It’s hard to think of a new design tool that’s generated more buzz than Paper over the last few months. Every new feature launch seems to light up X, and designers are constantly sharing what they’re making with it. Less than a year after launching, Paper is already used daily by designers at a growing list of companies, including Ramp, Vercel, Resend, and Lovable.

As Paper announces its Series A, we spoke with founder and CEO Stephen Haney about the story behind the company and his vision driving it forward. For Stephen, passion, depth, and shared values aren’t soft virtues you prioritize once the business is working. They are the strategy. They shape how Paper chose its market, how it hires, how it grows without a sales team, and what it decides to build next.

What we cover in the interview:

• The founder-market-fit bet that led Stephen to leave a good job with no validated idea

• Why Paper waited on AI, then built a canvas agents can edit directly in HTML, without taking designers out of the driver’s seat

• How Paper ships: single owners, six-week cycles, and “appetite” as the kill switch

• What it means to “hire people into their dream job”

• Why the best marketing doesn’t always look like marketing’

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Founder-market fit as a compass

Paper wasn’t Stephen’s first attempt to close the gap between design and code.

In 2018, he co-founded Modulz, a startup focused on designer-developer handoff. Along the way, the team built Radix UI, the unstyled component library that has since become foundational to modern web development. But while Radix found wide adoption, the business around it never quite felt like it was venture-scale. Stephen sold Modulz to WorkOS in 2022, where he spent the next two years leading product, helping the company grow and launching AuthKit.

As he started thinking about his next company, he kept coming back to the people he wanted to build for: “Whose problems do I want to solve? Who do I want to be on Zoom calls with, hearing about the issues they have in their day-to-day, and then trying to fix those? For me, that’s creative professionals.”

Stephen decided to leave WorkOS without a validated idea (something we typically wouldn’t recommend!). But what he did have was a strong sense of founder-market fit: the belief that you should build something you’d be happy working on for years, regardless of where it led.

“If you have great founder-market fit, your company won’t die, because you literally can’t. This is what I would do anyway.”

That mindset is especially important when things stop going well: “If you’re only thinking about your ARR, when it gets hard—and startups do get hard—you might give up, or pivot faster than you should. Doing something you truly love gives you a compass to live through the harder times.”

This time, he also chose to build alone, after years in co-founder setups and larger teams. “I love that there’s no alignment tax,” he says. “When you see something, you can just do it. You don’t need to talk to anyone.”

That’s how Paper began.

Building a design tool for the AI era

Paper is a design tool built around a simple idea: designers should work in the same medium that software is ultimately built in. Instead of creating static mockups that later get translated into code, designers work on a live HTML and CSS canvas that engineers and AI agents can edit directly.

That vision came from two early bets, both of which looked risky at the time.

The first was waiting to build AI. “You could raise a lot of money if you were an AI company,” Stephen says, “but we waited on AI because it wasn’t clear yet how it would help designers.”

That changed last December, when Stephen noticed designers doing something he hadn’t expected: prompting Claude Code from the terminal. “I was shocked. I didn’t think designers would be in the terminal prompting away in a CLI, but they were.” As we saw in our AI in Design 2026 report, nearly half of designers say they now ship production code.

It made sense in many ways. Getting directly in code lets designers build higher-fidelity interactive prototypes, experience product flows as they were created, and keep up with engineering teams that are shipping faster than ever. “The power of what it was giving you is just so great that you had to be there to get this power.”

The second bet was technical. Paper renders directly in HTML and CSS instead of relying on a proprietary rendering engine like most design tools. That means AI agents work in a language they already understand, editing designs by generating HTML instead of translating between formats while keeping token costs low.

The goal is to automate the repetitive work around design, not design work itself. “The human designer figured out the design, but they need to ship it in eight different ways, and there’s a lot of boilerplate in that. Let’s save them eight hours.”

As AI makes it easier to create software, Stephen thinks great design becomes even more valuable, not less. “There’s so much stuff out there that design is how you elevate above it. You can’t have B-minus design and elevate yourself. You have to have A-plus design.”

How Paper operates

Paper’s operating system extends across product, people, and how the company shows up in the world.

Build products like you’re writing a great book

Stephen thinks building software should look more like writing than construction: “When you build a house, you can throw a hundred people at it. If quality doesn’t matter, build the house.” But that’s not the case for design software. “The best design tool has always won throughout history, and I think that’ll continue to be true. When you write a book, more authors doesn’t make a better book.”

What that means is that each product area has a single owner—somebody focused on the pen tool, another on design tokens. Put one person on vector editing for the better part of a year and you get the best possible version of it.

Projects take place in six-week cycles that act as checkpoints, instead of deadlines. During those check-ins, Stephen looks at what he calls “appetite”, the team’s current energy and conviction to keep investing in something: “If you don’t have appetite for something and someone keeps working on it, it’s going to get weird. They’re going to be posting updates, you’re not going to be excited about it.” When that happens, it’s better to ship what you already have and move on.

The final piece is focus under constraint. With a small team, every hour has to go toward the biggest bottleneck to growth. The team recently shipped an MCP server that unlocked AI adoption and expanded the top of the funnel. Now they’ve shifted their focus to more practical gaps, like design tokens and cursor presence, that enterprise teams want to see before they’re able to fully adopt the product.

Hire people into their dream jobs

“Something we think about when hiring is trying to find people’s dream jobs,” says Stephen. “What’s the most perfect job for you?” The payoff is twofold: “One, you’ll geek out on it. Two, you’ll have so much energy for it.” It’s the same philosophy that led him to start Paper in the first place: when you genuinely love the work, it takes far less effort to stay motivated and do it well.

He looks for obsession paired with range, instead of narrow specialization. “You have to be patient, you have to have a small team, and you have to be actively reaching out.”

As an example, Stephen first came across Alex Harri, the software engineer who would later build Paper’s pen tool and virtualize its layer tree for performance, through years of blog posts Alex had written about vector editing. Over the next six months, the two got to know each other, beginning with a simple message from Stephen: “I think we’re into similar things...do you want to talk about vector editing?”

Pick the right investors

Stephen runs a similar filter on who’s on his cap table as he does with new hires. “You should be very comfortable texting with your investors. You want people who are values-aligned in your camp, because otherwise they’ll push you to do weird stuff you have to spend time explaining your way out of.”

In terms of pitching, his advice is to cut anything that isn’t true and strong. “People build a 30-page deck, 10% of the information is clearly wrong, the investor sees it, and the conversation is over. Say less. Our deck is almost nothing.”

Build fans by being one yourself

For their first real marketing push, the team went all out at Config—Figma’s annual conference in San Francisco—with 3,000 branded coffee cans, a dozen newsstands showcasing work from customers, 10 wrapped taxis, and two LED trucks circling Moscone Center. They even built custom claw machines, plus branded napkins and posters scattered at a Config after party. Everything, of course, was designed in Paper and built in-house.

Surprisingly, Paper doesn’t officially have a sales or marketing team, and Stephen half-jokes that he doesn’t fully understand why the marketing works. It does, though: the product has a devoted following, and his tweets routinely go viral.

His hunch is that it’s because the company is made of exactly the kind of people it builds for. “We’re all builders and designers and engineers, and almost everyone does both. That authenticity comes through.” When your values match the market’s, he says, “they’ll forgive missing table stakes if they believe in you.”

That belief is earned by care that shows up everywhere, not just in the product. Paper’s user education videos are produced in-house by Harcourt Allen. And it’s clearest where there’s no business case at all: Agu Seguí, the company’s founding brand designer, made an entire printed magazine exploring Paper Mono, the studio’s first typeface, and brought it to a team meetup. “I didn’t ask him to do this. There was no business outcome in mind. It was just, this is really fun, so let’s do it.”

Part of why so many designers have rallied behind Paper is that it’s abundantly transparent about what it stands for: “A professional designer might look at a design tool and ask, ‘is this tool for me, or is it trying to replace me?’ Paper is clear: we’re going to do everything in our power to support professional creatives.”

Key takeaways

Most of what Paper does traces back to the same instinct: build things you’d want to work on anyway, surround yourself with people who feel the same, and go deep enough that it shows in the work.

It’s why Stephen left a good job, why Paper renders in HTML, why one person can spend a year on a pen tool. It’s also why the marketing looks like designers handing out coffee at a competitor’s conference, or why someone prints a magazine just because they wanted to see it in print.

1. Founder-market fit is survival, not sentiment. Build the thing you’d do anyway. It’s the compass that keeps you from quitting or pivoting badly when the work gets hard.

2. Speak your medium’s native language. Paper renders in HTML/CSS, so agents can edit it directly at a fraction of the token cost. Fewer translation layers is a durable advantage.

3. Depth wins where quality is the product. More authors don’t make a better book. In craft markets, one person going deep beats a crowd going fast.

4. Hire for the dream job. Write the role for the person whose life’s work matches it, and be patient enough to wait for them.

5. Values are distribution. If you belong to the community you serve, authenticity does the marketing a sales team otherwise would.

A book that shaped Stephen’s thinking: Hackers & Painters by Paul Graham. While Paper isn’t a YC company, a lot of early Paul Graham and YC writing shapes how Stephen builds. “They’ve figured out how startups work. You take the parts that work for you and leave the rest.”

Where to find Stephen

• Paper: paper.design

• X: @stephenhaney

Hero illustration by Adam Dixon

A couple of years ago, Jonathan Arena was working on a book about interfaces. He wanted to map the evolution from physical dials and switches to touchscreens, and then try to sketch what might come next. But the book was really a way into a bigger question: if the medium itself is shifting, what should design schools be teaching?

We’d been circling that idea for a while: what the curriculum would look like, who would teach it, whether any program could realistically keep up with how quickly things were moving. Eventually, he realized the chapter he most wanted to write didn’t exist yet. The problems were still unfolding. So he set the manuscript aside and went to work on one of them.

At that point, Jonathan had spent more than fifteen years building products at Facebook, Cruise, and Patreon, rising into senior design leadership roles along the way. By most measures, he was in a comfortable stretch of his career: work he enjoyed, strong compensation, and a clear path to the next leadership role and the one after that.

Most people would have remained on that track, but Jonathan looked towards a different one. Today he’s the co-founder of New Generation, a company building AI-powered storefronts for retail brands. The path from design education to e-commerce infrastructure sounds like a leap, until you hear him describe the lily pads that connected the two.

What we cover:

• Why Jonathan left design leadership to start a company at this specific moment in tech

• How a book about interfaces led him from design education to e-commerce

• What New Generation is building with Kepler and why current e-commerce websites can’t keep up

• How brands are reacting to agentic commerce and why change management is the real bottleneck

• The emergence of the “prototype-native designer” and agents as synthetic user research

• Why this is the most exciting time to be a designer, and what that demands

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“I couldn’t resist participating in this moment as a builder”

Jonathan’s been searching for two things throughout his career: complexity and new interfaces. “The intersection of new business models and net new interfaces is my happy place,” he says. “I am on a lifelong quest to continually try to position myself in that aperture.”

At Facebook, he designed key aspects of the photos experience used by billions of people and later led the design team for Portal, the company’s first AI hardware product, where they built a new end-to-end operating system. At Cruise, he managed teams working on early versions of the driverless rider experience and AI tooling suite. At Patreon, he led Consumer Product Design across mobile, web, community, and the design system.

In a recent talk at South Park Commons, he traced that thread back to middle school, when he built a snowboard repair shop in his parents’ garage, got Burton to send him free gear, and later counterfeited a press pass to sneak into the US Open of Snowboarding. The takeaway from those early experiments: “You can just do things.”

For a lot of his career, that energy lived inside other people’s organizations. He’d been carrying a list of 150 startup ideas for years, but didn’t quite have the right convergence of timing + partner + problem.

The timing arrived with what he describes as a new epoch, similar to the mobile ramp-up of 2011 that produced a generation of companies, followed by a decade spent building out those primitives. Now the primitives themselves are resetting.

“Because we’re all kind of resetting and the technology is all new and the heuristics are all new, it’s almost easier now to excuse yourself and say: nobody’s further ahead than I am in exploring this stuff. I might as well be at that efficient frontier.”

The partner arrived through grad school connections: Adam Behrens, his co-founder, who studied philosophy and economics and aligned quickly with Jonathan on a shared thesis about AI reshaping the open web.

And the problem emerged from a deep exploration of design education. Jonathan’s been involved with RISD since graduating and co-founded HarvardxDesign, a design conference now in its thirteenth year. As he dug deeper into how interfaces evolve, and what designers would need to understand next, a pattern emerged. A handful of unresolved questions kept surfacing. One, in particular, wouldn’t go away: what happens to the e-commerce website?

Online shopping architecture hasn’t meaningfully changed in twenty years: search bar, filters, product grid, detail page, checkout. And yet those pixels carry enormous economic weight; Stripe’s checkout alone processes over a trillion dollars a year. It’s a massive business opportunity, and it sits squarely at the intersection of Jonathan’s long-running obsession: making software work how people want it to work.

The design school remains a long-term ambition. “If I really squint at what’s the professor that I want as a student, it’s somebody who’s summited Everest a bunch of times.” Founding a company, he says, is the best expression of a designer’s intuition: the chance to put it to the test without fitting it underneath other people’s ambition.

“As a founder, you are sailing your own boat in a big ocean and you can go wherever you want and put your intuition to the test.”

What New Generation is building

New Generation’s platform, Kepler, starts from a straightforward observation: e-commerce websites weren’t designed for how people (and increasingly, AI agents) actually want to interact with them.

On the brand side, the infrastructure is a mess. One cosmetics company New Generation works with has 47 different suppliers touching their website. Managing that ecosystem while trying to sell products is a grind. On the consumer side, keyword search is broken. Finding something specific in a large catalog means opening multiple tabs, clicking through filters, comparing across brands. Thirty minutes spent on what should take thirty seconds.

The fundamental shift Jonathan keeps coming back to: the currency of the internet is changing. It’s now denominated in asking questions. ChatGPT is three years old. Its interaction model (natural language in, structured answers out) is becoming the baseline expectation for how people engage with information. The vast majority of e-commerce websites haven’t adapted to that.

Kepler is New Generation’s answer. It has three core products:

• Agent Storefronts structure a brand's site so AI agents can read it, discover products, and display accurate results.

• AI Insights surface real-time data on how customers and AI systems interact with products: shopper intent measured through actual conversations rather than inferred from clicks.

• Conversational Storefronts let customers use natural language search directly on a brand's site, generating bespoke pages in real time.

The go-to-market is deliberately low-risk for brands. Rather than replacing an existing site, New Generation deploys Kepler as a single AI-powered page on a subdomain, ai.[brand].com. Brands route a small percentage of traffic there, run clean attribution tests, and measure the uplift against their existing experience. If it performs, they roll it out more broadly. If it doesn’t, the core site stays untouched.

In his SPC talk, Jonathan described the concept to a taxi driver in Vegas: “We were explaining our idea and he was like, ‘So you mean websites are stupid?’ And we’re like, ‘Yeah, basically.’”

How brands are reacting

Jonathan has a useful framework for how companies adopt AI, organized by risk exposure:

1. Tier one is individual, private use. You’re using ChatGPT for your own work. If it hallucinates or gives a bad answer, the consequences are low.

2. Tier two is team or company use. Slightly more consequential, as you’re trusting AI with organizational work, but still internal.

3. Tier three is public-facing. You’re trusting an AI service to interact with your customers, on surfaces that directly touch revenue.

There are two types of brands that tend to move first. Incumbent leaders with visionary leadership who want first-mover advantage, and “punch-ups,” nimble challengers using the technology to climb the ladder in their vertical. One example of this is Nike vs On Running.

It’s the middle group that shows the most resistance: brands that have spent 15 years hyper-optimizing conversion funnels, where product detail pages are treated as jewel boxes no one is allowed to touch. It’s difficult for them to imagine putting a generative, non-deterministic interface that hasn’t been approved through five levels of review in front of customers.

Jonathan says this is as much about change management as it is about technology. “If this was an easy thing to do, an obvious idea, then there really wouldn’t be a business opportunity for us.” The combination of education + trust-building + great design results in their moat.

But the math is compelling. Demonstrate even a few basis points of conversion improvement for a retailer doing hundreds of billions in revenue, and the argument makes itself:

“Do you like money? You’re a business. Do you like to spend it less? Do you like to make more of it? Okay, great. Let’s go.”

Designing at the frontier

How do you design features for a product category that barely exists? Jonathan spends roughly half his headspace each week on this.

Figma still has a role, but it’s shifted. It’s now a storyboard for internal alignment rather than the artifact translated into specs. The real work happens in live prototypes. New Generation’s founding designer, Nick, is what Jonathan calls a “prototype-native designer.” Instead of starting with static files, he cuts straight to working prototypes connected to the company’s APIs. He moves fluidly between visual design, front-end engineering, and shipping pull requests throughout the day.

“We’re all just product builders now. It’s the most fun I’ve ever had working because we don’t have to think like ‘that’s not my job, I can’t go there, I’m going to piss somebody off’ anymore.”

Agent Score grew directly out of this practice. Agents evaluate a brand’s website, another monitoring agent reviews the interaction, and the system generates a report card identifying what worked and what didn’t. Jonathan describes it as a kind of synthetic user research, a glimpse of a future where designing for agentic stakeholders becomes as normal as designing for human ones.

Jonathan himself has been pushed further into the technical side than at any point in his career. “I have learned more about coding and engineering in the past year of this company than in my entire career before.”

“Lucky you”: Jonathan’s advice for designers

The baseline for designers is rising. If you’re completely non-technical, the output you can achieve with AI tools today is dramatically better than what was possible two years ago. That’s great for many use cases. But it doesn’t address the frontier. The people pushing new boundaries, widening the gamut of opportunity for everyone else, are technical. “That’s where we want to be,” Jonathan says. “Not in the center where it’s not consequential.”

His practical advice for designers, drawn from both our conversation and his talk at South Park Commons:

1. Get a co-founder. You need an actual technical partner to build with: “it’s pretty bad advice to think you can do everything alone.” There’s real leverage now for designers to build coded, working things, but those are prototypes, not commercial-scale products. You also need someone emotionally to get through the journey. “It is a long journey.”

2. Stop waiting for the perfect idea. “I had carried around for a decade all these ideas and I had excuse after excuse after excuse why it wasn’t the right time, the ideal time, or worse, not the perfect idea.” AI has dramatically increased the speed of experimentation. A lot of the things that would have killed a company before can now be de-risked quickly.

3. Put yourself in environments where your ideas can be tested early. Share work before it feels finished. Seek feedback from people who will challenge you. Jonathan says being part of a community where he had to regularly demo progress and expose half-formed ideas played a meaningful role in shaping New Generation in its earliest days.

4. Understand the difference between taste and sensibility. Taste is personal: it’s what you like. And it can become a trap if you cling to it too tightly. Sensibility, on the other hand, is knowing what’s right for the moment, the context, and the user, even if it’s not what you’d choose for yourself.

One thing Jonathan keeps coming back to is this: the more generated our world becomes, the more we’ll value what’s unmistakably human.

As AI starts shaping more of what we see, the handmade won’t disappear. “We still are biological creatures and have eyeballs and a sense of hearing and touch,” he says. Designers have always made things people can feel. That doesn’t go away just because the tools get smarter.

I showed him a poster on the wall behind me during our conversation: letterforms made from individually placed paper clips by designer Ben Barry. Could an AI have generated something similar? Maybe. But the thing that makes it beautiful is the evidence of a human hand painstakingly placing every clip. Jonathan’s conviction is that we’ll see more of that appreciation, not less, as the generated world expands around us.

His closing line:

“Lucky you. You’re a designer now, graduating into the most exciting software time in human history. Damn.”

If you’re a designer building something new, or you know someone who is, we want to hear your story. Refer them (or yourself) here.

Hero illustration by Adam Dixon

Leif Abraham’s resume doesn’t read like a typical fintech founder’s. As a teenager in Germany, he taught himself design on a pirated copy of Photoshop. He spent his early career in agencies, pulling all-nighters for clients, building muscle memory around shipping under pressure. He tinkered constantly, co-creating viral hits like Pay with a Tweet and eventually founding And Co, a freelancer tool later acquired by Fiverr.

Public, the investing platform he now runs with co-founder Jannick Malling, grew out of that accumulation rather than a single moment of insight. The company reflects years of repetition: agency-derived discipline, running a startup that found product–market fit but didn’t quite become a breakout, and close observation of how internet-native users decide which products deserve their trust.

