, including an associate regional editorial role at Patch.com.

Those roles prepared her for a unique role for a journalist at the Des Moines Register, a newspaper she rejoined in 2015 as a storytelling coach. She helped the team turn reportable content into stories that improved engagement just as the newspaper began measuring, improving, and monetizing on its new digital platforms.

To further her interest in studying leadership, she enrolled in a workshop on the subject in Philadelphia where she met a colleague who recommended a fellowship at Stanford University. She learned more about the program, found it intriguing, and poured her heart into the application. She was accepted and she left the Des Moines Register position behind to begin the challenging fellowship in the heart of Silicon Valley - Palo Alto, CA.

Intersections

Stanford is a melting pot of personality traits. As one of the premier educational institutions with proximity to Silicon Valley, it attracts significant numbers of creatives and extroverts. Stanford’s program at John S. Knight Journalism Fellowship encouraged journalism leaders to develop themselves beyond storytelling and Lisa gravitated toward design thinking and the innovation process. She learned the technique of asking questions, discovering the problem, developing prototypes, testing, iterating, re-testing until the true solution to the underlying problem revealed itself.

As she armed herself with these new skills and presented her work to live audiences, feedback encouraged her to improve her presentation through improv. Improv, the skill of discovering and exploring conversation by deeply listening, making mistakes, responding to situations live on stage was new to Lisa but helped break down her self-preserving walls that inhibit complete discovery. Improv, it appears, was a favorite of startup founders and entrepreneurs who loved the process of iteration, improvement, show, and audience delight.

The new discipline was about to change her in new ways.

Bonfire

Upon graduating from the program, Lisa decided entrepreneurship was in the next desired career move. She launched her company, Bonfire, to help others deploy design thinking in their problem-solving work. Modeled after the backyard bonfires of her childhood, Bonfire brought together people to share ideas, problems, thinking and solutions. She collaborated with Chris Snider, a faculty member from Drake and others who knew principles of design thinking and were seeking a community of practice in Des Moines.

The community of practice grew just as new threat appeared over the horizon, a global pandemic. A group, inherently designed to foster collaborative work through proximity suddenly became the casualty of social distancing.

A journal-keeper at heart since her childhood, Lisa kept anecdotes, stories, and nuanced conversations close throughout these experiences, unknowingly building a body of work about to charge a different new endeavor.

Although Bonfire LLC was dissolved, her second company, Lisa Rossi Comedy LLC continued to develop material in the background.

Open Mic Nights

The passion for Improv ignited during her fellowship at Stanford led her to open mic nights across Des Moines. In contrast with the slow-simmer ideas traditionally receive in the Midwest, she had absorbed the fast-paced and iterative innovation habit on the west coast. She had honed other design thinking skills through Bonfire and leaned into the compendium of stories collected through conversations.

She began testing her material in 5-minute comedic routines. She kept record of what worked with the audiences and what did not. And just like her journalism of the past decade, she listened and told stories. The lessons she shared for jokes apply remarkably well to innovation and entrepreneurship:

You’ve got to subtract

You’ve got to let things go

You’ve got to let bad jokes go

You’ve got to let bad ideas go

You’ve got to let bad stories go

She brings continuous editing and honing to her stories of innovation and gravitates toward entrepreneurs who are doing just that. She tells the story of Zack Smith who created his company Stock Cropper to re-intersect livestock and crops working together in a closed loop, low carbon intensive, synergistic field arrangement. Finding that it didn’t appear to solve a customer need, he found success after quickly pivoting his technology toward people invested in chicken husbandry.

Improv’s lesson in entrepreneurship

The Improv practice coaches participants to discover ways to win the interaction, yet audiences tend to connect more with the appearance of loss on stage. The vulnerability demonstrated through learning and participation engages audiences and leaves them talking. Although talking about a failed business is far from humorous, improv’s lessons of letting oneself lose an argument, position, or opinion can be freeing to discover what’s next. Plunging into the uncomfortable space of not knowing what is next and choosing to discover can be exhilarating.

Lisa begins her stories for the Business Record with such ambiguity. Choosing to begin with being ignorant, she humbles herself with sources and materials and begins to learn anew. Her goal is to know more about the topic than will ever enter her published story, to write with her reader in her view, and whose response to reading her stories is generally a ‘wow, I had no idea’.

What’s next?

Rooted in the discipline of meticulous journaling, improv’s continuous unpeeling of an onion, a penchant for comedy, and a wealth of scenarios collected from varied life experiences, Lisa is now learning the art of writing a mystery novel. She is learning about the genre by reading voraciously, learning the form and structure of mystery storytelling. The busy mom of teenage boys appears to have found the perfect time to learn - in a cabin by a lake as her boys fish for the family’s dinner.

Why I think these stories are important?

Creative individuals live and work across the state, in rural communities, suburbia and urban centers. They are writers, poets, singers, musicians, photographers, YouTubers, authors, speakers, podcasters and so much more. The Internet has given them the world as a potential market, and many are creating their own versions of the Silk Road. The Okoboji Writers and Songwriters Retreat is one such venue where creatives assemble to share, expand, and hone their craft.

Most are independent, individual, and creative in their special spaces - be it a comfortable nook, an intimate stage, a pottery studio or even a car on the open road. They may not be building IPO-ready businesses yet are creating a life and livelihood unique to their need, passion, and initiative.

These past 5 stories have taught me a great deal, and I look forward to discovering others. In the meantime, however, I intend to return next with another big bang Iowa invention that remains virtually unknown outside select circles.

A momentary AI detour

With no foundational knowledge of music or instruments, I asked Google’s Gemini to “help me understand the role of a bass guitar in a band”.

I quote:

If a band is a building, the bass is the foundation—you don't always notice it until it's missing, at which point the whole structure collapses

If the bassist isn’t perfectly synced with the drummer’s kick drum, the song feels “sloppy” regardless of how good the melody

A band without bass sounds thin and small.

So, I prompted - “this sounds a lot like the role of early capital in a young startup. Am I hallucinating in thinking this?”

If a startup is a garage band, the CEO (vocalist) gets all the accolades, and guitarist the attention. The bass remains audible but in the shadow

Too much money is like too much loudness, when there is too much of either, the groove is gone

Even the best product (melody) needs weight of capital to fill the room

Perhaps the above is a stretch and professional musician colleagues from the will correct me. I get the sense the AIs weren’t hallucinating in extending this metaphor.

Innoventure Iowa

Much has been written about this entity, yet much remains misunderstood. What stands true, however, is the immense impact the organization has had on Iowa’s startup landscape across agriculture, AI, advanced manufacturing, biosciences, and pure technology companies.

The American Rescue Plan Act injected $1.9 trillion in economic stimulus nationwide to accelerate recovery from the COVID-19 pandemic via direct relief to individuals, businesses, and governments. A portion was earmarked for states to apply for funds used to spur entrepreneurship via State Small Credit Business Initiative (SSBCI). Iowa applied for and received $96M. Innoventure Iowa represents about 40% of those funds that are deployed in an evergreen venture fund model. Returns from the investments are designed to be reinvested in promising future businesses. Unlike traditional VC funds, InnoVenture Iowa didn’t raise funds from lots of limited partners, does not provide carried interest to its leadership team or the board, administratively reports via BioConnect Iowa to the Iowa Economic Development Authority and the United States Treasury, and will not distribute future earnings to any limited partners.

Since its inception, Innoventure Iowa has invested $13.4M of the $40M in its corpus. As with private venture funds, it has reserved $20M in capital for follow-on investments in successful portfolio companies. It is governed by an Investment Committee and is a strong partner to Iowa’s private venture ecosystem.

InnoVenture Iowa, like the bass guitarist, provides foundational support to startups. Companies within the targeted sectors apply to InnoVenture for funding consideration once they have secured a private/leading source of capital. Leveraging its significant corpus, it matches a startup’s private fundraising with a meaningful amount of capital.

Despite Iowans’ humility, Kaylee and her team find themselves elevating Iowa startups in the eyes of peers outside Iowa. Out-of-state venture funds with little to no exposure here in flyover country receive InnoVenture’s outreach to Iowa companies. The annual InnoVenture Challenge further platforms innovations in Iowa for investors who are increasingly traveling to Des Moines for exposure to innovations born here.

And through it all, Kaylee is on stage, hyping up the crowd with boundless optimism and contagious stage presence.

Origins

Kaylee grew up in Cedar Falls, daughter of Maureen (Mo) Collins-Williams and Dave Williams, and sister to Rob and Clair. Mom was the Director of Entrepreneurship Outreach at the University of Northern Iowa and her parents together owned their small business called Antiques of Marion, so entrepreneurship flowed through conversations. No surprise then, that a young Kaylee found herself with a $100 investment from mom to launch a dog walking business. That early push led her to $5/per dog per walk and gave her a taste for independence, trailing behind four to five leashed companions around the neighborhood.

Kaylee developed an interest in art. Her parents encouraged her to join band and choir in middle and high school, and she would often walk to Java Joe’s on Saturday mornings growing up to draw in her favorite seat by the window. She learned how art and skill evolve through time and practice. Poetry entered her life around this time and she found creative ways to blend the two, continuing these passions into college where she pursued a degree in English.

Music and Startups

Kaylee began working for a startup in Des Moines called VolunteerLocal with an office in the city’s entrepreneurial incubator, Startup City Des Moines. Lovingly called ‘the island of misfit toys’, Startup City was a regular hangout for Marco Santana, an early journalist focused squarely on startups and entrepreneurship for the Des Moines Register. Working on a story he asked, ‘how is playing bass guitar in a bluegrass band like building a startup’?

River Glen, her partner then and now well-known Iowa singer songwriter, had gifted Kaylee a bass guitar and taught her to play. She found herself closing her laptop each day at StartupCity only to open her guitar case to play gigs at night in a duo act with River. The parallel between the startup and band was obvious to her: in business and in music, you are always performing. As a startup team member by day and a creative at night, she was adopting the life-long entrepreneur lifestyle-constantly building, constantly selling, and constantly engaging with audiences. As in a startup, the artist was creating art live, in the moment, accepting the applause and the failure, winning or losing in the public eye.

Kaylee continued to compose music and lyrics in her mid-20s. She left the band in time, just as her personal repertoire and skill increased. She added an acoustic guitar to her collection and began writing her own songs.

Those failed or successful experiments added to the confidence now plainly visible whenever Kaylee steps on stage to hype Iowa startups. That learned experience is her constant reminder to take big risks and share your successes and failures. Hiding only prevents growth.

You won’t ever start if you don’t love your garbage

Our discussion meandered into Anne Lamott’s Bird by Bird. In it, Anne offers advice on overcoming perfectionism, tacking large projects, and finding inspiration in everyday life, all frame by her father’s advice to her brother to write a report, ‘bird by bird”. Building iteratively, the practice of embracing what worked and letting go the rest is what Kaylee calls loving your garbage.

What holds our community back is the innate fear of letting go. Zombie startups with failed hypotheses continue to struggle, afraid of letting go. Failed programs are kept alive for fear of negative news stores. Despite living in a culture of planting anew each spring, our entrepreneurial communities continue to irrigate and fertilize failed crops.

Kaylee’s thoughts resonated with my feelings on the topic. We aren’t shedding enough, which is keeping us from building enough. Kaylee shared her belief that ecosystems, including entrepreneurial ecosystems, need to grow like forests, wild and redundant. Healthy ecosystems thrive on feed what works and destroy what doesn’t.

Launching Eat Free Pie DSM

Kaylee has always had a penchant for volunteer work, and no shortage of charitable causes she cares about – perhaps no surprise she was drawn to (and spent nearly a decade of her life building) a software company designed to help people volunteer more easily and more often in their communities. I plan to bring you VolunteerLocal’s story in the future but, in brief, VolunteerLocal is an early company in Iowa’s startup ecosystem that boasts an international book of business and employs a small team here in Des Moines.

I asked Kaylee about Eat Free Pie DSM, a charitable event she started in Beaverdale in 2020 that has expanded city-wide in the last five years. The concept for Eat Free Pie was born from her elderly neighbor, Chuck Reed, who shared with her that he’d be isolating on Thanksgiving Day to avoid getting sick. He asked if she’d bake him a pie and she agreed, delivering it to him the next day from across their shared driveway.

It was her sister Clair who wondered if there were other immunocompromised people like Chuck who might find cheer in a free pie on Thanksgiving Day. The two sisters created a sign-up for their neighborhood (using VolunteerLocal, of course) and called their effort “Eat Free Pie”. Nearly forty pies were requested, baked and delivered by Kaylee, Clair and friends in that first year’s effort.

Despite the world’s miraculous reopening by Thanksgiving 2021, neighbors and friends wanted the community effort to continue. Last year, Clair and Kaylee delivered nearly 200 pies to residents all throughout Des Moines and were featured on Iowa Public Radio in an interview with Charity Nebbe.

Beth Howard, who at the time was creating a documentary focused on the role of role of pie in Iowa culture, pie’s unique place in Americana, and the role of pie’s analogous pastries in other cultures heard of this effort and connected. It is Kaylee, Clair, Maureen, Brenna, and multitudes of volunteers who are profiled in Beth’s amazing movie Pieowa.

Transitions

Kaylee has morphed more than once in the 15 years I’ve known her. The artist of her teen years remains active even as her investment team at InnoVenture delves deeper into the numerical and analytic pursuits of venture investing. She is naturally active with the startup community and the brainchild behind the upcoming “Iowa Startup Week” this fall, pulling together community, sponsors, investors, friends, and startups. She is still composing music, now for her one-year-old son, Gus, still illustrating and still baking pies every year with her sister for Eat Free Pie DSM. Kaylee is an optimist and a builder, and her impact continues to grow with each passing year, continuing her mom’s tradition of helping build Iowa’s entrepreneurial ecosystem.

Why I think these individual stories are important?

Creative individuals live and work across the state, in rural communities, suburbia and urban centers. They are writers, poets, singers, musicians, photographers, YouTubers, authors, speakers, podcasters and so much more. The Internet has given them the world as a potential market, and many are creating their own versions of the Silk Road. The Okoboji Writers and Songwriters Retreat is one such venue where creatives assemble to share, expand, and hone their craft.

Most are independent, individual, and creative in their special spaces - be it a comfortable nook, an intimate stage, a pottery studio or even a car on the open road. They may not be building IPO-ready businesses yet are creating a life and livelihood unique to their need, passion, and initiative.

Print “Hello World”

I’d like to continue exploring Iowa’s technologists in this article with someone who has spent nearly three decades exploring such blank canvases. Although I’ve known her longer as a member of my family and shared some of these experiences as a colleague, partner, friend, and confidant, I hope to share a part of her creative process as a technologist that few know beyond the Business Record profile in their 2023 Photo Issue.

The subject of this story is Erin Rollenhagen, CEO and founder of People Friendly Tech (previously Entrepreneurial Technologies), author of books Soul Uprising and Love at First Launch, an insightful and informative LinkedIn series, The Revolutionaries Notebook, and incredible paintings bursting with emotion, color and inspiration.

Let’s first visit the origin story.

Coloring within the lines

Erin secured a summer internship at the end of her freshman year and began administrative work in a technology company. The company of fortyish people was quite self-reliant with limited administrative work to occupy her day. A learner by passion and entrepreneurial at heart (both mom and dad are creative entrepreneurs), she picked up a book on the Java programming language from the company library and began exploring a different kind of language. The prosaic book must’ve had a profound impact because she returned to the University of Iowa with a switch to now study MIS.

Graduation brought her full circle to a career in software development at the same company. As is customary for small software teams, she became a part of a team who captured user input about their desired systems, designed the user-interfaces, programmed the underlying logic, presented to the sponsors, trained the end-users, and managed the product post-deployment. This 360-degree view of the user experience inspired the latent entrepreneur to forge a new future for herself in 2007, just as the world was about to encounter a global financial crisis.

Picking up her canvas

There is never a right time to start a new business except perhaps at the onset of an economic crisis. Incidence of entrepreneurship rises as big businesses falter and the motivated decide to bet upon themselves. Erin found herself in an executive suite, a euphemism for a 10x10 shared office amongst a sea of other independents running their businesses. She’d identified a need for billing and management software for small(er) independent law firms and contracted with her first customer.

She blogged to share the handful of mistakes made in the infancy of her business and their impact on how she evolved the young company. These insights, captured first in the blog and later in her first book, Soul Uprising, published in 2017 paint a candid picture full of vulnerability and discipline.

Through her own experiences creating and running Entrepreneurial Technologies, her book illustrates authentic leadership and resilience necessary to create the purpose-driven business. Personal anecdotes further make the business book part-memoir, part-instruction. I read the book nearly a decade ago, but my Kindle remembers what I found inspiring then. Those highlights remain true today as then in an entirely different life:

Feedback is good for sticking to the status quo. If you want to break new ground, you’re going to have to go against the grain

I got a harsh reality check one day when a colleague told me that my business wasn’t really making money unless we could pay me a fair salary and still have a profit on top of that.

Inspiration in Setbacks

A lot transpired since the publication of that first book. Entrepreneurial Technologies grew organically, engaging in customer relationships that honored the company’s ethos and a shared passion for success. Personal and professional challenges were consistent with growth of any business, but the company endured through the meaningful and trusting relationships with its customers and employees.

Although I had seen Erin’s artistic sparks at family gatherings through sketches and paintings before, she began sharing some of her larger canvases online. As she told Nicole Grundmeier of the Business Record in 20231, she was not only embracing the process of creating something beautiful rather than obsessing on a pre-ordained end-result. She was living the paradox of creativity where one must create something ‘ugly’ in order to create something wonderful.

Painting with a different brush

If you have followed this Creative Technologists series, you know I have a soft spot for polymaths who don’t just write code but also descend into its layers. As November 2022 brought consumer-grade AI to the masses, Erin began interrogating the technology from her customers’ point of view. Rather than just consume popular content regurgitated by consultants ad nauseum, she deployed a playbook of the past - study the science, inspect those who lean upon her for advice, prepare her perspective, and broadly share the learnings.

The lifelong learner enrolled in Wharton School of Business’ certificate program in Decision Making. As the world was hallucinating AI’s potential, she chose to condition herself and gain competence in the field, not just to satisfy her curiosity but also to imagine the innumerable ways in which those who trust her, employees and customers, could benefit from the newly acquired knowledge.

She knew there existed a segment of business who didn’t just want to do the work, they wanted to change the future through the work they did. Rather than a bland designation of product owners or customers, she chose to call such individuals and teams revolutionaries. And she began documenting this journey on LinkedIn as The Revolutionaries Notebook.

A particularly meaningful sentiment from the first post in the notebook is below.

What are the moments when the emotion kicks up a notch? Where’s the pain? Where’s the hope? Where’s the fear? You can almost always hear the pitch change in someone’s voice when they are talking, the moment when it flips from an analytical discussion to something they feel deeply. Pay attention to that moment - that’s where the opportunity lies. That’s the thing to prioritize.

The connections to hope and fear are powerful and embedded within each mammal’s amygdala. If we have evolved to instantly react to these emotions in matters of life and death, why ignore them in the software we write, experiences we design, stories we share, or photographs we capture? Erin’s paintings captured that for the walls in her home and her (then, to be) husband’s comedy club. Patrons of Teehee’s Comedy club were greeted with grand paintings with brushstrokes intrinsically connected to the improv on stage.

That’s another part about revolutionaries - they don’t exist in vacuums. A close friend and colleague with deep expertise in information and network security found her comedic voice and identity in that comedy club. I wonder if Antoinette was subconsciously inspired by the brushstrokes of her tech contemporary. I was reintroduced to poetry in the very room by the (then) CEO of Business Publications when her poetry was read aloud by professional stage actors at a Script-tease (not misspelled) event. I wonder if the actors found new inflections for Suzanna’s words in the art surrounding them.

Coloring outside the lines

Her paintings often feature bold colors and layered textures in contrast to the flat, minimalist "Material Design" that dominates our screens. Programmers laugh at ‘it’s a feature, not a bug’ in response to unexpected software outcomes. Sometimes, however, such unexpected features, the stray keystrokes and brushstrokes birth new textures and experiences in her art.

