Highly recommend taking a BAE Boat out for a few hours on the Alameda channel. Reminds me of the time when we took a boat out on Lake Como in Italy, except you can’t jump in the water in Alameda.

A thing on my mind:

I can’t believe I’m 38 and a half. I was watching clips from the guy who stops older people on the street and asks them what it feels like to be their age. One person said something like, “I don’t feel old on the inside, but on the outside I look old so that’s how the world treats me.” I don’t look old yet, but that dissonance would bother me.

The 30s did hit me pretty hard. I was telling someone you know you’re getting old when you wake up feeling like you got hit by a bus even though all you did was go to sleep the night before. That’s how I felt every morning in my early 30s until I started stretching. I remember when I used to make fun of the OGs on the basketball court for needing to stretch, now I’m one of the OGs stretching all the time, except I’m called “Unc” not OG, which is way less cool-sounding.

I’m grateful I have older role models to help prepare me for what’s to come. On Sundays there’s a group of 65+ folks who play basketball at my gym. The oldest guy there is in his 80s and he still runs from the top of one 3-point line to the other, getting touches catching, passing and sometimes even shooting the ball. He told me if you want to keep playing basketball, you have to keep doing basketball movements. Even when you’re on vacation, do some loading, jumping, lateral running, etc. because when you get older the body is more eager to say, “Ok, guess we’re not doing that anymore.”

Outside of stretching daily, I’ve also had to sleep more, eat clean, lose weight, and build strength and flexibility. It’s a lot of work, and you still lose at the end. “Father Time is undefeated.” I was joking with another OG on the basketball court that we have to do way more just to do the same things we used to do. I spend way more time stretching and strengthening just so I can play a few hours of basketball, for example. The experience of aging is how the universe makes sure that you don’t take anything for granted.

On the flip side, it’s not all that bad. The plus of getting older is that I’m much easier on myself now. My theory is that there’s a pain threshold you need to hit in order for change to happen. I only started taking my physical health seriously when I realized I was spending more time managing pain, illness, and fatigue than I was living. The same is happening for my mental health. After years of beating myself up for not being good enough, it’s finally starting to feel like it all hurts too much. I used to be proud of my stupid high pain tolerance, but not so much now if that makes it harder to change who you are.

I enjoy watching and admiring my friends as we all age together at the same rate. I remember us when we were 18, 28, and now 38. Most of us were, and still are, driven to perform at a high level. The nature of the drive may have changed, and we’ve ended up at different places in life, but we are all still pretty much the same people. Rather than constantly telling myself that I’m not good enough in this way or that, I’m finding myself saying there are a million ways to succeed and believing it because I’ve seen it. And of course, there are a million ways to define success.

I remember reading a book called The Monk and the Riddle back in college. I don’t remember much of it other than the takeaway to pursue a life that is true to you. I enjoyed it at the time because I felt like I didn’t like the academic game. When I talked to the upperclassmen who came back from their coveted internships, I realized those jobs were just another version of the same academic game. What spoke to me instead was to make up my own game, which I did by starting companies. But every game needs a way to keep score. The challenge has been keeping the score the score — part of what makes the game interesting — and not an indictment of my worth. What matters is staying fiercely committed to and convicted in my potential, whatever the score says.

A piece of content I recommend:

1. The Score on 99% Invisible

Speaking of games and keeping score, the idea comes up all the time in my work on Flow Club. Some kinds of scorekeeping enhance the playing experience, others can become detrimental. This is an easy listen that talks about it.

2. Knicks Give Their City Something New: Impossible Joy by Matt Flegenheimer from the NYTimes

It felt like an inevitability before the series began that the 7’6 Alien would assume his basketball throne ahead of schedule, but then Big Body Brunson and the Knicks played incredible basketball to give New York something they’ve been waiting for for 53 years. The best thing about this NBA championship is all the media that came from it, like this NYTimes article, this video, and these photos.

3. The Greatest Season in Baseball History on Baseball Doesn’t Exist

All about Shohei Ohtani’s time in Japan. How he told Japanese teams not to draft him because he wanted to go to America, and a team drafted him anyway but ended up putting him on a two-way player development plan that prepared him to do what he’s doing today in the Big Leagues.

4. How to feel more secure from The Gray Area with Sean Illing

This podcast interviews Amir Levine who wrote the book on Attachment Theory about how to feel more secure. His suggestion aligns with what I’ve naturally done over the years to just gravitate towards people who can be what he calls “CARRP” — Consistent, Available, Responsive, Reliable, Predictable. There are people who can be that and others who for whatever reason just can’t. Instead of being upset, simply move towards people who can.

5. When you can’t help but thrive by me on the Flow Club Blog

We’ve always thought about Flow Club as a “space” and not just a website or a digital product, and my job is to invite everyone I can to this space we are hosting so you can experience how being part of the right space can transform your life. Wrote a bit about the idea.

🤗

—

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

We went to the Bixby Bridge in February and saw these three guys got out of the car looking suspicious and walked quickly towards the middle of the bridge. I yelled “ARE YOU GUYS GONNA JUMP!?” and one of them turned around and told me to shush 🤫 because YEP!

A thing on my mind:

Did you know the word “pollyanna” came from a 1913 novel about a poor orphan girl? One Christmas, Pollyanna was expecting a doll from the charity box, but got a pair of small crutches instead. That’s when her father taught her “The Glad Game” — find something to be glad about in every situation, no matter how bleak. In the case of the crutches, Pollyanna decides that she’s glad because she doesn’t need them! That’s just the beginning — her life gets bleak. Pollyanna’s father dies, she’s mistreated by her aunt, and eventually she’s hit by a car that leaves her paralyzed. Through it all, she plays The Glad Game, and it rubs people the wrong way because she’s annoyingly positive in light of all the adversity.

The more I read about it, the more I admire Pollyanna and dislike how our society turned her name into an insult for people who are excessively optimistic. That’s exactly the position of her evil aunt! I admit to having made the same disclaimer in conversation, saying something like, “not to be pollyannish, but…” as if it’s so important to disclaim to be taken seriously... “Y so srs?” 🤡

I’m drawn to people who are like Pollyanna — people who can seem naive, almost child-like. They're quick to love, quick to feel joy, quick to get excited, as if nothing bad can ever happen to them. Being around them feels easy in a way I can't fully explain. Maybe it’s because they live like the big kids I believe we are. I think about this often because I can feel my inner child craving the same freedom to just be, but instead I push him down to protect him from the world. Maybe I learned sadness far too young and I’m still responding to it.

One of these sickeningly optimistic friends once said to me, “I’m just a lucky person,” and I thought he was delulu. But the more time I spend with him, the more I see it’s a belief rooted in how he lives. Where I might spot something bad on the horizon, he doesn’t even notice bad things that have already happened. When something does register, he reflexively spins any situation into a lucky one. When bad things inevitably strike and hurt him, they don’t stick. He might get down briefly, but he moves on quickly by noticing the next lucky thing to break his way. It’s remarkable.

I marvel at these kinds of people. Maybe they were raised well. I imagine a kid trying something, it goes wrong, and they look up. If what they see — over and over, hundreds of times — is a face that says “you’re okay, I’ve got you, keep going,” they internalize that. Not as a lesson they can articulate, but as a felt sense that the world meets their stumbles with support rather than punishment. After enough reps of that, they stop needing to look up. “I know I will always be okay” just becomes part of their core beliefs.

But even if you weren’t blessed with that kind of childhood, or if life has knocked it out of you, you can still build it yourself. I’ve done it with health. “I’m a fit and healthy person” is part of my core belief now, even though it didn’t come pre-installed in any way. I used to believe I’d always be weak and sickly. I just started wanting to believe in a different story, practiced healthy habits, felt the benefits reinforcing that belief, and at this point, even with occasional setbacks, I never question that I’m fit and healthy. If practice can rewrite that story, it can rewrite others.

That’s the lesson from Pollyanna. The Glad Game didn’t come easy to her either. When her father introduced the game, she couldn’t see anything to be glad about getting crutches. She said, “the harder ’tis, the more fun ’tis to get ’em out; only⁠—only sometimes it’s almost too hard⁠—like when your father goes to Heaven.” She still found a way to be glad. Her belief finally broke when she was hit by a car. Lying in the hospital bed, paralyzed, she couldn’t find anything to be glad about. That’s when the people she’s touched throughout her life showed up to tell her how much her Glad Game had changed them — and that restored her faith.