Public launched in 2019 with an ambitious goal: to become a serious, long-term home for self-directed investors instead of another speculative trading app. The company reached a $1.2B valuation in 2021 and now supports multi-asset investing across stocks, ETFs, crypto, bonds, options, and more.

For designer founders, Leif’s path will resonate because it’s shaped by iteration rather than inevitability. He’s been the agency designer, the freelancer, the operator of a scrappy SaaS product, and now the co-CEO of a scaled financial platform. Over time, that range led him to develop a set of practical filters—about customers, incentives, and personal fit—that now guide what he chooses to build.

In this conversation, we talk about:

• How working at agencies helped develop execution habits that compounded later through building companies

• How Public avoids the “next feature trap” by designing for belief vs novelty

• The tradeoffs behind moving from “snackable” UI toward denser, more serious interfaces

• The dinner table test: a simple way to evaluate whether a company and problem deserve years of your attention

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The early makings of a designer founder, found in the agency grind

Leif's years working at agencies shaped how he operates as a founder. Unlike product teams where deadlines can slip, agency work is unforgiving: the client shows up when they show up. If the work isn’t ready, you don’t renegotiate. You ship anyway. That helps build the type of discipline many founders only develop later, under far more pressure.

Agency work also forces a faster detachment from ideas. “You’re forced into experiencing your darlings die all the time,” Leif says. You learn to generate, test, and discard them without attachment.

There’s also a practical advantage for designers. Because they can build and test ideas themselves, they can fund early exploration through freelance work, buying time to learn before committing fully. “You can make something with your own hands and test it,” Leif says. “You don’t need to hire someone else to get started.”

Why building a great product isn’t good enough

And Co was a platform to help freelancers handle invoicing, contracts, payments, and the operational details of running an independent business. It emerged directly from Leif’s own experience doing client work and was built to solve problems he knew firsthand.

The product itself was thoughtfully designed and genuinely useful. The business, however, proved harder to scale: “It’s really tough to make that a large business,” Leif reflects, pointing to two fundamental constraints.

Distribution came first: “Performance marketing doesn’t really work for targeting freelancers.” Without a scalable acquisition channel, growth depended on partnerships and constant hustle.

Pricing sensitivity compounded the problem. “Any money they spend in a professional capacity for tools comes out of their own pocket.” At $20-30 per month, the business required massive scale to become meaningful—scale that was difficult to reach without solving distribution.

Looking back, Leif sees a deeper issue underneath both challenges: an imbalance between product craft and business mechanics.

How Public got started

After And Co, Leif knew he wanted to build something that could scale into a meaningful business and still reflect his values as a designer. Around the same time, his longtime friend Jannick Malling had also sold his company and moved to New York. They found themselves in a similar place, unexpectedly free to start something from scratch. Jannick began working on the idea for what would become Public, while Leif initially got involved as an investor while wrapping up his time at Fiverr.

The company launched in 2019 with a clear point of view on the investing landscape. Most platforms leaned heavily toward speculation, encouraging frequent trading and short-term behavior. Others focused on serving experienced investors, but at the cost of approachability.

Leif and Jannick saw an opportunity to build a serious financial service that felt modern and well-designed without sacrificing trust. For Public to play a meaningful role in how people build wealth, it needed to feel credible from day one. It had to be something people would trust with their life savings. This meant prioritizing credibility over clever features, and making sure that everything—from product decisions to how the company made money—focused on trust, incentives, and long-term alignment.

The case for seriousness in designing for fintech

In early 2022, Public made a decision Leif points to as a turning point. Inside the company, it became known as “level up”—a deliberate shift in ambition and audience, framed as a long-term bet. Leadership warned the team not to expect immediate payoff; the strategy was built on patience, with a two-year horizon before it would register cleanly in the metrics.

Rather than trying to be a platform for everyone, the company decided to narrow in on the top quartile of digital natives: people with enough financial fluency to care about fundamentals, enough conviction to invest for the long haul, and enough engagement to track markets beyond headlines.

The shift in strategy quickly surfaced in the UI. Leif frames the design problem as a balancing act: bring more sophistication into the experience without making it feel complex, and avoid “simplicity” that reads as lightweight or unserious. In practice, that pushed Public toward a more information-dense interface and a more restrained visual language:

• More data per screen (depth over snackability)

• Tighter typography (less emphasis on big, bold numbers)

• A stronger desktop experience, reflecting how committed investors prefer to manage money

If the shift looked “less pretty” in places, it was by design. Public’s internal rule (“UX over UI”) puts reliability ahead of polish. In a brokerage, trust is built through mechanics: whether the app stays up, whether customer support responds, whether workflows behave consistently, whether a trade confirms quickly, and whether the user understands exactly what just happened.

Public pairs that reliability with an unusually fast shipping cadence. Internally, they treat product velocity as a leading indicator of health. In 2025, the team shipped roughly one major new feature or product each week without increasing the size of its engineering organization year over year. They’ll continue to do that and more this year.

Turning users into advocates through emotional retention

Leif describes two different forces that keep customers loyal: utilitarian retention and emotional retention.

Utilitarian retention is straightforward. People stay because the product works, the fee is competitive, and the features are solid. Those are all important, but easy targets for competitors to attack. Someone can undercut pricing. Someone else can copy functionality. That dynamic creates what Leif calls the “next feature trap”: the belief that this next release will finally unlock durable growth. When it doesn’t, the cycle repeats.

Emotional retention means customers stay because they feel aligned with how the company behaves: how it treats users, how it makes money, and what it refuses to do. This kind of attachment is much harder to replicate.

He gives this example:

“If we meet each other at a bar and you pull out the other green app, my reaction shouldn’t be, ‘I like Public more because they give me a higher interest rate.’ It should be: ‘Whoa, whoa, what are you doing on there, Ben? You need to be on Public.’”

That emotional (and perhaps even irrational) reaction is what Leif believes separates products people tolerate from products people defend: “When someone sticks with you because they’re a believer, not just because of a feature, you suddenly get things like pricing leverage. And that’s also the best kind of marketing—when customers feel such a strong emotional connection to the company that it feels personal to them and suddenly they become advocates, rallying on your behalf.”

That shift from user to advocate is what allows a company to make harder, longer-term decisions without immediately losing its base. After the GameStop surge in early 2021, the company stepped away from payment for order flow for equities trades, a meaningful short-term revenue trade-off in favor of cleaner long-term incentives.

More recently, they ran a Wall Street Journal ad stating:

“Wealth is not won in a bet. If you’re looking for a broker that’s not also your bookie, we invite you to try Public.”

The dinner table test

Leif uses a simple mental model to assess whether he’s building the right company: Would I genuinely want to sit at a dinner table with my customers and enjoy the conversation?

When he asked himself that question about And Co, the answer wasn’t a clear yes. The imagined dinner conversation centered on late invoices and difficult clients; important problems, but not topics he personally felt energized by.

Public feels vastly different. “Now I sit there and nerd out about the markets,” he says. That contrast connects directly to another principle he holds tightly: being a power user of your own product. With Public, Leif actively invests, tracks markets, and uses the product the same way many of the company’s most engaged users do. That creates a tight feedback loop between what he experiences personally and what gets built.

What Public is building towards

Public’s next chapter builds directly on the principles that shaped its earlier decisions. Rather than treating AI as a novelty, the company is using it as core infrastructure by reducing friction, increasing clarity, and supporting more deliberate decision-making for self-directed investors.

Over the past year, Public has rolled out tools that let investors build and adjust portfolios using natural language. Users can create custom portfolios—effectively their own indexes—that live alongside traditional ETFs, without navigating multiple screens or products.

What comes next pushes further in the same direction. In 2026, Public plans to introduce agentic brokerage: user-approved automation for things like moving idle cash, rebalancing positions, or setting rules around risk. The system doesn’t act on its own. Investors decide the rules, and the software carries them out.

The arc is straightforward. Public is building for people who want to stay involved in their decisions while removing the busywork around them, shipping at a pace that compounds over time without chasing novelty. For Leif, that combination—agency discipline, user alignment, and a problem that passes the dinner table test—represents everything he learned from the long accumulation that brought him here.

If you’re a designer building something new, or you know someone who is, we want to hear those stories too. Refer them (or yourself) here.

Hero illustration by Adam Dixon

By any measure, Julie Zhuo had already made it. She’d helped define product design at Facebook while leading a design team of hundreds and written The Making of a Manager, now a modern classic on leadership. But what happens after you’ve achieved the thing you set out to do?

For Julie, the answer wasn’t to coast or climb higher. It was to begin again. After fourteen years at Facebook, she left to explore what it meant to build from the ground up. Today, she’s the co-founder of Sundial, a company developing tools that automate what the best analysts do so teams can make faster, smarter decisions.

Julie has always been a bridge between worlds: an engineer turned designer, a leader who still thinks like a craftsperson, a writer who turns experience into clarity. In this conversation, we explore how she made the leap from design leader to founder, what she had to unlearn along the way, and the advice she’d give designers thinking about starting something of their own.

What we cover:

• How Julie recognized it was time to leave Facebook and start over after 14 years

• Why she believes discomfort is a signal for growth, not a threat

• Her practical framework for taking the first steps as a designer founder

• The origins of Sundial and how early consulting work revealed the opportunity in data tooling

• What she had to unlearn from Facebook, from delegation to consumer instincts

• Why she and her co-founder chose to skip the CEO title

• Why most designers mistake fear for preference when it comes to starting a company

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Choosing discomfort on purpose

When I first met Julie, we were both designers at Facebook, part of a small group trying to define what “product design” even meant at a company moving at breakneck speed. She’d trained as an engineer, so stepping into design came with a heavy dose of imposter syndrome. “I felt woefully underprepared for every new role and just had to learn through painful mistakes.”

But that discomfort was also what fueled her growth. “I started to realize that maybe you have to feel like an imposter to get that satisfaction of growth when you look back. So I started to choose discomfort on purpose.”

Over fourteen years, Julie grew from engineering intern to VP of Product Design, leading thousands. The first half was marked by self-doubt and stretch assignments; the second by frameworks and leadership. But after a while, the learning curve flattened. “There’s not much difference between managing 200 people and 400.” With a new baby and a sense that the job no longer stretched her, she decided to leave, choosing discomfort on her own terms this time.

“Ignore the whispers that beckon you towards the easy wins. Work hard for yourself, for the joy you feel when you’re one step closer to the person you’ve always wanted to be, whether it’s getting in the dirt to make things grow, getting in front of a crowd to speak your truth, or going out to find love behind all those brambles.”

From Julie’s essay, Our Soul Needs Proof of Work

Choosing who to build with

When Julie left Facebook, she wasn’t chasing a specific idea so much as a feeling of curiosity: “I still wanted to go out and explore, to understand myself and learn, what am I made of? What do I really love in this world?”

Early in that exploration, she reached out to Chandra Narayanan, Facebook’s former Head of Analytics and later Sequoia’s Chief Data Officer. “We have very different brains. But we share values, and I trust him completely.” What started as a casual check-in turned into a decision to work together long-term, possibly for decades, before they even knew what they would build.

They talked about what the next thirty years might look like if they built a life of work together: making products, yes, but also teaching, investing, and giving back. That long view created room to dream without pressure. When COVID hit the day after their first consulting project began, they spent the next year doing remote, fractional work for a handful of startups, helping with design, product, and strategy.

A pattern emerged across those projects. “A lot of these companies just didn’t have good data practices. They didn’t have the metrics or the observability. They didn’t really know what was going on.” One day, Chandra suggested, “Why don’t we build some tools to help automate that process for our companies?”

They began prototyping with a few contractors in India and found themselves completely absorbed. “We just got really into it. It was so fun that we decided to make it real.”

Building Sundial

Sundial’s mission is simple to say but hard to achieve: automate what great analysts do.

The idea grew from Julie and Chandra’s shared experience at Facebook, where disciplined use of data was core to how products were built and improved. At most companies, leaders want clarity and control but translating business questions into analytical answers is slow and human-intensive. “The way organizations solve that problem is by hiring specialists. But we kept asking, why can’t a product do that?”

Their goal with Sundial is to make software that feels like working with an exceptional analyst, not another dashboard. As Julie puts it, “We’re trying to productize Chandra’s brain.”

They hadn’t set out to start a venture-backed company, but the scope of the problem demanded it. The data tooling landscape was already crowded—“a hundred logos, and we’d heard of maybe ten”—yet their ambition was to build something foundational. Today, Sundial is a 50-person distributed team across the U.S. and India.

On titles and hierarchy

Julie and Chandra chose to call themselves co-founders rather than take on formal CEO titles. They didn’t want hierarchy to get in the way of how people showed up or spoke up, especially with a distributed team and many teammates in India, where companies often lean hierarchical. “Between us we know how we’d break ties. But we didn’t want that to bias information flow.” The title choice helps keeps things flat while leaving room for clarity when decisions need to be made.

What she had to unlearn from Facebook

Julie literally wrote the book on management. But starting Sundial meant trading scale for scrappiness and unlearning instincts that had been second nature after 14 years at Facebook.

1. Stop defaulting to delegation

At Facebook, Julie’s leverage came from delegation. As a VP overseeing hundreds of people, her job was to think in systems: defining direction, aligning teams, and trusting others to execute. Founding a 0→1 company was the opposite:

“I had to unlearn delegating as a primary lever and get back to rolling up my sleeves. I’d gotten really good at talking about things, writing docs about things, opining about things. I’d gotten out of practice at actually doing the thing myself.”

At Sundial, that meant re-immersing herself in the work: writing specs, defining product flows, doing sketches, coding prototypes. “When you think about what has to happen for an engineer to build something, someone has to redline it. Someone has to decide the thousands of micro-decisions, like is this spacing five pixels or seven?”

It was humbling to realize how much her subconscious habits still defaulted to management mode. “You can know something consciously and still act out of instinct. I worried about micromanaging for years as I learned to scale teams. Then I realized that in the 0-1 phase, you don’t even get the luxury of building a larger team if you don’t have a good initial product. That must be micromanaged.”

2. Consumer instincts don’t translate to B2B

Julie spent her career building consumer products where she was the user. You trust your instincts, you design for emotional resonance, and you believe the product should speak for itself. “That’s the muscle you build as a designer. You want the work to be self-evident.”

B2B, she learned, runs on a different logic. “When you’re selling to companies, you have to tell a story. And the story is often more important than the product in that moment, because it’s about building a long-term relationship. The product will change, but the trust has to start now.”

Her old instinct was to rely on product-led growth, letting users discover and adopt naturally. But with enterprise data tools, that doesn’t work. “Most people inside a company don’t have the authority to share data or sign up for a new tool. You can’t swipe a credit card and start. You have to go talk to the people who can make that call.”

That realization reframed her understanding of design itself. “Storytelling and sales aren’t superficial. They’re part of how you help people believe.”

In a sense, Sundial forced her to return to the kind of builder she was before Facebook—to find growth again by starting over, hands-on, in the uncomfortable middle of things.

Fear ≠ preference

When I asked Julie why she thinks more designers don’t start companies, her response was:

“I think a lot of us confuse fear with preference. We tell ourselves we don’t want that life—the stress, the risk—but often it’s just fear. We’re afraid to want something and fail.”

Her own fear wasn’t about money, it was about messing up in public. “I had this deep, deep well of fear that if I failed, I’d be seen as a fraud by others. People would think I’m wasting my time and my potential. Admitting this fear to myself was important, because then the next natural question was: do I want to be the kind of person that shies away from things because I’m afraid of what people will think? Absolutely not! Once I could clearly identify this fear, I knew that the only to overcome it was to dive right in.”

Borrowed ambition

We talked about ambition too, how it forms and evolves. When I first interviewed Mark Zuckerberg back in 2007, I asked him what he wanted Facebook to become. He said, “We want to connect everyone in the world.” I laughed. Half the world didn’t have internet. He looked at me and said, “Then we’ll bring them internet.”

Julie smiled when I told her that story. “That’s what I mean by borrowed ambition. When you’re around people who dream that big, it changes what you think is possible. Eventually, that size of ambition becomes what you expect of yourself also.”

Julie’s advice for designers thinking about starting a company

I asked Julie what she’d tell a designer who’s thinking about starting something but isn’t sure where to begin. Her advice is practical:

1. Name the blocker.

What’s stopping you from starting? Is it money, skills, an idea, or a partner? Get as specific as you can here.

2. Test the idea with the market.

If your uncertainty is around the idea, talk to 30-50 potential users. Listen instead of pitching. Try to understand their pain points, their language, and what patterns emerge.

3. Make something others can react to.

Once you’ve had those conversations, create an artifact, whether it’s a memo, a short deck, or a clickable prototype. “Artifacts attract momentum,” Julie says. They give people something to respond to and a reason to engage.

4. Light a beacon.

Put your idea out there. Tell your story publicly and with clarity. Vulnerability is part of the process. It’s how you attract people who care about the same problem. “If you light a beacon, the right people will find you.”

5. Skill up in public.

Pick the skill you have no confidence in, then do it 100 to 200 times. “For me, it was sales. I just had to keep doing it until rejection no longer scared me, and I could really start to understand my own approach and the strengths and weaknesses I have.” Volume is the fastest teacher.

6. Figure out your runway.

If your blocker is financial, take a rational look at your situation. How much time can you give yourself to explore? If it doesn’t work out, you can always return to a job or find another. Knowing your true runway makes the risk concrete and manageable.

At Facebook, Julie learned how to lead at scale. At Sundial, she’s learned how to build from scratch again. Her career traces a simple arc: learn, lead, unlearn, begin again. It’s an arc many designers will recognize—the pull between mastery and growth, between what’s proven and what’s possible.

For Julie, the choice has always been clear: keep moving toward discomfort, or risk staying still.

If you’re a designer building something new, or you know someone who is, we want to hear those stories too. Refer them (or yourself) here.

Hero illustration by Adam Dixon

Six months ago, we launched Designer Founders with the goal to share stories from designers who’ve built successful companies to inspire more designers to start their own.

We’ve since published interviews with Evan Sharp (Pinterest, West Co.), Ivan Zhao (Notion), Al Hertz (Folio), Cecilia Uhr (Bezi), Chris Kalani (Phantom), Jeff Anders (Ambrook), Jessica Hische (Studioworks), Phil Vander Broek (Dopt), Robert Yuen (Monograph), Sam Hashemi (Felt), Brian Lovin (Campsite), and Filip Skrzesinski (Subframe)

Below, we’re summarizing some of the best advice we heard from these founders.

What came up more than anything, maybe unsurprisingly: how much the “being a founder” part overshadows the “being a designer” part. Multiple founders told us, with varying degrees of bluntness, that you’re not really designing anymore as a designer founder, at least not in the way you’re used to. But the same instincts that make great designers—understanding constraints, iterating quickly, making tradeoffs—are what make great founders too.

Chris Kalani: Validate while you still have a job

Chris was a solo founder with his first company Wake, and learned the hard way he didn’t want to do it alone again. When he started Phantom with his co-founders, they took a different approach: build it while still employed at their day jobs.

“Don’t just immediately jump into it. Build something, prove out the idea. Brandon and I were literally still at our previous company when we built the first version of Phantom. I worked on it for a year and a half before fundraising. By the time we were fundraising we already had a $100,000 grant from Solana Foundation and 20,000 users on the waitlist.”

This approach has been taken by others: Brian Lovin spent six months nights and weekends on Campsite, then took a three-month unpaid leave. For Studioworks, Jessica Hische had customers connect Stripe accounts pre-launch to filter to get a sense of intent.

You reduce financial risk, get actual user feedback instead of hypothetical opinions, and create leverage when it’s time to raise.

Jeff Anders: Look beyond your own problems

Jeff thinks designers should look past solving their own problems and focus on overlooked industries undergoing transformation.

“I’m really drawn to these legacy spaces that desperately need change, whether it’s farming or manufacturing, trucking or construction. They’re not doing things the way their parents did. And we need to help people adapt to that.”

Ambrook serves farmers and ranchers, a world Jeff didn’t come from. But he and his co-founders spent nine months listening—hundreds of interviews with farmers, ranchers, water board managers—before writing a line of code. The conviction came from understanding the problem deeply, not from living it personally.

Jeff also learned to stop pre-compromising his vision. “I need to go to bat for the most ambitious version of what design can mean to the company. Start from a visionary design angle, then compromise through working together—not the other way around.” Let others bring you back to reality. Don’t do it to yourself first.