In a recent entry within The Revolutionaries Notebook titled “Why Great Colors Can Still Make Ugly Software”, she encourages revolutionaries to adapt their brand palettes to shift the user experience. She encourages leveraging the power of color to add balance to a page or a mobile screen, testing the alternative ‘dark mode’ to free the user from the lightness of white. The complete article is a lesson in balance, creative energy, inspiration and immersion. I like it so much that I’ll link it again below 😊

Why Great Colors Can Still Make Ugly Software | LinkedIn

Tapestry of Work

Erin’s work continues to evolve in various media. She is an oft-sought guest on panels and keynotes, sharing her experiences and wisdom with audiences large and small. Her latest book was released just about a month ago. The book picks up from Soul Uprising and incorporates the revolutionaries from her LinkedIn series, delving deeper into the hopes, fears, emotions and actions necessary to build a great product. Although software runs through the book’s veins, the principles apply to building anything great with passion, purpose and people.

There are two vivid examples that make the book’s lessons memorable. The metaphor of red and green shirts instructs how a delicate dance between those who see the forest and have a vision to conquer it and those who identify with each tree in the forest and devise the plan to win them individually. Both are necessary and neither expendable, yet inadequate attention to the needs of the two can lead to perilous outcomes. The second vivid example is of visionaries everyone needs on their team including Journey Guides, Dragon Slayers, and the Simplifiers. My mind drove me to their analogs from Star Wars - Yoda, Luke and Obi-Wan respectively.

I believe the book is a wonderful parable worthy of an easy read before embarking on a product journey; I devoured it in a single day. The link here is to Amazon but the book may be available at your local book nook as well.

I’ll leave you with a piece Erin shared at the onset of Spring last year. The piece is titled “Pollination” and the acrylic on canvas was her inspiration to welcome spring on her own schedule, on March 1st (and not on spring equinox). If you want to check the validity of her decision, go search ‘meteorological spring’.

Why I think these stories are important?

Creative individuals live and work across the state, in rural communities, suburbia and urban centers. They are writers, poets, singers, musicians, photographers, YouTubers, authors, speakers, podcasters and so much more. The Internet has given them the world as a potential market, and many are creating their own versions of the Silk Road. The Okoboji Writers and Songwriters Retreat is one such venue where creatives assemble to share, expand, and hone their craft.

Most are independent, individual, and creative in their special spaces - be it a comfortable nook, an intimate stage, a pottery studio or even a car on the open road. They may not be building IPO-ready businesses yet are creating a life and livelihood unique to their need, passion, and initiative.

This story’s roots are in my coming across my friend, Timothy L. Johnson’s social post where he shared his nom de plume. He was describing a murder mystery series based in Des Moines, Iowa and I was intrigued enough to (accidentally) pick up the second book of the series. With both the first and second now in my “read” pile, I can comfortably say that I didn’t mess up the story line (much) by reading #2 first and am eager to read the third and fourth in the series due later this fall.

Although the links above are Amazon affiliate links, both books are also available for purchase at Beaverdale Books.

Late 1980s and 1990s

Tim and I were students at Central College in Pella studying Business Management and Computer Science respectively. Small college campuses create creative collisions, and we knew each other from such interactions in the computer labs. The connection continued as we both landed in the Des Moines area at Principal shortly after college, him programming, then product and project management and me as a programmer and network administrator. Pathways soon diverged and connections withered until I encountered his first set of books and writings in the late 2000s.

Our alma mater is rooted in the liberal arts and writing is encouraged and required across curricula. When we recently connected for this series, a story I was surprised to learn from him was about a writing assignment from my programming languages professor, one where he had to describe his calculations to compute the volume of a tetrahedron using a determinant matrix. The same professor also taught my programming languages class where, at the beginning of the semester, she creatively assigned our class a single (simple at its face) problem we were required to solve in the next ten weeks. The only constraint - we had to solve it in ten different languages, one learned each week. She honored and applied the ethos of the liberal arts widely even in computer science. While my liberal arts degree took me to the photography dark room to process film to fulfill the fine arts requirement, Tim found himself in art history classes studying, understanding, and verbalizing 20th century masters.

The Data and PM connections

The late 90s progressed into the 2000s and career trajectory kept Tim engaged in project management roles in the metro area. He used and created systems to ease his and client workloads, learning from different industries along the way. He taught related courses at Drake University and UW Milwaukee, inadvertently collecting material for a future just around the corner.

Companies large and small were beginning to recognize the amorphous data exhaust from the systems they’d been building over computing’s past few decades. An industry, about to be born, would christen new titles such as data engineer, data analyst, and data officers. Those, like Tim, in the midst of these ‘data transformations’ were about to be inundated with new terms - master data management, data warehouse, data lake, data scrubbing and waterfalls (pun intended) of data initiatives.

Tim found himself making sense of this deluge and began writing his process, systems, and technical thoughts into books. His first book, released in 2006 fictionalizes a project management scenario in Race through the Forest. It was followed the next year by Gust and three years later by SWAT. The three fables are fast reads that provide a peek into the world of corporate projects, politics, and systems thinking, especially for those who happily live simpler lives outside those worlds. I found myself mapping the book’s characters to friends and foes I’ve encountered through the years - the fables are real!

From Flashes to flash bangs

Tim was invited to join a SWAT team by a friend, a team commander in the city’s police force. He eagerly joined the group, learning techniques and observing activities including securing locations, assets, and property, deploying weapons when necessary. He asked and received permission to photograph the teams in action deploying tasers, flash bangs and much more.

He began observing the disparate personalities who surrounded him in these sessions. Recalling Stephen King’s On Writing, Tim realized these personalities were providing him ready characters for future stories. Although he had fictionalized characters in the first three books based upon real-life humans before, this set of personalities was new and different from the corporate environments. A notebook filled with potential characters was awaiting opportunity.

The Spark

Tim’s first three books are dedicated to his wife and two daughters. One of his daughters, Lauren who was at that time an employee of Salisbury House invited him to host a murder mystery where the murder victims were the only actors in the know. Tim had a great time observing the willing guests playing along as participants. He knew he had to do it again.

Lauren agreed and encouraged dad.

Tim found many more personalities and characters amongst the guests and continued to document them for future mysteries.

The Murder Mystery Book Series

Two town names on a highway exit caught Tim’s attention during a family drive to visit the Crystal Bridges art museum in Bentonville. The town names Drexel and Archie off the Interstate between Des Moines and Bentonville planted themselves in Tim’s mind as a cool first and last name of a character. His family in the car agreed and Archie Drexel was born.

The book series begins with Archie’s life upended by his wife’s passing, his two daughters beginning their adult lives anew, a new neighbor, a murder in the neighborhood and the ensuing investigation. I won’t share much more about the plot or outcome, but it became evident from the beginning that this book would explore a subplot of male friendships. Characters from SWAT, the murder mystery at Salisbury House, and Tim’s own life perform lead and cameo roles throughout.

Those familiar with Des Moines will find mental detours as they read this series. The first book’s characters drive through the western suburbs toward the south side. The second book’s murder is set squarely in the city’s pride and joy - the downtown farmer’s market. I was, in both cases, imagining the drives myself, inadvertently giving names to streets where the characters turn, the investigative location of a parking garage, and even the coffee shop.

Intersection of technology and art

Archie is a data consultant whose professional life is mired in a data transformation project. Unlike someone fully fictionalizing this part of the story, Warren Haddock (Johnson’s pen name), obviously speaks from experience. His descriptions of the data engineering workload, client expectation, finger pointing, and desired outcomes are surprisingly accurate for a novel. Similarly, the process of elimination to reach the murder suspect (innocent until proven guilty?) are almost ministerial in approach. No cliffhangers or big twists - rather a simple yet effective conclusion.

The surprise

The books carry the subplot focused on the three main male characters. Although there is a cast of female characters, the primary characters are experiencing life as new bachelors late in life. Capable and confident, they find compatriots in each other and develop a friendship bond necessary in solving the murder mystery. And it is through this bond they inadvertently fill a void in each other’s lives.

I think this surprising element makes the series worth more than a fictional tale. Male friendships, formed later in life, are surprisingly few in number and almost never referenced in fiction or non-fiction. The subtle subplot alone makes the books remarkable, and I whole-heartedly recommend them for your reading pleasure.

Why I think these stories are important?

Creative individuals live and work across the state, in rural communities, suburbia and urban centers. They are writers, poets, singers, musicians, photographers, YouTubers, authors, speakers, podcasters and so much more. The Internet has given them the world as a potential market, and many are creating their own versions of the Silk Road. The Okoboji Writers and Songwriters Retreat is one such venue where creatives assemble to share, expand, and hone their craft.

Most are independent, individual, and creative in their special spaces - be it a comfortable nook, an intimate stage, a pottery studio or even a car on the open road. They may not be building IPO-ready businesses yet are creating a life and livelihood unique to their need, passion, and initiative.

My Pandemic Hobby

I didn’t start a sourdough starter during the pandemic. Privileged with flexible WFH environment, touchless grocery and restaurant pickups, I spent free time on walks and TV. I found myself learning home appliance repair when the dishwasher, dryer and lawn equipment broke (yes, I was able to fix them all), just as the algorithm directed me to creators whose work felt intriguing. This story didn’t start during the pandemic but is the result of a hobby that began in the summer of 2020 and persists to this day.

I ended up following a handful of creators running real businesses through their YouTube channels. An interest began to develop in understanding the creators’ business models and their creative process. My favorites were and remain Sadia Badiei of PickUp Limes in the Netherlands, Steve Marsh from Montrose, Scotland, Zach Nelson of JerryRigEverything from Utah, and a few others.

This is the IowaTeslaGuy’s story, closer to home, from Marion, Iowa.

The Iowa Tesla Guy

I prefer Tesla cars regardless of the CEO’s politics and remain peeved at how impractical it is to use it without sufficient charging infrastructure in rural Iowa. As I contemplated a longer-range car and searched for charging alternatives in northwest Iowa, the YouTube algorithm suggested I watch IowaTeslaGuy’s journey from Cedar Rapids, IA to Boulder, CO. The video was a hands-free demonstration of the updated technology (link later in the article).

Distracted from my purpose, I watched the video with great interest as familiar sights of Hy-Vee and Kwik Star faded in the background and the car progressed east on I-80. I’ve traveled the route in my EV before and was contrasting my experience with his first stop at “The Corn Crib” off the interstate in Shelby, IA. The narrator & driver talked about the nuances of friendly stops along the route reached Boulder, sharing words, mannerisms, expressions and opinions in a very Iowan fashion - matter of fact, devoid of politics or negativity, clear and straightforward. The word friendly kept coming to mind.

I became a fan and watched several more of his videos over the months, upgrading my car along the way, partly marveling at the effortless storytelling mid-drive, the various cameras in the car recording his and the car’s moves, and the road. I found myself constantly contrasting my experiences with his, finding them resonant yet learning something new in each video.

Connecting

Consistent with my pandemic habit, I now wanted to learn more about IowaTeslaGuy. I easily found a website for a Jim Spencer in eastern Iowa as the host of the YouTube channel and Jump Gap Software, an independent app developer for Apple devices.

That’s when inspiration struck for this series to tell stories of technologists who are using artistic storytelling even as they engage in deeply technical endeavors in life. I had to know more. I dropped Jim a note requesting a meeting. Jim tentatively accepted the meeting request, and we hopped on a Zoom call late one Tuesday evening in February.

Jim, like many creatives you’ll meet, is a reserved personality. I had seen enough of his videos to know that he isn’t introverted but thoughtful. A teacher by mannerisms, his technical chops were evident in the videos. Talking to him I found him to be the son of a tinkerer and engineer from Davenport. During Jim’s high school years, as dad exercised his profession and passion on cars, motorcycles and made tools and dies for work, he was etching his own circuit boards in the family garage. With electronics in the blood, an engineering degree was his natural path.

This recent video below is a wonderful introduction to Jim, his contemplative and gentle teaching style. It chronicles a day in the life of an Iowan as he journeys across the state to his alma mater, Iowa State University, for a career fair. It is marketing gold that Tesla should really commission.

Jim received his electrical engineering degree from Iowa State University and was invited to an interview at Vector Corporation in Cedar Rapids. The control systems automation engineering job was a welcome offer in the middle of an unfriendly job market of the early 1990s. He worked on embedded controllers and software, obtained an MBA toward the turn of the century and continued to tinker in spare time.

This tinkering was simply priming him for the upcoming iPhones and the app store.

A hobby becomes a business

Though Jim self-describes his foray into app development for the iPhone as being “late to market”, his entry actually was quite timely. Books and online courses were freely available, and Jim complemented book learning with a free online app development course from Stanford.

He developed his very first app and launched it into the app store for $2. He vividly remembers standing in his living room, looking toward his wife in the kitchen when the app was sold to its first customer. The euphoria generated by this external stimulus wasn’t just social validation, it was also the beginning of the dopamine effect inherent in filling a customer need and receiving instant online validation.

That purchase by a Canadian user was the first of many. As Jim worked for Vector Corporation by day, by now managing others, evenings and weekends gave way to this hobby that quickly evolved into a revenue-generating business. The first application, a currency converter called Currency+ was purchased around the world and continues to be available on the app story nearly ten years later. Jim developed other applications to help track bills, his own kids’ allowance, chores, and even a retro arcade game.

Jump Gap Software became a real company.

A new hobby and business, however, were waiting just around the corner.

If work gives you pleasure, is it still work?

A big birthday mid-pandemic brought Jim to his next adventure, almost by accident. He had eyed Tesla cars for some time but wasn’t quite ready to invest in the expensive Model S. The year 2019 brought sportier Models 3 and Y to address cost concerns and Jim found himself ordering his car and driving to Illinois to pick up it up. Upon a whim, he decided to record his experience of that first drive in the Model Y.

The nearly eight-minute video, his first, is a raw discussion of the pickup experience of a car one orders sight unseen, learns to work with EV driving range, EV driving experience, and even autopilot on the 250+ mile drive home. He shares Iowa’s temperature swings, rural living and driving, owning a car with limited service-center availability, and charging along the way. And he launches the YouTube channel with a promise to share additional experience, advice, and takeaways.

That first video, posted over 5-years ago has 442 interactions from nearly 8,300 views. Although car videos and photography mostly use coastal drives, fantastic weather, and dreamy backdrops, Jim’s videos connected to faraway audiences as Iowa roads and weather present an unusual environmental mix familiar to many in other parts of the world. Jim’s subsequent videos become progressively educational, guiding on topics common to new car owners - charging, winter driving and range, over the air software updates, and even mobile service.

The power of the platform and his videos’ ubiquity became surprisingly obvious not too long ago. Jim and his wife were in Germany, charging their rental Tesla at a supercharger when a fellow traveler charging his own car appeared to recognize him. Much to the Spencers’ surprise, the traveler from Netherlands had seen his work, knew him as the IowaTeslaGuy, and chose to say hello.

This experience is often repeated in the EV community. Due to the 20ish minutes required for charging vs transactionally filling a gas tank, the time allows travelers to get out and stretch, walk, break for coffee or a meal and strike up conversations with fellow travelers. And yes, running into friends driving coast to coast at a random charger can become a welcome surprise!

How hobbies become businesses

Like an iPhone app providing a small but steady income stream through the Apple app store, YouTube videos also generate an income stream for creators through the advertising revenue generated by viewership, engagement, shares and subscriptions. As Jim’s subscriber count edged into the thousands, a new income stream emerged - third parties whose products complemented Tesla cars and who wanted access to Jim’s subscribers.

Sponsor and affiliate marketing is a strong component of many successful creators with advertising incorporated into their videos. As any listener of Paul Harvey’s radio shows remembers, even Harvey’s news stories back then contained influence and advertising. YouTube takes it a step further, allowing targeted marketing, granular data about the viewers, and of course, direct purchasing via affiliate links.

Though many creators become shills for advertisers, Jim’s videos retain an authentic and educational feel. He judiciously selects products that matter to him and his driving experience. As he moved from the original 2020 model to the latest 2025 Juniper model Y, he shared the differences, the capabilities and his driving experience along with new products for the new models.

A remarkable video, the one that introduced me to his channel is the previously mentioned drive from Cedar Rapids area to Boulder, CO, almost entirely hands-free in the car’s self-driving mode. Even if you aren’t a Tesla enthusiast, the video is a demonstration of advances in automotive technology delivered to share the experience and constantly changing capabilities of the car.

Next

As Jim Spencer advances toward the next decade, he can see himself retiring from one of the gigs. Traveling, recording and sharing experiences, and teaching are likely to remain a mainstay in his life. The business of creating has helped him expand into participating in and leading enthusiast communities. Much like hot-rod gatherings that spring up around the Midwest all summer, EV communities too gather in spirit of the American love affair with cars. Jim finds himself an unintentional celebrity amongst peers, a detour he simply fell into when choosing to share his car’s virgin voyage.

Why I think these stories are important?

Creative individuals live and work across the state, in rural communities, suburbia and urban centers. They are writers, poets, singers, musicians, photographers, YouTubers, authors, speakers, podcasters and so much more. The Internet has given them the world as a potential market, and many are creating their own versions of the Silk Road. The Okoboji Writers and Songwriters Retreat is one such venue where creatives assemble to share, expand, and hone their craft.

Most are independent, individual, and creative in their special spaces - be it a comfortable nook, an intimate stage, a pottery studio or even a car on the open road. They may not be building IPO-ready businesses, yet are creating a life and livelihood unique to their need, passion, and initiative.

I am grateful you are reading their stories!

Spouses often have a way of cutting through the fluff and Laurie inquired into what he intended to do and “love” in his imagined retirement. His response foretold the future:

Iowa Wine Growers Association reports that the Loess hills in Western Iowa was once a landscape of grape vines. Grape production grew in Iowa from the first vineyard in 1857 to sixth in the nation by 1919 (the inopportune year when Prohibition began nationally even though Iowa’s began four years prior). Production suffered through the rest of the century until early 2000s. French grapes remained the mainstay, accompanied by a handful of native American grape varieties. Jeff traces his genealogy via his great grandfather who immigrated to the US in 1881 from Wintrich, Germany. His family name lives on in the prominent winery in the Moselle wine region of his ancestral Germany-Weingut Quint.

Contemplating their past and future, The Quints focused on the lightly rolling region between Cedar Rapids and Iowa City for their vineyards and planted 5,000 initial vines in 2003. As the vines, a hybrid of classic French vinifera and native American varieties to survive the harsh winters and the region’s biology, matured, the Quints began planning their launch in 2004. That’s when realization struck about what might be more midwestern than corn as their crop instead.

In 2004, Iowans were importing nearly $350M worth of spirits. With corn specifically, we were producing and selling $4 worth of corn, only to receive it back in form of a $40 bottle of spirit.

The early 2000s were also a resurgence of interest in American whisky after a brutal two decades where bourbon and rye industries had been decimated. The storied Michter’s trademark, for example, had sold for a mere $250 in the prior decade!

Leveraging State Support

Iowa Economic Development Authority (IEDA) showed up as a valuable resource to the Quints. As distilling spirits requires a much higher level of licensing by the local, regional, state and federal authorities, IEDA’s support helped the distillery acquire their first still, establish the physical infrastructure required to begin distillation (after certification - as readers have learned from prior posts) and secure it from miscreants. In 2005, Cedar Ridge distillery launched1 as Iowa’s first distillery since prohibition.

Iowa has a distinction in prohibition. Even though farm distilleries abounded in the early days of the state with farms using locally grown wheat, rye and ultimately corn to distill spirits, the temperance movement impacted the state earlier than national rules. In Iowa, the legal sale of spirits stopped in 1916, four years before national prohibition bans2.