So I’m learning to let the kid come out and play, and to keep playing even when it’s hard. Like Pollyanna in the hospital, I’m lucky to be surrounded by people who laugh with me, who appreciate the kid in me, who have huge and loving hearts, and who model for me every day how to be the big kid I want to be.

A piece of content I recommend:

Shrinking Season 3 on Apple TV

I recommended Season 1 and 2, and now I recommend Season 3.

Bonus Content: How EJAE Wrote The Biggest Songs for KPOP Demon Hunters on Daniel Wall

This is in the category of “world-class people nerding out about their craft” that I enjoy watching. The connection to Pollyanna is that EJAE said “writing positive songs is actually really hard because you can get on the edge of being kind of cringey.”

Bonus Content 2: The Most Exciting Tournament In Sports on Baseball Doesn’t Exist

I really enjoyed this year’s World Baseball Classic. It’s still very possible this tournament completely goes away if Major League Baseball doesn’t figure out how to align everyone’s incentives to play full force, so I’m grateful I got to watch it.

Bonus Content 3: Shohei Ohtani’s Dream Sheet

This went viral late last year on X. Shohei used the Harada Method to map out the 8 pillars he needed to achieve his goal and the 8 actions to take to achieve each pillar. The best part is how he explicitly worked on his “karma.” That’s how you bend the universe to your will.

Bonus Content 4: David and I both wrote something about AI recently. David FaceTimed his 19-year-old self to talk about how we can make anything now and yet…we are overthinking too much of it still? I wrote about burning out from trying to get AI to be my all-capable assistant.

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I went to two more Dodgers games since the last newsletter. That’s three games this season!

A thing on my mind:

What is your objective function?

The most important question just got more important in the age of AI.

In our roles now as AI supervisors, our ability to benefit from this abundant intelligence depends on how clearly we define our goals. We need precise prompts and a clear sense of what success looks like. We have to know what we want.

And…if you don’t know your objective function, you are someone else’s objective. Just like how social media algorithms are trained to maximize our time spent on their platforms against our better judgment, soon enough everyone and everything we interact with in the world will leverage AI to carry out their goals. We won’t stand a chance unless we know what we want.

I recently caught up with a friend who runs a non-profit and barely takes a salary. I asked her why not increase her salary now that it’s successful. She said something to the effect of, “What’s the point of that if you’re already doing it for the mission?” The way she said it, her clarity of purpose stuck with me.

My co-founder David is similar. He’s deliberate. When he commits, it’s 200%. David practices “full send” as a matter of habit. I make fun of him for speaking in a definitive manner on questions that I didn’t think warrant a period instead of a question mark, but I know his strategy is to constantly force clarity.

Most people I know, myself including, could use more clarifying of their objective function. It’s frustrating to hear friends say they want something only to watch them act in ways that look like self-sabotage.

My weight loss journey is like that. I’ve been tracking my weight since I was 22 because I’ve been wanting to lose weight since I first experienced a dramatic weight gain at 16.

As you can see, every year or two I’d go on a diet, lose weight, plateau, and give up. This went on until February 2023, when my “why” finally became clear. I wrote about it in “Pain avoidance machines (Ricky Weekly #94).” The gist is that the pain from carrying all the extra weight finally crossed an unbearable threshold. I couldn’t give my best to the things I care about. Later that year, when I read Peter Attia’s Outlive and came across his question—“Do you want to be able to pick up a grandchild?”—that solidified my resolve. I want to live life to the fullest for as long as possible because life is too good to half-ass.

Thinking about times in my life when I’ve achieved major clarity, most required being pushed to the brink. That’s not ideal. You don’t want to need extreme circumstances to gain clarity.

I wish you could achieve clarity just by thinking longer, but, at least for me, that just falls way short. The next best thing is to act as if you are clear. Be like David. Use periods instead of question marks even if you are not sure. Behave like someone who knows what they want, and soon enough you’ll find out if it’s true because you’ll be moving. On the flip side, if you are not acting according to your wishes or haven’t gotten what you want (assuming it’s within your control), maybe it’s time to update your objective function.

Of course, life doesn’t always have to be so goal-oriented. Part of the fun is letting life reveal itself at its own pace. Goals are just how we play by exercising agency. The good news is that AI will lower the cost of acting as if. Our AIs will try to understand what we want even if we’re not sure, act as if on our behalf, and return with results to help us see if that’s what we wanted in the first place.

Here is a funny clip on acting as if and learning about yourself:

A piece of content I recommend:

Joe Liemandt - Building Alpha School, and The Future of Education on Invest Like the Best

Tech Twitter has been buzzing about Alpha School for a while. I first read a parent’s detailed review and thought it was great, and then this episode dropped and became a conversation topic amongst friends. As someone who brute-forced school and never thrived in that environment, there is nothing about the way school works that I’m tempted to keep other than the peer socialization component (especially the “welcome to the jungle” part). I’ve never had “that teacher” who changed my life / believed in me / saw my potential. I’ve never felt engaged. If models like Alpha School existed, I think I would’ve loved it.

Bonus Content: What Is Man, That Thou Art Mindful Of Him? on Astral Codex Ten

A funny post about building AI.

Bonus Content 2: The 3 Best Core Exercises on Squat University

I’ve been dealing with recurrent lower back issues until I started doing the McGill’s Big 3 every morning. Now when I sit, stand and move, I can feel my core engaged. That’s a new sensation for me even though so many people have told me to engage my core over the years while doing various exercises.

We have such different lived experiences that words fail us. It’s like when a dance teacher tells you to move your body a certain way and you’re like, “I didn’t even know it was possible to move your body like that…”

Other examples: I used to hate walking and never understood hiking as a hobby. Then I lost weight, my thighs stopped chafing and I started walking normally. Now I love hiking! I used to feel like I can’t control my eating. Then I eliminated most ultra-processed foods and simple carbs and realized that I can as long as I don’t consume things that hijack my brain!

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

The Dodgers were in town! It’s been forever since I’ve been to a Dodgers game. I go to lots of Warriors games, Giants games, and even went to a Valkyries game for the first time recently but NOTHING compares to cheering for YOUR team!

A thing on my mind:

I’ve been thinking about what it means to set healthy boundaries.

Without them, life’s daily “elements” seem to erode my sense of self. Boundaries are signals that I know what I need and that I value myself enough to communicate those needs clearly.

I used to think people who are sensitive about boundaries have limited capacity or adaptability. If someone got upset by harsh feedback, I’d think, “They just can’t handle the truth!” If someone needed personal space, I’d dismiss it as “rigid and inflexible.” If someone bulldozed others with their agenda, I’d label it “selfish.” I’m realizing that’s not it and wow was I judgy.

I wasn’t entirely wrong, though. Like a lot of people, childhood was painful. It felt like the world just wouldn’t stop hurting me, and no one answered my cries for help. At some point, I decided boundary-setting was a useless exercise. Instead, I needed to develop the capacity for pain and learn to adapt to any situation. You can imagine then when I met people who acted like everyone needed to respect their boundaries, I’d think, “wow it’s so unfair that they get to ask to be treated differently.” It’s even more infuriating when people would comply, myself including. I never got that treatment.

I’m realizing now though that just like capacity-building is a skill, adaptability is a skill, so is boundary-setting. Boundary-setting might be the more important skill because it isn’t just about survival; it’s about thriving. You get to learn what you need and demand it from the world. It’s giving main character energy.

For me, setting healthy boundaries involves:

1. Noticing when a boundary is being crossed

2. Confirming it’s genuinely a boundary issue and not just temporary discomfort

3. Establishing the boundary clearly to the offender

Noticing

The girl I’m dating is good at checking in with me to ask me if I’m okay with a plan or what we’re doing. She knows I’m eager to please but can get grumpy if I don’t get what I need. Her simple questions reveal how often I overlook my own discomfort. I usually struggle with answering if I’m okay, because I’m not sure! Instead, I default to the people-pleasing, “yeah, I’m okay” or even fake some enthusiasm to avoid disappointing people who want me to be happy. I’m sure we all do this from time to time. Still, her check-ins give me a chance to register if there’s an incongruence or unmet need.

Confirming

Even when I notice discomfort, it’s still difficult to tell what is a boundary and what is just a fleeting emotion (eg HALT: Hungry, Angry, Lonely, Tired) or something I can adapt to. For example, if travel disrupts my morning routine, is that boundary-breaking or can I simply adjust what I do? If someone’s comment hurts me, should I say something or am I too sensitive? If I complain, do I become the insufferable one?