Phil Vander Broek: Pick markets that pull you forward

After Dopt was acquired by Airtable, Phil looked back and saw what he’d do differently.

“I’d hunt for the same depth of problem, but inside a market already flush with budget and urgency, even if that means heavier competition.”

At Dopt, they built a product adoption platform that customers genuinely liked. But they kept hearing some version of: “This is a big problem for us...but it’s not on the roadmap right now.” Teams wanted the product, but because implementation required developer time, it often got deprioritized. That lack of urgency killed momentum.

Heavier competition often just means there’s real demand and budget already allocated. When customers are actively searching for solutions, you get natural tailwinds instead of constantly pushing uphill.

Are you a designer building something new, or know someone who is?
We’re always looking for more designer founders to feature, invest in, or partner with.

Refer a designer founder

Jessica Hische: Make decisions without a CEO

At Studioworks, there’s no CEO. Instead, Jessica and her co-founders each have veto power in their domain.

“We’ve been really collaborative about decision-making. We each have our columns where we have the most power. I have all the veto power on design. If I ever say, no, this is more important, it doesn’t matter what anyone says, my decision wins out. Chris [Shiflett] has more veto power in certain product decisions, and Sean has veto power in systems decisions.”

This structure works because they understood each other’s strengths before starting the company. They aligned early on roles and decision-making authority, which prevents endless debates and lets each person own their domain fully.

It’s a similar approach to Julie Zhuo at Sundial, who deliberately avoided naming a CEO to keep hierarchy from creeping in and to make sure decisions stay rooted in what’s best for the company, rather than who’s in charge.

Ivan Zhao: Keep it dumb and study history

Ivan is deeply skeptical of clever design at Notion. He constantly pushes the team to strip things down and focus on the golden path, the main flow that 80% of people will take.

“Designers spend too much time on edge cases. Most of the time, what matters is the dumbest path. Make that great. If someone’s drunk, can they understand it? You care about your design. Your pixels. Your product. But nobody else does. They’re tired. They’re distracted.”

He also thinks the tech industry doesn’t look backward enough. “If you study physics, you know who Newton is. But in tech? Most people don’t know who Engelbart is.” His counter-move: borrow widely. Study architecture from 1900 to 1920. Look at mid-century furniture principles. “Most of the people I know in Silicon Valley are thinking about this year, or the next five years. When you zoom out, you have so much more context.”

Evan Sharp: Lead with confidence you don’t have yet

Evan found himself as the 27-year-old co-founder of Pinterest, managing VPs twice his age, and he felt utterly unqualified. But he realized something that started to change how he led the company:

“I understand the soul and spirit of this product at a level of depth that others never will, because they didn’t give birth to it. If I could go back, I would give [my co-founder] Ben and myself a huge injection of confidence, to know that our values were the right values.”

He also learned how to teach teams the business value of caring something he’s also instilling in building West Co. now. “I spent years trying to make a logical case for design. I finally realized it’s about helping your team learn the business value of caring and figuring out how to structure your team so they can make design-centric decisions in a way that empowers them.”

Robert Yuen: Stop being so nice

Robert doesn’t mince his words:

“If I were to do it all over again, my advice would be: don’t be so nice. A lot of first-time founders are too nice. We want to please everyone. But your job isn’t to please everyone—it’s to build a company. Learn how to have those hard conversations, and you’ll get there a lot faster.”

At Monograph, an operations platform for architecture and engineering firms, Robert learned that being direct early saves everyone time. Brian Lovin learned the same lesson when he had to fire someone who told him: “Oh, you’re not a nice boy”—a reference to his podcast nickname.

A mentor reframed this as: “What do you want to spend your heartbeats on? Our time is limited, but that’s also true for people on your team. So it’s actually kinder to say, as early as possible, ‘We should do something else here.’”

Designers are trained to be collaborative. But as a founder, that instinct can become a liability.

Brian Lovin: Get your reps in

Brian kept reverting to his comfort zone in building Campsite, acquired by Notion in 2024: “just build the best product.” But as a founder, you have to wear lots of hats: sales, marketing, hiring, firing.

“I treated it like a video game. I’m bad at all these things, but every cold email is two experience points, every sales call is 20 experience points. You just do the reps.”

At some point, you need to decide: do you get good enough at these things, or find people who are great at them and delegate? But you can’t delegate what you don’t understand. Putting in the reps first helps you know what good looks like.

He also learned what founders are up against in 2025. When you’re on a sales call educating people about a new way of working, their next call is someone saying “I have an AI solution that will replace a department.”

“That’s what you’re up against. So if you’re going to do a big startup, go big. Dream big. Make a big thing.”

Sam Hashemi: Get designers involved in sales

Sam has an unconventional take on what would get more designers energized about company building:

“If we got more designers to close a deal, they’d be more excited. Not only did you make the thing, but you got someone to pay you money for it. It closes the loop. I had this experience as an intern at Salesforce. When I started joining the sales calls and seeing how my designs led to hundreds of thousands of dollars in sales, it completed the loop for me.”

He also learned to talk about pricing early: “There’s a big difference between is this a $5,000 problem for you, a $10,000, or a $100,000 problem. Talking about pricing is not a design skill. It’s something I had to learn, and it’s actually pretty key.”

Cecilia Uhr: Prioritize brand early on

Cecilia learned two critical lessons while building Bezi. First, in a world where everyone has access to the same AI models, brand becomes the differentiator.

“I believe that brand is becoming increasingly important in this new world of AI products. How you show up, how you communicate what you believe in, and the storytelling behind these values is how you differentiate your company in a sea of sameness.”

At Bezi, they went through a rebrand to match their pivot from a 3D editor to an AI dev tool: “We’re trying to imagine what Bezi feels like with this new product. A lot of the actual craft is going to come through product capability and personality, through the chat interface.”

Second, she had to learn when to let go. “Prioritization is really hard. As designers, we’re trained to craft the perfect experience. But startups are always operating under extreme constraints. You need to differentiate between deal-breakers and nice-to-haves. That’s a muscle designers need to build to ship fast and iterate.”

Al Hertz: Accept you’ll design less and plan accordingly

Al is honest about what you’re signing up for in becoming a founder.

“Being a designer founder is like being a founding designer, but with even less time for design. We’re all like: how do I find the time to do the one thing that I’m really, really good at? It’s hard unless you’re incredibly intentional about it.”

Robert of Monograph puts it more bluntly: “Balance doesn’t exist, nor should it be the goal. What you want is harmony, not balance. Harmony looks different depending on what week, quarter, or year you’re in.”

But as Al puts it: “Building a startup is exactly as hard as people say, and 10x more fun.”

Filip Skrzesinski: Design the company’s DNA, not just the product

Filip takes the idea further:

“Don’t start a company because you love designing products. Do it in spite of that. You won’t be designing in the traditional sense—you’ll be designing the company’s DNA. It’s the invisible work: how you organize, how you think, how you make decisions. The day-to-day reality becomes shipping quick fixes, sending outreach messages, writing docs. All tasks eventually get delegated or automated. But the hard work is deeper. It’s cultural. It compounds.”

He adds: “In the end, you’re signing up for something bigger than designing a product. Do it because you want to design things that outlive you.”

Looking ahead

We’re planning the next six months of Designer Founders, and we want to know what you want to see more of. Who should we interview next? What companies are you watching? What questions do you wish Ben would ask? Let us know.

In addition to more interviews featuring incredible founders, we’re also considering putting together guides on things like fundraising as a designer founder, founder-led sales, how to choose what to build, and finding the right co-founder.

If you’re a designer building something new, or you know someone who is, we want to hear those stories too. Refer them (or yourself) here.

Leave a comment

When it comes to product and brand, most early founders set the bar at “good enough.” This allows for speed and iteration as you figure out who you are and what you’ll build. Occasionally, we meet a team that sets a really high bar in one of those areas, believing that excellence there will be critical to their winning early on. And then, rarely, we meet a founding team that does it in both from day one. It’s a big bet but if you have conviction early, it can pay off. This is the story of one such company.

Before starting Ambrook in 2020, Jeff Anders and his co-founders Mackenzie Burnett and Dan Schlosser had already been building together for nearly a decade. They first met through the student incubator they ran at the University of Maryland and the collegiate hackathon scene. “It was always a known thing,” Jeff says, “that when the stars aligned, we’d start something meaningful together.”

That chance came in San Francisco. Mackenzie had sold her first company and returned to Stanford to study climate security; Jeff was leading design at Scale AI. Living through California’s droughts and wildfires pushed them to consider questions of natural resource management. Instead of jumping into solutions, they spent nine months listening—conducting hundreds of interviews with farmers, ranchers, and water board managers.

What they learned was that the biggest barriers to climate resilience were financial. Farmers needed better tools to track investments, measure on-farm practices, and manage increasingly complex operations. With payments experience from stints at Venmo and Facebook Marketplace, the team realized they were well equipped to tackle the problem.

Their mission is reflected in the company’s name: Am- (Latin for love) and -brook (a stream of water). Through Ambrook, they’d build modern tools and systems to strengthen the financial backbone of family-run businesses.

Today, Ambrook is building the financial infrastructure for American industry—starting with agriculture and expanding into adjacent, resource-intensive sectors. More than 3,000 operations across all 50 states use it to manage accounting, banking, invoicing, and spending, replacing paperwork and legacy systems with modern tools. The team recently raised a $26.1M Series A to help more family-run businesses grow their operations and make better financial decisions.

As co-founder and head of design, Jeff has helped shape a culture where design informs every detail, from field-ready interfaces farmers rely on every day to storytelling that treats the agricultural ecosystem with respect and depth.

I spoke with Jeff about building a company where everyone thinks like a designer, finding competitive advantage in underserved industries, and what it takes to build trust with rural communities.

Are you a designer building something new, or know someone who is?
We’re always looking for more designer founders to feature, invest in, or partner with.

Recommend a designer founder

Design in practice at Ambrook

For Ambrook, design functions as infrastructure: the layer that makes complex financial systems usable, trustworthy, and empowering for people who split their time between the field and back office. It’s also what helped the team, even in the early days, punch above their weight:

“Craft, quality, and brand are core to our mission of making finance accessible. Craft got us in the door and helped us build credibility as a fledgling startup in 2020.”

The design team has remained small but exceptionally strong. Jeff works alongside Ali Aas, who leads brand and creative; Calvin Ku, who works on product design; and frequent collaborators like graphic designer Adam Dixon.

Here’s a deeper look at how design shows up across the entire company:

Product design: Making complex tools usable in the field

Ambrook’s user experience starts with the reality of its customers. Most financial software is designed for someone at a desk with reliable WiFi. Farmers and ranchers live in a different world, as Jeff describes:

“I’m wearing gloves in the tractor trying to make a financial decision because my banker just called me in the middle of something I’m doing outside of the office. I need to be able to access my data, make decisions, maybe even process payments or initiate new business transactions.”

Centering the product in practical usability is paramount when you’re building tools that work for both the 70-year-old veteran farmer and the 22-year-old graduate ready to work on their multi-generational family farm.

This also shapes how the team introduces new technology. For many customers, Ambrook is the first time they encounter AI in their day-to-day work, starting with scanning receipts and bills, and soon expanding to uploading documents like deeds and water permits. To build trust, Ambrook deliberately puts users in control of the AI systems working behind the scenes for them:

“We do our best to scan things for you, but give you an extra confirmation step. Because even though we might be adding friction in places, we are showing you how the sausage is made. We’re showing you how we got to an answer.”

That small design decision can turn initial skepticism into confidence. As Jeff says, “We’ve seen so many folks who are initially hesitant about some of these newfangled things become really familiar with it and appreciative of the work and the design there.”

Brand: Building authentic connection

Brand is treated the same as product design: with empathy for the people it serves. Rather than the high-gloss look we see in so much software, Ambrook’s visual identity feels warm and grounded, with its earthy colors and approachable typography.

One of the team’s most distinctive choices is its use of film photography during site visits. The constraint of film changes how they show up with customers:

“It limits the time with cameras out when we’re hanging out with customers on their farm. It creates a certain filmic look that we’ve all grown to love, and it makes photography accessible to any team member.”

The resulting images aren’t perfect but they are lived-in and real. They signal to customers: we’re here alongside you, not staging an ad shoot from afar.

Storytelling, culture, gathering

Within Ambrook, storytelling and culture are treated as extensions of design. Jeff and his co-founders are as deliberate about how the company recruits and collaborates as they are about how the product looks and works.

“Mackenzie and I have been talking a lot about how we’re designing our culture. It’s not just that you walk in, see a great logo, and you’re set for life. We’ve been rethinking our recruiting experience, and a big shift this year has been putting content out into the world through a blog the whole team contributes to.”

That sense of design shows up in their spaces too. Engineer Jaclyn Chan describes the New York office: “Plants trail from the windowsills. Candles sit tucked between books and mugs. We gathered around sweet Pakistani mangoes at the vintage wooden dining table we proudly sourced from Facebook Marketplace.”

Ambrook is a distributed team, with offices in New York, Denver, and San Francisco and teammates working remotely across the country. While hybrid by design, the team makes it a priority to come together—whether on ranches in Montana or at an ecological research center in Sonoma. These visits and retreats are a chance to learn from the places customers call home and connect with each other.

All of this groundwork fuels how Ambrook presents itself externally. The company launched Offrange, a deeply researched publication on modern agriculture that reads more like a cultural magazine than corporate content. Their Series A announcement appeared as a reflective letter, and they collaborated with Stripe on a short documentary—each example carrying the same editorial spirit rooted in the culture they’ve intentionally designed.

Jeff’s advice to designer founders

1. Don’t just solve your own problems

Jeff encourages looking beyond the often-given “solve your own problems” advice to consider where design can create outsized impact, particularly in industries undergoing significant transformation:

“I’m really drawn to these legacy spaces that desperately need change in order to help people prepare for macroeconomic shifts happening to their businesses—whether it’s farming or manufacturing, trucking or construction. They’re not doing things the way their parents did. And we need to help people adapt to that.”

Rather than competing in saturated markets where excellent design is the norm, Jeff advocates for strategic thinking about fit—not just product-market fit, but founder-market fit and founder-problem fit. He sees opportunity in industries where design insights can highlight patterns and complement the expertise of those already doing the work.

For Ambrook’s founders, their obsession with business and environmental resilience was the pull that kept them working through the complexity of building financial infrastructure for agriculture and beyond.

2. Your role as founder = design evangelist

As a designer founder, Jeff sees his role extending far beyond getting the design work done:

“My responsibilities have expanded into people ops, culture, events, content, recruiting—all these things beyond the pixels. The best designer founders care about things outside of design and bring that design competency to everything else.”

This means intentionally spreading design sensibility throughout the company. At Ambrook, salespeople make product pitches using Figma. Engineers advocate for user experience decisions. Jeff trusts the team to be good stewards of the product and brand because they’ve invested time in helping everyone understand design’s value.

“In 2010, we were talking about design getting a seat at the table. Design absolutely has a seat at the table now. The challenge is getting all the other people at the table to share a similar design sensibility.”

3. Don’t pre-compromise your vision

As a designer founder, you often have to juggle many different hats at once, managing the responsibilities of both building a company and building a design team.

One of Jeff’s biggest lessons has been learning not to pre-compromise. As the person responsible for design’s vision at Ambrook, it’s his job to dream bigger and advocate for those initiatives.

“I need to go to bat even more for the most ambitious version of the design team and what we can mean to the company and to our customers. Let’s start from a visionary design angle and then through working together compromise.”

Instead of jumping to thinking about timelines or budget, imagine what you could do starting from the most visionary angle.

4. Build community before you need it

Jeff emphasizes long-term relationship building. He and his co-founders had known each other for over a decade before starting Ambrook, connected through running hackathons and design communities in the early 2010s.

“There’s something magical about that scene. Everyone who was running hackathons or joining design communities is now founding something incredible.”

He continues investing in community, most recently organizing groups of founder dads navigating company-building and parenting simultaneously.

5. Take time to reflect

The relentlessness of startup life makes it easy to stay buried in execution. Jeff has learned the importance of stepping back:

“Coming up for air more often is something I wish I did more. Taking stock of what we’ve accomplished and who are the people around me who I need for the next stage of the company.”

Jeff takes particular pride in making complex financial tools intuitive and helping legacy industries adapt to change. For him, this work represents something larger than building better software—it’s about enabling family businesses to thrive through generational transitions and economic uncertainty.

Design is central to that work. It’s what allowed Ambrook to build credibility early on, serve customers with deep empathy, and raise the bar for how design influences product, brand, and culture across the company.

Ambrook is hiring across teams. They’re building a more prosperous future for America by giving independent, family-run businesses the financial tools they need to grow and thrive. If you’re excited about untangling the intersection of tech, finance, and sustainability, consider joining the team.

Careers at Ambrook

Where to find Jeff

• Ambrook: https://ambrook.com

• LinkedIn: https://www.linkedin.com/in/jeff-anders

• X: https://x.com/jeffand_

Hero illustration by Adam Dixon.

Evan joined our design team at Facebook in 2009. One of my first memories is him asking if he could keep working on a side project. We told him, “your whole life is about to be consumed by working here, but if you want to find time on nights and weekends, by all means.”

Well, eight months later, the tables had turned. I noticed Facebook employees spending time not on Facebook, but on his side project: Pinterest. For a company building a product notorious for amassing attention, it was wild to see another product take that attention away from inside the company.

When Evan told me he wanted to leave to work on Pinterest full time, I didn’t sugarcoat it: “Evan, you may be making the biggest financial mistake of your life.” He did it anyway.

Well, Pinterest went on to become one of the most successful and impactful design-centric companies in tech, with projected revenue of over $4B in 2025 and over 500 million people who use it to curate their aspirations and plan their life. So yeah, it turned out not to be the biggest financial mistake he’d ever make.

Evan eventually left Pinterest in 2021, and is now building West Co. to create tools that help people live meaningful, connected lives. Drawing from religious traditions and communal rituals, he’s asking a different question than most founders: what if a company’s operating system was built for care as much as productivity?

This thread pairs with another pattern that has defined his critical career decisions: choosing love over logic. From walking away from Facebook to betting on ideas that felt irrational but deeply compelling, he has consistently shown the power of conviction.

We spoke about business value of caring, design’s ability to create gravity around new ideas, and how his new company harnesses the power of congregation to rebuild some of the human connection that's been lost in our digital age. Hope you enjoy.

Are you a designer building something new, or know someone who is?
We’re always looking for more designer founders to feature, invest in, or partner with.

Recommend a designer founder

From architecture student to Facebook designer to co-founder

“The whole time at Facebook, all I wanted to do was go work on Pinterest,” Evan reflects. “After a year, I decided that if I loved it that much, I should be working there full time. I let that lead my decision, and it worked out. It could easily not have worked out, but I wasn’t afraid.”

Walking away from potentially life-changing money to bet on Pinterest was “irrational,” he admits. But it established a pattern that would define his career: choosing love over logic, and internal pull over external pressure.

More than youthful idealism, Evan had learned that the most compelling products come from solving problems you feel viscerally. Pinterest succeeded because he and Ben were building something they desperately wanted to exist, not something they thought the market needed.

“You have to make yourself fall in love with something enough that you’re willing to overcome your fear. You have to fall in love with the idea of investing an irrational amount of energy and money and time or whatever it is into this thing. If you find something you love that much, you kind of need that amount of love to stick it out. It takes a lot of intrinsic motivation to see through the ups and downs and challenges.”

Leading with confidence when you’ve never managed anyone

For first-time founders, hiring and managing leaders with far more experience than yourself can be daunting. Evan found himself at 27, having never managed anyone, suddenly overseeing accomplished VPs from Google and other tech giants. The instinct is to defer or second-guess your authority: “On some level, I had this self-awareness of: I don’t know what I’m doing. I should not be managing this person.”

But your lack of management experience isn’t necessarily a weakness. As Evan discovered: “I understand the soul and spirit of this product and its values at a level of depth that others never will, because they didn’t give birth to it and haven’t been invested in it like I have.”

Evan’s advice on leading with confidence as a founder:

• Don’t discount what you know: “If I could go back, I would give Ben and myself a huge injection of confidence, to know that our values were the right values.”