Did you know that prohibition actually increased criminal activity in multiple ways? As spirits were “cooked” at home, the person usually in the kitchen also applied her cooking steps to this new recipe, tasting throughout the process and ultimately developing a taste for a liquid previously largely consumed by men. Bribing law enforcement became a survival prerequisite. Smuggling spirits on the state’s backroads and highways a necessity. A fascinating fictional tale in Moonshine by Moonlight3 by Iowa author Ann Hanigan Kotz imagines how this work might have progressed in Carroll County, IA. Similarly, Wayne Curtis’ book, History of the New World in Ten Cocktails, outlines the many second-order societal impacts of prohibition in America.

Chasing Passion

Retirement is often confused by the action of stopping work. Jeff, one of the lucky few, was able to articulate it as a part of life to being able to do what he wanted to do. His new career opened in downtown Cedar Rapids in 2005 next door to Ben’s Beverage Depot, a liquor store. Iowa law then didn’t allow spirit sales directly to consumers, blend cocktails with their own spirit, or provide a tasting room.

The relationships with IEDA expanded and the company found itself lobbying for its economic interests at the state capital. Iowa’s capital becomes a flurry of activity in the first three months of the year and Jeff, unable to afford a lobbyist, showed up on his young company’s behalf. The efforts over the next TEN years led to the changes that allow the company to sell its own spirit in their distillery shop (a must visit) and blend interesting concoctions at the attached bar, restaurant and wedding venue.

Unlike Scotch, American whiskies are consumed when they’re relatively young, often in 2 to 4-year vintages. Although aficionados today are grateful for the downturn of the 1980s and 90s when spirit aged unintentionally and only now commands significant premiums, Cedar Ridge’s early product was good and set aside for aging. Aging happens in rickhouses, warehouse-like structures designed to securely store 200- and 500-liter barrels filled with new spirit, often stacked 4- or 5-high on shelves made specially for their size and weight.

Rickhouses need to provide airflow for the angels to swoop down and collect their angel’s share, the approximately 2% of spirit that evaporates from the barrels each year. Airflow also allows the regional terroir to enter the spirit, giving the whisky its regional flavor (so, no hog lots near our favorite distilleries please). They also need to control against potential fire hazards by channeling spirits from burning barrels away from other facilities. Cedar Ridge was building a new building each year. In fact, on the cold March 2026 morning of my visit, earth moving equipment was busy working amongst the rickhouses and the main office.

The Art of Building a Business

Distilling and Aging whisky faces a significant challenge in its early years, no matter how wonderful the spirit. The brand must be built to be unique and recognizable, roll off the tongues of patrons in restaurants and bars, be visible in industry publications, compete against brands established over America’s 250-year history, and taste good enough to become a repeat order.

Jeff, as they built the company, remained employed in his role as CFO at Involta, a well-regarded and celebrated technology company since its launch in 2007. Involta grew significantly in the subsequent decade yet afforded Jeff sufficient time to build Cedar Ridge. By 2016, however, Cedar Ridge was no longer a side hustle and Involta was a large enterprise itself. Jeff felt it only fair to dedicate the next chapter fully to his baby and resigned.

A small business entrepreneur at heart and soul, Jeff often shares a lesson-built the business of your dreams in your spare time. If you aren’t willing to submit your spare time to your dream, you are not cut out to own and run it. A small business is like your child-until the child is securely asleep in their bed, you aren’t ready to go to bed either.

I agree! 40 hours/week on the paying job, the remaining 128 on your business.

Early Years

Sermons aside, the early years in downtown Cedar Rapids were quite entrepreneurial.

Once yeast has completed its work in the washbacks and spirit is ready to be distilled, the liquid is moved into a still and heated. Heat causes vapors to rise up the still and move through condensing coils to be converted back to liquid. This distillate arrives clear, concentrated and strong. After being separated into heads, hearts and tails, it is diluted appropriately for the targeted spirit.

Look through the porthole above - that’s spirit in the making as alcohol evaporates and is captured before water or other impurities have a chance to chase it

It is almost ready at this time to be sold as vodka. If the liquid in the still had been adjusted just so with juniper berries and other botanicals, it might be on its way to become gin. Or it can be diluted by the master distiller for oak barrels for a years-long rest in the safe environment of rickhouses to age as whisky. Naturally, the product sold by most distilleries in their earliest years, then is vodka or gin to provide early sources of revenue, to begin establishing a brand, and refine the manufacturing, operational, and distribution processes.

Cedar Ridge followed a similar trajectory, selling vodka and gin in downtown Cedar Rapids as the young whisky aged in barrels. Those early barrels, made of virgin oak at domestic cooperages and charred for the distillery’s unique recipe, allowed the spirit to obtain its character, color, taste, and identity.

Maturation

The company continued to mature alongside its whisky. It set itself a BHAG (big hairy audacious goal) to become the #1 selling bottle of Bourbon in Iowa. It is a BHAG because national names roll off tongues without effort and require significant advantages in taste, price, brand recognition, mixability, availability and fandom. This BHAG was finally achieved in 2020, and Cedar Ridge remains the bestselling bourbon in Iowa six years in a row.

Consistent across Iowa distillers I’ve researched so far, Cedar Ridge also remains an entrepreneurial distillery at heart. Unwilling to stick to a safe mash bill, labeling, bottle shape or size, expressions, maturation age, partnerships or barrels used for aging, Cedar Ridge’s products have garnered attention from national competitions which have awarded gold medals and ratings in the high 90s (on a 100pt scale).

Farm & Family

Cedar Ridge brings the familiar farm to table philosophy to its spirit. Although Iowa #2 yellow corn is widely available, and the company could grow right at the distillery, a significant portion of Cedar Ridge’s corn comes from his wife’s family farm an hour north of the distillery. Barley, rye and wheat, however, are sourced from elsewhere as the state’s primary crop has all but pushed those crops out in any appreciable quantity.

I think there is a day when local corn, rainwater, and cultivated yeast may yet find their way into the bottle. Though Jeff wouldn’t say, I have to believe that something secretly rests in one of the rickhouses, aging to compete with the hyperlocal single malt Scotches Cedar Ridge competes against.

In another family blessing, their son Murphy showed early interest in working with mom and dad as they juggled careers and a growing business. He worked with them on evenings and weekends, developing skills and mastery in the distillery operations. He wasn’t automatically offered a role upon graduation from college, however, and had to leave home to develop skills. He landed at the legendary Stranahan’s distillery, where he gained competence and experience working with a wholly different grain, rye, as he rose the ranks and won his own awards as employee of the year.

It was his experience working with the single grain, rye, that led to Cedar Ridge leaning into its single malt whisky. Jeff had developed his interest in single malts during a self-education trip to Scotland and found himself gravitating to the Balvenie double wood maturation processes. Nestled in Speyside on the picturesque banks of the river Fiddich, Balvenie is a highly regarded whisky and located a short walk from Glenfiddich distillery, home to its popular Solera cask finished single malt. Those two visits greatly inspired their work over the next decade.

Murphy remains deeply engrained in the distillery’s operations today. I was glad to have been served by Murphy during a farm to table dinner hosted by the Liberty St. kitchen restaurant in Pella last fall, where I first tasted the product of those visits to the Scottish countryside.

Single Malts & Solera Casks

These are words usually associated with specific Scotch expressions but have found fans stateside as well. Single malts are whiskies produced using a single grain in the mashing process. Where Bourbon mixes a minimum 51% corn with the remainder coming from rye, wheat or other grains, a single malt uses a single grain. Much like Stranahan’s or Templeton are made with 100% rye, single malt Scotches are made with 100% barley. Given Bourbon’s status as the American spirit, American single malt spirits remain unusual across the US.

Cedar Ridge has developed its single malt expertise but chose to not stop at the single malt alone. Knowing the wine world produces spirits and ages them in barrels and butts of varying sizes, they took a part of their spirit and aged it in imported barrels to borrow the unique attributes remaining in the barrels. The result are whiskies that exhibit the deep red hues of a Port Wine finish from Portugal, the subtle yet noticeable caramels and yellows from French Sauternes, Tokaji dessert wines from Hungary, event notes of peat and tobacco from a marriage of varied oaks.

These limited releases, part a result of experimentation and part controlled by the amount of barrel capacity, are sought after by collectors and worth the nose, palate and finish.

What’s next

The American spirits industry is, once again, feeling a bit of contraction. It isn’t all tariffs, however, as American tastes are undergoing change once again, young consumers choosing different beverages than their parents, cocktails circling toward clear spirits, and of course the effects of GLP1 drugs changing consumption overall. The industry that swung to significantly increasing production in the mid 2000s is now adjusting production for the market predictions. Yet, it cannot forget that it takes 4 to 8-years for a good whiskey to rest in a barrel to be ready for the consumer.

American spirits are also investing in developing export markets, markets sometimes more closed than the US. The Iowa craft distillers network continues to expand its influence in the state and across the US even as individual distillers introduce the brand to European markets just as whiskies from Japan, India and France join those from Scotland and Ireland on store shelves.

The distillery itself is a destination beyond whiskey. The spirits shop does maintain a collection of its available spirits and associated merchandise. I couldn’t resist buying my bottles of the single malt and a Glencairn glass (my preferred vessel of choice for whisk(e)y.) The restaurant serves up snacks and food and a new pizza kitchen, patio and live music ensure the rolling hills of Swisher Iowa have an additional element of entertainment and fun. A different Iowa than portrayed in most national media!

Go check it out!

Entrepreneurship is a full contact sport; one played by introverted dreamers who evangelize dreams with manufactured hallucination. Some conjure up realities from these dreams, some burn up while trying to achieve escape velocity, and some persist to an end. Others find a path through, seeking victory yet finding enlightenment.

I share the guest post below, with permission of course, by a dreamer I’ve admired for a long time. A creator who transforms stories from wispy clouds, introspection through complex drawings, and histories with roots in childhood memories. I hope you read Matthew’s journey through the end, and I’ll see you at the bottom of the page.

The Business Buffalo - by Matthew Smith

My life goes in chapters. One just ended.

Ten years ago, I walked out of my front door with a beard to my chest and hair to the middle of my back. It had been one year since the previous chapter had ended — a decade-long adventure in capitalism: selling insurance, running a real estate investment company, spending three years in a tech incubator building software to solve marketing problems. I even dipped my toe into live events (tuk-tuk racing) and ran a food truck called Powered by Fries.

But here’s what most people didn’t know about any of those businesses: I was on a spiritual journey. Business was just my ride.

My degree is in religious studies. For most of my young adult life, I had more questions than answers. Out of college, I wrestled with depression and a profound lack of purpose — which is exactly why I went into business. I was hoping to find my dream. A feeling of being alive again.

There’s something nobody tells you when you start dreaming. It’s not out there.

The language we use can send you on a wild goose chase — “chase,” “find,” “pursue.” But dreams aren’t out there. They’re in here. (taps heart)

I remember sitting in my twenties with a mastermind group called the Enlightened Millionaires — Mark Victor Hansen of Chicken Soup for the Soul and a real estate author named Robert Allen. It was, beneath all the inspiration, a sales call. They had us visualize: big house, pool, happy wife, happy life. Lock it in. Then they tied what they were selling to that locked-in dream.

It took me years to understand what had gone wrong. If you tie your heart to someone else’s dream, but your heart was never in it, you’ll spend your life dragging that deadweight around.

Here’s what took me almost fifty years to learn, and I learned it from a friend talking about his brother.

His brother was an eccentric who could do just about anything he put his mind to. One day he decided to take up sculpting. He spent weeks searching for the right stone — getting up close, studying the grain, the texture, the material — before he ever picked up a tool. Then, after about a month, he worked furiously until the most extraordinary thing appeared: a perfectly sculpted bison.

His brother asked him how he did it.

“The buffalo was always in there,” he said. “I just removed everything that was holding it back.”

It’s what Michelangelo said about his most famous work. He did not carve David. He simply removed what was not David.

That’s how dreams are revealed.

The rock that builds up around the buffalo happens over time. Eventually, you forget there’s a buffalo in there at all. When someone comes along and calls you by that name, it catches you off guard. You might even deny it. But something in you remember

That remembering shows up in strange ways. A friend of mine is a book doctor — but while she was working as a state investigator, she would always sneak humorous anecdotes into her official reports.

When I was restoring historic homes in Des Moines, I had more fun digging through the antiques and lost possessions of former owners — hunting for the hidden gem — than I did doing the actual restoration work. Joseph Campbell would call that following your bliss.

When I walked out of my house that day with the long hair and the beard, it was the end of a year in which God — the universe, whatever you want to call it — had taken a massive chisel to everything I thought I was.

Losing multiple businesses and starting over wasn’t the end. It was just the beginning of the next stage.

The next ten years would be the finishing work. Not the big chunks. The sanding and the polishing.

That’s how I ended up at Rocket Referrals.

Sanding and polishing your life is tedious work. Everyone loves a restored Victorian fireplace. Nobody wants to spend hours with a toothbrush and dental tools removing those final stubborn layers of paint.

What that looks like spiritually is learning to lean into uncomfortable truths about yourself.

For example: I had convinced myself I was an entrepreneur — back when I dreamed with the Enlightened Millionaires, and certainly with a trail of businesses behind me. Turns out, I wasn’t. What I actually excel at is pattern recognition, predicting where things are heading, spotting overlooked details that turn out to be critical, a stubbornness that won’t accept easy answers, and the courage to go where others won’t.

What I found at Rocket Referrals was that I was a better first follower than a founder. I’m not the one who builds the rocket. I’m the booster system that helps it get off the ground. And once we land on Mars? I’m pretty good at exploring.

I also spent those ten years confronting a lie I’d swallowed whole: the myth of bootstrapping.

The lucky ones who escape the garage and build a startup sometimes forget the mothers, the partners, the encouraging kids, the infrastructure of a country, the sheer luck of being born in a time and place where it was even possible. We tell ourselves we did it all by ourselves. It makes us feel superior. It makes a good story.

It took ten years of watching men in the insurance world take women for granted for me to see what I had been doing. Watching men delegate their executive function to more capable women — often paid a fraction of what they were worth. Sitting on calls where women were belittled and demeaned, only to watch the entire tone shift the moment I walked in. I’d heard people describe this. I hadn’t seen it, up close, until I had.

And I wasn’t innocent.

My wife should have left me years ago for the half-baked ideas and entrepreneurial risks I put her through. I knew that leaving wasn’t something she would do — not from the world we came from — and I took it for granted. I risked everything. Including her.

After a decade of being the face of all my businesses, I spent ten years in the background — helping build something, gaining perspective, learning consistency, watching the buffalo emerge.

In January, the Rocket Referrals chapter ended.

There are a few things I know now that I didn’t before.

In business, it’s easy to confuse market value with self-worth. We talk about value in purely transactional terms — ROI, multiples, equity. But in spiritual terms, your worth is immeasurable. You are both the buffalo and the sculptor. The buffalo is the body you’ve been given for this lifetime. The sculptor is your soul. And that soul is connected to something so profoundly infinite that no spreadsheet will ever capture it.

I also learned the power of a well-built system. I worked alongside two extraordinary builders who showed me how quality products create consistent, predictable results. On a personal level, that translates to self-knowledge — because blooming a cactus and blooming a rose require completely different soil, weather, and humidity. You can’t build your most effective system until you stop lying to yourself about what you actually are.

So after all that carving away, what does my buffalo look like?

I love researching how things work, why they work that way, and how they’re shaping our lives. I love solving big problems in ways that make people’s lives better and reduce suffering. I love systems that are loose but tight — I need both freedom and structure. I love telling entertaining stories about big problems and the people solving them. I love traveling to interesting places and meeting people who don’t see the world the way I do.

As for what’s next — I’m uncertain. Which is different than unsure.

I’m sure there’s an intelligence in this universe that’s growing me, the same way it grows the cacti and the roses. Part of my job is to be a good gardener for my own life. To take what I’ve learned on this spiritual business trip and put it to work — so I can bloom and bear fruit for myself and others. That means living in the tension between making it happen and letting it happen. Between the gardener and nature.

I’ve also learned that on these journeys, history doesn’t repeat — it spirals. I’ve had the chance to help my son get started in a career in life insurance. I’ve spoken to a startup building a Tinder for Real Estate — which, as it happens, was the exact idea I was developing in that tech incubator a decade ago. The universe, it seems, has a long memory and a sense of humor.

Wherever I land, it will be with people solving problems that relieve suffering — people who create space where others are valued not just for what they contribute, but because they carry that same divine spark.

If that sounds like where you’re building, I’d love to talk.

I met Matthew in early 2012 at StartupCity Des Moines, an initiative borne out of the community’s need for an entrepreneurial hub, an incubator to foster ideas in hands of entrepreneurs. Apple CEO Steve Jobs had called these entrepreneurs the crazy ones. We came to call the collective an island of misfit toys brought together by fate and a hunger for a shared experience.

Matthew pitched (and I saw) a reimagined idea for residential real estate. He was surrounded by others working hard to shift a marketplace governed by deeply rooted corporate interests and protected by one-sided regulation. He could spar with a fellow entrepreneur on her vision to disrupt predatory ticketing at music venues in one breath and shift to thinking about social discovery in the next. With an insatiable appetite for ideas, Matthew generated more ideas per day than anyone I have ever met.

I sought Matthew’s permission to share this piece because it exposes the mind of an entrepreneur. Regardless of society’s outward expressions that encourage and celebrate failure, we all know the encouragement and celebrations are bullshit. Risk takers are penalized and pilloried by employers, customers, investors and employees. Many are driven deeper into mental health challenges, and some choose suicide over seeking help. Vulnerability is easier spelled than accepted by society. Leaders among us choose to ignore early entrepreneurs “because most are going to fail anyway”.

Yet it is within the mind and hands of the dreamer, the entrepreneur, the creator, the writer, the preacher, the poet, the singer, the musician, the painter, the sculptor, the reader, the photographer, the lone protestor, the one who keeps getting up each time they’re knocked down that the world changes. Steve Jobs got it right when he said:

“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.”

―Steve Jobs

You can find Matthew at LinkedIn or better yet, at his website. While you’re there and ready to dig into some incredible history through his series on Substack, The Suriname Contra Affair and how he grew up next door to a dictator.

If you are lucky enough to know a creator in your life, find a way to support them-words, hugs, listening work wonders.

I am honored to be amongst an esteemed group of creatives, the crazy ones who choose to share through notes, photographs, poems, articles, stories, books, songs, recipes, and music. The Iowa Writers Collaborative keeps me informed and educated daily through its incredible diversity of thought. Come check it out and consider paid subscriptions to those whose work moves you.

I want to thank of the dsm Magazine for including my story, Slainte mhath, in the dsm dish newsletter. If you haven’t checked out this incredible newsletter of tastemakers and foodies, please visit and subscribe for free here.

But, thanks to a follow-up invitation from the distillery’s owner Kyle Doyle, let’s first drive back down to Cumming, Iowa for a second visit!

Background

The TL;DR of last week’s post is that Todd Dunkel experimented with making wine in the mid-2000s. Neither of his first two batches succeeded but his dad intervened before he’d dumped his second batch. Dad’s advice to distill brandy led him to obtaining a craft distillation license (#4 in Iowa!) and inspired him to try Bourbon, a decidedly more complex process and operation. He was able to acquire a 100+ year old building in Cumming, procure necessary equipment, seek and obtain a Bourbon distillation permit (#8).

Craft Distillation (in Iowa)

The wave of craft brewing wave had spread widely leading home brewers and winemakers wondering about spirits. Spirits, however, are a controlled product governed by myriad city, county, state and federal rules that establish physical requirements, certification, fire control, security controls, taxation, sales and much, much more. Those who grab a distillation still and begin converting wort to alcohol through distillation are technically breaking several rules and producing moonshine.

A part of licensing requires the building housing the still that distills spirits to be secured, inspected, licensed and approved for production. Further, the product they distill cannot just be sold via their tasting or retail operations as it must be distributed through a controlled spirits distribution facility. The facility must bottle their spirit only up to the limit allowed by their licenses. They must be labeled in accordance with the licenses issued and carry appropriate legends and warnings.