Clear boundaries requires clearly knowing what I’m willing to fight for. It's taken years and considerable self-sabotage to realize that maintaining my self-confidence is a critical boundary to being who I want to be. If a physical injury is your body telling you you’ve gone too far, my emotional resilience has kept my mind from telling me I’ve injured my heart.

Establishing

Noticing and confirming boundaries leads inevitably to the hardest step: communicating them. I'm relatively comfortable communicating the uncomfortable (“I feel” statements help). The difficulty lies in the decision itself—deciding that I'm worth fighting for. If I don’t value or trust myself, I won’t genuinely advocate for myself. I have to believe deeply that “I deserve to be me” and can occupy proper space in the world. I’m practicing this now.

Acknowledgements

This was hard to write because I’m still processing it, but recent interactions with these friends have deeply influenced me:

• Jason coached me to “let Ricky cook” by getting out of my own way. His story about being too resilient to physical pain in gymnastics made me wonder if emotional resilience could similarly become harmful.

• Ryan reminded me that my younger self balanced thoughtfulness with bold, intuitive action. He used to say, "Protect your swag!" Today I think the kids would use the word “aura.”

• Kat and Amanda: Going on trips with them this summer opened my eyes to what healthy boundaries can look like.

• Nikil: For writing about how to live a confident life and setting a good example of someone who knows his worth.

Even random sports podcasts have influenced me (probably Baader-Meinhof):

Jeremy Lin said he should’ve spoken up earlier to Kevin McHale. Gary Sheffield said speaking up against rookie hazing taught him that he can demand respect.

“I guess I got my swagger back!” - Jay Z

A piece of content I recommend:

The Materialist written and directed by Celine Song (Past Lives)

Past Lives was my favorite movie of 2024, so I had to watch Celine Song’s latest—and it did not disappoint! Past Lives explored longing for a multiverse of what-ifs. all those coulda, woulda, shouldas we carry until we surrender and embrace the present. The Materialist dives into the infinite possibilities of the present and how we struggle to decide what’s truly right for us. “Dating is hard and love is easy,” but can—or should—you trust what’s “easy” when your brain tries to protect your heart by trying to check all the boxes?

Bonus Content: Ocean Vuong Was Ready to Kill. Then a Moment of Grace Changed His Life from The Interview, New York Times

When this interview dropped, my friend Katie and I both separately listened to it right away. Then Katie called me and I said, “Ocean Vuong on The Interview!?” She was like, “Yessssssssss.” That’s how good it was.

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I went on a bachelorette party trip! I feel special being part of a bridal party. Boys and girls can be so different it’s a fun topic to think about.

A thing on my mind:

Whenever I’m down about work, I like to say to myself, “I CHOSE this.” It’s a powerful reminder of my tremendous luck and privilege to do what I love to do, and that I can always choose something else.

Then I ask myself if I still love what I do. People have asked me, “is this your life’s work?” I hope it’s not that serious. Sounds like a trick question to me, as if we are only meant to do one thing. My answer is always, “who knows!”

I fell in love with startups in college. 15 years later, I know much more about it and I still love it. Most days I wake up excited because I get to do something challenging that has potential to teach me something about how to shape our world. Business is a big, competitive game with very few rules that affords me maximum degrees of freedom and scorekeeping to tell me what I’m made of. Can I fall out of love with it at some point? Sure. It’s really hard and I’ve sacrificed a ton. So I have to always be checking to make sure it’s still worth it.

Am I good at it? No. Not yet, at least. I’m not nearly as good as I believe I could be. One of the hazards of this job is that you can’t easily get the reps to improve a particular skill (ie if your startup isn’t scaling, you don’t get to work on hiring skills). Another one is that the actually important skills are too meta* and hard to work on (eg seeing opportunities and knowing how to capture them). Either way, regardless of how good you get, luck plays a very significant role in the outcome, which makes this all very unsettling but also very appealing. You have to constantly be working to figure out what actually matters for your business, charting paths to your best ability for those around you, and being willing to run full speed ahead of everyone knowing where you’re going is most likely off the cliff.

Should you succeed as a founder, you’d have created a system. You can hire employees to operate with reduced uncertainty for a predictable result, and they get to showcase and refine their skills in that context to produce the result more effectively. But at the end of the day, the uncertainty is only reduced for everyone in the system to the extent the business is successful. Job security is a fantasy. Markets are alive and changing faster than ever. Just over the last few years we went from one of the longest bull markets in tech to massive layoffs due to economic uncertainty and AI disruption. The founders are the ones staying up every night in good times and bad studying the market and thinking about the customers to figure out how to move in the direction of opportunity. Founders trade certainty and security for resilience and agency.

Still, founder life is hard. I’m plagued by insecurities. What’s been useful for me over the years is to stop believing in the successful founder archetypes. Bill Gates. Steve Jobs. Jeff Bezos. Mark Zuckerberg. Elon Musk. Their successes have led to an entire industry pattern matching for roughly the same type of brilliance: intellectual horsepower/rigor, precociousness, brazenness/daring, visionary-ness, a little unhinged with a side of the tism. As an ambitious nerd, this is admittedly what made Silicon Valley feel like home to me. These are qualities historically undervalued by society. But it’s a trap to think they’re the only attributes that hold any predictive power. For too long I’ve discounted many of my strengths for not matching up to this archetype. Now I know better. Among all the pattern matching, founders and companies need to be differentiated enough to win. I think for me to really do that well, I need to embrace who I am.

*Footnote: the “meta” skill of business is not so meta according to this article by Cedric Chin. It’s a different type of learning that you can think of as “sensemaking” — useful when learning from real world experiences where feedback loops are noisy, delayed, might not even exist. There are ways to get better at “sensemaking” through constant reflection and being agile enough about updating your priors. Here’s a related article from Brian Lui on the dangers of tight feedback loops. Really, really cool stuff.

A piece of content I recommend:

Why Relationships Die & Which Ethnicity is WORST in Divorce on Flagrant by Andrew Schulz and Akaash Singh

I’m a new fan of Andrew Schulz and Akaash Singh, so I’ve been gobbling up all their content. The podcast’s pretty sweet. Good comedians have superpowers because they can cross the line and take conversations to places they don’t normally go. The topic of divorce is not something people like to talk about and here’s two and a half hours of it in exhilarating depth with a wide variety of perspectives. Another good episode is the one with 50 Cent talking about…Diddy. Yup. They’ve also talked to politicians like Bernie Sanders, Pete Buttigieg, Eric Adams, Vivek Ramaswamy if you’re into that.

Bonus Content: I have a bunch this time, so a sentence to introduce each.

• If you love San Francisco, you’ll love this explainer of SF’s map and how it came to be.

• This is like Jiro’s Dreams of Sushi but for ramen lovers.

• A Chinese YouTuber interviews her grandfather about growing up in the communist revolution. I think this is a pretty rare first-hand account.

• A very adept conversation about trauma between Peter Attia and Jeff English.

• A fun reminder that we are the source of our problems (and the title of this newsletter).

• If you’re looking to eat better, Eric Topol interviews Kevin Hall who used to be a Senior Investigator at the NIH and looked into ultra-processed foods, among other things in our food environment.

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Went on a breakfast date with my friends’ kid (and her parents). We loved watching bigger kids and trains go by!

A thing on my mind:

I’m at Thorough Bread and Pastry enjoying their almond croissant (one of the bests in the city). This is my 100th Ricky Weekly. Even though it hasn’t been a “weekly” for some time, it still gives me joy whenever I make the time to write what’s on my mind to share with you all. The fun is in how writing helps me think. I always have a lot of thoughts swirling around in my head. They keep swirling because I feel like if I just pull on their threads a little more, they’ll reveal something about themselves that will change the way I see the world.

I had mentioned that I might stop writing this newsletter at No. 100. The thinking at the time was to pivot myself into higher impact projects in my free time. I crave impact and was belittling this newsletter for its mostly selfish nature, but maybe that’s too harsh. When I look at all the things that make me happy, writing for fun is right up there near the top. The desire for higher-impact work is still burning, so I’ll do that anyway, but I’ll also keep writing here.

So, what’s been on my mind?