• Teach the business value of caring: “I spent years trying to learn how to make a logical case for design. I finally realized it’s about helping your team learn the business value of caring, and figuring out how to structure your team so they can make design-centric decisions in a way that empowers them.” One example of this philosophy in action is how the team redesigned the business onboarding flow to better serve small businesses alongside larger brands.

• Lean on mentors: “If you’re working with a mentor, reach out when you need help and don’t self-censor. Often people are very nervous. It’s kind of like being in high school and texting the person you have a crush on. You overthink every interaction. That dynamic manifests often in these professional mentorship relationships. It’s understandable, and it’s also just a waste of energy.”

How to build a design-centric company

That confidence Evan found as a young founder became essential as he helped shape Pinterest into a truly design-centric company. When we previously asked how the company achieved this, Evan explained:

“The trick for us is to build a company that makes money as a result of every single one of our disciplines operating at the highest level. Building a product in service of a business is the only way to make something long, long, long term. Like people say, Apple is a design company, which it is, but really that means everyone is doing an amazing job at their craft. We’re trying to tie the value of our product to every function - engineering, design, support, content, marketing, sales, all of them - doing high-quality work.”

Design’s superpowers are threefold, according to Evan:

1. Care that users can feel: “What I think it comes down to is just care. I see that with other founders like Brian Chesky at Airbnb. When you use a product and you can just tell that someone cared about your experience. Did they care about you as a user? What parts of you did they care for?”

2. Inventing new products in new spaces: “There are so many products that have never been invented that could really help people. Designers have the ability to do this. If you can find that kind of idea, you get to build a very different kind of company. It’s not just chasing some market share and some existing thing, it’s creating new market share.”

3. Generating gravitational pull that draws the right people in: “One of the superpowers of design is creating desire.” Instead of filling funnels with prospects and optimizing conversion rates, “with design, you can refine something you’re in love with, and it develops a gravity. People start to show up out of nowhere to work on it because it has this draw, this pull. It’s so in a designer’s power to sit down and make something beautiful that brings people in.”

💡 Look for the “disciples of why.”
Evan uses this phrase to describe mission-driven people already captivated by the question your product is trying to answer. “Designers tend to be more loyal to humanity than to any given company,” he says. They don’t need convincing; they feel it viscerally. When searching for a co-founder or people to join your team, look for:

• People who’ve worked in or researched your problem space

• Side projects or open-source work in the same domain

• Motivations rooted in why the problem matters, not just what the solution is

Knowing when to leave

“One of the least discussed chapters is leaving your company. Many founders wait too long. It feels scary to step out of the story that has made you successful and move into a complete unknown.”

Even as Pinterest flourished under these principles, Evan found himself at another crossroads. Despite the company’s massive success, he felt called to step away and grow as a designer and product builder. In a move that echoed his earlier leap from Facebook, Evan left Pinterest in 2021 to return to the fundamentals of craft, learning and rebuilding his approach to design from the ground up.

Once again, it was a move driven by internal conviction rather than logical reasoning: “Because I had never finished architecture school, I had felt like I’d never truly learned my design craft. I’d always dreamed of learning under somebody whose craft I respected, soaking in their process, their values, and their way of working. What does that way of working feel like?”

Evan’s advice on knowing when to leave:

• Test if you love an idea enough to overcome fear: “You have to fall in love with something enough that you’re willing to overcome your fear. You need that amount of love to stick it out.”

• Listen to your need for growth: His decision came from the feeling that, despite building an incredibly successful company, he’d never fully developed his design craft. If you don’t see yourself growing in the ways that matter to you as a founder, it may be time consider a new path.

• Don’t wait for logic to give you permission: Both of Evan’s leaps - leaving Facebook, then Pinterest - looked irrational from the outside, but were guided by a steady internal compass. “I was taught to follow my curiosity and I was pretty uncompromising about that. I made a series of pretty poor (on paper) financial and career decisions that ended up working out for me.”

“Curiosity has helped me be successful, whatever that means, more than any other quality.”

Applying ancient wisdom to a modern team

This pattern of following internal conviction over external logic led Evan to his most ambitious project yet. In recent years, his exploration of consciousness and spirituality led him to ask:

“What could I build that might help address just some of the terrible devastation of the human mind and heart that we’ve wrought in the last 15 years? I was so in love with the idea of trying to build something around that that I decided to bring together a small team and see what we could do.”

Rather than looking for answers in the present, he turned to history, as Notion’s Ivan Zhao has also done. “Most of the people I know in Silicon Valley are thinking from the perspective of a very zoomed-in timescale. They’re thinking about this year, or the next five years. When you zoom out, you have so much more context on what’s happened and why.”

That zoomed-out view revealed that “a lot of wisdom is also stored and transmitted by the world’s great religions and spiritual traditions. Specifically in the United States, it’s been stored and disseminated through the technology of congregation. Congregation has really fallen apart in the last few decades. We f*cked it up with the phone.”

Seeing this gap between ancient wisdom and modern disconnection, Evan knew he’d found something he could fall in love with enough to overcome his fear of starting over. His new company West Co. - started with Twitter co-founder Biz Stone and an impressive team of designers, technologists, and scientists - is building tools that strengthen our inner lives and revive that lost art of congregation.

That philosophy starts within the company’s own culture. At West Co., the team operates in two key ways: First, they weave time-honored practices into their daily work, connecting their personal growth and wisdom to what they’re building. Second, they live their mission: if the goal is helping people lead more purposeful lives, then the company itself must embody that same intentionality in how it operates.

Here’s what those principles look like in practice:

• Connecting the rhythms of work with the rhythms of nature by planning around seasons (e.g. spring, summer) instead of quarters

• Attending to how they want to be together by reflecting on shared commitments as a team

• Connecting life and work by meeting every couple of weeks in small groups

• Cultivating awareness of longer time frames and lineages by sharing photos of ancestors and lighting a candle each day

By rooting their culture in these intentions, West Co. aims to foster care, connection, and purpose - reminding us that even in tech, the deepest sources of wisdom may be found by looking back.

In many ways, these practices trace back to a collaborative project Evan had been part of years ago, where hundreds of rituals and practices from religious and cultural traditions around the world were cataloged in a spreadsheet. For a deeper dive into this research, you can take a look at the spreadsheet here.

“Now we’re entering a time where we don’t remember that the point of life is to be in synchrony with the world around us, and we have a real risk of pushing the planet to a terrifying place. It’s time to cast off that spell of the Industrial Revolution and reintegrate with an older way of working.”

The thread that connects it all

Looking across Evan’s journey, from Pinterest’s focus on inspiration to West Co.’s spiritual technologies, there’s a consistent thread. His approach is a reminder that the most enduring work is rooted in genuine attention and a commitment to serve others.

“Craft is just work with care,” he explains. “You can make something, but if you really care about it, you’ll craft it. Craft is the word that, to me, embodies care.”

Looking ahead, he’s clear about what matters most:

“I think future me will have wanted me to do my best to serve people and to treat everybody well along the journey in building something I feel genuinely proud of.”

It’s a philosophy that challenges the typical Silicon Valley narrative of growth at all costs. Instead, Evan suggests something more radical: that building with genuine care and following what you love might not only create better products, but better companies, and perhaps, a better world.

Key takeaways

1. Care is the foundation of great design. Craft is simply care made visible, and users can feel it. Evan emphasizes that showing genuine care is more persuasive than abstract arguments about design’s value.

2. Confidence shapes leadership. Evan wishes he and Ben had trusted their instincts earlier. Owning their values would have empowered their teams and reduced the tendency to defer to outside experts.

3. Designers can create gravity. Prototypes make ideas real and desirable, drawing in co-founders, hires, and collaborators. This pull is often stronger than abstract recruiting or pitch decks.

4. Rituals can transform culture. At West Co. the team plans by the seasons, reads a covenant, meets in small groups, and honors an ancestor table. These simple practices reconnect work with larger rhythms and meaning.

5. Founders must love their idea irrationally. Evan left Facebook for Pinterest not because it was logical, but because he loved it. That love provided the persistence needed to endure years of uncertainty.

Hero illustration by Adam Dixon.

Jessica Hische has built a legendary career that spans from lettering for Wes Anderson films to designing stamps for the USPS, establishing herself as both a New York Times bestselling author and one of the most recognizable names in design. Now she’s channeling that expertise into something different: Studioworks, a suite of business software designed specifically for independent creatives.

The idea came from her own frustration: existing tools for managing creative businesses weren’t built by people who actually run them. So Hische and her three co-founders decided to build their own, without investors or a traditional corporate structure. They’re bootstrapping, staying small, and building what they wish they’d had as working creatives.

What we cover:

• How Jessica got her start in design and lettering

• Why necessity is the mother of invention when it comes to web design

• How Studioworks’s co-founders make decisions without a CEO

• The case for bootstrapping over taking VC money

• How Studioworks built revenue from day one

• Jessica’s pragmatic take on using AI in creative work

Designer Founders

Inspiring more designers to take the leap of entrepreneurship.

By Designer Fund

Key takeaways for designer founders

1. Find your own funding. Bootstrapping has benefits. Venture funding isn’t always the right move for all companies and all founders. Consider if you might be able to move more nimbly if powered by your own resources.

2. Build the tool you wish existed. The idea for Studioworks came from Jessica’s own frustrations running a creative business, which helped made the product specific and the positioning clear.

3. Charge early. Studioworks skipped the free trial and asked users to connect Stripe accounts pre-launch, which helped filter for real intent and gave the team signal on what features actually mattered.

4. Build loyalty with your earliest adopters. Your first users are taking a risk by paying for your product. Consider rewarding them with a lifetime founding member discount, or other benefits that will turn them into evangelists for your brand.

5. Learn the tools before you negate them. Take the time to learn how to use new tools so that your decisions are coming from a place of knowledge, not fear. Treat AI like any other tool. Jessica uses AI where it helps (e.g. verbal ideation, prototyping) but draws a hard line when it compromises the craft.

Are you a designer building something new, or know someone who is?
We’re always looking for more designer founders to feature, invest in, or partner with.

Recommend a designer founder

Below is an edited transcript of the full conversation:

What led you to become a lettering designer?

Growing up, I loved drawing. It’s the one thing that has always given me joy. As a kid, I would draw for seven or eight hours a day. Even though I grew up in a small town and didn’t know what an art career looked like, I knew that I was going to be an artist.

I was really lucky to go to an art school that didn’t force you into a major when you first got there. I took graphic design for the first time as a sophomore and realized that I’m a very 2D person. I love all 2D mediums. Even in my sculpture classes, I basically ended up making 2D carvings or drawings on any of flat surfaces. I even did this really ambitious project in ceramics where I made 200 tiles that all had hand-carved dates and facts on them, and my teacher was like, “This isn’t really like what we were going for in terms of you taking a class within the 3D discipline.” Even in my painting classes, I’d get told my work was so graphic.

I was also not your typical art kid. There are artists who are always artists, and they have a lot to say about a lot of things. I just wanted to draw all day, and it didn’t matter what I was drawing. My passion was not necessarily about the subject or the feeling—it was about the doing. I really liked the idea that I could be given a project or a problem to solve, and that I could make art in response to that. I love constraints. If you give me an open brief and tell me I can do anything, I just freeze.

I also had a drive to learn new skills on my own. You learn X so that you can make Y. That’s always how I’ve worked. Part of that is, I went to kind of a scrappy school. I didn’t grow up surrounded by a lot of art, and it was expensive to hire other people. I had to find my own way through a lot of things. I’ve always tried to learn as much as I can on my own, to do the work as best I can on my own.

All of that led me to lettering. I realized I was best suited to illustration as an art form, and that I liked projects that were in response to problem solving.

You’re one of the most well-known working lettering artists today. How did that come about?

The reason why I ended up being such a big deal within lettering is because there were very few people doing it at the time that I started. It had kind of fallen out of favor after the 80s and 90s because of the massive explosion of display type that you could use on computers. Then people realized there were way too many options to sift through on their own and that they needed to hire a professional. There were a few of us who discovered this medium in 2007-2008 who were incorporating a lot of lettering into our work as illustrators or designers, which helped it emerge as a discipline on its own within this new context.

When did you start getting exposed to the digital design world?

When I graduated in 2006, it was a turning point for web design. It was one of the last years of Flash being the thing. It was also the early years of Blogger. I wanted my blog to look like my website, so I started using the WYSIWYG editor, which led me to CSS manipulation. Then I moved my portfolio website and completely rebuilt it in WordPress. I ended up building a whole bunch of WordPress websites one year, and they got messed up by viruses because they were all on one Rackspace and accidentally got cross-pollinated. And so then I had to rebuild them as static HTML sites, which got me into PHP and jQuery. I had a button on my website for a while where you could turn my whole thing into “teen girl mode” or “field notes mode,” which was a jQuery style switch thing where it swapped out the regular CSS file to one of four other insane CSS files.

It sounds like you were really interested in the web as a medium. What drove that?

I have just always really loved playing around with the web as a medium because I’m kind of an instant gratification gal. I was lucky I started getting excited about bespoke little web stuff right when other people were really excited about doing bespoke little web stuff too.

I was driven by this idea that people are going discover and see my work through the context of my website, so I wanted my website to always be the truest reflection of who I am, what I’m interested in, and showcase my work in the best way possible. Plus, as an independent creative, it’s not like I have like an available web developer in my back pocket that I can pay $20,000 every year to redo my website. So I felt I had to learn that skill myself.

Did you ever think about going in-house with a company?

I’ve talked about this a bit on the internet, but I’m a recent ADHD diagnosee. Looking back, Ive realized that I’ve basically created my career to exist in symbiosis with the way that my brain works and focuses. To join a company, I think I’d have to have a very, very trusting boss who would basically give me free reign to pursue the all the things I want to do.

How did the idea for starting your own company emerge?

It had been a while since I had done a fun web project, and I was starting to feel excited about possibilities again. I wanted to make resources for designers again, in a way that would help shape their businesses.

I randomly reached out to my old studiomate Chris Shiflett because he loves doing little bespoke projects for niche audiences, and we had a really exciting two-hour conversation. We put a pin in it at the end, because we realized we would need a whole team to help make our ideas a reality. Then a week later, the two developers that he had just worked with on a project both quit their jobs the same day, reached out to him, and were like, “hey, do you want to build something together?” And so he called me up and said, “hey, you know that thing we were talking about that we said we couldn’t do right now because we need a real team? I think we might have a team.” It felt like such kismet.

It quickly went from a side project to “oh my god, I think we’re starting a company.” It all felt right though. You know how it goes when you start something and you feel excited about it, but then it’s like you hit this vein of gold, when you were looking for something totally different? Then once you hit that, you realize there’s this whole ocean of good stuff underneath it? All of a sudden, it’s like you’re drinking the most intense Kool-Aid you’ve ever had in your whole life about the new thing that you’re excited about.

How do you know when you’ve found that “vein of gold” idea?

I’ve had enough things like that happen in my life where you can just feel how things that were misaligned have suddenly come into alignment. That’s the moment—run with it!

With Studioworks, it’s felt like that the whole time. We’ve been working on building the first part of the product, which is an invoicing and payments platform, but there’s so much more. We want to build a complete business management product for small studios. We’re trying to solve all of the problems that come up as we grow.

What sets Studioworks apart from the competitors?

One of the things that’s really unique about what we’re doing is that we’re not trying to attract our customers’ clients as our own customers. We basically white label our whole website to look like our customer’s, so when their clients interface with paperwork via Studioworks, it just looks like they hired this crazy custom backend to manage everything.

That’s what gets me really excited—you’re paying not very much each month to look like you paid someone tens of thousands of dollars to make this custom backend for you.

As a company of co-founders, how do you make decisions without a CEO?

We’ve been really collaborative about the decision-making. We each have our columns where we have the most power. I have all the veto power on design, for example. If I ever say, no, this is more important, it doesn’t matter what anyone says, my decision wins out. Chris has more veto power in certain product decisions, and Sean Coates has veto power in systems decisions. We all weigh in on all the things, but ultimately, whoever is in charge of their vertical has the final decision on that issue.

How are you funding Studioworks?

It’s self-funded. Chris and I have been splitting the bills—under $15K each so far, mostly money for lawyers.

It’s definitely been a challenge because Chris, Sean, and I have families to support. Chris is basically a single-income household with three kids (his wife is a school teacher). I’ve had more flexibility because of passive income channels and having a high-earning partner, but because so much of my time has been dedicated to Studioworks this year I’m not doing as much client work, which still makes up the majority of my income.

How are you thinking about pricing and revenue?

It’s a revenue-in-the-door-from-the-jump situation. We had a pre-launch signup period in which Founding Members can sign up, connect their Stripe accounts, and be ready to go at launch but are not charged until that time. There were just under 1,000 Founding Members when we launched the private beta, and we’ve only had about 60 cancellations. These folks are paying $29/month for life—at public launch, the price jumps to $39/month for all new signups.

We’re still working out how we entice people to sign up with that higher price point. We don’t want to do a free trial and get a bunch of false information about who’s interested and who’s not. We have a few incentives we’re exploring—one is a referral program in which members can “give” a free month to new folks and once they convert to paying customers they get a free month in return. It’s similar to Dropbox’s model in which you would get free space for referring folks to the platform.

How are you thinking about company growth? What happens if Studioworks gets big?

Because we don’t have to grow like crazy as a company, we don’t have to build for every person on earth. We can just make the thing that matters the most to the people that would benefit the most from it, and not chase the money in every direction.

Building on that, our model for customer acquisition is going to be quite organic. We don’t have this plan to do a big splashy marketing thing because we don’t want there to ever be a sudden flood of customers—we want to be able to scale more slowly and organically. Our immediate goal is 3,000 customers. If we can get to 3,000, we are rocking and rolling. Then everybody makes a decent salary.

We’ll hire as needed to handle the influx of people, likely in customer service to field incoming questions and issues. What I what I don’t think I ever want to be is a hundred-person company. I’ve always had a real pull towards keeping overhead low and just being able to be nimble. When you’re responsible for keeping that many people afloat, it’s much harder to do that. I could definitely see a future in which we have 15-20 employees, though.

What does success look like 5 years from now?

Even if we don’t plan to grow beyond building for graphic designers, I would love for this to be something that all people in artistic disciplines use. It just makes your paperwork look awesome—super pro.

As a designer founder, how are you thinking about the role of AI in your work?

I don’t think it’s ever been a smart move to decide to not learn about something if you’re afraid of it, or think it is going to have a significant impact on your field.

Whether or not you’re into AI, you have to understand it very significantly in order to decide to opt out of it. You have to know what you’re opting out of and to be able to defend those reasons who want to pay you—or require you—to use it. Personally, I need to test the fences on this and understand everything that it can do. Where it makes sense in my process, and where it doesn’t make sense in my process.

I also had another thought about this recently. I was in the process of releasing the new version of my book, In Progress, which is a compendium of my work. As I was looking through the first version, I thought: what do I want the book of my work to look like in 20 years? Sure, having some 3D work and AI experiments makes sense, but if that’s all of the work, I feel like it would be really hard for me to feel my own hand in the work anymore.

I’m using that as a north light in how I use AI as a tool. I make sure that even if I’m using AI to help prototype or test textures, ultimately I feel like I have the most control over the final output of the work. It’s all about control, feeling like the final version of the work has been given a very fine-tuned polish by me. As long as I can do that, AI may find its way into different crevices of my creative process.

What are some of the ways you’re using AI today?

I often use AI for verbal ideation, when it comes to writing and coming up with concepts. Trying to spitball different words for “common terminologies within volleyball” for example. Really specific stuff like that.

I’ve also been vibe coding a bit on the Studioworks marketing page. Basically, “help me write a jQuery thing that when you touch this button, it does this thing over here.” It’s sort of like when you learn a new language and you can’t speak it, but you can understand it being spoken—I know the general semantics of the code enough to be able to read and understand it, but I couldn’t write it from scratch.

I also think AI will be helpful for prototyping in my work. I can give it a prompt, which can give me a prototype to share with a client to communicate the vibe I’m going after for a photoshoot, for example. But I don’t think AI is going to produce the final output, or the final work—it’s more about prototyping.

How do you think these emerging AI tools are going to change the design industry?

The story behind the work and the story behind the person making the work is going to matter even more than it ever has. Even more than the influencer era.

That’s fine by me because I love being a person out in the world. I do get worried about folks that want their work to be separate. Not everybody wants to have their face on the internet all the time, sharing what they’ve created. But I think AI is going to make that a requirement. The things that are going to have value are the things that will have a strong story behind them.