In many ways, distilleries are like startups, investing heavily long before any revenue can be achieved from sale of the product. The equipment required includes mash tuns, fermenters, spirit still, spirit safe, sanitation equipment, barrels, bottling equipment and much more. This early investment required serves both as a deterrent for random production of spirits and as a way to test the mettle of wannabe distillers. By the time distillers achieve the regulated pathways, they are so heavily invested and ready for revenue that many begin distributing the earliest product condensing from the stills - vodka.

Early Days

Kyle Doyle, the current owner of Iowa Distilling Company (IDC) tells me that Todd came at distillation with the GSD (get shit done) mentality inherent in many entrepreneurs. He hustled to obtain his licenses and facility in Cumming. He created the product and achieved distribution rights. Then came the challenge faced by every startup - generating demand.

Bourbon and Rye are the primary spirits across America. In IA, Black Velvet Canadian Whiskey sold over 355K gallons in 2023 right after Titos Vodka’s 420K gallons as the top two most sold spirits in Iowa (Iowa ABD, 2023). Consumers know these brands by name and instinctively ask for the familiar name and taste. A craft distillery, on the other hand, produces spirit that’s uniquely new and distinctive in nose, palate, and finish - its flavor. A palate that for many must be developed.

Todd and his master distiller, Adam Cox, had developed the product and found their complement in Kyle Doyle who acquired the company in 2017 and began the effort to market the product across the state. Kyle had earned his stripes in marketing and sales, and I originally met him when he joined Plains Angels angel-investor network. His acquisition of the company prompted me to visit his distillery in a town I once frequented when visiting Adam and Abby’s restaurant and their sumptuous Sunday morning New Orleans-styled brunch.

The Spirits then

Walking into the young distillery was a unique experience. I could see the equipment behind a wall and grab a seat at the bar. That’s when I learned idiosyncrasies of Iowa law - the products I was about to sample may have been produced behind the wall but had to travel to the state distribution warehouse and reacquired by the distillery for samples and sales to customers and nearly double in price due to taxes and distribution cost. We sampled craft Vodka, Bourbon and Rum - all differentiated from the big names - my cup of tea.

Though not my go to spirit of choice, I tried their Vodka and found it pleasant on the palate - none of the burn that accompanies the spirit in its purest form.

The next item I tried was Rum, a spirit whose use dates back to the earliest days of the colonies but is best known across America today as the spirit mixed with Coke and consumed in great volumes across state fairs, college campuses, dive and home bars alike. Iowa’s (and America’s) taste buds are most familiar with Captain Morgan Original Spiced Rum, the third largest selling spirit in Iowa (Iowa ABD, 2023). IDC’s Caribbean Styled Steel drum reminded me less of Captain and much more of a favorite from India - The Old Monk. The flavors were reminiscent of citrus and florals and less of syrupy sodas. Yum.

My final bottle that day was the lead product - Bourbon - America’s all-American spirit. Before I describe it, you should know I prefer peaty, smoky Scotch Whisky (yes, without the e) distilled from barley and aged in Scotland. Tasted neat, those spirits carry nose and palates of leather, seaweed, ocean, salt and millennia old organics from the soil. Bourbon, on the other hand, generally derives its sweet and smooth palate from corn and rye. Yet, this particular whiskey was alcohol forward, hot on the nose and sharing caramel and vanilla derived from the virgin American Oak casks it had rested for two years. The bourbon’s sweetness arrived a bit later.

I bought all three bottles - master salesman that Kyle was to identify my taste and serve the products in order of influence!

Marketing the spirits

It is a significant marketing challenge to introduce a craft spirit to audiences used to big brands and their flavor. The company decided early to bring mixologists to the tasting room and begin using mixers that highlighted the spirit’s characteristics. For example, cola which overpowers the nose and hides Caribbean styled rum’s citrus notes was set aside for citrus fruit to elevate the spirit and experience. A sommelier sampled and guided the distillery to replace the plastic drinkware with glass as plastic lent the ethanol-forward smells in advance of the spirit. Since a significant majority of taste enters the body through the nose, ethanol from the plastic cup had to be removed from the experience.

The distillery decided to punch above its weight and entered its 4th batch of Bourbon into competitions. That early batch was still completely hand-drawn, bottled, sealed, labeled, and packaged but the team believed in the product to compete. The LA International Wine and Spirits competition evaluated the spirit and awarded it a Silver award in the category. A reason for not achieving Gold was the judges’ perception of heat - the feeling of the spirit on the nose, palate and finish - derived largely from the higher concentration of alcohol in the spirit - the ABV.

All distilled spirit is diluted before being moved from still to cask and bottle and IDC’s Bourbon was bottled at 90-proof (45% ABV). This raised a classic entrepreneurial dilemma - they could easily lower the spirit’s ABV by diluting it further from 90-proof to a more common 80-82. Not only would it create more bottles and more revenue, but it could possibly help them win Gold. Competition judges, sampling large numbers of other spirits at lower ABV would also not be surprised at the inherent hit from higher ABV. IDC’s customer feedback, however, urged caution. Their Bourbon club, a group of buyers who bought options to buy early production runs wanted the higher ABV to retain the spirit’s taste.

Customer preference prevailed and IDC Bourbon continues to be bottled at 90-proof.

The distillery today

Cumming, Iowa is experiencing growth and expansion in hands of entrepreneurs Steve Bruere of The Peoples Company who is establishing an “Agrihood”, a neighborhood rooted in agricultural traditions of Iowa. His significant financial and personal investment is developing mixed-use commercial spaces, homes of varying sizes and space, dense multi-family housing, retail, and office. A modern eatery sits a stones-throw from Iowa Distilling Company and a stop on the bike trail. Live music, community, BBQs, and tacos all serve a diversifying and growing culinary experience.

The distillery has automated its bottling, labeling, capping and even laser printing batch and bottle numbers. A 6000 sq. ft. rickhouse (large warehouse for storing and aging whisky barrels) is within walking distance and ready for growth. The distillery’s products are available now in all 99 counties across Iowa and labels like Prairie Fire are forging their own paths. Me, a purist and snob, sampled Saints and Sinners quite tentatively and, loving it unadulterated with a mixer or ice, had to purchase the bottle for its gentle Apple Pie nose and taste.

The Country Gal Moonshine was the last bottle on the table, and I was no longer tentative in my approach. Tasted. Loved. Added. It may be labeled moonshine, but it remains assuredly legal with all taxes paid!

I am a proud member of the Iowa Writers Collaborative, a growing eclectic collection of independent voices who share their varied interests, passions, and divergences under the watchful mentorship of Julie Gammack and a cadre of teachers and mentors. Check out their work at this link.

Regular readers are probably wondering why I am presenting a story about spirits, especially on a day when many are choosing to forgo something for the next forty days. Candidly, as the number of tech histories diminishes, this may serve as a transition toward stories of technologists who live a double life as creatives with other art forms. I will interview one such creative technologist later this evening (Tue, Feb 17) and will try to tell their story soon.

In the meantime, however, I welcome feedback from new readers and regulars alike.

A Couple of Hundred Years Ago

There were no iPads or minicomputers in the decades preceding Iowa’s birth. Although corn was the preferred crop for Native Americans on this land, the European immigrants brought wheat seeds and, by the 1840s, expanded wheat into Iowa’s cash crop and milled this flour for their bread. Iowa rivers also provided ready water velocity to power the mills that crushed grain into flour. Vestiges of those water-powered mills remain as historical markers in Eastern Iowa, then the hotbed of wheat and flour production. Their location was also critical as access to the might(ier) Mississippi which allowed for easy shipping.

Wayne Curtis’ book, “And a Bottle of Rum: A History of the New World in Ten Cocktails”, chronicles the midwestern states wheat production to satiate the needs of growing populations of the eastern seaboard. As immigrant and refugees to the new land increased exponentially, so did the need for more grain. Grain destined for the east had to travel by horse back across the Appalachian Mountains, an expensive and backbreaking (for the horse at least) task.

A different desire, helped along by America’s farmers, was brewing simultaneously. The enterprising Midwesterners, using any available excess in stills to distill alcohol, encouraged replacing rum with their American spirit. Realizing that they could fit far more quantity of alcohol than grain or flour, they began transporting the whisky across the plains.

The single packhorse that once moved four bushels of grain began carrying six times the grain in distilled form. The whisky was a more reliable currency, and filled the role of legal tender, medicine in form of anesthetic and sterilizer, and to neutralize the bacteria in drinking water.

Distilleries and Farming communities

Scottish refugees, displaced by the clearances of the 18th century, brought their whisky production know-how to the United States, the Dutch brought Gin, and the Scandinavians beer. Distillation was a natural household chore on the farm and consistent with farm ethos, nothing went to waste. Excess harvest went to the still, bringing with it the unique tastes embedded in local water and soil. Some of those pot stills from the mid-1800s remain visible in antique shops and early distilleries.

I was inspired about this topic in the tiny town of Cumming, Iowa, just south of Des Moines and home to Iowa Distilling Company. The town is reinventing itself through the work of several entrepreneurs today, modernizing as an agrihood, while maintaining its decidedly agricultural identity. Two of the earliest entrepreneurs in this class might be Todd Dunkel and Phil Bubb.

The Accidental Distiller

Todd, like many others in the mid-2000s, experimented with home brewing and winemaking. Both were quite inexpensive hobbies to start requiring less than a $100 investment in equipment, easily procured raw materials, a focus on cleanliness and a healthy dose of patience. He made a batch of wine that (ahem) didn’t quite work out. (I empathize - my first attempt at making a Cabernet Sauvignon resulted in a decidedly bubbly Cab and most of the 30ish bottles went down the drain). When Todd’s failed second batch was about to meet the drain, his dad intervened and encouraged him to use the alcohol to produce brandy.

Brandy required distillation, a process unlike beer and wine that was governed by state and federal rules. Todd took advantage of recently relaxed rules for craft distillation in Iowa, applied for, and received license #004 to begin in his garage with a newly acquired still. The bag of wine was distilled into brandy, and in typical product development methodology, a minimum viable product (MVP) was at hand. His interest, however, was Bourbon, not brandy which required a little larger operation.

As you drive a mile or so east of I35 into Cumming, you encounter a stop sign with a smattering of shops, a 100ish year-old building, and the end of a bike trail. The old building on the northeast corner of the intersection was for sale. He acquired the building, applied for a bourbon permit, #888, and acquired the necessary gear. Armed with his belief that Iowa grows the best corn in the world and a love for Bourbon whose mash bill is required to contain a minimum of 51% corn, he began the process of distilling world-class whisky.

They received the licenses required to produce distilled spirits in 2010 and are now recognized with a native distilling license which affirms that their aged spirits are distilled and aged in Iowa.

From Craft to Process

Craft brewing, winemaking and distillation are an art-form. Smell, taste, visual cues and instinct play a huge part in producing the desired product. As one scales, however, a consistent taste and experience become key for the casual and experienced customer.

Art begins to invite science into the process.

For example, milled grain is one of the first steps in the process, carefully separating the husk, grits and flour (grist). A ratio of about 20/70/10 allows for balancing filtration, fermentation and starch when washed and rinsed with water in a mash tun. Measured volumes of water are applied at varying temperatures in two or more washes to extract just the right amount of starch from the flour and to allow enzymes in those starches to convert to simple sugars.

One or more water rinses optimally extract sugars from the grist and excess water retained for subsequent processes. The grist now transformed to draff also remains a viable by-product as animal feed.

Each element - the ratios, water temperature, volume, time in contact with grist, and reuse are monitored by distillers and aided with technology calibrated for individual recipes.

Yeast is added in precise measures and at optimum temperature to the sugar-water mixture and the liquid rests in a washback to let the yeast begin its work. Hygrometers, manual or automated, monitor the process, awaiting the moment fermentation is complete. Math, Physics and Chemistry may have begun the process in the mash tun, but Biology is the driver in washbacks. It is time to begin separating alcohol from the rest of the mixture in a still.

Distillation generally occurs in copper stills. Artisans who forge stills swear by the tastes imparted by the stills’ unique shapes, bends, bumps, turns, heights and lyne arms. Precision Chemistry and Physics determine when and how much alcohol vaporizes within the still as the liquid is heated, how far up the still’s neck it rises, how it is cooled and collected for aging. The tempest in the kettles is a marvel to observe in making of this spirit.

Biology reenters the picture as the alcohol from the stills is moved to barrels. The provenance of the wood governs manufacturing of the new barrels. Coopers char the barrels the inside to a precise depth (levels 1 to 5) to awaken the wood’s constituent characteristics, again specific to the recipe. The resulting char allows extraneous compounds to be filtered out of the spirit as it ages even as they lend familiar notes of vanilla, butterscotch, bananas and other fruits to the resting spirit. And finally, as angels extract their “angel’s share”, through natural evaporation, the constantly changing concentration of the spirit become the focus of the master distiller’s work.

Dude, that’s all Art - Where is the Tech?

Technology is the underlying beat in a distillery. Each step of the process is carefully calibrated to maintain quality, consistency, and repeatability. Water’s physics, sugar’s chemistry, yeast’s biology and their interplay are a carefully calibrated dance under the watchful eye, nose, taste, touch of the distiller. Slight variations in environmental temperature, volume, char, boil, weight, moisture, color and time can be disastrous or worse, explosive. Although only the most expensive and expansive factories are truly automated, millions of gallons of spirit move through craft and factory distilleries daily through a mix of modern and antiquated technology.

To the regulators, at least, the most important measure is the number of gallons bottled as spirits are taxed and controlled at the source of production, distribution, and sale. Nearly half-a-billion dollars are transacted in spirits sales in Iowa.1

Do you want to learn more?

This is the audience participation part of my request - do you want to learn more about this Iowa industry? Do you want to know what happened with Todd Dunkel and his company at the four-way stop in Cumming, Iowa? Where do native distilleries fit in our consumption pattersn? What happened to the prohibition era rye whisky that became all the rage in Iowa fifteen-ish years ago? Does Iowa whisky hold a candle to bottles from Kentucky? Can you envision a private bottling with a carefully tuned recipe (perhaps an Okoboji Writers Collaborative Spirit)?

Or was this enough of a detour and I should stick to my knitting in technology?

I am a proud member of the Okoboji Writers Collaborative, a growing eclectic collection of independent voices who share their varied interests, passions, and divergences under the watchful mentorship of Julie Gammack and a cadre of teachers and mentors. Check out their work at this link.

Doug Wilson discovered a need for such a convening platform for mental health professionals. Let’s rewind a couple of decades to learn this entrepreneur’s journey.

Best Laid Plans Disrupted

Doug Wilson was living in Indiana and working for the behavioral health division of the pharmaceutical giant, Pfizer, in the mid 2000s, calling on clinics delivering psychiatric care. He would often hear clinics inquire if he knew of doctors seeking alternate opportunities. He’d make those connections when one was available, cementing not only a valuable relationship with the doctor but nearly guaranteeing a long-term relationship with the clinic served.

He enrolled in an MBA program in the late 2000s as he continued to think about a lifelong dream of running his own business. An assignment to develop a business plan led him to think about telemedicine and telehealth, services then in relative infancy due to the specialized hardware and connectivity required.

Although starting his own company wasn’t in his plans, fate intervened. Pfizer’s patents for the very pharmaceuticals he represented expired and the division was shuttered, displacing Doug in 2011 when the world was just recovering from the recent financial crisis. Entrepreneurship rises in times of economic uncertainty and Doug knew it was time.

He, like many others who’d been dreaming of entrepreneurship while being previously employed, decided to take the leap. Leveraging his family’s existing connections to Iowa, Doug and his wife moved from northwest Indiana to Iowa and Doug registered his new company, eVizzit, LLC in January 2012. The company later adopted the name Integrated Telehealth Partners (ITP) in 2017.

Funded by the severance check and supplemented by random gigs, Doug continued to diligently build his company while looking for funding to scale. He sought connections to entrepreneurial support organizations (ESOs) who could help him steer his business and fill the need for small office space. He found the West Des Moines Business Incubator, an effort of West Des Moines run by Clyde Evans and Jo Eckert, who facilitated several connections including to a future business partner, David Gion.

Equally valuable were connections who became mentors. Dr. Robert Caudill, a psychiatrist at the University of Louisville and one of the early leaders in telepsychiatry, generously volunteered his time to provide guidance from both a clinical and operational perspective in the earliest stages of the company. Similarly, Jonathan Neufeld helped him understand the changing trajectory of telehealth resource centers, regulation, and reimbursements.

Funding, however, remained elusive and Doug sensed an end of his dream, when he was encouraged by the West Des Moines business incubator to meet Mikki Stier. In his mind, that would be the one final meeting before he shuttered his dream.

The Spark

That pivotal meeting with Mikki Stier, then head of public and government relations at Broadlawns hospital led him to state representative Renee Schulte. Renee introduced Doug to Bob Lincoln. Bob was the CEO of the County Social Services Mental Health and Disability Services (CSS MHDS) region. Bob was helping the state transition from a county to regional system for behavioral health services and expanding their reach. He recognized the value telehealth could provide to far-flung rural regions despite the highly proprietary and expensive technology of the time (2012 was a different era for remote meetings).

A stumbling block remained. ITP was relatively tiny and large hospitals don’t just handover large-scale contracts to unproven small businesses. Recognizing ITP’s value, however, Bob introduced Doug to Chris Hoffman of Pathways Behavioral Health of Waterloo to the table and facilitated the funding for Pathways to partner with ITP and bring its solution to the regions. Bob, CEO of the first such region became a champion for the company.

The career that began with Pfizer in 2003, took him through the MBA at Kelley School of Business - Indiana University, and brought him to Iowa to launch ITP in 2012, had now delivered him the dream of running his business. ITP remained at the West Des Moines Incubator and began growing with servicing this new business model.

The Business

Behavioral health professionals, like in any other field, can have excess untapped capacity, especially when they live and work in remote areas themselves. ITP began building a network of providers willing to make their excess capacity available to hospital and clinics elsewhere. ITP built the technology to manage this ‘marketplace’ and hired the providers as 1099 contractors.

Nearly 60 county jails and 70+ hospitals across Iowa leveraged ITP’s providers, connecting the provider to someone seeking care. As such care needs often arrive unannounced to these facilities, ITP services became highly desirable and critical, especially in rural and remote areas that were mental health provider deserts and rarely had psychiatric services available from within their medical staff.

As some providers hailed from outside Iowa and occasionally required licensure and insurance themselves, ITP facilitated their ability to become certified and provide the requisite services. The marketplace, thus, took care of both sides of the market, cementing its value in the eyes of both entities.

Over time, as the company grew, so did the complexities of managing flexible and varied availability schedules. Many of the 1099 arrangements have transitioned to full-time employees of the company. A growth in services required by children and adolescents, immediate and residual effects of the pandemic’s impacts, and societal isolation has also led to expanded need for ITP and similar providers’ services.

Funding

ITP raised a round of angel investments in 2017 and, in full disclosure, members of Plains Angels including myself, were minority investors in the round alongside executive members of the company. The company used the funds for growth, both in operational and medical staff. David Gion, a serial entrepreneur in the Des Moines area joined the company’s executive team after exiting his own construction software company, Canvis.

A period of quiet execution followed, with little heard from the firm in the central Iowa startup circles during the following two years. Although schools could’ve been a growth area, the bureaucracy of long sales cycles posed a risk the company chose to avoid, focusing instead on rural clinics, hospitals and jails expanding to over 200 facilities within the state.

The company continued to innovate from within. Nathan Vorm was the company’s first non-physician hire and became a multi-talented resource. He recognized the complexities inherent in proprietary hardware to deliver telehealth and built ITP’s own custom cart, an admirable yet complex solution. Recognizing their own small size and complexities of building hardware, they ultimately didn’t commercialize the cart (presciently, as web-based telehealth was just around the corner). Nathan delivered information technology support, identified new business opportunities, managed billing, accounting and customer support.

By 2019, ITP had reached the level of maturity that attracts strategic buyers and merger partners. Having exited their relationship with Pathways Behavioral Health, they were now a profitable and independent business.

Transition

Psychiatric Medical Care (PMC) based in Nashville, TN was a private-equity backed entity, formed to provide intensive outpatient group therapy program for older adults. Their product, Senior Life Solutions, was accretive to ITP’s telehealth services and envisioned as a complement to their service model. ITP brought a critical element to PMC-the psychiatric and medical professionals employed by the organization greatly appealed to PMC who had relied upon contracted services only until 2019.