I’ve been re-learning that I have agency. A new friend was remarking that I am a high-agency person, which matches my own self-narrative. But a closer examination would show that I contradict myself and act low-agency in lots of situations. If there’s benefit to choosing differently to produce a better result and I don’t choose it, that’s infuriating. Of course, easier said than done. Being high-agency feels virtuous because it’s hard, like waking up at 5 and starting your day with a workout. It’s not the end-all, be-all of course. Nothing ever is. But re-learning that I have agency in many more situations helps me practice it more frequently.

I’m un-learning that I have to hold myself to sky high expectations in all aspects of life. For as long as I can remember, I’ve set a very high bar for myself. The reasons are complicated, but the consequence is I’m always failing and beating myself up over it. I was watching the latest season of F1: Drive To Survive, and Fred Vasser described Charles Leclerc as “over-motivated” and that struck a chord. Obviously very different context but the idea that you can be “over-motivated” is a nice reminder. In an email with my friend Jason Shen, he wrote, “Research shows that beginners need positive feedback and reinforcement, while experts benefit more from constructive criticism about gaps they need to address” as a way of reminding me that I can be more adaptive with how I set expectations to not deprive myself from ever being a beginner. I’m a beginner in almost everything I try to do!

I’m learning that I might have an “addictive personality.” I was being very self-critical with my fitness coach about falling off the weight management horse for two weeks when it was only supposed to be a weekend. Not the first time it’s happened, so he pointed out that I may have an addictive personality and will experience more polarized behaviors. For example, after two years of work, I got to a point when I’m “on” (the proverbial horse) I can stay very disciplined and eat a healthy diet, but when I’m “off” I swing hard in the other direction and engage in unhealthy behavior that can verge on disordered eating. Depending on how long I had to stay disciplined, what my brain needs to feel like I’m really off is a lot more than just a cheat meal or two or three. Combine that with the addictive chemicals in bad food and my other addiction to beating myself up when I’m down…things can get out of hand. I’m not sure if “addictive personality” is even a real thing but it does explain a lot outside of my relationship with food and why I prefer a simplicity, a bit of structure, and minimal living. Either way, it’s useful learning to help inform adaptive strategies.

A piece of content I recommend:

An Expertise Acceleration Experiment in Judo and Mental Strength in Judo, Mental Strength in Life by Cedric Chin

It was intriguing to read about someone’s journey to compete in high-level Judo in their mid-30s after taking more than a decade off from the sport. The most striking part to me was how the author’s coach identified “mental strength” to be a limiter to his progress. The author writes a successful business blog, which takes mental strength to accomplish, so I would’ve thought the same mental strength would translate to working on Judo if he’s completely dedicated to it. That’s too simplistic. This is what got me to email my friend Jason who knows the author, and he reminded me that our attributes (eg mental strength) are domain-specific.

Bonus Content: Court of Gold on Netflix

USA vs Serbia and USA vs France were two of the best games I’ve ever watched in my life so just to re-live those two games would’ve made this worth watching but it definitely delivered way more. If you love basketball, you’ll love this. Fuck it we ball.

Bonus Content 2: Another Harry Mack Freestyle. Enjoy!

@alex.ontiktokRick Glassman gives a task to Harry Mack: come up with a “Girls At Guggenheim” freestyle — amazing! Is there any other rapper that could do something like this? #flowstate #freestyle #rappers #hiphop #improvisation #podcast #legend

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🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Found a mushroom, a banana, and a shark at the farmer’s market.

A thing on my mind:

“What’s your biggest fear in life?”

A friend asked me this recently. At this age, a lot of my fears have subsided. I don’t feel much more courageous, but I’ve stopped spooking myself as much as I used to.

I told my friend my biggest fear is not living up to my potential. Not becoming the best version of who I can be. I know I sounds like a typical overachiever. How would I even know if I’ve reached “my potential?” All the conventional markers of success are arbitrary. Startup IPO? Win the EGOT? Own a home? Build a loving family? Just different games of our choosing (or “different adventures” since “games” feels like a neg and I don’t mean to trivialize how we find meaning).

For me there’s no finish line, meaning I’d probably have this intense desire to be better until I die. Striving is a lifestyle preference, and playing the startup game to challenge myself still feels right because it has a tight feedback loop. I’m challenged to be better every single day.

As part of the improvement, I’m working on overcoming moments of FUD more quickly. When I feel FUD, experience has shown me that there’s something valuable on the other side, but I don’t feel like I’m moving swiftly enough through them. So really, like FDR said, “the only thing we have to fear is fear itself.”

Jeff Bezos’ Regret Minimization framework resonates. I don’t want to look back on my life and regret not doing what I want even if it’s scary. I’ve been really enjoying the latest Silicon Valley mantra, “you can just do things” because it’s a wonderful reminder.

Talking to my friend about how I arrived here, I can give you countless stories but the original sin was probably spending my entire childhood hiding in fear and helplessness until I took control and began living. I remember the day like it was yesterday. I was 14, and it felt like someone flipped on the light switch. I realized that I can poke life and mold it to make it better. Only after that did I start to really perceive the world, register the experiences, and remember the people. Everything I have today is because of that fundamental realization, so the goal is just to get better at the poking and molding.

A piece of content I recommend:

Jerry Seinfeld on Blocks w/ Neal Brennan

There’s not one thing that stood out in this conversation. The whole thing was great. I love it when comedians talk to each other because to be good at their job they have to see life very clearly, from all the angles and all levels of depth. Even better they’re both writer types, so they can articulate what they see.

Bonus content: I saw someone recommend a book called “Don't Believe Everything You Think” and thought the title was great but I’m probably never gonna read it. Then Baader-Meinhof took over and I started seeing similar ideas everywhere. Here’s a good clip from Mel Robbins on how ruminating or venting to friends can be counter-productive, asking what if you simply do not allow it?

Here’s research that suggests we can inhibit negative thoughts and improve our mental heath:

Bonus bonus: This Frank Ocean cover together with drone shots of LA is immaculate vibes. Reminded me of HBO’s Insecure.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

This is the first floor of the new Eslite Spectrum in Xindian, New Taipei City. I like visiting Eslite to remind myself of what is possible in business. What is Eslite? Imagine a Barnes & Noble that not only didn’t get crushed by Amazon but thrived by transforming itself into a shopping mall for the kind of people who like bookstores. Everything from the design of the stores to the retailers they bring in to the non-book products they sell differentiate them from a generic mall to attract people who want the smart sophisticated taste associated with a bookstore, and every mall is anchored by one of their bookstores that still get a ton of traffic, making up 30% of their revenue. They’re known for operating the world’s first 24-hour bookstore, which is also how they built their brand.

A thing on my mind:

I used to follow a journalist named Taylor Lorenz. Earlier this month she posted this in the wake of the United Healthcare CEO shooting:

I was shocked. Our healthcare system is broken and people are angry, but are we at a point in human society where it’s okay to publicly imply support for murder? It’s disturbing (and yes, so is people getting denied life-saving coverage, but only one of the two feels like a new development).

Taylor Lorenz expounded on her post in her newsletter and went on Piers Morgan where she said she felt “joy” in the CEO’s murder, before walking it back later in the interview.

I understand her point. I love reading Internet comments, and the screenshot she shared contained the same comments I read following the shooting and honestly found morbidly funny.

I’m guessing Lorenz sees herself as the voice of the Internet. She got her start reporting from the formerly obscure corners of the Internet, like Tumblr, that were responsible for a lot of the dank memes that ended up permeating our wider culture. I get it when she says,

Let me be super clear: my post uses a collective ‘we’ and is explaining the public sentiment. It is not me personally saying ‘I want these executives dead and so we should kill them.’ I am explaining that thousands of Americans (myself included) are fed up with our barbaric healthcare system and the people at the top who rake in millions while inflicting pain, suffering, and death on millions of innocent people.

Part of the problem here is the Internet is longer just obscure. It’s obscure for some, and a massive stage for others, with the algorithm increasing elevating more content out of obscurity. Lorenz’s posts get millions of views, so her account definitely functions as a stage, and we expect people on stage to talk like they care about keeping our fragile society intact (same reason people find cable news and things Trump says dangerous), or at least give ample warning when trying to say something nuanced and potentially incendiary.

The other part of the problem is that words are both meaningful and meaningless at the same time, and the Internet accelerates both the conflation and dilution of meaning. Lorenz’s defense is that she is simply highlighting the sentiment of the Internet, suggesting we should treat the Internet like people say we should treat Trump, “take him seriously but not literally.” It’s serious but not THAT serious. But how were we supposed to know that? The contexts we typically use to figure out how to interpret things has collapsed and become meaningless, and so we’re left with just the words themselves.