Do you have any advice for other designers looking to become founders?

You don’t need to go looking for problems to solve. Usually there’s a problem within your own life you’re dying to solve—and no one has solved it.

The people that have had the most success are the people who just make the thing they wish that they had. The thing is, you are not that unique. So if you make things that are just for you, they’re actually for quite a few people. There are probably 2,500 people on Earth that are carbon copies of me, and I just have to make things for those people. And if they like what I’ve made, then people that are 80% like me might like it, and people that are 70% like me might like it—and suddenly you have a large audience you’re making things for.

Just find problems in your own life to solve. Worst case scenario, you can feel good knowing you solved a problem you had.

Books that helped shape Jessica’s journey

• The Creative Act by Rick Rubin

• Arbitrary Stupid Goal by Tamara Shopsin

Where to find Jessica

• Website: http://jessicahische.is

• Threads: https://www.threads.net/@jessicahische

• Instagram: https://www.instagram.com/jessicahische

• LinkedIn: https://www.linkedin.com/in/jessicahische

More recent interviews:

Al Hertz didn’t set out to build enterprise software. He started by designing posters for his band. But looking back, there’s been a consistent thread: building tools that help disparate systems work together—first for musicians, then developers at Plaid, and now hospitality teams at Folio.

Today, Al is co-founder and head of design at Folio, a supplier management platform that’s raised a Series A to help hotels operate with less friction and more soul. Unlike most B2B software, Folio feels delightfully human, complete with satisfying sounds when you reorder inventory and drag-and-drop interfaces that just make sense.

In our conversation, Al shares how six years at Plaid taught him to make incompatible systems work together, why hospitality and design share the same DNA, why the best co-founder relationships develop over years of working together, and how small teams can use AI tools like Cursor to punch above their weight.

Designer Founders

Inspiring more designers to take the leap of entrepreneurship.

By Designer Fund

🗓️ Heads up: We’re hosting a virtual session on Thursday, August 28 on how startups can find, attract, and win over great designers. We’ll share what’s changed with the talent market in 2025, with tips and examples for founders and hiring managers alike. RSVP here.

Are you a designer building something new, or know someone who is?
We’re always looking for more designer founders to feature, invest in, or partner with.

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Key takeaways from the conversation

1. Map your career backwards to find your throughline forward. The path to becoming a designer founder is rarely linear. Look back at your past career decisions, like Al did, to gain a better understanding of what drives you—then build your next venture around that core thread.

2. Learn by embedding yourself in a startup early on. You don’t have to go all-in on starting your own company right away. Finding a job at an early-stage company and experiencing hypergrowth firsthand provides invaluable insights you can apply when you launch your own venture.

3. The best co-founder might be someone you already know. Like Al and his co-founder Kate, growing a relationship over years gives you insight into how someone thinks under pressure. Look for overlapping interests and complementary strengths in people you genuinely enjoy working with.

4. B2B software can and should be delightful. Just because your customers are professionals doesn’t mean your product should be boring. Small details, like drag-and-drop reordering, subtle animations, or context-aware guidance, make enterprise software feel more human and memorable.

5. Use AI as a force multiplier. Startups can adopt AI tools faster than large companies. Tools like Cursor let small teams punch above their weight and prototype/ship quickly.

How did you become a designer?

I wanted to be a musician first. My small high school in Pennsylvania had computers with Adobe Illustrator, and I got hooked when I realized I could make my musical pursuits seem way more legit if I made posters, album artwork, and websites for them.

It became obvious to people in my circles that I was good at it, so I started getting asked to do projects for others. I’d say yes to random things, like building a website even though I had no idea how to write PHP. That’s how I learned.

The breakthrough moment was around 2012 when I started working with musicians like Lee Martin on projects that used new APIs in creative ways. We created this experience for a Swedish band called Little Dragon where you’d go to a website that said, “Little Dragon has something very important to tell you but they forgot your phone number.” After you entered it, it would trigger a video of the band picking up the phone, timed perfectly to when your actual phone would ring so you could hear their new song. We were recreating the intimacy of playing songs to friends over the phone.

That’s when I became hooked on capital-D design—building software that makes people feel genuinely connected to something.

Looking back at your design journey, from Gumroad to Plaid, what’s the throughline?

Looking back, there’s been a consistent thread: building technology that empowers creative acts. Before Gumroad, it was about celebrating musicians. At Gumroad, the definition widened to all kinds of creators. With Plaid, it took a left turn to focus on developers building financial software. And now with Folio, it’s come back around to what I call “the mother art”: I love hotels and want to serve them.

One great thing I learned at Plaid is: how do you build software that makes other things in software more interoperable, especially when those things might not want to be? The financial system, especially in the United States, is not something that’s inherently open. That’s something I really wa

nted to play with, technologically speaking.

How did you decide on hospitality for Folio?

I needed to do at least two out of three things, with the third coming into sharper focus as we build:

First, I wanted something that played to my unique strengths. Specifically, making incompatible systems work together seamlessly.

Second, I realized I can work on something for years if I love who I’m working with and who I’m working for. The people working in hospitality clearly deserve great software. The nature of hospitality is service, but the people providing it aren’t getting the service they deserve from their tools.

Third—and this is the most important—hospitality is really the same as great design. I’m paraphrasing Danny Meyer from Setting the Table, but service is when something is happening to you—hospitality is when something feels like it’s happening for you. Great design is when something is done so well that it feels like it was made exactly for you, even though it’s designed for millions.

How did you and Kate Adamson decide to work together as co-founders?

It was very quickly clear that Kate and I decided we wanted to work together. She started at Plaid as one of the first go-to-market hires and at that time we worked a lot on special pitches. We pitched to get Apple to use Plaid for the ACH verification authentication flow with Apple Card. Plaid also had a culture around quarterly hackathons, and Kate was always one of those people that would have her own team, but she would also create like five other teams at the same time. She had so many ideas that were compelling, and it jumped out at me that she had a really powerful way of being a creative leader.

After we both had left Plaid, we decided during one of our regular breakfast meetings to build something together.

We definitely went through a maze to land on the right idea. We started with some core principles around what mattered to us. The main one was about serving local economies and small businesses. The first decision we made was not, what are we working on? It was, who are we working on it with? And that meant, what customer are we serving?

💡 What this means for you: Don’t leave finding a co-founder to chance. Make a running list of colleagues you admire and revisit it regularly. Sometimes the best partnership is hiding in plain sight among the people you already trust and enjoy working with.

How do you balance being a designer with being a co-founder?

Being a designer founder is like being a founding designer, but with even less time for design. Otherwise, it’s very similar. We’re all like: how do I find the time to do the one thing that I’m really, really good at? It’s hard to do that unless you’re incredibly intentional about it.

I have to focus on time management quite a bit and carve out time to just go design stuff—whether that’s doing research or generating ideas or polishing pixels just before launching a new feature—because I very much love jumping into code, now more than ever.

I have to balance that with my responsibilities as a founder. My role is very much focused on leading our product engineering design motions. Right now there are five of us writing code. Then we have operations and go-to-market with Kate, Gen, Greg, and Omar. We’re at an inflection point where we’re going to have to get a little bit more structured, but for the most part we’re just focused on: what’s going on this week, what are we building?

The main principle that I’m leaning on right now is that the best way to make product decisions is to visualize ideas and prototype. I’m a big Cursor stan.

💡 What this means for you: Set aside intentional blocks of time for deep work. Treat these sessions as non-negotiable meetings with yourself. The creative breakthroughs that set your product apart are most likely to happen when you regularly make space for focused, uninterrupted design.

How do you bring soul into B2B software?

My favorite thing about enterprise software is the bar is pretty low, and that’s a great starting point. Not to make it marginally better, but to start from first principles: we want to make this super easy to use, like how everyone knows how to use an iPad without instructions.

Here’s a concrete example: You can create shopping lists on Folio, which hotels use for complex menus and inventory. We noticed these lists need to be organized by shelf order—“shelf to sheet”—so staff can efficiently gather items. We built drag-and-drop reordering, but then asked: what else might make this delightful? We added a satisfying sound every time you move items around. Small details like that make the experience feel more human.

Our customers benefit from consumer-grade design principles because hospitality requires business-to-business tools that still feel personal and intuitive.

What role is AI (artificial intelligence, that is) playing at Folio?

AI has helped us imbue delight into our product with the scrappy resources we have as a startup. A little over a year ago, my designer friend Stefan and I were both copy-pasting from ChatGPT into VS Code—we were laughing about doing the same ridiculous workflow.

Now with Cursor, the ergonomics keep getting better. As a startup, we can adopt these tools faster than large companies, and our nimbleness becomes a competitive advantage. AI lets our small team focus on prototyping and shipping rather than getting bogged down in repetitive tasks.

💡 What this means for you: Don’t get stuck trying to craft a perfect AI roadmap. Instead, identify the most repetitive or tedious task in your workflow and focus on automating that. Whether it’s cleaning up design specs or generating code snippets, small wins add up and free your team’s creative energy for the work that actually matters.

Any advice for your past self starting out?

I would tell myself (because this is something I was curious about) that yes, building a startup is exactly as hard as people say—and 10x more fun. It requires dedication, determination, consistency, thoughtfulness, and integrity. But it is so rewarding. The connection to people, to your customers, to creativity, to whatever motivates you…those are the big things.

The advice I’d give someone considering this: just do it and go without fear. Be aware it’s as hard as they say, but it’s also a lot more fun.

Books that helped shape Al’s journey

• Reboot: Leadership and the Art of Growing Up by Jerry Colonna

• Setting the Table by Danny Meyer

Where to find Al

• LinkedIn: https://www.linkedin.com/in/heyal

• Website: https://hey.al

• Folio: https://folio.co

We’d love to hear what you thought about this feature. Let us know, and if there’s someone you’d like to see featured next, recommend them here.

You may have heard the story of the company’s early years: rebuilding the product four times, nearly running out of money, and taking five years to see signs of traction. Notion has grown to more than 100 million users, but the questions remain the same. How do you keep a product coherent as it grows? How do you make decisions that hold up over time? What does it mean to build with taste?

Below, we’re recapping Ivan’s fireside chat with Andrew Lee from our Designer Founder Night in San Francisco earlier this year. He shares his Ivanisms: deeply-held ideas that shape how he builds, from his reverence for history, to how he thinks about tradeoffs, to building products with lasting coherence and taste.

Note: Notion is hiring for designers in San Francisco and New York. Great opportunity to hone your skills inside a company that treats design as a first-class discipline.

Designer Founders

Inspiring more designers to take the leap of entrepreneurship.

By Designer Fund

Are you or someone you know an aspiring Designer Founder? We're always looking for more Designer Founders to feature, fund, or partner with.

Recommend a designer founder

1. Keep it dumb

Ivan is deeply skeptical of clever design. He constantly pushes the Notion team to strip things down and focus on what matters most: the golden path, or the main user flow that 80% of people will take.

“Designers spend too much time on edge cases,” he says. “Most of the time, what matters is the dumbest path. Make that great.”

That principle shows up everywhere, from interface decisions to internal debates.

“If someone’s drunk, can they understand it? You care about your design. Your pixels. Your product. But nobody else does. They’re tired. They’re distracted. They’re going to scroll past it.”

The team doesn’t optimize for polish up front. They optimize for exploration. Designers at Notion will copy-paste a UI 20 different ways just to see what falls out. “Eventually, the right answer becomes obvious.”

His favorite metaphor: the Chinese buffet. You don’t get attached to any one dish. You put a lot out there, let people try, and trust that the best thing will stand out.

2. Build systems, not a suite of features

If you’ve spent time in Notion you’ve probably noticed the LEGO metaphor everywhere. Content within the platform is made up of “blocks.” Employees mark anniversaries by adding a new block to their stack. Their first conference was called Block by Block.

It’s no surprise, because Ivan sees Notion like a LEGO set. Instead of a stack of features, it acts as a system. The building blocks inside the platform include elements like text primitives, database tables, images, callouts, and embedded files. They’re intentionally designed to be modular and moveable so a database can live inside a page, which can live inside a list, and so on.

“When you add a new LEGO brick, it might pollute the whole thing,” he says. “So you have to think system-first.”

The team is building across a lot of product areas—docs, tasks, databases, calendar, and email. Each one has to make sense on its own, but also work together as part of a larger system. That does, of course, make every decision a little riskier as a small change in one part can easily throw off the rest.

This is why Ivan spends so much time balancing tradeoffs. Not just inside the product, but across the org. APIs, incentives, system constraints. “It’s especially tricky because we’re not trying to build just one product.”

3. Company building = constantly making tradeoffs

For Ivan, being a founder is a lot like being a good designer. Both require making the best possible choices within constraints.

“Starting a business, solving a design problem, or a technical problem…they’re all the same. You’re making tradeoffs.”

Early on, Ivan and his co-founder, Simon Last, repeatedly scrapped entire product versions when complexity overwhelmed users. "Don't be afraid to start over," Ivan has said, reflecting on how progress came only after they radically simplified. Ivan found guidance in Notes on the Synthesis of Form, a 1964 book by architect Christopher Alexander, who argues that good design is about systematically mapping out problems, understanding the materials you have available, and making the best compromise within existing constraints.

Ivan sees that same logic everywhere: A designer choosing between text and icon in a 200-pixel-wide component. A founder deciding between a bottoms-up or top-down go-to-market. A PM evaluating Python libraries. “The shapes are very similar,” he says. “You’re working with constraints. You’re trying to let something live.”

This mindset has shaped Notion’s culture. From its early days, the team stayed intentionally small—even reaching unicorn status while the team was still only a dozen people—so decisions were quick and everyone stayed close to the product’s core vision.

For founders and designers, it’s worth regularly asking: What are my real constraints? What am I willing to sacrifice to make this simpler? Is this feature or decision truly serving users, or just adding noise?

4. History is your hidden advantage

Ivan points out how little the tech industry studies its past.

“If you study physics, you know who Newton is. But in tech? Most people don’t know who Engelbart is.”

Douglas Engelbart invented the computer mouse, but his deeper contribution was a radical vision: computers should augment human intellect. He saw software as a flexible medium that helped people think better, not just work faster. Ivan has called Engelbart Notion's “patron saint”, revealing how deeply this philosophy shapes both product and culture.

This vision permeates Notion's design. The block structure reflects Engelbart's belief that users should construct their own tools, not fill out templates. The product's modularity stems from his idea that software should adapt to human thinking, rather than forcing thinking to adapt to software.

Ivan draws from other historical wells too: Alan Kay's dynamic media, early-20th-century architecture, mid-century furniture design. Walk through Notion's office and you'll see design books beside engineering texts, Eames chairs beside whiteboards—reminders that history holds forgotten solutions.

His counter-move: borrow widely and look sideways. Study architecture from 1900 to 1920. Examine mid-century furniture principles. Learn from computing pioneers who saw software as a medium, not a tool.

5. Taste and agency are what remain

The words “taste” and “agency” seem to come up in half the conversations about AI and creativity these days. They risk sounding like empty placeholders, but Ivan offers a clearer breakdown in which he sees product and company building as shaped by three forces: capability, agency, and taste.

Capability is your raw skill. AI is already supporting a lot of this through designing screens, writing copy, generating code.

Agency is your ability to push through. “To start a company, you better be able to hustle. Just push through stuff.”

Taste is what determines which direction you push. “It’s whatever draws your inspiration. But don’t just look in front of you like tech people do. Look sideways. Look into the past.”

It turns out, good taste isn't as subjective as we assume. The best tastemakers are pattern recognition machines who've absorbed vast cultural knowledge to predict what discerning audiences will value—something AI systems could eventually replicate.

But as Ivan and Julie Zhuo discussed in their conversation, the highest form of taste goes beyond prediction to movement making. The most significant tastemakers take social risks, championing unfamiliar work and convincing others of entirely new ways of seeing greatness.

Taste is refined the same way a palate is. You start with red vs. white wine. Over time, you start distinguishing Chardonnay from Albariño. Early Bauhaus from late Art Nouveau. Features that feel “fine” from those that resonate emotionally.

But how do you actually develop taste in software?

Start by treating software not just as a user, but as a critic. Ask: What about this feels good? What breaks the flow? How does it handle complexity or edge cases? Follow the work of designers and product teams you admire.

Most importantly, build things. Side projects offer irreplaceable firsthand experience with tradeoffs, friction points, and quality standards. Even small projects teach you to recognize “good.”

6. Design should show up everywhere

Ivan toured over 20 buildings before landing on Notion’s new office, a 1907 post-earthquake structure in downtown SF. “We liked this one because it had some sense of history. Most offices are just glass boxes.”

When I visited, I could see why he chose it. The interior feels more like a craftsman home with wood-paneled walls, warm indirect lighting, and carefully chosen textures. No steel sheet to be seen.

And then there’s the green rule.

“We don’t allow green furniture,” Ivan says. Not because he hates the color, but because it doesn’t mix well with other tones. “You can’t control where people move things around. But if you cut green from the palette entirely, everything still looks okay.” This means no green plants, either.

Strict, maybe, but it reflects the same logic behind Notion’s product: reduce interference, preserve harmony, and let the system scale without falling apart.

To close, here’s Ivan’s encouragement to designers:

Where to find Ivan:

• LinkedIn: https://www.linkedin.com/in/ivanhzhao

• X: https://twitter.com/ivanhzhao

• Notion: https://ivanhzhao.notion.site

One of the things I appreciated most about talking with Cecilia Uhr was how much her story reflects the reality of being a designer founder today. She started out doing packaging design in art school, exploring her curiosity about how people experienced a product, not just how it looked. That instinct has carried through everything she’s done since: agency work, AR/VR at Oculus, and now co-founding Bezi. Bezi’s current product—a Unity dev assistant powered by real-time AI context—wasn’t where they started.

In my recent conversation with Cecilia, she walked me through their pivot and the tough decisions that come with trying to build something useful in an emerging space. We also talked about the shift from agency to product work, learning to prioritize as a founder, and why customization is the next big frontier for AI products. There’s a lot in here for anyone figuring out how to build under constraints, trust their taste, and adapt when the work demands it.

What we cover in our conversation:

• The strengths of an agency background

• Cecilia’s lessons from transitioning into tech

• Knowing when it’s the right time to launch your own company

• Founder skills designers already have—and the skills they need to learn

• How to weather hard startup decisions

• Cecilia’s biggest learnings in building Bezi

• Why brand and storytelling are more important than ever for AI companies

Designer Founders

Inspiring more designers to take the leap of entrepreneurship.

By Designer Fund

How did you first get into product design?

I went to an arts high school where I majored in visual arts. As much as I loved drawing and painting, I realized it's really hard to make a living off being an artist, so I pivoted to design.

At that time, the idea of “product design” was just beginning to emerge. I didn't really know what it meant, but I knew that I liked designing experiences. In one of my college packaging design classes, I realized I was less concerned about the aesthetics of the package and more interested in the experience of someone opening the package. What is it like seeing the package on the shelves, picking it up, and interacting with it?

When you first started working, you chose the agency route rather than immediately getting into tech—what appealed to you about that?

I like doing a lot of different things. Going the agency route, I wanted to get a breadth of experience rather than just working on one feature for several months. I wanted to be able to work on the brand, the website, and the product all in one place.

Looking back, that was the right choice—at least for me. There's a certain level of grit that comes with working at an agency. There’s a healthy competition with the other designers you work with, and you’re working a ton of hours. You get to try a bunch of different things, and you build a good portfolio because you're pumping out so many concepts.

What made you switch to tech?

I wanted to be closer to the work. At agencies, you're tasked with coming up with a concept and after you hand it off to the client, you don't see it or touch it again. Sometimes the idea gets mutated along the way—sometimes for a good reason—which can be disappointing.

I wanted to be part of the whole process: collaborating with engineers, getting user feedback, and iterating on the product. I wanted to see things through to the end, not just hand them off.

So I started looking into ways to get into the tech industry. I was lucky—I didn't have any AR/VR experience at the time, but I ended up at Oculus. I started off as a visual designer, and then transitioned over to a product design role.

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What were some of the things you learned going from the agency world to a software startup?

Agencies are usually optimizing for awards and recognition because that's how they get clients. That's the mode that I was operating in when I joined Oculus. I was so excited by the possibilities of the product. And then of course one of the big mistakes I made was not taking technical constraints into account. I came back with all these ambitious concepts for new user onboarding, showed them to the engineers, and they were like, “yeah, that’s not going to happen.” It just wasn’t technically feasible.