PMC acquired ITP in 2019, providing liquidity not just to the ITP executive team but also to angel investors who in-turn reinvest returns from such exits into other startups.

The subsequent pandemic was an accelerant to adoption of telehealth. As the world became accustomed to mobile and desktop video conferencing for work, family, and play, medical professionals found themselves serving a larger number of patients in ever larger geographic areas.

Doug, like many ‘exited founders' (yes, this is a formal term for those who successfully exit a startup) could’ve simply cashed the checks and retired to warmer climates. Driven by his passion for behavioral health services, he chose, instead to stay with PMC and grow the business. PMC continues to grow, now with a recent second PE firm led recapitalization that helps facilitate organic growth as well as inorganic M&A.

What’s next

State regulations differ across borders for licensure, insurance, prescriptions, and service delivery. As behavioral health delivery may involve family intervention, patient self-check-in at hospitals, law enforcement and even involuntary commitment when self-harm may be suspected, the myriad regulations must be evaluated prior to connecting a medical professional to a potential patient. Doug and team remain in their West Des Moines office (albeit now in a hybrid mode paralleling their own product) to expand the ways in which their technology performs its work.

What Doug’s business plan at Kelley had envisioned nearly 15 years ago has come to pass in his care yet much work lies ahead. Behavioral health interventions cannot way a multiple week wait common when seeking professional health. Similarly, these services are expensive, cash-payment at service, even as many patients rely deeply upon Medicaid.

Despite the many changes influenced by the pandemic, challenges and vestiges of the past remain. Potential requirements for patients to be seen in-person at pre-set frequencies is often impeded by distance. Prescribing medications under the Drug Enforcement Agency’s potential supervision is another impediment to timely delivery of care.

As I left Doug’s office amidst light flurries and thoughts circling around telemedicine, behavioral health care, affordability and entrepreneurship, I was glad for Doug’s layoff from Pfizer. His story reaffirmed my long-held belief - entrepreneurship rises when economy falters. He thrived, experienced a double-whammy - layoff during a financial crisis.

Perhaps that is what inspires his grit and commitment to patient care.

I am a proud member of the Iowa Writers Collaborative, a cohort of writers, and artists who contribute their creativity to a global audience.

Those thinking about wellness are discovering myriad ways to manage through. Some seek professional intervention for support while others engage in reflective interventions to illuminate a way to wellness. This is a story where one family’s work is leading to an approach as implemented by a startup in our enterpreneurial community.

This story is slightly different for another reason. I am the steward of a group called Plains Angels, one of several angel investor networks in the state whose members seek startups whose message resonates with their investment priorities. Although I am not an investor in the company, our group does have an active investment in BRIGHTN, the subject of this story.

A bit of back story

Jeff Johnston of Cedar Rapids was a wealth advisor with a robust career in finance. His practice employed nine individuals who collectively helped people manage nearly $800MM in wealth. His family comprised of his wife and three boys, and life was on a steady and comfortable trajectory until tragedy struck.

On the morning of October 4, 2016, Jeff received a phone call no parent imagines receiving. A child’s body is considered the greatest weight borne by a parent in Hindu culture and Jeff would bear such a weight that morning. His son had just succumbed to a drug overdose in a hotel room. He was a mere three weeks from the arrival of a daughter.

The family continued to work through grief and trauma even as they picked up the pieces of life with their granddaughter. Jeff’s wife bore that trauma differently, and lost her own life a mere five years later. Jeff’s own perseverance wearing thin, he recalls that his family almost buried him in this period of grief.

His life’s purpose, however, was yet to be revealed. He wanted to become a better, not bitter, man and wondered if there was something beyond wealth advisory for his life’s purpose. A passion had taken hold in him in these years to make the world better through improved mental health. He now recalls how the phrase below became his mantra

Purpose becomes Passion when it is Personal

He sold his wealth advisory business, the podcast and TV show and dedicated his remaining life to improving mental health for others. The name for his new company came from Brighton, the daughter of the son he lost-he removed the ‘o’ to create BRIGHTN, both honoring her and protecting her privacy.

Introducing BRIGHTN

Accustomed to helping clients create a financial plan for life, Jeff directed energy toward mental wellness planning via an app. With a significant population of GenZ individuals reporting mental wellness challenges, he instinctively knew that a comprehensive planning application could improve adherence to medical treatments and focused his energy on such an app.

BRIGHTN, the company and app, are a subscription service distributed directly, through health plans, schools, and therapists. It prompts its young members to see the optimism of the day and to find beauty and connection to the world. It seeks to know and track the user’s mood, encourages journaling within the application, and works to shift the user toward a growth-driven mindset.

Guided by a team of clinical advisors and mental health professionals, the small team launched the app in the summer of 2025. They engaged Portland Trail Blazers and Sacramento Kings’ players Kris and Keegan Murray, respectively, to provide motivation as ambassadors in the program and began seeking early users and group contracts.

Nearly 25 million words had been journaled by users by the end of July 2025 (by contrast, there are only about 650 words in this story at this point). Nearly 20% of the app’s users persisting their use past 30-days, more than double the rate of persistence of comparative therapies. A recent pilot study showed improvement in sleep, lower anxiety and depression, and three times more social connection than the control group.

Reaching Users

They have expanded their reach to insurance and pharmacy groups and added generative AI to the journal for better and more intelligent conversation. The user can engage with the app in a chat much like other LLM experiences via ChatGPT, Gemini, Copilot and more except that these conversations are kept private and do not inform the underlying LLMs with the journaled content.

The app does not provide medical advice or pharmaceuticals, relying instead on the user’s medical professionals to provide those services. The company’s recent partnership with Des Moines-based OpenLoop further highlights their ability to provide access to care yet remain further upstream with prevention.

Gamification is the name given to an approach to increasing engagement. Where social media engages through addictive doomscrolling, apps (Duolingo prompts anyone?) have deployed game principles to bring users back and Brightn is bringing app-specific gamification to keep users engaged. By integrating financial well-being with mental health, the app also brings front and center an instigator of challenges to mental well-being for the GenZ cohort.

What’s next

Brightn’s history is still being written so I’ll replace my usual retrospective with a prospective view. Startups such as Certintell, Integrated Telehealth Partners (ITP) and OpenLoop are actively delivering medically-inspired products to audiences in Iowa and beyond. ITP has already experienced an exit acquisition and Openloop is whispered about as one of the rare unicorn startups from Iowa.

BRIGHTN has generously offered interested readers a trial via the link below. The link will direct you to the download pages if you’re reading this on your phone or to their website if from the desk

I am honored to be a member of the Iowa Writers Collaborative, a cohort of writers, photographers, poets, artists and musicians who contribute their entrepreneurship and creativity to a global audience. A visit the Iowa Writers Collaborative promises to be enriching

They were using email :)

Long before there was Gmail or Hotmail

Long before Gmail, Hotmail, or Yahoo (all still in-use by this Substack’s subscribers), email traffic largely traveled on proprietary email services. The user-interfaces were optimized for transmission efficiency over friendliness, even on emerging user-friendly platforms such as the Macintosh computer and its Windows and DOS counterparts. A few products experimented with desktop-based user-friendly mail applications, launching precursors to the likes of Outlook and other apps of today.

Des Moines, Iowa was relatively distant from these email developments.

Except however, for CE Software, a company that had restructured and rebranded itself from selling computer hardware (as Computer Emporium) at retail into a software company. Though the pattern of shifting from hardware sales to software products would repeat time and time again over the next two decades, Computer Emporium’s transition into CE Software may be one of the earliest instances.

Their future flagship email product was yet to be needed, discovered or born. They focused their attention to software for Macintosh computers and began working on tools and utilities that resolved everyday annoyances for the end-user.

A wonderful archive of CE Software

Although much appears to be lost about CE Software and my attempt to seek the founders for an interview failed, a single bibliographic citation led me to the Des Moines Register archives at the Des Moines Public Library. Kathy Bolten, a business writer for the Register and Gary Fandel, photographer, captured the key moments of the company’s history in the Metro Business Section on April 9, 1990, which became my primary source.

History doesn’t repeat, it rhymes

The citation, however, inadvertently led me down another path reminding me that history doesn’t repeat itself, it often rhymes. Stewart Butterfield1, the founder of photo-sharing app Flickr, once found a new career in creating a gaming company, Tiny Speck, after selling Flickr to Yahoo. Tiny Speck’s first major product, a game called Glitch launched in 2011. Though Glitch failed to gain sufficient traction, the development team’s communication platform became legend in computing circles.

The Glitch dev team kept up with each other via messages posted on internal channels on a platform they’d developed for internal communications. As they shuttered Glitch, they released this communication platform to use by outsiders. The product, a Searchable Log of All Communication and Knowledge became known as SLACK and is now a de facto communication standard.

That’s the rhyme in 2014. Back to 1981 Des Moines.

Games

Kathy’s interview in the Des Moines Register leads us to Don Brown2 who joined the transformed West Des Moines software company as a partner. He was the brainchild behind much of the company’s software, including two games - a text-based adventure SwordThrust and Eamon, a role-playing game series. Unlike Glitch, these games found significant commercial success and were ported from Apple II to PCs, Atari computers and the Commodore 643.

As the game business delivered steady revenue and Don’s ambitions widened, the company pushed deeper into the emerging Macintosh ecosystem. What followed was a burst of experimentation: small utilities that solved real problems for early Mac users. Desktop Accessory Mover, MockWrite, MockPrinter, MockChart, and MockTerminal weren’t just products — they were proof that CE Software could spot gaps in a platform and fill them quickly. The tools eventually became bundled as MockPackage and their growing reputation drew the attention of larger publishers. One of CE’s utilities, MacDesk, never even made it to market under its own name; Borland snapped it up and rebranded it as Sidekick, a sign that the company’s instincts were resonating far beyond Iowa4.

Quickmail

As CE Software grew, so did its needs for streamlined communications. It led to the development of its most successful product over nearly two years to help internal communications. The original approach of shouting messages to each other in the early 1980s followed by the ubiquitous Post Its no longer worked for the nearly thirty person company. They looked at the commercially available software from Microsoft and Apple and found that neither worked for a company their size. Developers, being developers, decided to write their own.

The product they developed for internal use was good. Having supported the community of users across the Apple platform for multiple years, they knew they had a winning product worth commercializing. By 1989 they commercially released the first version of Quickmail. Although a utility software, another product Quickeys would remain a successful product by units shipped for some time. Quickmail, however, rose quickly in overall revenue, providing nearly half of the company’s overall $2.9M annual revenue per the April 1990 Register story.

The 1990s

Microsoft introduced Windows in 1985 in response to Apple computer’s success amongst creatives and passionate home users who loved the Apple graphics user interface. There was a widespread joke at the time that Microsoft never got anything right for at least three versions and Windows 1.0 was no exception. Windows 3.0, released at about the same time as Quickmail, however, found a footing and began making appreciable inroads into business environments. Its 1992 release of Windows 3.1 finally brought reliable networking to the desktops. CE Software added a Windows version of Quickmail to its arsenal of products in 1992, supporting a peer-to-peer messaging platform without need for a mail server, thus perfectly modeled for a small business.

Although the history behind the “why” appears lost, the company began running into delays and issues with release 2.6 of Quickmail in 1993. Though stories blame the divergent strategy of supporting Windows and Mac, alas only a conversation with the founding team could reveal the actual reason. Regardless of the reason, CE Software experienced a layoff that year, resulting in staff reductions of 7%. The 100+ person software company was back below 100.

The rapid software release cycle of the late 80s slowed considerably with version 3.0 release in 19955, and a pro version in 1997 covering Mac and multiple versions of Windows6. A version was even planned for Microsoft’s flagship server product, Windows NT even though, ominously, Microsoft’s own mail server, Exchange, was well on its way to establish corporate beachheads.

2000s

The company chose to access capital from the public markets via an initial public offering. Completed on Jul 28, 2000, CE Software began its public life on the OTC. Modern day startups don’t even consider going public without hundreds of millions in revenue. However, even in 2000, a company as small as CE Software appears to have run into filing complexities as exhibited by multiple delays in their regulatory filings within their first year as a public company7

With financial difficulties compounding over the years, significant maturation of competitive products from multiple vendors, the increasing use of Internet hosted email from Hotmail and Yahoo and growing popularity of self-hosted email on Linux servers, CE Software recognized a need to liquidate. It found a buyer in a new California company, Outspring software. The transaction was completed on the last day of 20038. Outspring Software continued to sell and support the product for nearly five additional years, finally succumbing to technological obsolescence and suspending sales in July 20089.

The company founded in 1970s as one of the region’s earliest retailers of computer products, one that successfully and presciently executed a transition to software and developed a cult-like status through software was at its unfortunate end.

Why record this story?

It is easy to capture successes with wildly profitable exits and riches distributed to owners, employees, investors, bankers, and shareholders. It is hard to revisit similar history when missteps, competitive forces, market maturity or myriad other reasons lead to a product or company’s demise. If we don’t visit this history, however, we stand to lose the lessons embedded within.

Lessons such as CE Software’s recognition that hardware sales are linear but software can be exponential. Lessons like focus (on Apple/Mac) can allow a company to excel even in uncharted waters. Lessons like distraction (Windows) can be lethal.

I am attempting to seek other failures, some occurring over decades and others in short few months or years. Such stories are hard to read and heart-wrenching to record in the entrepreneur’s voice yet must be recorded and remembered.

It is up to us, the historians and participants to remember the legacy of the entrepreneurs who went before us, to honor their work, not as a funeral for their companies but as a celebration of life - of what they achieved and how they unlocked future generations of customers, investors, employees and cheerleaders.

Born on a dairy farm in Northwest Iowa, Dawn selected an admirable path for herself. Her passion for math encouraged her to enroll at the University of Iowa as a math undergraduate in the early 1990s. She was exposed to the field of computer science and felt there was a future she might just create in the burgeoning field. She envisioned a career in teaching and set a course for post-graduate studies and an eventual doctorate. Life’s gifts included three young sons for the academic. Life’s twist, however, saw her husband’s departure from the family, a setback in Barry’s paradox.

A consummate learner with motivational messages at the ready, she asked me if I knew the most influential person between 1000 AD to 2000. I got it wrong and I invite you to think about it for a moment.

Changing Tracks

DEDE Inc was registered in 1997 and financed with capital from investors to begin providing software engineering services through a small group of programmers. Disrupted from her academic pursuits, it was this firm where Dawn sought and found employment. Leveraging her newfound skills she became a programmer. As was customary for many software firms of the time, the group of 9 employees wrote software for a variety of companies, bringing technology to those whose expertise lay in Iowa’s broad industries.

Corporate life is often like a car on cruise control. Employers large and small set the company’s direction, perform sales and customer management duties, and the employees deliver to the company’s strategy. Until a roadblock causes the cruise control to disengage.

Busting the Roadblock

The 9 employees showed up to locked doors at the company one morning. To employee and investors’ surprise, the founder had abandoned the company. Employees knew of the owner’s extravagant lifestyles but didn’t expect to suddenly be unemployed. Dawn, with the farm kid’s resolve and agency, chose to attack the problem.

As the investors now owned the company, she approached them with an offer to run the company but not as an employee. Thirty-three years old and amongst the youngest of the nine, she would run the company and earn her ownership via vested stock over time. Her vision and goal was to own the company outright and provide the investors with their capital and gains in exchange for 100% ownership.

The investors had no desire to run a software company or be responsible for “the nerds”. Facing a win-win, they agreed and Dawn stepped in as President of the company, unlocking the door to employees who had been her peers just days before. She had chosen to rely upon the power of her agency to seek what she knew could be hers rather than wait for a future to be decided for her. All eight chose to stay under Dawn’s leadership and Genova Technologies was reborn. She was a thirty-three old first-time businesswoman.

Focused, Organic Growth

The team adopted servant leadership as their approach to work and sought win-wins through a period of near-explosive growth. Dawn describes her preference to drive and navigate the boat through turbulent waters because it felt scarier to not be in control. Learning and running the business was like facing buggy software, something they knew how to manage – learning to see and debug the business in stride.

Her chief technology officer, a veteran of the company recently asked her about why none of her competitors from thirty years ago remained in business. He rebutted Dawn crediting luck with no one surviving on luck alone for three decades. Reflection provided the reason – they had always sought solutions where neither the customer nor employees lost in a negotiation. By focusing each conversation on a win-win, to be the best engineers for the best customer outcomes, assured them continued growth.

Dawn paid off the investors who had trusted her their original investment with a handsome 3x return on that investment. She never borrowed any capital from any investor or funding source, ensuring that business growth was organic, profitable, cared for customers and employees, and delivered on promises.

The nine-person company would grow to 225!

Disruptions

Growth wasn’t devoid, however, of roadblocks. Rockwell Collins was one of the company’s primary customers when the nation faced 9/11’s impacts. As a federal contractor, Rockwell also retrenched and Genova’s business appeared to waver. A lesson that Dawn would repeat to an MBA class years later, present-day curses can lead to future blessings. 9/11 forced her to look broader at the industry in her Cedar Rapids backyard and on the national scale.

She diversified.

One such diversification was winning a bid for work with CMS (Centers for Medicare and Medicaid). Winning a brief engagement worth $17,000, the software firm expanded to Baltimore and began servicing a client itself about to experience significant growth. It also allowed her to take a principle-driven approach to software development to CMS.

The BOSS (Business Objective Software Supplement), the company’s ethos that balanced business objectives with software supplements, ensured that neither software purity nor business drivers alone governed a project. She was able to show their approach and its value to CMS who adopted the principles, helping grow that part of the business to millions in revenue and influence. This success provided an unusual insurance policy for another roadblock ahead.

As the financial world imploded

Dawn had entered technology business on the cusp of the dot-com crash followed near immediately with 9/11. As the business’ footprint grew to nearly 225 employees in 2008, a different, less-predictable tsunami arrived with a diagnosis of multiple sclerosis for Dawn. As MS impacts each patient differently, Dawn had to begin planning for the unpredictable future, inadvertently setting in motion a plan for longevity. She began mentoring and guiding employees to also become business managers just as she looked to sell those pieces of businesses that were not directly strategic.

The healthcare/CMS arm of the business, a profitable enterprise attractive just as Obamacare was becoming a possibility under the new government, was attractive to potential buyers. The focused growth had created an insurance policy that could be sold. Booz Allen Hamilton, a global consulting entity bought that part of the company, bringing Genova back to an Iowa enterprise, now with a more manageable sixty-ish employees. Genova retained its defense and technology businesses.

The company’s products continued to be varied and strategic for its customers. Dawn talks lovingly and longingly about products such as the mobile laundromat payment system, developed for a valued customer. She talks about other projects where it was better for Genova to steer a customer away from developing a product already on a death-march. Though that left money on the table, it created a multi-year trusted customer relationship.

She also speaks to the ideas of recognizing value. Citing another project example, she shared how they studied and learned value of a seat on an airplane using variables such as day and time of flight, its origin and destination, fullness of the aircraft, and more that went far beyond the cost of flying a seat in the aircraft.

On that early desire to teach

Dawn didn’t end up getting her doctorate or teach computer science. However, a colleague recognized her as a lifelong learner who freely imparted knowledge. Dawn was invited to speak to MBA students at the University of Iowa, inadvertently fulfilling the early dream. She was finally in front of the class. Some of the lessons imparted through that class and conversations include:

Entrepreneurship and business ownership isn’t working just a few hours – it is choosing which 80-hour block to dedicate to the company week after week. It is a continuous exercise of service, modeling, delivery, management, reflection, and humility.

Entrepreneurship is for those who seek control over their destiny. It involves stress – our reaction to obtaining and maintaining control. It contrasts with frustration, felt by those employed by someone else and whose destinies are controlled by someone else’s decisions. Neither is inherently wrong, nor easily interchangeable.

Today’s curse is tomorrow’s blessing and each roadblock is a software bug waiting to be debugged.