The problem with just words is that they are rarely precise. Take for example of what a “college degree” means:

I was one of the people in college that switched from a harder major to an easier major, and yet I graduated with the same “Stanford degree”—as long as you don’t squint too closely. Just by saying those words, I can let you confer all of the positive associations onto me and adjust your behavior accordingly, even though in reality the words fail to communicate anything about the degree of my academic accomplishments (or lack thereof). Words suck, and yet we need them to understand the world, so there exists arbitrage opportunities. A small arbitrage is what I did: take the easy road to an undergraduate Stanford degree. A bigger arb would be taking a Stanford Online or a GSB Executive Education program and putting “Stanford” on your LinkedIn.

Politicians and businessmen arbitrage the meaning of words all the time. In order for ideas to build mass appeal, they have to lose resolution in order to co-opt all positive associations and elude all nuance. You have to turn them into a Rorschach test. “Immigration Reform” is good because it deports illegal criminals, or good because it ends all immigration into the country, or good because it more sensibly manages our borders, or good because it expands H1-Bs visas for top talent to join us? Yes.

I have a “meditation practice.” You might think I sit for a long time with a teacher, you might think I’m super zen, you might think I go on silent retreats. I’m not going to dispel you of any of those positive associations about my ability, but in reality I have a free Calm subscription through Kaiser and sometimes listen to a three-minute “meditation” while walking home. Calm as a business succeeded partly by co-opting the aspiration of people to meditate and diluting its meaning in the name of democratizing access. It’s not bad. I think it’s a net positive for the world but still doesn’t change the fact that being able to say “I meditate” or “I’m a meditator” without doing the traditional work associated is a big part of the appeal.

The Internet accelerates this by collapsing contexts, amplifying voices, obscuring identities, creating echo chambers of everyone who have the same answers to your Rorschach test, and adding a powerful incentive of “attention points” that you can convert into money. There are accounts that are obviously in the business of riling people up with engagement bait like @TylerDurden and @realDonaldTrump, and then there are accounts that are less obvious and more insidious, like someone using a real-sounding fake name—and again, Donald Trump. These engagement-bait accounts are “art imitating life,” but because we can’t tell what is real, we take the words at face value. Our reality warps, and life ends up imitating art. I’m worried words are just going to become more meaningless as this progresses.

A piece of content I recommend:

Shrinking Season 2 on Apple TV+

After season two this show it is joining the ranks of my favorite shows of all time! Up there with Mad Men, The Expanse, The Wire, Insecure, Dave, Silicon Valley, Sherlock, Narcos: Mexico, Ted Lasso. I think it’s as good if not better than Ted Lasso at delivering pleasant, light-hearted yet emotionally sophisticated television, but I prefer this Jason, his style of humor, and 30-minute episodes. Can’t wait to see how they do Season 3.

Bonus content: How did the first democracy die on Search Engine

We live in a democracy with all these rules that seem to barely work at best, and people often want to change the rules or dismantle it altogether in favor of something else. Hearing how the first democracy came about and went away was a good reminder of why we have what we have today and why it’s still so very fragile.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

After visiting Portugal last year, we went to Spain this year on our annual friends trip. My heart is full and I hope we can keep this up. This is how I remember our trip, just non-stop smiles (to the extent Jun knows how to smile without showing teeth).

A thing on my mind:

The night before my flight home from Spain, my friend's two-year-old hugged me goodbye and cried. I was caught off guard and told her it was okay while fighting back my own tears.

A few weeks ago, I called a friend to catch up on my way to the gym. She tracked me down on Find My and showed up in person. I didn't have that much time to talk to her, and she was okay with that. I was surprised.

Every day, I go to work and marvel at my co-founder's determination, work ethic, and intelligence. I am amazed that he's still here, despite all my shortcomings.

I'm working on recognizing the countless ways people love me. My problem is that I am so, so surprised by them. Me? You love me?

I don't know if it's because, deep down, I don't think I'm worth loving. Intellectually, I understand that everyone deserves to be loved. Simply existing should be enough. But that didn’t feel like the case growing up. Over the years, I've become more certain that I was loved, but that love simply couldn't reach me at the time. Parents are people, and people are flawed.

I had to grow up very quickly, and part of growing up meant deciding that I didn’t need love. I channeled my energy in more productive directions, like trying to improve my life or at least control what I could. That sense of agency saved me, but I never stopped longing for love.

I’ve developed a number of personality traits that help me win love, only to reject it because I'm afraid. I'm ever the people-pleaser. Whatever situation I'm in, I want to make sure I'm wanted. I do that by making you laugh and taking an interest in you. It’s not fake—I truly enjoy most people's company, and I can easily see what is lovable about every person.

But when you start to show me love, I run. Pay me a compliment, and I deflect with self-deprecation. Take an interest in my life story, and I will share with you the same version of the story I tell everyone—one that helps you get to know me but also spares me from having to engage my deepest emotions. Even this newsletter is, in a way, an exercise in dancing the line between storytelling and true vulnerability.

But this hurts. Not being able to receive love hurts. It hurts me and affects how I show up every day. I show up not really believing in my worth. It also hurts everyone who loves me but can't reach me. Some people are limited in how much they can love, but even those with seemingly infinite capacity—people who nag, annoy, and pester me every day with gestures of love—still struggle to break through. Unlike when I was growing up, this time the problem is me.

So, as I said, I'm working on better recognizing all the ways I'm loved so I can practice letting those feelings register. One of the best things about ChatGPT is that I can just ask it to give me 100 ways friends can show love, and it will, and then I can ask for 100 more. Here are a few examples:

• Listening intently when I talk, and remembering details.

• Offering advice or perspective when I’m struggling, without judgment.

• Making plans around my preferences (e.g., choosing a restaurant I like).

• Taking an interest in my interests, learning about things I care about.

• Including me in group plans, making me feel part of their circle.

• Asking for my help or advice, valuing my perspective.

• Making time for me, even when they’re busy or stressed.

• Spontaneously doing something kind, like grabbing my favorite snack.

• Giving me space when they sense I need alone time or rest.

I don't know how long it’ll take to feel a sense of progress here. I don't even know how to measure progress for something like this. I'm scared because engaging my deepest emotions is terrifying. Last night, I talked to a friend about this very feeling. We discussed "givers" and "takers" in love, and he said, "Taking is vulnerable because you are not in control." Yeah.

Receiving love means opening myself up to the possibility of heartbreak. By savoring and relishing love, it becomes more difficult to ignore the fear that it could all go away. I want to absorb love, let it change me, and learn to trust that even if it all disappears, I will still be okay. Wish me luck.

A piece of content I recommend:

Culinary Class Wars on Netflix

People tell me they love the The Bear because it’s a show about what it’s like to be devoted to your craft, but I couldn’t stand watching it because it’s too anxiety-ridden. I do love content about people at the top of their game though so I’ve been raving about this Korean reality show that pits 50 up-and-coming / hidden gem chefs against 50 Michelin / well known chefs.

Bonus content: Esther Perel: How to Find, Build & Maintain Healthy Romantic Relationships on Huberman Lab

The way Esther Perel re-interprets and broadens the common ways we talk about relationships is a masterclass in perspective, like pointing out that it may be better to recognize that in the West we now have two or three relationships or marriages in our adult life, and some do it with the same person, but the relationship has to change. Or disentangling the idea of love from the idea of desire.

Bonus content 2: Trump and the Art of the Bullshitter on Honestly with Bari Weiss

I wanted to meet Trump with curiosity the first time he got elected. I couldn’t categorically reject the guy just for being vile because he’s a vile guy with massive appeal. Well, he just won again, and this podcast was insightful. It talks about Kayfabe.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Went to Hood River, Oregon with friends in July. It gets harder to spend quality time with people as you get older so I’m cherishing these moments.

A thing on my mind:

“Did you have a good day?”

Someone recently asked me how I’d define a good day and this is what I came up with.

A good day is a day where…

• I am at the top of my game with things that are in my control

• I am contending well with things that are not in my control

• I am living life in full color

Things that are very much in my control are things like when I go to bed, when I wake up, what I put in my body, how much I move my body, and what I spend my time doing. When I think about “bringing it” everyday, this is what I think about.