That was a hard lesson to learn. I remember at the time feeling very small, asking myself: why didn't I think of this? But when you're working at an agency, you don't think about that at all. You're just like, how do I make the most eye-popping, awesome experience possible? And that's just not how it translates to the software world.

When did the idea for Bezi start to take shape?

Bezi stemmed from personal frustrations between me and my later co-founders, Julian Park and Denys Bastov, and needing to find a way to collaborate with them while working at Oculus. As a designer at the time, there were a few options for designing AR/VR experiences. You could work in Figma, a tool you're familiar with, and try to mock up 3D-esque designs—but these wouldn’t truly be able to replicate a sense of space, distance, or speed of movement. You could try to mock it up in Blender, but you’d end up having the same issues—seeing something 3D in a 2D frame. Or you could learn a hardcore game engine like Unity to actually be able to design in 3D. The problem with that is that it’s not something already within the designer’s skillset—or even job description—so many designers are allergic to learning it.

So, we built a web-based, collaborative editor that made it easy to design and prototype experiences in 3D. We initially did it on the side on nights and weekends, excited by the idea and having fun exploring where it could go.

When did you know it was time to start your own company?

It was a building feeling rather than an inflection point. It's not like we were trying to get users or anything at the time. We were just focused on trying to solve our own problems. We eventually reached a point where we realized we were more excited about this than what we were working on in our day jobs. We were also frustrated with the layers of approvals and how slow things were moving. We decided to go all-in on building this new company.

How did you decide on the roles each of you took when launching Bezi?

It came pretty naturally to us and I think that’s because we had worked together before. We understood each other's strengths, what each of us was interested in and what we were not interested in. For me, coming from a design background, it made sense to take the lead on design and product.

You ended up shifting Bezi’s focus away from being a collaborative 3D design tool to being AI-powered dev tool. Walk me through that process.

For the record, I still believe that the first product we were building will become useful at scale at some point. The hard thing about that is that AR/VR is so dependent on hardware and technology. So if the hardware isn't there yet, if these AR glasses can’t function like we need them to, then mass adoption doesn't happen and we can’t be successful. It’s entirely out of our control.

We asked ourselves: does it make sense to keep working on this, or should we tackle this from a different direction?

Honestly, it was a really hard decision—probably the hardest decision that we as a company have had to make. We decided to move away from the 3D editor that we had been building, while still focusing on our mission of making it easier for people to design experiences and games. That's the new product that we're building right now, and we're leveraging some new technologies I’m really excited about.

What helped you make that transition?

The startup journey is all about sequencing and prioritizations, and sometimes you just need to make hard decisions. We had to do a lot of introspection, and decided to have a small 'tiger team' that prototypes the new product in the beginning. The rest of the team was business as usual during this phase, and we shifted the whole team around to work on this new product as we saw promise.

As a team, we had to learn a lot. None of us had experience with AI or LLMs. We had to look at a lot of existing products out in the market, understand how things work, and just try. It was a lot of prototyping, and a lot of trial and error. My hope is that what we had built before can be integrated into this new product, which could make it really powerful.

What were some of your existing skills that have translated well to being a founder?

I worked on brand and marketing materials when I was at agencies, and that helped a lot as we built Bezi. I made the logo, designed and built the website, all of that stuff. If I didn't have that experience, I would be struggling a lot more now. I believe that brand is becoming increasingly important in this new world of AI products. How you show up, how you communicate what you believe in, and the storytelling behind these values is how you differentiate your company in a sea of sameness.

At Meta, I learned a lot about how to work with cross-functional partners like engineers and product people—understanding what their roles are, why it's important to the company, and how that all ladders up to business goals. I was able to use that knowledge to understand what we’re missing, so I know what to hire for.

What skills have you learned as a founder?

The weight of decision making, and prioritization. Those go hand in hand because you need to make decisions on what you're going to prioritize and that could sometimes determine the trajectory of your company.

One of the things that designers actually struggle with—and I'm speaking from firsthand experience—is that prioritization is really hard. As designers, we're trained to craft and design the perfect experience. We call it the happy path for a reason! You want to make sure that people have a really good experience and they're able to achieve their goals in your product.

The truth is that startups are always operating under conditions of extreme constraints. So it's very unrealistic for designers to get everything they want in a feature or a product. In those cases, you need to be able to differentiate between deal-breakers and nice-to-haves. It's challenging to let go of some of these things that you know will make a delightful experience, but that aren’t integral to the product or to the feature, but that’s a muscle designers need to build to be able to ship fast and iterate.

Do you have guiding principles that help you make the right decisions around what to prioritize at Bezi?

When it comes to high-priority features, we always need to figure out: what is the main goal that the user is trying to achieve, and will not shipping this specific thing deter the user from getting to that point? Or are there ways that they can get around that will still help them achieve their goals? So if it does allow them to do that, maybe it's not a P0, maybe it's a P1 or a P2.

An example of this is our onboarding experience. This might be controversial because the onboarding experience is your product’s first impression, but the product we're building now relies less on an onboarding experience because it's already so intuitive. It's a chat interface that most people are familiar with. Who doesn’t know how to message someone, right? Because Bezi’s core experience is so intuitive, we decided to cut the onboarding experience.

Once we shipped this first version of our product, we got feedback that some people needed instructions on how to connect their Unity project. So we built it in a day and shipped it. This new small improvement cut about 90% of the negative feedback around onboarding.

That’s a good example of where you need to identify a quick improvement you can ship to help 90% of people get what they need to use your product. And then over time, when you have more resources, you can refine it.

Even though you might have a smaller audience than Oculus or Meta, it can feel like product decisions are even more important. Why is that?

At a tech company of that scale, even if you make the wrong decision, it's usually not existential. Google ships hundreds of products every year, and they scrap 90% of it. They have the resources to be able to do that. For a startup, if you make a wrong decision, it could be existential. That's something I grapple with every day.

You have to be sure that the decision you're making is the best decision at the time, and that you understand what the risks and the consequences might be. I can't remember who said this, but it resonated with me a lot: some decisions are one-way doors, and some are two-way doors.

You also need to learn how to decipher what is actually important. It’s a key skill for a founder to have because if you don't, everything is urgent. Everything is a crisis and your team will feel that.

What has been one of your biggest lessons in building Bezi?

When you’re building a 3D design tool, you’re essentially competing with products like Maya or Autodesk—products that have been around for decades. Unless you reach somewhat of a critical feature parity, your platform is useless to people because they can do it elsewhere much faster. Design tools are just generally incredibly difficult to build, and I have a lot of respect for anyone who's doing it.

One of the mistakes that I made early with Bezi was trying to get to that feature set without a highly prioritized strategy. I wish that we had started with a more solid work-back plan from where we want to be, but it's a lot harder in practice when you're getting feature requests left and right.

How do you think about the role of craft in a startup?

My designer Daniel Marqusee and I had a debate about this recently where we were talking about the word “craft.” I do think it's a very overloaded word that needs to be defined specifically or else it can be weaponized a little bit. Often, people will say, “We need a higher level of craft on this.” And then you’re like, “What do you mean by that?” And they can’t clearly define it. You need to be intentional about what kind of experience and feeling you want to evoke in your users or your customers—and that can look a lot of different ways.

What role does AI play in your brand and storytelling?

Nowadays everyone's kind of working with the same materials. Everyone has access to the latest models, and we can kind of bend and mold them how we want them. AI has leveled the playing field.

What we’re focused on now is how do we test the limits of the model, and how do we make sure people can achieve their goals going through it? Brand and storytelling play a bigger role than ever. In a world where everyone's building a chatbot, how do you stand out? You need to invest in how you tell your story.

We're going through a rebrand where we're trying to imagine what Bezi feels like with this new product that we're building. A lot of the actual craft is going to come through product capability and personality, through the chat interface. It's been really interesting because we're talking about how do we want Bezi to feel—and it's no longer just about aesthetics.

What are some of the biggest challenges of designing with AI?

I think customization is going to be the next frontier of AI products in general. Because you can have a very distinct personality for your product, not everyone's going to be happy with it. Remember when OpenAI shipped this new update to the personality where it was very proactive? People hated it.

I’m thinking a lot about how we allow people to customize their experience. To set not only the personality, but also the rules and instructions for how they like to be interacted with. Designing that is really interesting because it’s something that hasn’t really been possible before.

There’s going to be a tension between the brand personality and what we allow people to customize. You need to have a point of view that people can tie to your brand and your product—but you also need to give people enough leeway to be able to customize their experience and interactions with your AI.

How do we bridge that gap? I don't know what the right answer is right now. It's something that we're trying to figure out. I'm also seeing every company in this industry try to figure that out too. That's why a lot of companies are going this neutral route, because then it can be filled with whatever meaning the user wants it to have. But that also has its pitfalls. You can start to blend in.

What’s inspiring you these days?

I’m having fun trying all the cool products that people are putting out. Some of the most interesting ones currently are node-based creative tools (ComfyUI, Flora, and Weavy), and seeing how chat interfaces are evolving (ChatGPT, Claude, Gemini). That's what I love to do—trying to figure out why the team made certain decisions and what the product is capable of doing.

With the amount of new products and models coming out every week now, it's absolutely insane. But I think that’s what makes it a really exciting time to be a design founder. The playing field has leveled out. You can try a lot of different things to see what works. We’re at an inflection point, and I love that everyone is learning together.

Books that have guided Cecilia

1. Building a Story Brand by Donald Miller

2. Traction: How any Startup can Achieve Explosive Customer Growth by Gabriel Weinberg and Justin Mares

3. Originals: How Non-Conformists Move the World by Adam Grant

4. This is Service Design Doing by Marc Stickdorn

Where to find Cecilia

• LinkedIn: https://www.linkedin.com/in/ceciliauhr

• X: https://x.com/UhrCecilia

👋 Are you a designer founder building something new, or do you know someone who is? Refer yourself or someone else here.

Partnering with Notion was a no-brainer. With a designer founder at the helm (Ivan Zhao) and over 35 former founders on the team, Notion has become one of the most design-forward companies in tech, setting the bar for product quality, craft, and taste.

For the first of two fireside chats (the other with Ivan; recap coming soon) I sat with Brian Lovin. Brian’s journey from Facebook and GitHub to founding Campsite—which was eventually acquired by Notion late last year—is exactly the kind of story we need more of: not a perfectly polished success story, but an honest look at the messy, human side of building something from scratch.

I’m excited to share the recording of our full conversation with you all. You can also keep reading for a written recap + transcript.

Takeaways from the conversation

You have to get good at what you're bad at, sales and tough conversations included

There’s a tendency for designer founders to stick close to what they’re comfortable: designing the product. Brian approached the uncomfortable parts of the job—sales, marketing, firing—as skills he could build with practice.

“I kept reverting to ‘just build the best product.’ If you build it, they will come. That was really challenging for me.”

“I treated it like a video game. I'm bad at all these things, but every cold email is two experience points, every sales call is 20 experience points.”

He also had to grow out of his nice designer identity.

“In design, we're often very nice to each other. I still struggle with giving direct feedback without feeling like an asshole. But when I think about the people I respect most, whose feedback I seek—it's the people who tell me the truth without sugarcoating it.

“A mentor used this phrase with me: ‘What do you want to spend your heartbeats on?’ Our time is limited, but that's also true for people on your team. You don't want other people to waste their heartbeats either. So it's actually kinder to say, as early as possible, ‘We should do something else here.’”

Don’t confuse initial traction with long-term fit

Campsite had many early fans and even sold big contracts. But ultimately not enough end users used it. What excited the buyers (design leaders) didn’t translate to daily behavior.

“We’d sell big contracts…but individual contributors really didn’t like posting work-in-progress to what they saw as a big unknown audience.”

Eventually, Brian and his co-founder realized the product was drifting from what they truly wanted to build.

“At some point, my co-founder Ryan and I looked at each other and asked, ‘Is this what we want to do?’ The answer was increasingly no.”

Use side projects to build conviction before going all in

Brian worked on Campsite for six months on nights and weekends, then took a three-month unpaid leave from GitHub to see if the pull to start was real.

“Start a side project first and work on it for six months…By October, I felt I’d de-risked it enough—I had customers, users, and six months of conviction.”

In 2025, you're up against AI-level outcomes

Founders these days aren’t just pitching incrementally better workflows. Buyers are comparing you to AI solutions promising 2–5x productivity improvements.

“[Your prospect’s] next call is someone saying, ‘I have an AI solution that will replace a department.’ That’s what you’re up against. You're educating people about a new way of working.”

The journey is worth it, even if the end result isn’t what you hoped for

Even if you don’t end up building a unicorn, the personal growth and learning are meaningful on their own.

“Face your fears…the journey itself has incredible value, even if the outcome isn’t a billion-dollar company.”

Transcript

Here's our full conversation, edited for clarity:

Ben: Brian, you're one of the few people I know who actually experienced Facebook's internal Pixel Cloud tool firsthand. Can you tell us how that influenced the idea for Campsite?

Brian: Pixel Cloud was this internal Instagram-like tool where Facebook's design team posted work in progress—mocks, prototypes, everything. When you joined Facebook, it was like walking into the museum of Facebook. You could go all the way back through the archives and understand what people had tried, what they'd explored, who did what. Everyone had a profile, including people who'd left the company, so you quickly understood the DNA.

But it became more than an archive. It was this daily ritual—I'd check it on the bus ride home to see what people were working on. “Oh, that person's doing something cool, I should reach out.” It had this competitive energy too. You could see who viewed your post, and everyone wanted “the Zuck view.”

When I left Facebook, there was no more Pixel Cloud. You'd join other companies and ask, “Where are the designs?” “Oh, it's in a Slack channel somewhere, or maybe a Dropbox folder.” You couldn't find anything, couldn't understand how the product came to be. That frustration just built over time.

Ben: So that became the first version of Campsite—trying to recreate that internal design sharing experience?

Brian: Exactly. We wanted to build this feed for designers to share work, give feedback, have visibility across teams. We worked on that for a year and then had to pivot.

Ben: What worked well in that first version?

Brian: When we announced we were joining Notion, three or four customers reached out asking if they could buy the product. That told us we'd built something a small number of people really, really loved. Design leaders would tell us their teams wanted to do better work because they were using Campsite. That felt incredible.

We had a high bar for craft—we'd nudge pixels for hours. We built an awesome team of five people, and everyone had this insane bar for taste, detail, and listening to users. Having engineers who cared about craft meant I could focus on sales, marketing, and figuring out SOC 2 compliance.

Ben: But something clearly went wrong with that first version. What happened?

Brian: It was brutal. We'd sell big contracts to design directors and VPs. They'd nod through the whole pitch, saying, “of course I want my designers sharing more work, I want visibility, I hate these biweekly email updates with one screenshot.” But when it got implemented, individual contributors really didn't like posting work in progress to what they saw as a big unknown audience.

They'd think, “The CEO might see this, so I can only share highly polished stuff at the very end.” The more we tried to address the behavioral and psychological barriers, the more we ended up building private channels and silos. We were basically rebuilding Slack.

The moment I knew we had to pivot was when we closed a six-figure deal—about $23,000 per user. I was excited about the revenue, but the usage just wasn't there.

Ben: So you pivoted to building a team communication tool. How did that go?

Brian: We spent months building this comprehensive platform—docs, chat, video calls, posts, all rolled into a single feed. Working at Notion now, I see how much our philosophy aligned. We were frustrated with using five different tools to communicate one idea. You make a doc, share it in Slack, then hop on a call to discuss it. It felt insane.

But we essentially built a Notion-Zoom-Slack-Google Docs competitor all at once. Startups would say, “Yes, this will be our full-stack communication tool,” but as soon as we went upmarket, companies would say, “We only want posts” or “We only want docs.” The suite was too much to change at once.

Ben: That's a challenge I see with a lot of designer-founded companies—building at the intersection of teams where it's unclear who actually pays for it.

Brian: Exactly. None of them end up paying for it. At some point, my co-founder Ryan and I looked at each other and asked, “Is this what we want to do? Are we on track to build something we actually want to accomplish?” The answer was increasingly no.

Ben: As you reflect on the journey, what assumptions were off or what blind spots did you have?

Brian: I'm a product person. Building software is my happy place. But as a founder, you have to wear lots of hats: sales, marketing, hiring, firing, positioning, sending cold emails. All stuff you find uninteresting and are terrible at initially, but you're the only person who can do them.

I kept reverting to “just build the best product.” If you build it, they will come. That was really challenging for me.

Ben: You mentioned earlier that someone once told you “you're not a nice boy” when you had to fire them. Can you tell that story?

Brian: [Laughs] I used to run a podcast, and my co-host gave me this moniker “nice boy” because I was just a nice person. It stuck and became my Twitter bio. So I had this perception of being nice, and then you get in a room with somebody you have to fire, and they're like, “Oh, you're not a nice boy.” I was like, “No shit.”

Ben: That's interesting because this is the second time I've heard this advice. Robert from Monograph told me if he could go back, he'd tell himself “don't be so nice.” There's something about the designer archetype—we have to be collaborative, and you can't collaborate if people hate you. But that's not necessarily the founder's job.

Brian: A mentor used this phrase with me: “What do you want to spend your heartbeats on?” Our time is limited, but that's also true for people on your team. You don't want other people to waste their heartbeats either. So it's actually kinder to say, as early as possible, “We should do something else here.”

I still struggle with giving direct feedback without feeling like an asshole. But when I think about the people I respect most, whose feedback I seek—it's the people who tell me the truth without sugarcoating it. In design, we're often very nice to each other. Crits become “Oh, that's a great idea, but actually what if we...”

Ben: How did you go about learning sales and marketing when those weren't your strengths?

Brian: I treated it like a video game. I'm bad at all these things, but every cold email is two experience points, every sales call is 20 experience points. You just do the reps.

I also learned later that you can hire coaches for things you're bad at. Other founder friends told me they hire sales coaches who shadow them on calls as background participants, then debrief afterward. I could have done that earlier.

Ben: What advice would you give someone thinking about starting a company?

Brian: Start a side project first and work on it for six months. See if you still really like it. With Campsite, I did nights and weekends in spring 2022, then took a three-month unpaid leave from GitHub to see if I actually wanted to do this full-time. By October, I felt I'd de-risked it enough—I had customers, users, and six months of conviction.

I find myself in situations where I can't help but start the thing. You leave Facebook, you leave money on the table. You leave GitHub, you leave money on the table. But there's this deep core pull to solve the problem, even if it fails. If you're feeling that pull, I think it's okay to listen to it.

Ben: You had a great point about what founders are up against in 2025. Can you elaborate?

Brian: A mentor critiqued Campsite perfectly. He said when you're selling a team communication tool, you get on a sales call and start with “Let me tell you about my philosophy for team communication.” You're educating people about a new way of working, asking them to switch tools, maybe for an incremental productivity boost.

But you have to know that when you hang up, their next call is someone saying, “I have an AI solution that will replace a department” or “make people who previously couldn't do something now able to do it.” They're selling 2x, 3x, 4x, 5x productivity improvements.

That's what you're up against. So if you're going to do a big startup, if you want to raise money, go big. Dream big. Make a big thing. Your competition is doing the same, and it's not enough to introduce a philosophical change in how people work.

Where to find Brian:

• https://brianlovin.com

• https://www.linkedin.com/in/brianlovin

• https://x.com/brian_lovin

AI has fundamentally shifted the playing field for designers who want to build products. With the tools available today, you can ship faster and with smaller teams than ever before, no longer constrained by eng bottlenecks or lengthy approval processes. The question isn’t just whether this changes everything for designers who want to start companies, it’s whether you'll move fast enough to take advantage of this historic moment.

Phil Vander Broek and Filip Skrzesinski offer two vantage points on this shift. Phil’s first startup, Dopt, was acquired last year by Airtable, where he now leads AI design. Filip is in the thick of building Subframe, a new UI design tool. One has the perspective of having been through the full cycle, while the other is building in real time.

What connects them is the conviction that good products come from understanding what’s actually worth building, and the shared belief that AI has created a brief window of opportunity for designers that won't last forever.

What you’ll learn from Phil and Filip:

• Why early discovery should focus on pain-hunting, not validation

• How to get honest about customer signals and urgency

• Why picking a bigger, competitive market can be the smarter move

• What it really means to design a company, not just a product

• Why designers should take advantage of this AI window

1. Go pain-hunting to figure out what to build

Phil Vander Broek and his co-founders had everything going for them: eight years of shipping products together at Dropbox, Amplitude, and Productboard, plus the deep trust that comes from that shared history. Their first startup idea—a pandemic-inspired collaboration tool—fell apart in weeks.