No one wants to be sold what the entrepreneur wants to sell - people buy buy what solves their problem. The entrepreneur needs to understand the customer’s problem and describe the solution in the customer’s words. Listening is, therefore, one of the most important skills an entrepreneur needs to build to be able to sell anything.

Nobody will come give you something if you aren’t willing to go ask for it. Bravery in the ask often stands beside the fear inherent in the ask.

Coming full circle

Genova Technologies was born when a displaced employee’s courage reopened an abandoned business. It grew through the new owner’s medical diagnosis when it was thrust into forced succession planning. It has remained viable in the intervening years even as Dawn reduces her workload through transitioning responsibilities to her employee managers.

This January, the business has transitioned yet again. It left Dawn’s hands for those of certain employees who have acquired the company from her and will now run it in their stewardship. They will write a new story for the three-decades-old business as Dawn looks at it from the vantage point of her retirement. She proudly and rightfully retains the title of Founder, Partner and Senior Advisor.

She recollects thoughts she’d shared from the Technology Association of Iowa’s Prometheus award stage when recognized as the “Woman in Technology” in 2006. She credited the four men in her life – her three sons and the then and current husband – for being her greatest cheerleaders, unthreatened and supportive. Flipping the statement “behind every successful man is a supportive woman” she reflected that “behind her honor was an equally supportive husband”, one who remains by her side through these changes.

The Most Influential Person of the last millennium

Johannes Gutenberg launched the information revolution through his printing press. The information revolution is neither stagnant nor evenly distributed in its past and is unlikely to be predictable in the future. It is up to the dreamers, thinkers, and tinkerers to create its future.

I am honored to be a member of another startup community, the Iowa Writers Collaborative. Its voice is led and amplified by another type of entrepreneur - writers, photographers, poets, artists and musicians who contribute their creativity to a global audience. A visit the Iowa Writers Collaborative promises to be enriching

This post is slightly longer and better read in the Substack app/website rather than your email client. Email may cut off before the valuable lessons learned are presented fully.

The first two installments discussed stories of the Global Insurance Accelerator and the New Bohemian Innovation Collaborative. This final installment is a story of wins and losses, euphoria and regrets, experiments and results. I alluded to this story in the Origins section of my Thanksgiving week post and how a chance meeting led to the creation of several components of Central Iowa’s entrepreneurial ecosystem. As with any memoir, this post is derived from my memory and could be inconsistent with others’ as I unravel this thread. Although Mike Colwell’s and Christian Renaud’s review comments are within, I invite others with additions or corrections to place them in the comments for the benefit of history.

Let’s begin with a nod to the shirt designed by Ben Milne that symbolized StartupCity Des Moines’ Lean approach to ecosystem building far and wide

Proof, Java Joes, Amici, Tacopocolypse, Peace Tree, Garlicpalooza

Iowa’s startup community was searching for a home in late 2010. The two years leading up to my lunch meeting at Proof with Mike Colwell and Christian Renaud were filled with efforts to start an entrepreneurial community in downtown Des Moines at coffee shops, restaurants, and music venues.

Long-time (9 months, but a lifetime in this stack’s age) readers will recall the nascent Impromptu Studios community established by Dan Shipton and team. As Impromptu neared its end, others hungered to pick up the mantle and maintain momentum. Christian Renaud, then CEO of Palisade Systems, was already supporting entrepreneurs in the community. He hosted Ben Milne and the nascent Dwolla in Palisade’s office and was dreaming of a larger space for greater creative collisions amongst entrepreneurs to duplicate his experiences at Cisco in Silicon Valley.

The weeks following the lunch are a blur. Christian and I built a blueprint for an incubator, spreadsheet-ed a financial model, forged new friendships (including our own), and begun fund raising. Iowa’s economic development landscape supported our three-year vision, and over the subsequent nine months, we were able to garner funding support from the State of Iowa, City of Des Moines, Polk County, and the Greater Des Moines Partnership (The Partnership) with access to and incredible support from Debi Durham, Terry Vorbrich, county Supervisor E.J. Giovannetti and CEO Martha Willits, respectively.

The organization’s name, Startup City Des Moines (SCDSM) and the logo, a modified anvil, were unveiled on December 9, 2010, forging a new start for our incubator. Our model assumed that participants would contribute a portion of their company’s equity to the incubator, become residents in a shared space, mentor and grow together. A related assumption was that their successful exits via sale/merger would provide new funds to sustain the organization. The Partnership assisted us in securing 10,000 square feet in downtown Des Moines in the Bank of America building.

This section’s header is a nod to the earliest locations and entrepreneurs who contributed to the community through place, food and beverage. Though, sadly, none exist today, the contributions of each were critical in bringing people together, securing their place in this history.

The early years

An essay from Andreesen Horowitz derisively refers to this period as when “ways of working were diffusing out into the world beyond Silicon Valley”. Then, as now, the valley’s elitist feeling was that true technology could only be built in the valley.

However, other ambitious entrepreneurs from elsewhere in the state shared our dream. Amanda Wood and Andy Stoll came from Cedar Rapids and shared their work from eastern Iowa and, more importantly, told us about Startup America, a parallel initiative underway in Washington DC. They motivated us to join forces with Startup America and launch Startup Iowa alongside SCDSM.

Startup America was led by Steve Case of America Online and Scott Case (unrelated) of Priceline. Steve & Scott, in their new careers, envisioned a three-year plan to spur entrepreneurship across America by tapping into states’ strengths in hands those states’ entrepreneur leaders. Andy and Amanda brought a detailed playbook from Nashville where Startup America had helped establish StartupTN.

The SCDSM plan and funding were also a three-year strategy so adopting and adapting StartupTN’s plan for Iowa to connect to a national strategy felt right. Startup IA launched simultaneously with SCDSM’s ribbon cutting in Des Moines with Scott Case, Jay Byers and numerous city and state leaders present. SCDSM’s 10,000 sq ft filled with hundreds from many walks of life. The community was on fire and local print and television media began reporting weekly on its activity.

Eight companies officially joined SCDSM and signed over equity to begin working on their products. They began meeting with mentors and advisors who pushed and prodded, cajoled and inspired the young companies. The space became a “community center” complete with a pool table, wall to wall whiteboards, food and drink. Ideas flowed from residents and guests alike.

Why All the Excitement

Not everyone searches for another job when the economy contracts and layoffs affect livelihood. Some start small businesses and simply stop being employed by others. Others equate business formation risk with employment. Although entrepreneurship, in aggregate, has been declining in the US since the 1970s, partly driven by the necessity of healthcare benefits and increasing wages in low-unemployment states, the pattern of increased entrepreneurship during economic downturns remains true.

Early 2010s in Iowa brought an economy feeling delayed effects of the 2008 financial crisis, the possibility of health insurance availability under Obamacare, the decreasing costs of launching tech-centered businesses with ubiquitous cloud computing, and congressional attention on starting businesses with specific legislation such as the JOBS Act of 2012.

Iowa was an unlikely place for entrepreneurial activity with a twist. Coverage of Iowa’s entrepreneurial activity reached a crescendo as Lynn Hicks and Marco Santana’s voices put startups on the front page of the Des Moines Register’s business page and, on more than one occasion, above the fold of the front page. Kyle Oppenhuizen of the Business Record developed deep stories and brought startups to the paper’s cover originally graced by CEOs and leaders of area corporates. Geoff Wood added written and podcast coverage via his Silicon Prairie News web channel which further attracted attention from traditional and tech-first national outlets. Iowa’s own startup darling, Dwolla, continued to capture national attention which added to the aura of Des Moines as a startup hub.

It is what led Jay Byers, by now CEO of The Partnership, to exclaim that Des Moines was punching way above its weight, and he lent his formidable social media presence and love for Des Moines to the startup community. An entrepreneur and musician himself, he was also ever-present to the community’s need, meeting entrepreneurs, adding their voice to the Partnership’s Washington advocacy on high-skilled immigration, JOBS act, patent reform and much more.

Celebrity sightings

Media and press bring celebrities. In addition to Startup City hosting Ashton Kutcher and Ben Milne for an investor’s perspective on Dwolla, interesting guests appeared in this 10K sq ft space. In May 2012, Brad Feld led one of the most meaningful discussions into the early morning hours. A venerable venture capitalist from Boulder with what was once his seminal work in the Boulder Thesis, Brad had led a session on building entrepreneurial ecosystems at the Thinc Iowa conference that morning. Generous with his time, he’d offered an hour-long fireside chat with ecosystem members over pizza and beer. The hour stretched to two, then four, ultimately ending about nine hours after it started. I, along with many ecosystem leaders can trace our learnings and work methods to those hours.

The Iowa National Guard had just established Kosovo as a sister state and Major Mike Wunn of the Guard requested SCDSM to host and introduce Iowa’s startup ecosystem to the Kosovar President. We were so different from the standard business community that we couldn’t even honor the US Secret Service’s demand for a phone tap - we had no landlines! We subsequently hosted delegations from Ireland and Israel, US Senators and Representatives, the Chief Information Officer of the United States, economic developers from Iowa counties and neighboring states, and hundreds of students from colleges and universities.

All proved to be distractions from our core purpose as you’ll see next.

Why did StartupCity Des Moines exist?

Entrepreneurs.

The distractions, some of our own creation and others a product of recognition beyond our four walls, increased rapidly. We were often asked about our PR agency, our marketing professionals, and our spokespersons pitching to news and media sources. Of course, there were none. All attention was earned media, our blogs, tweets, posts, and the startups talking about the Des Moines ecosystem.

Not all events were PR. Some that impacted the community then and now arose from the days of building, namely, Startup Job Crawl, Startup Weekends, OpenIowa, open coworking, education, and Socratic mentorship.

Startup Job Crawl was an event intended to expose college students from ISU, Iowa, UNI and numerous private colleges to the startup community. Growing startups such as Dwolla pitched themselves to students to offer them a path toward employment at smaller companies here rather than leaving the state for the coasts. Several of those individuals, including Diana Wright, Scott Herren, David Ziemann and more arrived in the job crawl wave, found a home and became engrained in the startup community.

Startup Weekends, a phenomenon that began in Boulder, CO and spread worldwide was already active in Des Moines. StartupCity and its available community space allowed it to grow to over 100 participants for multiple years. Members of the planning community then, including Andrew Kirpalani, Levi Rosol and others remain active and productive members of the broader entrepreneurial, angel investor and mentor community today.

The early 2010s were also a special time in public data when the Obama administration consolidated government data via a single federal data portal. The initiative was led by the first Federal CIO, Vivek Kundra, and spurred the creation of state and local data portals nationwide. Iowa’s initiative, data.iowa.gov under data cazr Scott Vanderhart’s stewardship was already a frontrunner. SCDSM hosted the first statewide open data initiative and solicited entrepreneurial ideas to develop solutions upon public data. Entrepreneurs tested unique ideas such as automatically reporting a pothole when a smartphone detected a bump while in motion in a car. Even the then Lt. Governor Kim Reynolds became involved, spending time with each team late into one evening of the event.

Each such event was an energy producer - invigorating the community, engaging the engineers, designers, dreamers, builders and community supporters.

What Got in the Way

Our core purpose was to deploy the nearly $700,000 in community investment to spur innovation and test viability of a sustainable ecosystem. Christian and I were volunteers. We were paid out-of-pocket expenses and had a future stake from sale of member companies, after the public entities had been paid in full. SCDSM expenses went primarily toward hosting events for the community, rent, utilities and travel when necessary. None of the monies from public entities were used for direct investment in the startups as we focused on connecting our startups to sources of private investments and investors.

Strike 1 - startups need external funding to grow

Another purpose for us was to highlight the successes amongst our cohort of 9 companies, Present.io, Pikuzone, Tikly, Real Estate Fan Pages, Sharewhere, Meidh Corporation, Posterzen, Jobsite Unite, and staffNinja to motivate others building companies in garages, basements and spare bedrooms. SCDSM connected with entrepreneurs in the metro area, to those from Fairfield to Spencer, Council Bluffs to Iowa City, Sioux Center to Pella. Yet, in a state with consistently low unemployment and even lower access to investment capital, the density of startups remained light. As the economy began improving, that density fell further.

Strike 2 - startups feed on energy from more and diverse founders and risk takers

The business model we’d constructed for SCDSM, coupled with the financials necessary for long-term sustainability were increasingly showing stress fractures. By early 2014, we could see the model’s chances of success evaporating and SCDSM’s organic unsustainability.

Strike 3 - startup successes increasingly take 7+ years to achieve

We had other distractions of our own making as well when we encouraged entrepreneurial ventures across food and beverage. Early 2010s saw an introduction of craft beer and we hosted brew-off competitions. We hosted after-parties after the Technology Association’s Prometheus awards with pizza and drink. The adult playground also had food and beverage available anytime day or night and at times it resembled a frat house.

Strike 4 - work and play may mix, but within boundaries

Managing the ever-growing community interaction fell on the shoulders of our two community managers in the three-year existence - Becky Mollenkamp and Danyelle Crowell. Their skills in herding the hundreds of cats, producing blogs and articles, meeting startup and later coworking needs were crucial for our existence. Thankfully, the community manager role has since transformed toward a program manager role, now focused on primarily supporting the startups toward their needs and less the parent.

Strike 5 - even three person organizations require job function clarity

Writing on the Wall

We shared the growing unsustainability of the business model with our funders, investors, community and public that the economic model wasn’t going to be successful. What we saw as failure of the model, however, was seen by many in the community in reverse - a phenomenal success. Having spent nearly $400,000 we had attracted attention at a scale unimagined by traditional PR and marketing campaigns. We were asked to continue through the end.

We declined as our goal was to test the value of an incubator in the middle of the city’s core, one that brought entrepreneurs together, connected them to resources, built a networked ecosystem, and relied upon their success to sustain the entity. Continuation beyond the three years required new sources of funding - whether as a non-profit seeking foundation support or as an entity supported by public funds.

We informed our supporters that we’d initiate an orderly wind-down, selling all assets, and returning all remaining funds to the public entities. There appeared to be no precedent for such a return of public funds. The Partnership came up with a strategy to revert the funds, and a shutdown process began in 2Q2014.

Shutdown City

As with each quarterly report submitted to the funders and posted publicly during the life of SCDSM, we promised to share all lessons learned in full view of our stakeholders. A Shutdown City moniker was applied to the series of events and papers that emanated from within and included,

Mentors - in an era of paid advisory groups and consultants, more than a dozen leaders from within the community answered the call for mentors. The first sixteen individuals below with trusted skills in entrepreneurship, software development, education, marketing, fundraising, investment banking, venture capital, government funding volunteered time and talent to the young companies. That volunteer spirit is multiplied today into hundreds accessible to startups across Iowa.

An industry vertical accelerator - we learned that an all-purpose accelerator was not viable in 2013 Des Moines. However, the region’s strength in financial services, insurance, biotechnology, and agriculture presented opportunities to launch an industry-specific program with corporate investors engaged in the entity. We researched plans for a biotech incubator in Des Moines and an Ag Tech accelerator in the northern suburbs. A brief ultimately led to the creation of the wildly successful Global Insurance Accelerator. An Agtech focused accelerator was also launched in 2017 to complement the GIA’s success but was found duplicative to other more successful regional ag accelerators and decommissioned after four cohorts.

An angel network - Although John Pappajohn’s Equity Dynamics fund was well-established and invested, and Craig Ibsen was making incredible (yet slow in his view) progress toward the State’s first state-focused venture capital fund, there remained a need for a network of high-net worth individuals in the city interested in investing in young companies. I am grateful for six individuals who randomly gathered one afternoon at SCDSM for coffee and formed Plains Angels. Sheldon Ohringer brought deep learning from Colorado to Des Moines, joining JD Geneser and Paul Juffer of UHY, Chris Sackett of Brown Winick Law Firm, Mike Colwell of The Partnership, and Christian as we collectively stewarded the group for its first several months. Plains Angels remains an active investor network in our community.

Gravitate - Geoff Wood asked a poignant question during one of the many shutdown city town halls - where would entrepreneurs convene if SCDSM went away? Answering his own question, he created Gravitate in the Midland Building on 6th and Mulberry (now home to Surety Hotel) before returning to the street level of SCDSM’s physical space. Gravitate remains the core of the city’s entrepreneurial activity!

Corporate Connections - There was much disdain in the shutdown city events for our corporate citizens who, for the most part, had remained disengaged. However, Torey Maerz of Rocket Referrals (now ClientCircle) challenged the room with - “don’t we all (startups) want to sell to corporate clients and some even become the very corporate entities when you grow up? Then let’s work to fix what didn’t work.”

NewBoCo/Iowa Startup Accelerator - Eric Engelmann sat in a corner talking to individuals, 1:1, about the Des Moines startup community during one of our many events. A consummate learner, he sponged the lessons from each person he spoke with, informally and with curiosity. I like to believe that he may have avoided some of our missteps in designing the entrepreneurial ecosystem in Cedar Rapids.

Wins and Losses, Euphoria and Regrets, Experiments and Results

I’ll be brief in this eulogy. Much was learned by the city and the entrepreneurs from the SCDSM experiment. Eleven years later, I have regrets that we didn’t pivot to make something new work. Yet, I know that had we continued, we would’ve broken a cardinal rule learned from the fireside chat with Brad Feld.

It is easy for a community to venerate those who start something disruptive and attract positive attention. Having seen it in other communities he had nurtured personally in Boston and Boulder and others observed from afar, Brad cautioned against a CEO of the startup community. His printed and spoken exhortations asked for startup communities to be led by entrepreneurs with a twenty-year vision. Each twenty-year vision resetting each year to look 20 years ahead. StartupCity in 2013 was the de facto executive office of the startup community and Christian and I had become default CEOs. We needed to step back, and the shutdown made it happen.

The lesson I’ve taken away from the experiment, its results, successes and failures is to not penalize the experimenter when such experiments fail. Although I’d love to delve more into the lesson in a future post, for now, suffice to say that had Debi Durham, Jay Byers, Mike Colwell, Terry Vorbrich, the Polk County Supervisors, Lynn Hicks, Marco Santana, JD Geneser, Chris Sackett, Jason Stone, Connie Wimer or our innumerable supporters chosen to penalize us or disengage with the startup community then, Iowa’s startup community would’ve been forever kneecapped.

We are a thriving community today because they internalized the lessons learned, adopted and adapted new strategies, hired those who understood the long arc of time and investment, and remained vigilant believers.

You, the reader gets to decide if this final story of 2025 is one of ruin or one that laid a concrete foundation for the future.

I am honored to be a member of another startup community, the Iowa Writers Collaborative. Its voice is led and amplified by another type of entrepreneur - writers, photographers, poets, artists and musicians who contribute their creativity to a global audience. A visit the Iowa Writers Collaborative will be enriching

StartupCity Des Moines, focus of the forthcoming Part III of this series, was in the decommissioning process, and the Global Insurance Accelerator, focus of Part I of the series was its formative, pre-launch phase. The Kauffman Foundation-sponsored One Million Cups was regularly convening entrepreneurs around cups of coffee every week. Startups were being recognized for Technology Association of Iowa’s Prometheus awards and startup profiles had become a mainstay in the Des Moines Register’s business section as well as the business weeklies in Des Moines and Cedar Rapids.

Eastern Iowa energized and anew after 2008’s devastating floods was experiencing its own entrepreneurial resurgence. Today, it is time to dig into their community serving work.

Humble origins

The Cedar River flooded the city of Cedar Rapids in 2008, and the ensuing recovery brought community together in unprecedented ways. Eastern Iowa was never stranger to software or hardware technology companies and maintained its concentration of deeply technical resources, despite the low density of companies seeking exponential growth in the region, and across much of the Midwest. Yet the flood recovery sparked something new and different.

I met Eric around in 2013 just as he began a series of road trips across Iowa, collaborating and learning from his peer entrepreneurs and entrepreneurial support organizations from his neighborhoods of Cedar Rapids, Iowa City and Cedar Falls to well as new friends in Des Moines, Ames and beyond. He found himself at coffee shops and IEDA offices, from legislators to economic development chambers.