Then there are the things not in my control that I’m saying, “BRING IT ON!” My emotions and my customers are examples of these things. Building a startup pushes me down negative emotional spirals all the time, and I am practicing getting out of them faster and reducing their occurrence overall. Instead of feeling even worse when my productivity gets derailed by these emotions, if I’m practicing new strategies, it can still be a “good day.” Similarly, customers don’t have to buy and keep buying what I sell, but if I am executing in a way that gives me new insights about what makes them more likely to buy, that still is a “good day.”

And while I’m doing all this controlling and contending, a good day is only a good day if I’m also living life in full color. That means fully engaging with all the things I love about life. San Francisco’s had an amazing summer so far and I’m walking all over (I did the Double Cross Trail recently), spending time with people I love, and pursuing whatever I’m curious about.

I’ve only recently started distinguishing things in my control from things that are not because building a startup has broken me too many times. My ambition means I’m willfully unrealistic about what is possible. My default is to reject rules, no’s, and ways of being if I think things can be better. But that also means I am constantly disappointed in myself in my inability to make fast enough progress.

I think my pain tolerance and scarcity mindset have held back my progress. I’d just beat myself up and suffer rather than changing my strategy to ease the pain. But now I know I can move a lot faster making myself suffer less. I can stage out my ambition to let myself get positive feedback along the way. Instead of writing off every good thing as “not good enough,” I can learn to recognize them as real points on the scoreboard. I can choose to see the game as the first quarter and not running out of time.

A piece of content I recommend:

Hillbilly Elegy by J. D. Vance

I’m eight years late to this book. Regardless of how you feel about the guy now, he wrote a very good book that described how privilege works in our society in all of its complexity much better than I ever could. It’s a topic I’m very interested in and have written about in the past. Sendhil Mullainathan’s research on scarcity is my next area of exploration.

Bonus content: 30 For 30: American Son by Jay Caspian Kang

I wasn’t old enough to know much about Michael Chang but I think he was something like a Jeremy Lin of tennis back in the day. The part that struck me the most in the documentary was when Arthur Ashe wrote a letter to him as he was rising to prominence to tell him what it was going to be like as a minority.

Double Bonus: September 9, 2024 New Yorker Cartoon by Asher Perlman. I thought this was funny.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I went to an adult basketball clinic for Asian professionals called Breakaway and got coached by Marshall Cho who just coached the Nike Hoop Summit earlier this month. I discovered more stories about being the only Asian face, getting cut by the team, not speaking up, and from the coaches I learned about the power of role models and bridging gaps through basketball. Shout out to Peter Ahn for turning his dream into something for the community.

A thing on my mind:

I’m considering ending this newsletter at issue #100 because I want to be more “goal-oriented” with my writing again. Sometimes you just want to have fun and enjoy the process, and other times you crave results and improvement. I think I’m ready for some results. I want to write more about 1) Flow Club and 2) consider a follow-up to my viral essay from 2016. I’d need to spend more time on them and care about their impact. The stakes will be higher but it’ll still be fun, just Type 2 Fun.

My favorite quote is from F. Scott Fitzgerald, who wrote that “the test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” In light of recent anti-war protests, some of which spilled into my community, I’ve been thinking about how one develops and continues to develop this ability. I went to read the source material and learned that F. Scott Fitzgerald wrote what he wrote only to say that he had lost that ability in his later years. Fascinating!

Fitzgerald described his belief in his twenties and thirties this way:

“I must hold in balance the sense of the futility of effort and the sense of the necessity to struggle; the conviction of the inevitability of failure and still the determination to ‘succeed’ – and, more than these, the contradiction between the dead hand of the past and the high intentions of the future.”

But then he “cracked” and lost it in his later years because of “too much anger and too many tears.”

So how do you develop this ability to hold two opposing ideas and sustain it?

A clear answer to me as an immigrant is to keep living in America, the land of contradictions. I don’t know how it feels to have only known the American model, but I’m constantly comparing what’s happening in American society to Taiwan.

Take for example the debate about how SAT scores unfairly disadvantage underprivileged kids because rich people can pay for tutors. When I heard that, I immediately thought about how American colleges at least try to incorporate multiple factors through personal essays, recommendations, extracurriculars, in addition to grades and test scores. In Taiwan, you get a college entrance exam, and where you go and what you get to major in are almost entirely based on how you score on that test. It’s more meritocratic in one way, but it defines merit very narrowly and expects the entire society to fall in line with that definition. The American system is trying harder to incorporate more definitions of merit, but that invites many, many more contradictions that we must hold in our head, debate when necessary, and continue to function.

Last week, Biden signed the bill to force a TikTok divestiture from ByteDance or face a ban in the U.S., but his social media team plans to continue posting on TikTok to reach younger voters. That appears hypocritical because humans have consistency bias, but Americans seem to have the least of it. Reminds me of the documentary Waiting for Superman that talked about how American kids ranked #1 in confidence despite ranking 25th in math and 21st in science among 30 developed countries. Taiwan has already banned TikTok and prohibited any government worker from using the app. If anyone important in the government were outed for using the app, I can only imagine the tremendous backlash calling out the hypocrisy because it’s a collectivist society.

The fundamental contradiction is that America tries to have it all when having it all is an impossible task, but I don’t know a more compelling alternative.

Even F. Scott Fitzgerald “cracked” because he couldn’t find the success he had experienced earlier in his career, and the world seemed to be moving away from him as a novelist. “Holding opposed ideas” is hard work and very taxing, so we need to see our conditions improve, our dreams becoming true, and more positive reinforcement from our communities to keep the dream alive even when most evidence point to the contrary. The American Dream is an attractive story so you don’t need that much evidence, just enough to keep up the Kayfabe.

A piece of content I recommend:

Justice: What’s The Right Thing To Do? from Harvard’s Michael Sandel.

Speaking of TikTok, the time-waster app put me on this Harvard lecture series called “Justice” and I watched all 12 lectures in a week. What hooked me was this discussion about affirmative action from lecture 9. I’d recommend starting there and going back if you’re intrigued.

Bonus: “The best sports drone video you’ll ever see” from the Chicago Cubs.

Can a drone video make you cry? Yes if you love baseball. Even if it’s not your team. Even if you’ve grown apart. You still and will always love the sights, the sounds, and the stories. Sports are memories, and they are usually memories shared with friends and family. Watching sports help you access those memories, because while they keep changing they also stay the same. Watching a player break a record or win a game reminds you of when you watched another player break a record or win a game. You remember that time from your life, who you were with, and how you felt. Some of the people are not with us anymore, but you remember how excited they were when the exciting thing happened.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

There’s this house on McAllister that puts up a hanging artwork every month. I heard the person is getting pretty old and may not be able to do this much longer so I began taking pictures and videos every time I see a new one. I plan to put them all together at some point because they make me happy!

A thing on my mind:

I’ve been trying to lose weight for more than a decade. Here’s a graph of my weight since 2010.

The quick background is that I gained 80 lbs, from 140 to 220, over the course of my four years in high school that basically ruined my health, and I’ve been unsuccessfully trying to bring my weight under control ever since.

In the last 12 months, I’ve lost 42 lbs (170) and I’m on track to hit my target of 50 lbs (162). This is the lowest I’ve weighed since I was 16 so I thought I’d share the secret to my success.

Here’s the secret: “People don’t change unless they have to,” and I’ve finally had to because of OLD AGE. 😂

I’m in my mid 30s now, which is old enough to feel all the aches and pains. I like to joke that the most disappointing part about aging is waking up in the morning with pain in the part of your body you never knew existed. I’ve had to really manage my pain with daily stretches and strengthening exercises, but even with that, I’ve suffered more injuries on the basketball court that seriously jeopardized my ability to keep playing. That turned out to be a very credible threat to my happiness and made me realize how I really needed to slim down in order to stay physically active for as long as I can.

Beyond muscular and skeletal aches and pains, old age is also amplifying general discomfort enough to change my cost-benefit analysis on all sorts of things. The classic example is how quickly you recover from alcohol. I felt that in my mid-twenties. In my mid-thirties, they’re things like eating greasy or salty foods or consuming too much sugar. I’d feel uncomfortable or sluggish immediately after, enough to erase the pleasure I used to associate with delicious foods. On the flip side, if I eat healthy and clean, I’m able to notice how much better I feel. That wasn’t the case when I was younger.