“The space was crowded, the signals were weak, and conviction disappeared,” Phil recalls.

A former colleague gave him simple advice: restart discovery and ask people for their top three problems. No pitching, just pain-hunting. That single prompt led them to scrap everything and run a proper discovery process.

They ran 60+ interviews in three waves. The first 20 conversations with product and growth leaders surfaced a shared pain point: driving user adoption was painfully hard, and existing tools felt bolted on. The next 20 calls helped shape a potential solution through mockups and prototypes—one engineer was so interested he volunteered for weekly co-design sessions. A final batch of 20 calls confirmed their ideal customer was engineers, not PMs.

“That discovery process gave us the conviction in the opportunity and the story to close our seed round,” Phil says. "The false-start forced us back to first principles."

The result was Dopt: a product adoption platform used by companies like Superhuman and Productboard to build onboarding flows and in-product assistance.

The takeaway: Don’t interview to validate your idea. Do it to find an idea worth validating. Phil’s team could have saved months by being more ruthless about abandoning their first concept.

2. Don’t slow down after discovery

Phil's biggest lesson: Even with a solid discovery process, there were opportunities to move faster. Each phase of learning could have been more compressed, with decisions that stretched into months when they might have taken weeks.

Before product-market fit, you’re racing to answer three questions: Who are you building for? What pain do they desperately need solved? Can you deliver something distinctly better they’ll pay for?

At Dopt, those questions unfolded in three phases: first, learning that while engineers were the users, PMs were actually the buyers; evolving the product to actually solve adoption problems for PMs; and finally re-imagining it with AI to unlock in-app assistance. Looking back, Phil wishes they’d moved through each phase faster.

So what does moving fast actually look like? Phil points to two things:

1. Be ruthlessly honest about signals. “We should’ve been more honest about whether users were banging on our door or putting skin in the game.” That means talking to customers every week and looking for signs of urgency. Are they offering feedback unprompted? Committing to a pilot? Signing on as design partners? If not, it's time to reassess your assumptions.

2. Launch more often. “Get the word out until something resonates and sticks and users start coming.” Don’t wait for perfect positioning. Momentum comes from shipping and seeing what gets a real response.

The takeaway: Speed of learning beats perfection of process. The market will teach you faster than any amount of internal deliberation.

3. Pick a market that pulls you forward

Even with the right problem and strong execution, Phil now believes there might have been opportunities to scale faster had they chosen a different market from the outset. Looking at other companies in Dopt’s cohort, many were solving problems for go-to-market teams, customer support, or building pure developer tools—massive, proven markets where the pain is often urgent, budgeted, and well understood.

“They’re competitive, for sure,” Phil reflects, “but I’ve come to believe that can actually be a feature, not a bug. Competition often just means there’s real demand, and in many of these categories, there’s still plenty of room to build something better or more focused—especially now with how AI is reshaping workflows.”

The moment his team began to realize their market might not be as urgent as they'd hoped was when they kept hearing some version of: “This is a big problem for us…but it’s not on the roadmap right now.”

“We got that over and over again,” Phil says. “Teams liked what we were doing, but because implementation required developer time, it often got deprioritized. That kind of delayed urgency is tricky. It introduces friction unless you have enormous volume or extremely high pricing, neither of which we had in the early days.”

This lack of urgency didn’t hurt their early fundraising, as investors were excited by the idea of a new platform for driving product adoption, but it did make long-term momentum harder to sustain.

With Dopt, it wasn’t just a positioning issue—it was more foundational: what should the product be, and who exactly is it for? They aimed to serve both PMs and developers, which reflected a real shared problem, but also created challenges around focus and go-to-market clarity.

“In hindsight,” Phil says, “we optimized for uniqueness in an area where the pain was very real but wasn’t on this quarter’s roadmap enough. Today I’d hunt for the same depth of problem—but inside a market already flush with budget and urgency, even if that means wading into heavier competition. When a huge number of customers are actively searching, you get free tailwinds, faster cycles, and cleaner data on what’s working.”

The takeaway: Choose a larger market with burning pain, even if it means more competition. It’s much easier to build momentum when your customers are already urgently looking for a solution than trying to carve out a niche in a quieter market.

4. Start a company in spite of your love of designing products

Filip Skrzesinski didn't leap into founding a company—it was “slow fermentation.” Years of working with systems: process-driven artwork, Markov chains before LLMs, visual languages built from component libraries and brand identities.

He left his job with no plan and no safety net, but realized he’d already been quietly working toward this moment for years. When he met his co-founders Irvin and Adam, it clicked immediately. Subframe started as a compulsion by people just crazy enough to build a better design tool from scratch.

But here’s Filip’s counterintuitive advice: “Don’t start a company because you love designing products. Do it in spite of that.”

“You won't be designing in the traditional sense—you’ll be designing the company’s DNA,” he explains. “It’s the invisible work: how you organize, how you think, how you make decisions. How it feels to work there, to use what you're making, to believe in it.”

The day-to-day reality becomes shipping quick fixes, sending outreach messages, releasing product emails, writing docs. All tasks eventually get delegated, automated, or made irrelevant. But the hard work is deeper. It’s cultural. It compounds.

“In the end, you’re signing up for something bigger than designing a product. Do it because you want to design things that outlive you.”

The takeaway: Before you start a company, ask yourself: Are you excited about designing products, or designing how a company thinks, decides, and feels? If it’s just the former, consider staying in a design role.

5. Know when to go with your gut and when to just ship

Filip’s first job was working for Justin Maxwell, a designer-founder who became his mentor. “I saw the unglamorous side of early startups: you're in a windowless office, letting go of brilliant ideas that fizzle, and still showing up the next day to try again.”

But he also learned “the toolkit every designer-founder ends up reaching for: intuition, craftsmanship, and delusional confidence. You reach for these when you have no data, no traction, and no idea where you’re going—especially then.”

Above Justin’s desk was a quote from Charles Eames: “Innovate as a last resort.”

“Most of the time, this is the move,” Filip says. “Ship the defaults, optimize for speed. Intuition is a catalyst, but I like to say ‘I don’t know’ a lot. Shipping is knowing.”

But it’s a balancing act. At Subframe, some details matter deeply: “We're designing a tool people work in all day, so how drag and drop feels, how microinteractions enable flow states—that matters.”

Other times, you pursue ideas born from raw, long-term conviction, even when they look contrarian: “like rethinking how designs get handed off as code, or resisting chat-based AI to find more nuanced, contextual interactions.”

The key is knowing when to reach for the right tool. Where you choose to focus is also what you’re choosing to ignore.

The takeaway: Save invention for what truly needs it. Most of the time, shipping fast beats being clever. As Filip puts it: “What do I wish I’d known? When to reach for the right tool. And I’m still learning.”

6. Why more designers should build now

Both Filip and Phil see this moment as uniquely urgent for designers.

Filip frames it as a generational shift: “Designers have founder instincts. But for a long time, the market didn’t reward design because building software was hard. The empathy, care, and clarity designers bring got filtered through technical constraints.”

Those barriers are collapsing. For the first time, designers have direct access to software as a medium, controlling not just how it looks, but how it works. "You’re not just building with frontier models; you're competing with them. This is the first time technology might outrun my imagination."

Phil sees the same gap: “AI’s raw capabilities are racing ahead while the experience layer lags far behind. Creating AI products that feel amazing and trustworthy demands new design patterns the old playbooks can't provide.”

This is where designers have their edge. “Designers bring the taste, judgment, and craft to invent those patterns and can bake them into a company’s culture from day one,” Phil explains. “I think it’s an amazing time to be a design founder.”

The takeaway: Now is the time for designers to start companies. AI has removed the technical barriers that once required permission or extensive resources. Start building now while the experience layer still lags behind raw capabilities.

1. Be ruthlessly honest about early signals. Are customers banging on your door or putting skin in the game? If people aren’t offering up their time or reputation (e.g. unprompted feedback or committing to a pilot), it might be time to reassess.

2. Choose markets that pull you forward. Phil’s insight: “I’d hunt for the same depth of problem, but inside a market already flush with budget and urgency, even if that means heavier competition.” When customers are actively searching, you get natural tailwinds.

3. You’re designing a company, not just a product. The real work goes deeper than product design. As Filip puts it: “You’re designing the company's DNA—how it feels to work there, to believe in it.” Tactical work gets delegated; cultural work compounds.

4. The AI window won’t stay wide forever. AI has removed technical barriers while the experience layer lags behind. Both founders see this as a historic but brief opportunity. The question isn’t whether to start, it’s whether you'll move fast enough.

• Recently added to DesignerFounders.com: Jony Ive, Julie Zhuo, Danqing Liu

• Omada Health went public last week—our first portfolio company to IPO 🥺

• We also joined Linear’s Series C!

• Carly Ayres on why everyone is suddenly so thirsty for designers

• Weavy launched with a node-based approach to AI image and video creation, combining multiple AI models in one tool. Watch our demo to see it in action

• Soleio and Indie.VC released a new video series featuring design pioneers at the frontiers of tech, designer founders included

Hey everyone,

We’ve been heads down launching our new State of AI in Design report, and we’re back with more designer founder stories! If you haven’t had a chance to check out the report yet, it’s packed with insights on how design teams are navigating the changes brought on by AI—from where it’s actually being adopted in workflows to where current design tools are falling short, plus tactics to help designers adapt without getting left behind. Let us know what you think.

We’d also love to hear from you: If you're a designer founder or hoping to become one, what topics would you like us to hit on? What do you wish you knew about starting a company? Founder-led sales (which Sam touches on below), finding a co-founder, figuring out what to build? Drop us a note in the comments.

Thanks,
Ben

View the State of AI in Design report

As part of our ongoing Designer Founders series highlighting designers who’ve built companies from the ground up, like Robert Yuen and Chris Kalani, we spoke with Sam Hashemi, co-founder and CEO of Felt.

Before Felt, Sam built Remix, a planning platform used by city agencies to design smarter public transportation systems. The product scaled to over 350 cities in 17 countries before being acquired by Via for $100M.

Now, with Felt, Sam is tackling a new challenge: making map creation as intuitive and collaborative as design tools like Figma. Backed by a $15M Series A that included Designer Fund, Felt is gaining traction as the go-to mapping platform for modern teams.

What we cover in our conversation:

• Lessons as a two-time founder

• The right balance of listening to your vision versus customer feedback

• Rethinking hiring and interview processes

• What happens when startups go bold with their brand

• The importance of finding your “CEO community”

• Why more designers should close the loop with sales

Designer Founders

Inspiring more designers to take the leap of entrepreneurship.

By Designer Fund

What was the decision process like between leaving Remix and starting Felt?

I wasn’t planning to start another company right away. Remix had been a long journey, and after the acquisition, I thought I might take a break. But there was this lingering frustration I couldn’t shake. Every time I needed to create a map—to share information, communicate something, collaborate—it felt unnecessarily hard. The tools weren’t built for how people actually work today.

Maps are such a powerful medium. They hold so much information and context, but most tools require a level of technical knowledge that cuts out a huge number of people who could benefit from them. I started wondering why maps weren’t more like other creative tools. Why couldn’t they be collaborative and intuitive, like Figma or Notion?

That question stuck with me. The more I thought about it, the more it felt like a problem worth solving. That’s really what led to Felt. It wasn’t about jumping back into building just for the sake of it. It was about scratching a very specific itch that I hadn’t seen anyone else tackle in the right way.

You’re a two-time founder. What have you learned your second time around?

How to hire people. When I was building Felt, I was religious about doing a long interview process. I was really trying to suss out every candidate, and it was a four or five hour deal every time. I found, in time, that that was not particularly predictive. A candidate could do really well in the interview, but it didn’t necessarily mean they would do great at the company, and vice versa.

At Felt, we’ve inverted the process. It’s a much lower interview bar. We start with a one or two hour interview. Then we try to get people in for a two week trial—actually join the business and work for a week or two.

Not everyone can do it. It depends on your lifestyle, but I think that more people post-COVID are in these much more flexible situations and are willing to try it. But it gets us much more high quality folks who are culturally-aligned, working-aligned, style-aligned. It's been a complete shift in our hiring approach.

Interviews are just not very predictive. So you just have to get in and do the job. I'm a big advocate now of having some kind of work trial. It's much more informative than an interview.

How has being a designer shaped the way you lead and make decisions as a founder?

Earlier in my career, I thought the goal was to design the best possible product from a craft perspective. Every detail mattered, and I wanted everything to be perfect. That mindset helped me develop high standards, but it also made me more focused on execution than outcomes.

Becoming a founder forced me to think differently. Suddenly, design wasn’t just about what something looked or felt like. It was about how well it worked in the context of the business, how quickly we could ship, and whether users were actually getting value from it. Trade-offs became a big part of the job.

That shift also changed how I lead. For me, design shows up in every part of the company. It’s not just in the product—it’s in how we structure meetings, write documentation, and communicate as a team. I still spend most of my Wednesdays on design reviews, which helps me stay close to the product and show the team that quality matters.

But I also try to stay pragmatic. Design is only as important as the problem it solves. If it’s not the differentiator in your market, it might make more sense to lead with something else. At Felt, it is the differentiator, so we invest heavily in it. That’s a decision every founder has to make based on what kind of company they’re building.

Any big mistakes you've made that you'd want other designer founders to avoid?

Finding the right places to really double down on your vision, and finding the right places to listen to customers. At Remix, I was kind of always in between—trying to integrate them and getting muddled in the process.

Now, I’ve tried to be clear about what I’m doing. There are parts of the work where I’ve declared, this is my vision and I’m just going to do it. This is where the product is going, and I see it coming together even if our customers can't see it yet. Whereas in other areas, I’m very open to what customers are saying and I allow myself to be surprised by what they say and do and care about.

This approach gives you the best of both worlds, instead of having to water down your vision, you know? Steel your vision and really push hard on it. Then be open to everything else—customers, and metrics. Because customers will always tell you they want a faster horse.

What other business lessons did you learn?

I should have talked more about pricing. Because the question of “does this solve your problem?” that doesn't necessarily answer how big a problem it is for your customer.

Talk early and often about pricing. I’ve even had to continue learning that here at Felt. There’s a big difference between, is this a $5,000 problem for you, a $10,000, or a $100,000 problem for you?

Talking about pricing is not a design skill. It’s something I had to learn, and it’s actually pretty key when you’re talking about all the other problems you’re solving.

What role does brand play in the success of a business?

Brand can be particularly powerful. We had a good brand at Remix, but I think we could have pushed the boundaries much more. We’ve tried to do that at Felt because brand is a way to stand out as an early stage business.

Be really bold in your brand—especially the early days. I think it's unlikely to harm you and it has a lot of potential upside to just be a little bit crazier on the brand front. You get good talent. You'll get more attention to your product. You'll eventually distill the brand down to its core and mature it as you grow the business.

What role does design play in how you run a company?

Design is not just in the product. It’s in everything. It's the sales process. It's in how you talk about the product. It's in how you hire. It's in the culture.

You also have to make sure design is an important differentiating value in the market that you’re going after. If it's actually not a differentiating value, then it’s better to differentiate in your sales or engineering, or something else.

At Felt, we’re building a creative tool that’s like using Figma for mapping. So the design details, the care and craft that goes into it, are a highly differentiating factor. So even just focusing my time on hiring really high quality designers that can continue to execute at that level of design means that the business succeeds.

I still spend more time than probably the average CEO does on design. I spend most of my Wednesdays on design reviews.

How did you learn to be a CEO?

How I did this at Remix and how I’m doing it at Felt are a little bit different. The first time, I was more focused on getting a department-specific adviser. So, a marketing person who I trusted and could have a meeting with every week to provide some validation if I was on the right track and thinking about marketing in the right way.

This time, I’m more focused on building a CEO community and getting a pulse on things. For example, what shifts or trends am I missing? If designers are all of a sudden using AI to do their work, I don’t want to miss that trend. I’m currently part of two different CEO groups, and we meet once a month and talk through what's going on.

Getting a coach when I was a first-time founder was really helpful, too. Once we scale past the size of my experience at Felt, I think that getting a coach again will be really useful.

What advice would you give designers starting a company now?

If you want to be a designer founder, it’s going to be a big uphill battle—but it's really satisfying on the other end. You come away with superpowers. You can build products you've only dreamed about because you have a whole team aligning around your vision.

As an early designer, the part that excited and frustrated me the most about my work was that I had a vision, but that I couldn't quite pull it off with just myself. As a CEO, you have a huge team to help you achieve your vision. It's kind of like the dream of a designer, I think, that you can dream the world and then, faster than you expect, it comes to life. If you're willing to take that uphill battle, there's a big reward at the end.

How do you think we can get more designers to become founders?

This is going to be a weird answer, but I think if we got more designers to close a deal, they'd be more excited. Not only did you make the thing, but you got someone to pay you money for it and get excited about it. It closes the loop. I had this experience as an intern at Salesforce. When I started joining the sales calls and seeing how my designs led to hundreds of thousands of dollars in sales, it completed the loop for me. It’s really energizing.

I think if we get designers to be more involved in the sales process, more of them will want to own the whole thing and be more encouraged to jump into the founder journey.

Books that helped shape Sam’s journey

1. You Can't Be Neutral on a Moving Train by Howard Zinn

2. Art & Fear by David Bayles and Ted Orland

3. A House Is a House for Me by Mary Ann Hoberman

1. Design your own hiring process. What works for another company might not work for yours. Don’t be afraid to try a new format, like Sam did, with asking candidates to join the team for a week or two, to see how they work.

2. Get clear on your vision. Customers can’t always imagine what you’re building. Be clear on when you’re following your vision—and when you’re incorporating customer feedback.

3. Be bold with your brand. An eye-catching brand can help your startup stand out, stay top of mind with customers, and even attract talent. As Sam advises, you can always refine the brand as your company grows.

4. Get comfortable with talking about pricing. Sam says he is still learning how to drill down on what customers are willing to pay for a solution. It isn’t something designers are trained on—but it impacts everything they build.

5. Find your support system. As a second-time founder, Sam has found a “CEO community” he meets with monthly to keep abreast of trends, so that he can continue to grow as a leader.

6. Is design actually your differentiator? Be honest about the role design plays in your product—if design isn’t a differentiator, your design skills won’t be much of a superpower. If it is, make sure to invest. Sam dedicates an entire day each week to design reviews.

As part of our ongoing Designer Founders series highlighting designers who've built successful companies, I sat down with Robert Yuen, Co-founder and CEO of Monograph.

Designers and founders can sometimes feel like they're cut from entirely different cloth. But Robert challenges that idea. He believes the same instincts that make someone a great designer also make them a great founder. And that the risks you take as a founder aren't actually that different from the ones you take as a designer.

Before starting Monograph, Robert spent over a decade as an architectural designer. He experienced firsthand the frustration of running complex projects without the right tools. Rather than wait for a solution, he built one with his co-founders.

Today, Monograph is a modern practice operations platform that helps architecture and engineering firms manage budgets, schedules, and project delivery—all in one place. It supports over 12,000 architects and engineers managing $14.5 billion in project fees. On average, firms using Monograph see a 21% revenue increase and 20x ROI in their first year.

Robert’s story demonstrates that when designers deeply understand the industry they're working in and pair that domain expertise with grit, tenacity, and tolerance, they can build category-defining companies. He's been able to solve for a niche that turned out to be anything but small, through consistent execution, day in and day out.

What we cover in our conversation:

• Why Robert and his co-founders started Monograph

• How living the problem led to building the right solution

• Lessons learned in going from architect to CEO

• Why “balance” is a dangerous myth for founders

• The common mistake he sees first-time founders make

Designer Founders

Inspiring more designers to take the leap of entrepreneurship.

By Designer Fund

Below is an edited, easy-to-read version of our full conversation:

Let’s start with the big question: Why do you think there aren’t more designer founders in the world?

You and I believe that the characteristics, skills, and traits of a great designer match almost one-to-one to what would make an incredible founder. But I see a disconnect—the kind of risk designers are used to taking in a project isn't always seen as the same kind of risk required to build a business. And that disconnect scares a lot of designers away.

My advice to any designer at that edge is the same: embrace it. Don't be afraid. You're already equipped to solve these problems. And they are the same problems.