His developing vision ran parallel to those of the Global Insurance Accelerator in some ways and diverged in others. He envisioned an accelerator to host startups across industries and customer segments to spur innovation and bring new companies to the region. Embedded within this vision was to provide a means for latent talent to experience entrepreneurship with a support structure.

The Iowa Startup Accelerator (ISA) was born in 2014 and brought ten companies to Cedar Rapids, three from Iowa, two from outside the US, and the remaining five from other states. Each participated in the program, learned the process of modeling a business for exponential growth, structured financial models, engaged in mentoring sessions with current and past founders, and prepared for graduation day (demo day in startup parlance) on Nov 6. At least three of the ten remain viable businesses today under their original name & ownership or post-acquisition.

Expanding Support Systems

Accelerators surround business founding teams with a managing director, a program manager, curricula, mentorship, access to investors, and members of the community vested in the company’s success. Attention on the founding team and company are a core principle of most accelerator ethos and service providers simply selling their wares to these young companies is verboten. As accelerators mature, therefore, services needed and sought after are either built from within the accelerator or partners carefully curated.

ISA recognized additional skills and services needed in-house for the incoming teams to the ISA and the larger community. It had formed a non-profit entity concurrently with launching the accelerator, named it the New Bohemian Innovation Collaborative (NewBoCo). This entity not only housed the ISA but also became home to the new service organizations. It began by addressing the three key areas of need for any founding team as they near graduation from an accelerator - space, money and talent.

Space

The ISA started on the second floor of Geonetric’s office building and teams worked there throughout the program. As graduating teams are expected to move out to their own spaces to make room for the next cohort and programming upon graduation, space for them became a need. Dispersion can result in lost camaraderie built by members of the cohort who spent 90-100 days working near and with other so proximity was key.

Andy Stoll and Amanda Wood were strong members of the community and ran Vault Coworking, one of the earliest coworking spaces in the state. From the onset of their space, they recognized a need to expand their community and sought connections across Iowa and beyond (more in next week’s StartupCity Des Moines story).

They saw the collaborative opportunity with ISA and relocated their coworking space into Geonetric’s building, bringing the idea and prospect of creative collisions closer. This provided an option for graduating teams to move across the hall and continue to work in and expand the entrepreneurial community. Their infectious energy was a catalyst in growing the ecosystem further, boosted itself by proximity to their people - entrepreneurs.

Although Andy and Amanda now work on projects within the Kaufmann Foundation umbrellas, Vault coworking continues to operate today and supports day passes, annual memberships and month-month agreements for short and long-term stays.

Money

The best accelerators guide the startups to lay a path toward commercial success and exponential growth toward an exit. Unlike building sustainable, lifelong & lifestyle businesses, accelerators by and large focus on companies that can be grown toward an exit to return a profitable exit quickly. This isn’t simply a perverse incentive, rather a recognition that accelerate-able companies consume larger amounts of capital, do so quickly, and carry a higher risk of failure than small business.

Startups do not generally qualify for small business administration loans as they often don’t have assets to collateralize, need far greater amounts than economic development program loans and grants, and must find private capital to match available support from state of Iowa programs.

In collaboration with Plains Angels, NewBoCo launched the Corridor Angels Investors to find and educate accredited investors in the region about startup investments. This effort in 2015 led to the subsequent establishment of ISA Ventures, a $22M venture capital fund to provide strategic financial backing and support for high-growth companies.

Talent

Much of technology history is punctuated by a lack of sufficient resources to create, deploy, support and expand technological products. As the gap grew between available and necessary resources, numerous agencies and businesses identified means to introduce technology to younger students.

NewBoCo recognized this need and created its own programs to educate students, teachers, and non-teacher adult education programs. Its DeltaV code school deployed the bootcamp method to provide rapid and immersive education in technologies at startups and corporates. They also recognized the need to equip teachers with necessary computer science education skills. Focusing on kids, they brought the global CoderDojo programming workshops via a local chapter to the region.

Each of these programs was designed to solve a long-term problem of adequate resources to enable companies being born in the region to stay and grow here.

Learnings from this program unearthed another opportunity, one referenced in the Geonetric article some months ago. A modern approach to technology and innovation is rooted in Agile principles popularized in 2021. NewBoCo developed the curricula for extending the very practices they were teaching startups during ISA’s program and at Geonetric to corporates statewide.

The Latest Addition - Novy Venture Studio

Venture Studios are a natural evolution from accelerators where founders who dream of a world-changing idea build a company. Venture studios pivot on the idea slightly, bringing seasoned and bespoke partners to the founding team behind an idea. Novy Ventures is Eric and team’s latest addition.

They review ideas submitted for commercial viability, often as long as an accelerator program itself. This vetting allows iterative idea-refinement before a dedicated research and validation period with prospective customers and subject matter experts in the field. As ideas move through this refinement funnel, the winning, single, idea is chosen for investment.

The investable idea is converted into a formal company and receives up to $1M in investment from Novy Ventures to facilitate the product build, brand and marketing, sales and revenue strategy and scale. The goal throughout this phase is to build the nascent company toward an exit to an acquirer or become a standalone company.

Eric, David and team have done this before with team of founders who walked through the ISA. Critically, in this phase, the founders and Novy members become one with mission and incentives aligned even stronger for mutual success.

Leadership

Eric has shown an ability to attract and grow talent to elevate NewBoCo. Operating the organization with long-term succession in mind, his team comprised David Tominsky as program manager in 2014 and remains in a leadership role today at Novy. Aaron Horn joined in 2017 and served in various roles including Eric’s successor to the executive director role until 2023 when Jill Wilkins stepped in to the role.

He has grown it from a 2014 P&L of $292,000 to nearly $2.9M in 2023 with significant financial and operational support from community and corporate partners. None of this could’ve been possible without significant financial support complementing Eric’s own blood, sweat, tears and windshield time on I380, I80, and I35 when he wasn’t traversing state highways and gravel roads to angels.

The team’s structure is influenced by agile and Scrum principles, allowing the non-profit to operate with the flexibility and high-velocity execution as with a startup. This agility allows NewBoCo to rapidly pivot and launch new programs to meet emerging needs in the ecosystem demonstrated by more than a decade’s work.

In Closing

It is heartening to see that the New Bohemian Innovation Collaborative isn’t done writing its story and continues to innovate, true to its name, at home and across the state. Its leaders and team members remain invested in spurring and growing entrepreneurial ventures and are constantly finding new ways, partnerships, and people with a shared purpose.

This entrepreneurial support organization remains critical to the state’s economic development future and thus worthy of public and private support.

I am honored and proud to be a member of the Iowa Startup Collective whose focus on entrepreneurs across Iowa inspires many. I am equally honored and proud to be part of the Iowa Writers Collaborative whose nearly 100 members share a depth of knowledge, education, inspiration, opinion and essays to an ever-broadening audience. I hope you check out both.

I recognize the numerous other new and experienced organizations focused on parallel efforts and promise to revisit them in subsequent months. Let us open December with the Global Insurance Accelerator. As with any memoir, everything until the section titled “v2.0” is my memory and could be inconsistent with others’. I invite those with additional facts or corrections to please place them in the comments for the benefit of history.

The story, like many technologies, is separated into three cycles led by three different managing directors. Although the program appears similar from the outside, the three cycles have achieved distinct stages of maturity. Consistent with the approach to versioning technology releases, we begin with the beta.

The Beta launch

Can something come before birth? Conception, of course :). Though more reasons for conception will become clearer in the Startup City chapter, the origins of this accelerator go back to late 2013 when Christian Renaud and I were capturing and documenting our goings-on at SCDSM and publicly sharing them on a quarterly cadence. One reflection I shared was an acknowledgement of a growing trend of accelerators and how the region could benefit from a vertically-focused accelerator which tapped into the inherent strengths of our community. Christian, simultaneously, reflected upon and researched a concept to tap into the region’s visible biotechnology ecosystem. We explored concepts for financial services (fintech), insurance (insurtech) and biotechnology (biotech). Those reflections, papers and designs provided great fodder for academic discussions and explorations (such as walking through defunct theaters on 5th and Locust in Des Moines to imagine them as impossibly expensive wet labs for biotech research in the downtown core).

Jay Byers, then CEO of the Greater Des Moines Partnership (GDMP), asked if he could keep a copy of the two-page vertically-focused accelerator. I agreed. He would resurrect it about six months later as we shared a beverage on court avenue and ask if it still held interest as he had an idea to explore. He proposed we convert the proposal into a short deck and discuss it with as many insurance company CEOs as possible to obtain feedback and offered to open as many doors as his position could influence. Mike Colwell, then leading the entrepreneurial initiatives for the GDMP, took charge on the deck and prepared a short deck consistent with Guy Kawasaki’s template from the Art of the Start.

Accelerator research

Jay went about opening doors to nearly 81 insurance CEO offices from the nearly 400 companies conducting insurance business across Iowa. Just as he made his phone calls, Mike and I began talking to accelerator programs about logistics, lessons learned, best practices, costs and mentorship. We received wonderful guidance from the industry behemoth, Techstars and adopted its mentor manifesto nearly verbatim.

We also studied recently retired accelerators. Accelerators led by Sprint, Nike and Disney were three such retirees sponsored by a single corporate entity. We learned about non-profit accelerators and how profit-focused startups needed a profit-focused environment and mindset. We also learned of the cardinal sin - that an accelerator with a single-minded focus on raising money from investors didn’t lead the startups in its care toward sustainable profitability.

We also learned that the financial models behind successful accelerators had a multi-year commitment for capital, with the most successful ones seeking commitments of $5-$11 million before getting started. Knowing that such multiple millions was practically impossible in Iowa, a bespoke financial model was developed from scratch.

v1.0 - April 2014

Jay had us ask Larry Zimpleman, CEO of Principal Financial Group, for the first meeting. Anticipating a two to three month wait to secure time on a Fortune 500 CEO’s calendar, we thought we’d have ample time to plan. Larry’s office offered us a slot the very next afternoon. He met us with Principal’s CIO, Gary Scholten, and listened patiently to the deck. Then, in incredible prescience and commitment, promised the entire ask, $100,000 per year for three years with a condition that the board would be formed as a group of equals with Principal having an equal position on the investor board. Shortly thereafter, Principal appointed Doug Fick, CIO for its US Life and Benefits business as the board representative.

Naturally, this commitment lent substantial wind to the sails and we proceeded to the next meeting with Jeff Russell, the CEO for Delta Dental of Iowa. Jeff, no stranger to innovation in insurance AND financial services welcomed Principal’s condition, saw the value for the proposed accelerator and secured Delta Dental’s support. He also volunteered to serve as a candidate to the accelerator’s board of directors.

The accelerator fully launched soon with critical support from five other leaders - Grinnell Mutual Reinsurance Company, Farmers Mutual Hail Insurance, IMT Insurance, Farm Bureau Financial Services and American Equity Investment Life Insurance Company.

Structure

We had proposed and planned a financial model comprising a minimum of 7 insurance companies as investors, each committing to investing $100,000 annually. We planned a $50,000 investment in up to 7 startups annually leaving $350,000 for operating the accelerator. Our three-year budget approximated $2,100,000 and was considerably lower than suggested by research. Yet it appeared achievable and we persisted.

We also planned a single managing director to start - an individual who was an entrepreneur with history of mentoring, guiding, building and a belief in the mentor manifesto. Knowing such a unicorn would be hard to find, I began serving as an interim MD as we initiated a nationwide search for both the best person to lead the accelerator and startups to form its inaugural class.

Inaugural Managing Director

The MD for an accelerator is the glue that binds startups, mentors, investors, community members, media, onlookers and peer accelerators, thus requiring an experienced juggler. In the accelerator’s formative years, the juggler needed to be especially skilled with a dose of humility, ingenuity, energy and likeability to transcend the varied audiences. The search netted us several candidates from across the country, but each applicant fell short on multiple criteria.

We were at a frustrating end to our search where we simply hadn’t located any individual meeting all our unicorn criteria. As we discussed restarting the search over coffee at Friedrichs Coffee in Urbandale, Jeff asked if we had performed any outreach to individuals we knew to be qualified even if they weren’t in the market. We thought of one who surely wasn’t in the market but at Jeff’s insistence decided to probe his interest.

Mike made the call and, much to our collective surprise, Brian Hemesath was dreaming about such a challenge. He quickly rose as the candidate we sought and and assumed his role in Nov 2014 as the Global Insurance Accelerator’s first managing director. I transitioned to an independent director role, joining Sheldon Ohringer as the second independent director to the GIA’s board of directors. The team continued searching for the accelerator’s inaugural class.

Inaugural Class

The program was designed as a 100-day intensive to conclude with a demo/pitch day at the Global Insurance Symposium (GIS) in Des Moines. Backtracking from the pre-set date for the GIS, the start date for the accelerator fell to mid-January. Bringing startups from around the world to snowy, icy Iowa for a 100-day program became a running joke, one that would prove fruitful toward a truly immersive program.

Although several online communities served as directories for new startups, the first applicant was a referral from Craig Ibsen of Next Level Ventures. Three ISU engineering students Morgan Hampel, Tyler Fox and Justin Coaldrake pitched the idea for an electronic health record for speech pathologists. Several others followed soon thereafter via portals, referrals and direct outreach.

Despite early resistance to inclusion of Clinicnote, the speech pathology EMR into the accelerator, Clinicnote, the first pitch became the last entrant to the 2015 cohort and remains a viable company today. Pablow, a startup run by two brothers - one in Australia and another in Germany traveled the furthest and remains a part of the Iowa entrepreneurial ecosystem today.

Board

We underestimated the power of the accelerator’s board of directors for its future. The governing board quickly transformed into a powerful glue through its expertise and industry networks. Consisting of the two independent directors named earlier and a representative from each of the seven insurers who funded the accelerator, it received input and attention from a diverse set of industry voices. Most investors appointed a deputy to the board and to each team’s credit, the primary and deputy often attended the board meetings, creating a natural transition and succession plan.

The board also became the initial mentors along with several industry voices they solicited to develop into mentors. Through Brian’s leadership, the mentors brought insight, experience, connections and minefields to avoid.

The board also took several actions in that inaugural year under Jeff’s leadership, actions that had palpable effects in Des Moines and on insurance hubs around the world. The board audaciously decided to call itself the “Global Insurance Accelerator” and not simply an Insurance Accelerator or a Insurtech accelerator and begin a practice of finding and inviting startups from around the world.

Contrart to most accelerator programs, the board worked to emphasize the importance of a positive income statement during the program. This direction to income statement from a balance sheet shifted focus for the startups on generating revenue early from real customers rather than just an ability to raise money.

But the most impactful foundation laid by the board, one quite revolutionary at the time, was for competitors and unrelated insurers to come together as a team of equals around a shared purpose and identity. They welcomed and adopted an antitrust statement while simultaneously remaining a collaborative. They represented life insurance, employee benefits, reinsurance, ag insurance, property and casualty, and dental insurance.

Demo Day 2015

The inaugural class graduated in April 2015 at the annual global insurance symposium, held then at the downtown Marriott. Teams presented the companies they were building, one after another to a broad audience of industry representatives. Even a wayward fire alarm couldn’t stall the momentum that had been created just a few short months prior. The GIA had placed itself in the center of all things innovation in the insurance industry.

Branching and Growing

Unwilling to rest on the laurels from its first year’s success, the GIA began expanding its approach and reach. Brian and board members expanded to industry conferences and spoke about their experiences. ACORD, Insurtech Connect and others provided audiences receptive to and surprised at the collaboration. Although Des Moines’ role in global insurance was known, Brian’s memorable uniform - a Raygun shirt with the slightly irreverent slogan - Des Moines, Hell Yes - put it front and center.

Brian also recognized the growing influence of mentors, a need to carefully invite, welcome, vet, nurture and continually curate the accelerator’s primary asset for the startups. He designed the job description for and onboarded Megan Brandt to begin serving as the accelerator’s program manager where she formalized the mentor program and became a constant presence for subsequent classes.

The roster of investors and board members waxed and waned with time, and Brian led five classes of startups, eventually transitioning back to his entrepreneurial venture, Volunteerlocal in April 2019.

v2.0 - 2018

As the accelerator changed and grew, so did the needs from his chief executive. Four cohorts had expanded the accelerator’s financial footprint, its portfolio of investments in the startups, requests for alternative terms for the accelerator’s investments from prospective members and more. Brian’s replacement, thus, couldn’t be a simple replacement, rather one who filled the changing needs of the job.

I had transitioned away from the board by this time and found the board’s selection of Nicole Cook Gunderson significant. She brought an investment professional’s perspective to the role of the managing director. Brian’s foundational work had taken the training wheels off the accelerator and Nicole could now add growth fuel. To her credit, she maintained Megan’s role and remit in this next stage.

v3.0 - 2022

Another transition was in the works by 2022 as Nicole began a transition full-time to venture capital. ManchesterStory, a Des Moines-based venture capital firm focused on investing in insurance, financial services and health focused startups became her new home for role as Principal. Megan Brandt was also considering a career change and found an opportunity at Maple Studios, a West Des Moines-based hardware and engineering services coworking space and incubator.

Dan Israel, Principal’s relationship manager to the GIA found the opportunity intriguing and became the leading candidate for the accelerator’s third MD. He joined shortly after Nicole’s transition and continued the evolution of accelerator to its hybrid program state, opening up its approach and prospects to more global organizations. The accelerator also continued to attract attention of more mature Insurtech companies who complemented startups equally eager to innovate in the industry. Megan’s role was filled by Jess Louis to continue curating the mentor program, modifying and selecting program resources, and operating the accelerator’s daily activities. With eight cohort of startups with varying fundraising events, executive transitions, product matrices and more, another role became apparent, and Jenny Gruenisen rounded out the team as the alumni director in stewardship of the portfolio.

A Decade of Success

The inaugural board had learned from the lessons of Nike, Disney and Sprint accelerators and diversified its investors across multiple insurance segments. Though some investors withdrew as others joined, the accelerator continued operating through an uncertain decade in the startup, investing and insurance industry.

The period saw a global pandemic disrupt supply chains and thus replacement costs for roofs, cars, and building materials. It saw a rise and fall of early-stage investment capital in the startup community with rise and fall in financial markets. The period experienced impacts of climate change wreak havoc on the home and auto insurance markets in coastal regions through hurricanes and floods, and on home, crop, auto and flood insurance in the Midwest through catastrophic storms, tornadoes and hail.

Rather than reiterate the recent history, I’ll link to the GIA’s tenth anniversary report below as it provides a comprehensive lookback on its people and their pursuit of innovations in insurance, a necessary component of our life in modern society. The GIA’s superpower remains its cross-industry leadership, investment, prescience and constant innovation.

Closing thoughts

Our insurance footprint and investment aren’t happenstance. The expertise in building great insurance companies extends back into the city’s history for over a hundred years and complex support networks built across academia to government over that period. Drake University, ISU and Iowa provide leading programs in actuarial science, preparing students from as far as Malaysia to lead changes in insurance.

Government and Economic Development strategies to continually bolster this leadership in insurance is similarly multi-decade story of investment. The Iowa Insurance Division, under commissioner Doug Ommen’s leadership, is visibly open to collaboration with established insurers and startups, his and his team’s commitments evident in active participation with the GIA and entrepreneurship-focused events. The Global Insurance Symposium began well in advance of the GIA’s formation and provided a global stage for the first cohort. Governor Vilsack even brokered a commitment and relationship between innovation and insurance in 2001, swapping a premium discount for a tax credit. Several insurers continue to honor that commitment, investing in accelerators, venture funds, internal and external innovation.

It is easy to take the GIA organization, its investments in insurance innovation, and its ability to draw entrepreneurs from many corners of the world for granted. Doing so, however, is done at our own peril because just like the startups in its ever-changing cohort of classes, the GIA also requires continual attention and refresh, especially as well-funded organizations near and far attempt to copy and better our playbook.

After all, in the words of Intel’s late CEO Andy Grove, only the paranoid survive.