Through this experience, I’ve learned how motivation is closely related to pain. My motivation to lose weight has always been vaguely about improving my overall health and energy so I can pursue what I love, which comes from having experienced the pain associated with poor health that held me back from doing what I want. That is as opposed to, say, wanting to lose weight so I can look good. In fact, even though people have called me fat, that never much bothered me because my mom always told me she liked chubby men. So, this is making me think that we’re all just pain avoidance machines and we may not have as much free will as we think we do over our motivation or why we do what we do.

To take advantage of this insight, I’m using weight loss as a way to avoid another type of pain — the pain of feeling worthless. Feeling worthless is a deep seated fear I have and why I’m motivated to achieve. Making progress on the scale is an easy reinforcement of my ability to achieve, especially compared to the high variance game of startups. Thinking this way has actually made me more resilient. Instead of getting discouraged by every weight loss plateau or whenever I blew up my diet, now I simply put the work in to bring myself back, and I always am able to, which is very confidence inspiring!

A piece of content I recommend:

Harry Mack & Lamorne Morris (New Girl meets 8 Mile) on TYSO with Rick Glassman - #243

Couple things about this podcast. It’s fun and irreverent. It’s the only podcast that I’d watch because of the great visual editing. But mostly Harry Mack, Lamorne Morris and Rick Glassman are a perfect trio because they all freestyle rap and have incredible chemistry. Since it’s a long video, I’ve linked to the part you should watch if you’re only going to watch some of it.

Bonus: Harry Mack (Freestyle Rapper. He's incredible!!) on TYSO with Rick Glassman - #195

I got so interested I went to watch this other interview Rick Glassman did with Harry Mack. There was still a ton of goofing around and freestyle rap but also really interesting discussions about the craft of freestyling and comedy.

Bonus Bonus: Sisyphus and the Impossible Dream by Casey Neistat

If you liked reading about my weight loss journey, you’ll probably like this video from Casey Neistat.

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Double rainbow!

A thing on my mind:

I was watching a YouTuber talk about the movie Past Lives and it really stuck with me. He showed a clip of Nora telling her husband Arthur that she feels so “not Korean” when she’s with her childhood sweetheart Haesung, but also “in some way, more Korean?” Later in the scene, Nora says how she has “Korean American friends” but Haesung is “Korean Korean.” But my question is, “what about Nora? How does she identify?”

I moved to the U.S. when I was 11, around the same time as Nora. At the time, all I wanted was to fit in. I picked up the language, the culture, and made friends with kids of all colors until I blended right in. When I got older and we started using labels to describe ourselves (probably around college?), I labeled myself Taiwanese American, or just Asian American. That seems to be the label that lets me fit into American society while feeling like I belong to a smaller tribe at the same time.

The Asian American label feels true most of the time. I’ve even written extensively about it. I get the Asian American experience of feeling like a foreigner in both America AND Asia. I get why a mediocre movie like Crazy Rich Asians had to be a big deal. I get Linsanity. I get #StopAsianHate. I get it.

But I also don’t get it. At a recent dinner for Asian Americans to talk about our relationships with our family, I felt very different from the other participants. I don’t get the sadness of not speaking your parents’ language fluently. I don’t get the pressure to achieve in order to be loved. I don’t get the feeling of abandonment of being raised by grandparents because parents were busy. I don’t get the guilt from the parents’ sacrifice to be in this country. I mean I get it but I don’t, or at least I was looking for something else to be shared with the group that is a big part of who I am. I found it in Past Lives.

Is Nora “Korean American” or “Korean Korean”? She’s both and something else at the same time. This is the quote that hit me from the YouTube essay:

There’s a unique emotional displacement that happens to people who migrated when they were old enough to have forged memories of life in their homeland but still young enough to be remolded by a new environment. As the years mount, and you become someone else somewhere else, that previous existence, now so distant from your current reality, begins to fade into a corner of your subconscious covered in the cobwebs of nostalgia.

- Carlos Aquilar, The Wrap

Nora’s something else because she remembers being Korean Korean and was old enough to have imagined a life as a Korean Korean, and then she moved and consciously became “someone else somewhere else” while her previous Korean existence is still there, tucked away and “covered in the cobwebs of nostalgia.” Nora lives on in her new timeline, carrying this previous part of her that she thinks about but rarely talks about. It comes up sometimes, like when her husband Arthur tells her that she dreams in Korean and how that makes him feel like there’s this part of her that he can never understand. Not because of the language barrier, but because that part of Nora is Na-Young (her Korean name). It comes up when she talks to and eventually reunites with Haesung, but Haesung is just a bridge to the memory of when she was Na-Young. Nora meeting Haesung reminds me of my visits to Taiwan. Everything is familiar — the sights, the sounds, the smells, the food of course, the warmth of the people. But I no longer go by the name I had growing up. I visit as “Ricky” and my Mandarin now has a slight American accent that gives me away sometimes. My “past life” lives on only in my memory and in the person I am today. That’s the nostalgia, but it doesn’t have to be the wistful kind. It just is what it is, and it can even be sweet.

A piece of content I recommend:

Past Lives

Yeah I wrote about it so of course I recommend it. I saw it in theaters and thought it was great, but wasn’t thinking this hard about it until I started watching the YouTube essays about it and the cast interviews.

Bonus: Nostalgia, Ultra by Frank Ocean

Every year or so I’d revisit Nostalgia, Ultra and listen to the whole album. I’d do it more often if it wasn’t so difficult since it’s not on any streaming service. It was Frank Ocean’s first mixtape and I remember loving it so much that I was kicking myself for turning down my friend Sean’s invitation to go all the way to San Francisco to see him perform at a small venue. Frank Ocean blew up afterwards so I’ll probably never be able to see him perform on a small stage.

Bonus Bonus: Flow Club 2023 Thank You Video

I woke up the morning of January 1, 2024 to this surprise thank you video from the Flow Club community. It was the best way to start the new year, and I wanted to share that joy with you all. Happy New Year y’all!

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I helped marry David and Amanda with the power vested in me!

A thing on my mind:

I think about “feedback loops” all the time. Great products give people what they want, quickly. Bored? Open TikTok and you’ll be instantly entertained. Want an air fryer? Open Amazon and you’ll find the top air fryer within a few seconds, and it’ll arrive at your doorstep tomorrow. You get feedback on your desires so quickly that you’re not even sure you really want the air fryer and there it is already on your doorstep. Positive or negative, that’s kind of the magic of technology. AI promises to shorten that feedback loop even more. I write this newsletter to help me understand my thoughts and connect with my friends. The process of writing one word at a time helps me think, but once I get better at working with ChatGPT, I probably will just have a conversation with the AI and when I’m satisfied, I can ask the AI to share a piece of writing in my style with you all. That’ll probably be easier (and Ricky Weekly can actually come Weekly), but it’d feel very different for me and for you if you knew that’s how I’m doing it. I write for the “experience.” The experience of struggling to understand my thoughts well enough to express them, and the experience of sharing what I find out with you and have you recognize the thoughtfulness, enough to maybe elicit a connection or response. Of course, this is not to say AI-powered products can’t also create this experience for me. In fact, that sounds like an extremely fun project to work on.

I was listening to The Daily episode about Ozempic/Wegovy, and one of the interviewees who lost a ton of weight said something that stuck with me. She said, “It’s the first time in my life that I’ve ever felt normal. I kept saying this must be what skinny people feel like. This must be how normal people’s brains work…this is what a healthy relationship to food actually presents as.” This stuck with me because it’s exactly what people with ADHD say once they get on Vyvanse/Adderall. They’re floored because whatever was “wrong” with their brain gets chemically switched off and the feedback loop is so immediate and clear that it’s almost shocking. As someone who has expended an inordinate amount of energy managing my own weight and even more helping others manage their attention through Flow Club without pharmacological intervention, the prospect of these “miracle drugs” like the GLP-1 compounds represents the holy grail that no software solution can really compete with.

And so just like writing with AI, if you pull forward the future just a little, it comes back to what gets lost if the basic needs and wants become easy to attain. Will we become more discerning about what we truly want? I’m not just trying to produce a document like meeting minutes, I’m writing to enjoy the experience of understanding my thoughts, learning to express myself and making a connection. It’s a bit more complex with managing weight and attention. I want to manage my weight to improve my healthspan, but in addition to shedding the pounds, it’s also about becoming a healthy person and the process helps create that identity. Similarly with managing attention, how much of the desire is about simply acquiring the ability to pay attention to what you want, and how much is the story we want to believe about ourselves as self-sufficient and capable beings.

I don’t know, but the TV show Westworld is making a lot of sense to me now.