Take this example: how do I, as a designer, solve a financial problem when I'm used to solving a design problem? The process doesn't change. You still go through discovery. You still ask sharp, specific questions. You still iterate your way to a solution. That same process applies to sales. It applies to fundraising. It applies to hiring. It applies everywhere. It's absolutely a transferable skill.

You have to embody an attitude where you're constantly learning. Accept that everything you do is the first time you do it. When we first started, my only resource was Google. I had to learn finance, legal, operations, hiring. As you grow, your toolkit should expand. The founder network at a $1 million business is very different than at a $20 million business. Always ask: is your toolkit evolving with you?

“The first hurdle is just recognizing that the kind of risk you're already taking as a designer is the same kind of risk you'd take as a founder.”

You started your career as an architect. What pushed you and your co-founders to start Monograph?

When I was a practicing architect, the design process was the part I loved most. But everything around it—budgeting, coordination, operations—was painful. We were working on complex buildings using outdated tools and spreadsheets. It didn’t make sense. I felt like our work deserved better tools. Monograph came from that pain. I wanted architects to be able to focus on their craft, not waste time chasing down invoices or managing projects in Excel.

Before Monograph, my co-founders Moe Amaya, Alex Dixon, and I were running an agency. We were a team of architects who had become designers and hackers—building tech for other tech companies and, on the side, helping architects digitize their workflows: dashboards, intranet systems, timesheets. Over time, we realized we wanted to go all-in on building for the people we cared about most—our friends in architecture.

Monograph actually started as a subscription-based website-building platform for architects. We designed it to be a drag-and-drop interface that made it easy to edit content, choose fonts, and arrange elements. We even offered beautiful, responsive templates and a free concierge service.

While building this, we noticed architects had a deeper problem. Most firms had no clear way to track time, manage budgets, or understand how projects were performing until it was too late. That's when we pivoted and launched a really simple time tracking app just for architects. One client asked us to build a productized version of something we’d made for another firm. That was the lightbulb moment. We realized these operational problems were systemic across the industry.

How did it go from side project to a company?

We were reading a lot about Basecamp and Mailchimp, companies that bootstrapped alongside consultancies. So initially, we didn't even consider the VC model. We bootstrapped Monograph for a while, working on it nights and weekends while running the agency.

Then came the “oh shit” moment when Monograph was taking up more time than the agency. Either we go all-in, or we stop. We chose to go all-in.

Was there a turning point where you felt, okay, this is working?

There wasn't just one moment. I remember getting emails early on from architects saying, “This is exactly what we've needed for years.” That felt like real validation. When we raised our first round, it gave us the confidence and resources to move faster. Then we raised from Base10, who really understood the space, and that was a big signal we were onto something meaningful.

How did you navigate the transition from architect to CEO?

When we started, we had complementary skillsets. I was the one who enjoyed talking to people and had been responsible for bringing in agency contracts. My co-founders were incredible at product and engineering.

We quickly realized for this project to take off, we needed capital. Since I was already comfortable with the client-facing aspects, it made sense for me to step into the CEO role and focus on fundraising. I'd never worked in tech, but I figured I could learn. I spent thousands of hours watching YouTube videos of YC pitches.

There's a romanticism around being an architect. You go through seven years of school, internships, licensure…your identity is wrapped up in it. Letting that go was a real emotional shift. But seeing the impact helps. When architects tell me Monograph helps them finally understand their business, it reminds me why we do this. I'm still practicing architecture—I'm just designing systems instead of buildings.

What role does design play in how you run the company?

Design is everywhere. For us, it’s not just about how the product looks. It’s how we run meetings, how we write documentation, how we communicate as a team. We try to design everything with intention. That includes the company itself.

For example, our leadership meetings follow a highly structured format based on a modified Level 10 Meeting. This structure helps us pinpoint issues, iterate quickly, and continuously to solve the needs of business today.

I think designers are good at zooming in and zooming out. You have to sweat the details but also think in systems. That mindset is incredibly useful when you’re building a company.

Why do so many software companies treat design like an afterthought? Design is not decoration. It’s how you solve complex problems clearly.

I was an architect before Monograph. Architects have an extraordinary ability to zoom in and out very quickly. That mindset shapes how we build at Monograph: in our values (“design-driven” is 1 of 6 values), in our product (built for clarity and simplicity), and in our team (co-founded by architects).

But we’re not building software. We’re designing for the professionals responsible for our homes, schools, and hospitals. And they don’t need software. They need elegant solutions that work like they work, remove friction, and turn chaos into control. If A&E firms are distracted away from design, the built environment suffers.
– from Robert’s LinkedIn

How do you stay close to your users while scaling?

We don’t build anything in isolation. Every feature starts with a conversation. We won't build it unless we have at least two or three customers who will co-develop it with us. It’s not just “does the customer want this?” It’s, “will they sit down with us and help shape it?”

That approach is rooted in our background as architects, where problem-solving starts by listening well, deeply understanding the problem, and designing with people, not just for them. You see that in how we work today—architects and engineers trust us to hear them, and they see their input reflected in rapid product improvements.

We also host monthly webinars, have an open Slack channel, and hold monthly design partner calls. It's always a conversation.

We believe A&E firms deserve world-class service—because that’s what they deliver to their clients. For us, that means fast support, hands-on onboarding, continuous feedback shaping the product, and access to industry experts who share practical insights to help firms grow. That level of care is part of why so many customers mention how much they value that Monograph is built by architects who actually listen and help them move forward.

How do you balance the many roles you need to play as a founder and CEO?

I don’t like the word balance. If you’re starting a startup, you should never use that word. Balance doesn't exist, nor should it be the goal. The goal should be to find extreme alpha and extreme leverage. Within that chaos, what you want is harmony, not balance. Balance suggests splitting things 50-50, but harmony looks different depending on what week, quarter, or year you're in.

At the stage we’re at, it’s my job to set the goalposts – where we’re going. I don't need to be in every design meeting or iteration. But I do need to define what good looks like quarter over quarter, year over year. That's my responsibility across every department.

Specific to the CEO role, I do think there has to be a certain level of grit, tenacity, tolerance to be in that position. Because that’s the job: you have to make decisions even without the data. It’s about making risky calls. That is a very uncomfortable spot to be in, and you're in that spot every day.

But the reality is that if the objective is to continue to grow the business as big as you can, as fast as you can, incremental gains are never gonna get you there. So this means you're gonna have to make risky bets—and the size of the bet proportionally changes.

What would you tell your younger self about starting a company?

If I were to do it all over again, my advice would be: don’t be so nice. A lot of first-time founders are too nice. We want to please everyone. But the faster you overcome the weight of “it’s not your job to please everyone” (and it’s actually not even your job to please anyone) the better off you’ll be. Your job is to build a company. Learn how to have those hard conversations, and you'll get there a lot faster.

What's next for Monograph?

We’re doubling down on collaboration. The way architects and engineers work together across firms is broken. It’s still email threads, outdated file sharing, scattered spreadsheets.

So we’re building the tools to fix that. We want to make it easy for different firms to collaborate in real time, stay aligned on budgets and timelines, and actually work as a team—even if they're not under the same roof. That’s the next frontier for us.

We’re still early in the journey, but we’re excited. There’s so much more to build, and we know who we’re building it for.

Robert’s favorite books

1. Revenue Architecture by Jacco van der Kooij (“I think every Designer Founder should learn a little bit of sales.” – Robert)

2. Powerful: Building a Culture of Freedom and Responsibility by Patty McCord

3. Traction: Get a Grip on Your Business by Gino Wickman

4. Atomic Habits by James Clear

1. Deep domain expertise is your unfair advantage. Robert’s experience as an architect helped him identify problems that weren’t obvious to outsiders. When you've worked in an industry, you understand its pain points firsthand.

2. Start with side projects. Monograph began as something that was built while Robert and his co-founders were running an agency. Similar to the advice Chris Kalani gave in our previous interview, you don't need to make a dramatic leap—start building on the side and see what gains traction.

3. Focus on one problem first. They also didn’t try to solve everything at once. What started as a simple time-tracking tool to address a specific pain point, later expanded into a broader platform that solved end-to end needs for architects and engineers.

4. Build with users, not just for them. Monograph won’t build features without at least 2-3 customers actively participating in development. This approach keeps the team focused on solving real problems rather than imagined ones.

5. Have the tough conversations. “Don’t be so nice” is Robert's blunt advice to his younger self. Building a company requires making decisions that won't please everyone and trying to make everyone happy slows you down.

• Newly added to Designer Founders: Tiya Gordon (it’s electric), Aaron Epstein (Creative Market), Shiz Aoki (BioRender), Imran Chaudhri (Humane)

• Nan Yu on why AI adoption is a UX problem

• Designer-founded Canva is now the highest-valued female-led startup in the world

• A class on prototyping with Cursor, built for designers and non-developers

Hero illustration by Adam Dixon

This is a defining moment for designer founders, especially as AI makes it easier than ever to build great products. We just launched Designer Founders to celebrate successful designer-turned-founders and share their stories and insights, in hopes of empowering more designers to take the leap into starting companies of their own.

From Facebook to Phantom: A designer's journey

For our first conversation, I sat down with Chris Kalani, Co-founder and CPO of Phantom.

Chris began his career at Jive Software, moved on to agencies building products for Microsoft and Nike, and then joined Facebook's design team working on growth, graph search, and Messenger. Inspired by the common pain points he encountered, he founded Wake, a design collaboration tool for sharing work and obtaining feedback.

After Wake was acquired and eventually shut down, Chris took a three-year detour at crypto startup 0x, where he met his future co-founders. Together, they started Phantom—a cryptocurrency wallet that now stands as the world’s leading platform in the space, with 15 million monthly active users, $25 billion in assets, and a recent $150M Series C at a $3 billion valuation.

Here's what we covered in our conversation:

• Finding the right co-founders and why it matters

• Why Chris chose to be CPO instead of CEO the second time around

• How designers can learn business fundamentals

• Why you should validate your idea before quitting your job

• Shifting your mindset from designer to founder

Finding your co-founders with intention

Having been a solo founder at Wake, Chris was adamant about the importance of choosing the right co-founders for Phantom:

“I learned through Wake that founding a company alone was much harder, and I decided I never wanted to do it by myself again.”

This sentiment echoes what we've seen repeatedly: founders sometimes struggle not because they lack vision or product sense, but because they try to do it alone. At Phantom, with three co-founders, they could divide responsibilities according to their strengths: CEO, CPO, and CTO, allowing Chris to focus on what he does best.

His advice for finding ideal co-founders:

• Work together first. Chris founded Phantom with people he'd already worked with: “We already had a lot of experience working together at our previous company. This helped us move faster to start building and capitalize on the unique moment in the market.”

• Align on values explicitly. “We sat down as co-founders to have direct conversations about our intentions, the kind of company we hoped to build, and what motivated us.”

• Do a “retro” on past experiences. “We literally did a retro on the lessons learned from our previous experience working together–identifying the things we wanted to avoid along with the things we wanted to carry over into our new culture.”

• Look for complementary skills. “Find co-founders who complement your strengths—whether on the business side or the technical side—and fill in the gaps that will help your company succeed.”

• Check your personal compatibility. “You need someone who you'll want alongside you through the highs and lows—who cares just as much and can help pull you out of the slumps when things get hard.”

This intentional approach to co-founder selection is something we've seen repeatedly in successful companies. The strongest founding teams are built with care and deliberate alignment.

Playing to your strengths: Why Chris chose CPO over CEO

When I talk to designers who are hesitant about starting companies, they often picture themselves as CEOs responsible for everything. However, after his experience running Wake solo, Chris opted to become the Chief Product Officer at Phantom, a move that let him focus on what he does best. Rather than managing every aspect of the business, he chose a role that leveraged his deep design and product expertise.

“I knew from my experience with Wake there were parts of being a CEO that I didn’t enjoy. I remember wishing someone else could run the company so I could spend 100% of my time focusing on product.”

For designers considering the founder path, this is liberating: being CEO isn’t the only way to lead. Many designers might find greater fulfillment in product leadership roles where they can stay closer to the craft, focus on the user experience, and build and lead product teams.

When I asked Chris about ensuring design remains valued when he's not CEO, he mentioned it hasn't been an issue because design excellence was central to their strategy:

“[Design] was just so ingrained in our decision to start the company. All our competitors were difficult to use, so a big part of our strategy—and our DNA—was to actually care about design and make crypto incredibly easy to use.”

Bridging the business gap beyond design skills

One of the biggest hurdles for designer founders is the gap in business fundamentals. We've seen this repeatedly in talented designers who can create beautiful, usable products but struggle with aspects like go-to-market strategy, user acquisition, or financial modeling.

Chris was candid about the challenges of focusing exclusively on design, that led him to become a founder for the first time.

“I was so married to the idea that I wasn’t developing the other skills you really need—like marketing, sales, company building, how to get distribution, how to develop the business, or how to be an effective leader.”

This gets to the heart of why many designers hesitate to become founders. They've spent thousands of hours mastering their craft but often lack exposure to business fundamentals. And unlike technical co-founders who might have built side projects with monetization models, designers rarely get that business experience through their craft alone.

“At a large tech company, even as a senior designer, you’re not always part of shaping the vision or strategy behind what you’re building. You might not have a clear view into the 'why' or the business objectives. But when you’re a founder, you’re responsible for all of it—you’re the one developing the vision and driving the strategy.”

His advice for bridging this gap: you should be “thinking like a founder” even before you become one. Some ways to do this:

• Be curious about the whole business. “I always look for this quality when we hire almost anyone: do they understand the company they're coming from? How deeply are they thinking about what they're working on? Why they're working on it? What the strategy is?”

• Read extensively. “I read a ton about other companies, their challenges and evolutions over time. For example, I enjoy learning how Google or PayPal worked in the early days seeing what lessons I can draw.” (📚 recs below)

• Talk to people in different roles. “Get to know other teams like customer support or sales, learn what they do, and what they need to be successful.”

• Question why decisions are made. “People should be asking ‘why’ to understand what's going on. It's a good indication that they're plugged in and they care about what they're working on.”

There's also a mindset shift required here. Chris suggests designers might benefit from embracing more ambition:

“I think designers need to realize the power they have to influence things and sell ideas. Doing so can lead them to have a massive influence on a company at the highest level.”

Validate before you launch

Perhaps the most actionable advice from our conversation was Chris's emphasis on building and validating your idea before going all-in:

“Don't just immediately jump into it. Build something, prove out the idea. Brandon (Phantom's CEO and co-founder) and I were literally still at our previous company 0x when we built the first version of Phantom. We didn't quit, but still had a good sense of what we were building and why. I worked on Phantom for a year and a half before we started fundraising.”

There are several advantages:

• Reduces financial risk. You're still getting a paycheck while testing your idea.

• Gets you real user feedback, not just theoretical assumptions.

• Creates leverage for fundraising. When you do raise, you have traction to point to.

With Phantom, this paid off significantly when it came time for their raise:

“By the time we were fundraising we already had a $100,000 grant from Solana foundation and 20,000 users on the waitlist. We had something tangible to show.”

Chris had followed a similar approach with Wake, working on it for a year and a half before raising. This gives you time to refine your idea, build early momentum, and approach investors with confidence rather than desperation.

For designers, this approach plays to your strengths. You can create compelling prototypes, get them in front of users, and iterate based on feedback - all skills you already have. You can start this process now without waiting for the perfect time to quit your job or raise money.

Chris's journey from Facebook designer to two-time founder offers key lessons for designers considering starting companies: be intentional about finding complementary co-founders; validate your idea while still employed; bridge the business knowledge gap beyond design skills; and consider which founder role truly leverages your strengths.

Chris’s recommended books

• Zero to One by Peter Thiel

• The Hard Thing About Hard Things by Ben Horowitz

• How Google Works by Eric Schmidt and Jonathan Rosenberg

What's coming next

Chris’s story is just the first of many we'll be sharing. In future newsletters, we'll continue interviewing designer founders at different stages. Let me know: Who should we interview next? What specific topics do you want us to explore? Nominate an amazing designer founder you know by replying to this email or filling out the form at the bottom of this page.

What we're reading

• Nikita Bier's tweet on why having a designer separates companies that execute and those that can't: “At the end of day, products live and die in the pixels: it's what the users see and tap. And without someone shepherding that process, you are effectively wandering the desert blind.”

• David Hoang on how designers can develop business acumen: “‘Embrace the entrepreneurial spirit’ is one of my design philosophies. When constructing teams, I like having designers who've started their own companies or worked at an early-stage startup.”

When we started Designer Fund in 2014, it was a special moment for designer founders. The world was filled with many antiquated, multi-billion dollar companies nearly everywhere you looked. This led to an incredible opportunity for companies with better software products to come in and take market share from incumbents. Companies like Airbnb, Pinterest, Instagram, and Gusto emerged during this historic period, attracting users with products that were dramatically better than existing solutions.

What made that era special was that building online products and services had become cheaper and accessible enough that many more people could participate. Historically, when a fundamental technology reaches a certain maturity, value creation moves “up the stack” towards the product and design layer and it creates a massive opportunity for folks to differentiate there. We saw it happen with mobile. We saw it happen with SaaS. And now, that moment has come to AI.

The Design Opportunity in AI

The last few years have seen the creation of incredible underlying AI technology. As companies leapfrog each other, users have bounced from product to product, chasing more robust technical capabilities.

However, while we continue to see improvements, the difference between the underlying tech in top AI companies is decreasing. And, as the gap between competing AI innovations narrows, the product experience will become more of a deciding factor for what products people use.

For example, in a world where dozens of different AI models can create high quality images, designers won’t choose their image creator based on the model, but rather on the rest of the product offering. They’ll choose a creative tool that will let them make precise refinements, integrate into their other tools, or effectively collaborate with their team.

This new environment where product experience exceedingly matters more plays beautifully to the strength of designer founders. Not only that, these new development tools make it easier than ever for designer founders to build products faster and with smaller teams, making it one of the most compelling times ever for designers to start technology companies.

Why Aren't More Designers Becoming Founders?

So we’re left wondering: why? Why aren’t we seeing hundreds of designer founded companies every month?

After talking to numerous designer founders over the past couple of months I’ve come to a few key insights as to why designers aren’t becoming founders right now:

1. Perceived lack of skills + knowledge. Design is a specialized vocation. The best designers spent thousands of hours mastering their craft around interaction design, prototyping, and product building. This means unless a designer has specifically sought out to develop their knowledge around how to build and run a company, they believe they’re ill-equipped to do so effectively.

2. Lack of confidence. When designers begin to contemplate becoming founders, they not only believe they lack fundamental knowledge but also fear they don’t have the ability to gain those key skills in the future. The belief is that what makes them great designers - craft, product building skills, etc. doesn’t translate to learning how to build an effective sales org or how to come up with a well-devised product strategy. This myth leads many would-be designer founders to opt out of even considering the founder path.

3. Lack of visible role models. Despite an increasing number of successful designer founders, design as a vocation still does not celebrate founder success the same way engineers celebrate Mark Zuckerberg or Larry Page. If you need proof simply go to a room of design students and ask them to name five successful designer founders of tech companies. My bet is you’ll get a roomful of blank stares. We simply don’t do a good enough job of celebrating exceptional designer founders and helping designers understand what it took for those folks to succeed as founders.

Announcing Designer Founders

The good news is that all three areas can be effectively addressed, and starting today, we’ll be ramping up our efforts to transform this landscape.

Today we’re announcing two new initiatives towards that goal:

1. The release of designerfounders.com. We’ll be celebrating successful designer founders, capturing their insights, and making them easily accessible to anyone.

2. The launch of our Designer Founders Newsletter. The newsletter will go deeper with original founder interviews, startup tactics, and opportunities specifically for designers starting companies.

By sharing the stories and insights across these two formats we hope to inspire the next generation of ambitious designer founders to take the leap of entrepreneurship and equip them with the tools they need to succeed.

Take it to the Bank

Designer Fund is ready to support the ambitious designers who are prepared to embark on this entrepreneurial journey. We plan on investing millions of dollars over the coming years in companies with designer founders and bringing along a like-minded network of funds and angels who will invest many millions more. Our time has come once again. If you or a designer founder you know is ready to build something extraordinary please reach out to us.

The coming years will be historic for technology companies and society. Designer founders will play a pivotal role in creating companies that better serve humanity and help people live their best lives. This moment calls us to rise up and build that future together.