Much like the word’s biological origins, an ecosystem grows over time through consistent nurture and care. Brad Feld coaxed attendees at the Thinc Iowa event in 2012 to think of our (then) infant entrepreneurial ecosystem in 20-year time horizons on a sliding scale with each subsequent year starting a new 20-year cycle. As our team wrapped up the conference and I drove home, Brad’s comments resurfaced.

This reflection, in the spirit of Thanksgiving, recognizes several individuals and organizations who have impacted the ecosystem over the years. A man-made list such as this can never be complete as memory will undoubtedly fail but I hope those I inadvertently miss will forgive me for the omission.

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Origins

My opening question for interviews that inspire this Substack’s stories generally seeks to know the origin story - not the day the entrepreneur started the company but rather when inspiration struck. For my point-of-view and work in the ecosystem, mine was in 2010, during a brief walk on the skywalk connecting Mercy Hospital to a parking garage. I was leaving a meeting with Mike Colwell after helping a physician entrepreneur seeking the State of Iowa demonstration funding support. Mike and I had just become acquainted in that meeting and his question “I’ve never met you or know of you - who are you and why you’re helping this physician” began a multi-decade friendship.

I told Mike that I had recently exited my successful entrepreneurial venture and was now looking to help other technologists looking to get started in their entrepreneurial journey. Much of my prior decade was focused inward on customers largely outside Iowa. I frequented downtown DC or Sacramento more than downtown Des Moines. In 2010, I barely knew any part of the Iowa technology or entrepreneurial ecosystem.

He asked if I was open for lunch as there was someone else who was working to do the same. He texted Christian Renaud and the three of us met for lunch shortly thereafter. That lunch became the catalyst for my induction into the ecosystem.

Placemaking 2010-2012

In my “Bookends of Silicon Sixth Avenue” story published here on March 18, 2025, I talked about the seeds of this ecosystem sown by Dan Shipton and friends. I referenced then that the ecosystem began to grow under heavy investment by Ben Milne and his Dwolla team and Geoff Wood and his Des Moines outpost of Silicon Prairie News.

A larger cohort was growing around Ben and Geoff, and I was surprised and gratified to learn of their big-tent approach. No one seemed to question my motive, interest, commitment, desire or ability but simply welcomed me into the mix with invitations to the nascent community’s events.

This would become an early lesson: adopt a big-tent approach, make the table bigger and trust first. A test of this lesson was at hand - Startup Weekend Des Moines 2011 when the event’s organizers Shane Reiser, Levi Rosol, Andrew Kirpalani and others expanded their table for me.

Startup Weekend, a global phenomenon that brought together entrepreneurs, mentors, service providers, sponsors, and the public for a 54-hour marathon building session was regularly hosted across Iowa and in Des Moines from 2010 to 2015. In one of its reincarnations, the entire 54-hour weekend was spent building public works applications. We used openly available government data and extended the connection between the entrepreneurial community and government through the State’s lead data guru, Scott Vander Hart. The effort piqued (then) Lt. Governor Kim Reynolds’ interest enough that she engaged with the startup teams late into the night.

This series of events proved a magnet for attracting current and future ecosystem leaders into a small space where they coexisted for the weekend, eating, sleeping, cleaning, working, dreaming and building together. Although many dissipated at the end of the event, many of today’s ecosystem builders can trace their origins into the ecosystem to one of these events.

Engaged Entrepreneurs

Brad Feld’s guidance to us in 2012 was to build an ecosystem that was led by entrepreneurs and actively resist the urge for the rise of a “CEO of the entrepreneurial community”. Getting individuals who are already deep into building startups to also build ecosystems is nearly impossible, yet many arose and remain connected. Brad Dwyer of Hatchlings and now Roboflow, Andrew Kirpalani then of Workhound and now as an angel investor and mentor, Levi Rosol of We Write Code, Erin Rollenhagen of People Friendly Tech, Casey Niemann of Agrisync, Ben Milne of Dwolla, and now Brale, Brian Hemesath of Catchwind, Tikly, Global Insurance Accelerator and now Volunteerlocal are just a few of the many.

Each is a gentle yet brutal guide - eschewing Iowa nice for directness, mentoring with grace and empathy for the region’s newest entrepreneurs. Though in their second, third or later rodeos, they continue to share wisdom with new entrepreneurs.

Academic Institutions

Innovation-driven enterprises are often birthed on research campuses where students and faculty ideate for the future and commercialize inventions and discoveries. The numerous programs and support systems at Iowa and Iowa State complement the statewide John Pappajohn Entrepreneurial Centers (Iowa, Iowa State and others) and those at Iowa’s private colleges.

Government and non-government agency connections

The entrepreneurial ecosystem in Iowa is inextricably tied to local and state government (as you saw with Scott Vander Hart and Kim Reynolds above) and non-government agencies. Three deserve a callout for their connection, support, and consistent engagement.

The Iowa Economic Development Authority (IEDA) under Debi Durham’s leadership has maintained a series of entrepreneurial support programs throughout her tenure. Working closely with Governors, legislature, and business leaders, Debi believes in and supports this ecosystem with presence, team, and financial support whenever possible. IEDA continues its support for programs that unlock low-interest loans and royalty agreements for entrepreneurs and financial support for programs like the Iowa Angel Investor summit mentioned at the opening of this article. Debi’s team members, Anna Lensing, Megan Brandt, Anne McMahon remain ever-present and supportive of this ecosystem.

The Greater Des Moines Partnership is the other influential entity with incredible influence on the entrepreneurial community and has persisted its support through three consecutive CEOs. CEO Martha Willits initiated this when she hired Mike Colwell and funded entrepreneurial support in 2007. Her sponsorship must’ve rubbed off her successor and our dear friend, Jay Byers, who added his contagious energy and doubled down by actively expanding the ecosystem throughout his vast network. He handed the CEO reins to Tiffany Tauscheck who similarly champions the entrepreneurial ecosystem.

Two suburban entities stand out for consistency - the West Des Moines chamber and the Ankeny EDC. Jo Eckert and Clyde Evans of the WDM Chamber became friends of the entrepreneurial community, extending support from the western suburb through coworking spaces and sponsorship. In a parallel but different move, the Ankeny EDC gathered a group of angel investors from its community and complemented a different statewide effort for increasing angel activity. Ankeny Angels continues today as an entity and a partner to the statewide efforts under Joey Beech’s leadership.

Risk Capital - venture, angels, friends & family

We’ve discussed a bit of the history of public, private angel and angel group funds, venture capital and institutional capital sources recently in Medicis of the Midwest I, II and III, but gratitude for increasing investment bears summarizing here. Beginning with John Pappajohn’s personal commitment and extending through Matt Kinley’s work first at John’s Equity Dynamics and later his and David Miles’ ManchesterStory, the incessant and often thankless work by Craig Ibsen and his colleagues, Dave Tucker and Liz Keehner, of Next Level Ventures and Eric Engelmann of ISA Ventures, we may not have the growing venture ecosystem in Iowa. Harris Vaccines and Smart Ag’s successes led founders to reinvest in the Ag Innovation ecosystem via Ag Startup Engine putting other ag-first ventures on a path to success.

I’d be remiss in not mentioning the nearly 100 members of Plains Angels angel investor network who view, consider or invest in startups culled from nearly 600 applicants annually or those part of FIN Capital, Ankeny Angels, Ames Seed Capital and numerous other private groups that listen to entrepreneurial vision, invest in the founders and help build businesses from barely an idea.

Entrepreneurship Coalition (EShip Coalition)

I started this note mentioning Diana, a colleague and instigator of a 12-person cohort she formed in 2021. The dozen she curated represented a diverse (geographic, age, gender, background, experience) cohort who attended a two-year program at MIT to accelerate entrepreneurship regionally. Though we could’ve parted at the end of the two-year program, she polled us to continue or disband. The group chose to continue, voluntarily, and now comprises many original and new members. The coalition boasts educational events, storytelling, advocacy and inspiration for others as its current initiatives. The tent, in spirit of the 14-year-old lesson, remains big and open to others. This Substack, along with those of 11 other writers originally came together as a collective meaning to tell startup stories to raise cultural awareness for entrepreneurship, to decouple the word entrepreneurship from its culturally negative meaning of unemployed.

Independent voices

As is normal for any entrepreneurial venture, there remain supporters and cheerleaders who opt to work outside the tent, lifting entrepreneurship in their unique ways. Ben McDougal captures caffeinated conversations via his podcast and books. A revolving team of volunteers at 1 Million Cups Des Moines gathers entrepreneurs on most Wednesday mornings since fall 2012 and continues to ask and answer its originating question - 'what might you achieve if you gather entrepreneurs around a million cups of coffee in cities around the world?’

Clashing Journalists with Startup-y People

The earliest startup community found friends in a few journalists. Lynn Hicks and Marco Santana of the Des Moines Register, Kyle Oppenhuizen of the Business Record, Geoff Wood and his team at Silicon Prairie News were instrumental in putting Des Moines on the national startup stage. In Jay Byers’ private and public motivation to us, that podium was punching way above our weight, but he didn’t see that as a limiting factor - he saw it as aspirational. That aspiration and work have landed this documentarian in a community of professional journalists who capture and tell stories in poetry, prose, film, narration, photography, baking, novels and song.

The startup community now shares voice with nearly 100 creatives of the Iowa Writers Collaborative - entrepreneurs all, creating and honing their craft as they influence their fellow creatives. I am honored to call them peers and teachers.

Looking back 15 years and at Brad Feld’s coaxing to think in 20-year horizons, I know the Central Iowa community absorbed that lesson. I could’ve never imagined what has become of this, my, community. And cannot imagine what successors will make in the next 20. I only know that it will be richer, broader, healthier, and welcoming in the hands of the dozens named here and the nearly 160 who showed up at last week’s summit and their mentees to come.

And for that I am thankful. Happy Thanksgiving, all!

I reported in last week’s Rugged by Design story that a 2x recognition by Inc 500 is hard to do and a hattricks elusive. We meet a company today who hit that hattrick AND followed it for three consecutive years on the Inc 5000 list in a spirited conversation with Frank Russell, a serial and successful entrepreneur. The story upholds the original hypothesis of founders creating companies, finding successes, and reinvesting through diaspora that continues to impact Iowa technology.

The Changing Face of Learning

Increasing complexities of work, new technology, interpersonal skills, regulation, compliance, legal, and cross-border interactions altered the practice of continuous education in the workplace. Apprenticeships, technical schools, sales training, job instruction and onboarding brought us from the Middle Ages to the post-World War II expansion, but the modern era is punctuated by a practice organized under the human resource umbrella.

This industry of collecting, consolidating and imparting knowledge began integrating (then) current technology of overhead projectors, transparencies, round-table discussions and entered rapid change as innovative educators introduced just-in-time training with bite-sized learning modules and simulations, board games and consultative approaches to exploring new ideas.

As the industry embraced technologies, entrepreneurs were inspired by innovations at the edges. The centuries old practice of human-led education was about to be disrupted by the humble video cassette recorders (VCRs), satellite and, ultimately, the Internet.

Meet Frank

The son of George Russell II, Chancellor and President of the University of Missouri system, Frank Russell was just completing his Masters degree in 1977 at the University of Illinois when he found a role to train others on a system called Plato at the Center for Advanced Computation. This job introduced him to Control Data Corporation of Minneapolis until he was convinced to move again to Des Moines. Joe Batten, author of the best-selling book “Tough Minded Management” and CEO of Batten, Batten, Hudson, and Swab convinced him to leave CDC for this prescient move. The whirlwind early career had Frank traveling Monday-Thursday to client sites, barely returning home to see his family. An opportunity presented itself in 1980 for him to create the Iowa management training system for the State of Iowa in Governor Robert Ray’s administration, one that would create a cascade of creative experiences.

Two years of public service led to the North American Chief Learning Officer opportunity at Massey Ferguson (those of the red tractors) followed by the Chief Operating Officer role at American Media. By 1986, Frank had seen nearly a decade of various client sites, industries, technologies and training modalities. It was time for something of his own. His COO role had exposed him to raising money for the company, the newly honed skill critical to his next step in the journey.

He sought early investment from an angel, Terry Mealy, and launched Excellence in Training Corporation in 1986. The company leveraged the state’s tax advantages available to limited liability companies investing in specific lines of products such as those matching Frank’s skillset - training films. The company produced its videos on VCR tapes and shipped them to customers.

Unlike the business of a trainer present in front of their students, thus limited by their own time for growth, the ease of use and ubiquity of VCRs provided the company the means to scale. Growth followed in the next decade, and the company became attractive for its reach and intellectual property. It was acquired by Westcott Corporation of Dallas in 1997 with Frank and team joining the company as employee operators. Carl Westcott, an investor and innovator himself, continued to invest in his acquisition’s growth, and writing was on the wall that operations would ultimately end up in Texas. He believed in this scaled approach to learning but hadn’t quite embraced a different means of delivery beyond tapes and DVDs on the horizon.

It was time for a new chapter.

Retire or Reboot

Although Carl had found inspiration about training via satellite and grew that part of the business organically and inorganically via acquisitions, he found the prospect of training via the Internet unlikely. Frank, on the other hand, was ready to make the jump into this next medium. He redeployed proceeds from selling Excellence in Training to launch his new company, GeoLearning in 1997. Having previously providing a return to his angel investor, he was able to convince Terry to come alongside as an investor in this new venture as well.

GeoLearning’s first product became Geo3, a hybrid DVD and Internet based training product for leadership development. This proof of concept worked. In the meantime, they had acquired a NY company whose training product was instructional design booklets that guided students to “jump” to sections in the booklet based upon their answers. This manual hyperlinking lent itself perfectly to branching online training and the next iteration of Geo3 was born with the acquired company’s 20ish booklets.

GeoLearning continued to innovate and listen to customers and prospects at conferences. The voice of the customer at the first online learning show told him of the growing presence of Learning Management Systems (LMS), suites of products that not only delivered instruction but also tracked employee progress through training pathways and allowed employees to jump between static resources and dynamic training. Before he would jump into developing his own LMS, however, Frank came across Frank Berry of the UK who happened to offer a solution. They landed upon a joint-venture model that allowed both to grow with creatively investing in each other’s successes.

From Bricks and Mortar to Clicks and Mortar

This growing industry in 2000/2001 was dominated by large corporations who developed and sold product suites to deep pocketed buyers. The corporate buyers had established vendor relationships with the global brands and trusted them “behind the firewall”, operating within the corporate buyer’s network. GeoLearning neither had the deep pockets to develop the entire suite of products nor established relationships to reach inside the corporate networks.

However, they were convinced their strategic direction to deliver their intellectual property over the Internet via the browser was the future. They also knew the incumbents’ adoption of staid user experience wasn’t likely to excite the future buyer. They chose a new playbook, learned from a teen-dating site and adopted an early version of skeuomorphism from the site’s Canadian developer.

Much like some video games based in familiar structures such as homes or offices or the original iPad’s Books app that resembled a bookcase filled with book, this approach introduced a virtual office environment at launch. The user could choose “elevator buttons” to move to the library or training rooms. This interface that virtualized the training center and began marketing themselves to HR professionals instead of technology buyers. They avoided the bloody battle over price or company size and successfully licensed their products.

Critical Junctures

A strength for the company was the relationship between Frank and Terry as CEO and angel, respectively. Terry represented patient capital at work, guiding and securing additional capital as and when necessary. Unlike the first venture, Excellence in Training, where extended family’s assets were deployed alongside Frank and Linda Russell’s, GeoLearning deployed the couple’s capital alongside Terry’s before securing private equity and venture capital. The initial growth through nearly $22M in personal and patient angel capital allowed the team to make mistakes before $32M in professional capital was raised from Fidelity Investments (Volition Capital). A new growth stage was at hand.

As with many serial entrepreneurs, it was clear throughout the interview that Frank’s purpose came from the constant innovation. Maintaining close connection to his closest confidants was a catalyst in the creation of GeoLearning after Excellence in Training, his CFO on the entrepreneurial journey for almost as long has his cofounder wife, Linda.

Signals of Growth

Their trajectory of growth mimics the J-curve sought by startups everywhere. The product suite improved from the Geo360 in 2000 to add prerequisite training, dynamic reporting, skills and competencies, learning analytics, certifications, workflows, single-sign-on, dashboards, widgets, universal search and dozens of additional features. The decade between 2000 and 2010 also saw numerous awards and accolades from local and national entities.

The first Inc 500 recognition arrived in 2004, followed by two others in quick succession. Inc magazine soon began recognizing America’s top 5000 companies and GeoLearning was inducted into the prestigious list for three more years. The Technology Association of Iowa recognized GeoLearning as the Software Company of the year in 2010, Technology company of the year in 2006, and Frank as CEO of the year in 2009.

Diaspora

The GeoLearning team also comprised at least three notable technologists - Brad Rasmussen, Brandon Carlson, and Matthew Edwards. These members of the company’s diaspora impact Iowa technology via their own service and education.

Brad now serves as one of the longest serving members of the board of directors of the Technology Association of Iowa and was recently honored as the CIO/CTO of 2025 by the association. He is the CIO for Merchants Bonding company.

Brandon created and leads LEAN Techniques, a consultative training practice which brings modern product management practices to small and large enterprises through embedded education, consultative strategy and culture development, software development and delivery and online publication.

Matthew created and leads Trility Consulting, a 2x Inc 5000 inductee itself, and a provider of professional technology services in data engineering, AI, cloud engineering and DevOps. Trility was also recognized as Technology Association of Iowa’s Technology Company of the Year in 2024.

Revenue, Key Metrics and Exit

GeoLearning grew through a global team of 240 full-time employees with headquarters in Des Moines. Revenue approached nearly $38M in 2010 and was projected for $49M and $65M in the upcoming two years. The customer list of nearly 700 companies boasted prominent names such as Google, Dell, Wells Fargo, PayPal, Time Warner, Crate & Barrel and Kaiser Permanente.

Something we continue to struggle with as an entrepreneurial community in Iowa is corporate support for homegrown companies. As I reviewed the list of customers in company decks, I was disappointed to not locate any prominent Iowa companies.

2011 represented the ultimate pivot for Frank and the company. The Des Moines Business Record reported on Jan 6, 2011 that SumTotal Systems, Inc had acquired GeoLearning Systems Inc. SumTotal, a Florida-based company reportedly the largest LMS provider at the time was continuing in its strategy of rolling up successful providers in the LMS space.

The 2011 acquisition represented a rare exit greater than $100M of an Iowa technology company. Sadly, Terry, the angel who saw Frank’s vision and guided him along the way passed away a month later in February 2011.

Rest, Reboot, Restart

Once again, the serial entrepreneur didn’t rest long. Although life and circumstance had afforded Frank a comfortable future and Linda fully expected Frank to retire, he had ideas brewing for another professional life beyond GeoLearning. As Frank couldn’t simply relaunch another GeoLearning post-acquisition, he wondered if his previous employees were likely to be displaced by the acquirer and if those facing a layoff afforded outplacement services. Hearing “no”, he sought and received the acquirer’s permission to provide such services for free.

Prositions, Inc. was born as a non-competing entity to deliver outplacement services to employees facing a layoff from an employer. Although it has since been rebranded as Outplacement Pro, it continues to provide those envisioned services.

Frank also branched new companies, RobinHood HR, fractional HR services for fast-growth companies. He has written a remarkable eBook, “Fast-Growth Playbook, a Practical Playbook for Founders of Rapid Growth Companies”, one I was able to preview in its pre-release version. It is a concise guide for founders building high-growth companies and provides bite-sized lessons on employee experience, intentionally building and living a culture, building people-focused systems, leadership planning, customer focus, and evolution. I was moved by how art (below) influenced a chapter in the company’s life and will leave the readers to discover the meaning in Frank’s eBook.

I have permission from Frank to share the eBook with Founders and leaders who have read this far and are interested in learning from a serial entrepreneur with several decades of successful builds, exits, and incessant passion for technology entrepreneurship.

I am grateful for the incredible Iowa Writers Collaborative community which inspires me through its vastness of expertise. Find your inspiration here.