A piece of content I recommend:

Loki on Disney+

Marvel’s Phase 4 has been pretty underwhelming so far, except for Loki. Season 2 was especially amazing.

Bonus: The Acquired Podcast

I’ve recommended an episode of the Acquired podcast before, but I think it’s the only podcast other than Heavyweight that I’d drop everything to immediately listen to as soon as it comes out. If you are a business nerd and you don’t know about Acquired, let me put you on it. Start with the Costco episode.

Bonus Bonus: Everything Jung Kook right now.

I wasn’t a BTS fan because they just felt too foreign to me but what JK is doing right now is kind of amazing. An Asian man successfully combining Michael Jackson, The Weeknd, Justin Timberlake and Usher, singing in English with sexy lyrics and dance moves. This is the first truly sexy Asian man I’ve seen breaking through mainstream American culture and I’m here for it. Just watch this friggin’ video.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I’m in San Fran…errr Lisbon, Portugal this week visiting friends I haven’t seen in ages. Here they are, showing me the Golden Gate Bridge (of Lisbon). We’re driving an hour north to visit wine country later this week. It’s like I never left SF!

A thing on my mind:

There are two kinds of people — the full-hearted and the broken-hearted. Well, I can’t confirm if the first kind exists, maybe relatively, but I’ve definitely felt their presence. Full-hearted people live life with agency. They start with what they want and exert on to the world. They go inwards-and-out. Broken-hearted people walk around looking for missing pieces of their heart. They interact with the world with fixing their broken heart as the primary agenda. Will you love me? Do I belong? Show me I’m okay? They act outwards-in. Because they don’t know where the missing pieces are, they take in the world and react with little agency or control.

I’m one of those broken-hearted people and I’ve been on a journey to re-build my agency. I know my tendencies. I pick up on every breath, twitch, gaze when I interact with people, looking subconsciously for their approval that I am okay. I try not to act on them by dulling my senses. I’ve developed a confident demeanor, a sense of humor, and a practiced vulnerability, all to not let my broken heart take over and fill it with things that look like they help but actually don’t.

I’m curious about full-hearted people. One of them once told me that his confidence comes from knowing that he will be okay at the end of the day. Simple idea, but it frustrated me to no end that I can’t say the same for myself. If it’s a matter of ability, I’ve survived it all, even thrived some. If it’s resources, I’ve got enough and I am extremely resourceful. But being okay is not about any of that. It’s about feeling okay. That’s why I was moved enough to write about finding a home in Taiwan a few issues ago, because part of feeling okay is knowing you have unconditional love:

…I realized I’ve never felt like I had a “home,” defined as a place where I know I have people who love and support me unconditionally. The good news is that there is a place like that in Taiwan, IF I choose to let it be home for me.

A huge number of things I’ve done in life were for the purpose of finding the missing pieces of my heart, only to learn that I’m not going to find them no matter how hard I try. For example, I’ve spent time every year since I was 18 reconnecting with my mom to make up for her absence growing up, and every year, I learn that what is lost is lost. It comes out in small ways, like how she stopped calling me by the nickname I had as a kid, so I can only hear that familiar sound in my memory. Life is a one way street.

Kintsugi is a Japanese art form that takes broken items and repairs them with gold-dusted laquer. The idea is that instead of hiding the fact that the item was once broken like you would in a regular restoration, the laquer not only holds the pieces back together stronger than it ever was, it shows off the gold color to represent the beauty in having survived. I love the idea, but I think it’s wrong if you have to find the missing pieces.

The bad news is the missing pieces of your heart are missing forever. The good news is they are missing forever and you are free to ask yourself what you actually love, and let those things be the new pieces to complete a new heart. The challenge is you miss your old heart so dearly. You just want to go back to when you felt whole. You might not even know what you love because you’ve never had enough agency to let yourself explore that question. You’re afraid. But you’ll find them, and when you do, try as hard as you can to let those things love you, too. Let them be a part of your new heart.

I have a relationship with my mom today that’s different from what I was looking for, but it’s meaningful. I’ve built a “home” of amazing friends around the world. I’ve discovered my love for building companies. These are all things that I want to incorporate in completing my new heart, and I’m learning to accept and love this new heart as much and even more than my original heart.

A piece of content I recommend:

This American Life 811: The One Place I Can’t Go

Comedian Atsuko Okatsuka jokes about being “kidnapped” by her grandmother to America when she was a kid, and goes on a quest to find out from her family the story about why she had to leave Japan and her father to come to America against her wish. Found it interesting because of the parallels to my upbringing.

Giving you one more food for thought as you listen to this episode. I have a theory about immigrants that basically goes…if you are fleeing some f’ed up macro situation like political persecution, war, crime or just a generally poor country, then you fit the immigrant narrative we often talk about here in the US. But if you immigrate from a developed, stable country where life is pretty good for most people, then either you are extremely ambitious, or it was you who f’ed up and you are running away from some micro situation you got yourself in. In that case, our immigrant narrative, where sacrifices were made and hardships were experienced for the betterment of the next generation, doesn’t really apply.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I went to see Dear San Francisco at Club Fugazi. Incredible how much they were able to do from a tiny stage. Highly recommend!

A thing on my mind:

Whenever friends talk about having children, I like to play a game where I guess how many they’d want. The answer is almost always the same number they grew up with, and the rationale never sounds that sophisticated. If you grew up with siblings, you might say, “wouldn’t it be lonely to be the only child?” If you were an only child, you might say, “one is enough because I was happy!” I feel like I can play the same game and guess how you’d want to raise your family. In a city or suburb? In an apartment or a house with a backyard and a pool? Nuclear family? Extended family? Public or private school? Divorce ok? Religion? How much of your career are you willing to sacrifice? I’m ignorant here because I haven’t had to step through these decisions, but my guess is that it might be difficult to think about them from first principles because the stakes are so high. It’s easier to simply copy-paste the model we grew up with if we think we turned out ok.

And then there’s the trauma. If church f’ed you up as a kid, no-church might be a non-negotiable for you. If dad wasn’t around or never showed any love, you might choose to be very present and affectionate to make up for what you didn’t get growing up. A big public school could’ve given you the toughness and personality you are proud to wear today, or it may have scarred you enough that you’d never want to subject your children to that kind of brutality. So it seems like, on top of copy-pasting the parts that worked, we also have non-negotiable reactions to past trauma.

I like thinking about how we come to want the things we want, especially something as consequential as starting a family, but it’s also a bit scary. I think I turned out fine, but I don’t have any desire to copy-paste the “model” I grew up with. While common, my upbringing was not considered “normal” or what a family should look like by the dominant American, Christian-based, family values. That’s scary, but I soothe myself by watching a wholesome Taiwanese reality show that follows a different family’s story every episode. Single-parent, divorced parents, deceased parents, estranged parents, same-sex, cross-cultural, cross-border, differently-abled, multi-generational, adopted, blue collar, white collar, religious, non-religious, etc. and every episode shows me that anything goes and any arrangement can be okay. Taiwan is still a traditional Confucian society, but because of its counter position against China and obsession with freedom, there’s a market for a show like this to highlight the society’s diversity of values and infinite possibilities. That’s encouraging to me.

On my own, I’ve also collected stories from friends and acquaintances that go against the traditional family narrative, like stories of people who decided against marriage and/or starting families, or people who chose to be nomadic with children, homeschool parents, families where one parent works abroad but still loving, etc. I wish there were more positive stories to show a wider variety of ways to live life successfully rather than stories that prey on our fears and insecurities about living life different from the norm.

A piece of content I recommend:

The quest for psychological perfection by on Substack (h/t )

Thanks to my friend Jason Shen I am now a fan of Dr. Gena Gorlin’s writing. Many of the topics she writes about are the same ones I’ve thought or even written about, but I clearly don’t understand them as well as she does.

This particular article talks about the idea of “perfectionism,” how it’s been maligned by society, and separates the “drill sergeant” (aka arbitrary standards) and the “neurotic” kind of perfectionism from the “builder’s ideal” where the perfectionism stems from simply caring about excellence.

Building the Builders

The quest for psychological perfection

Image credit: “Pneuma,” © Kelsy Landin…

Read more

4 years ago · 41 likes · 2 comments · Dr. Gena Gorlin

My bonus rec from Dr. Gorlin is her article on “Vision or Delusion?” (Part 1, Part 2). If you compare them to what I’ve written in the past about this topic, you’ll notice a big gap in my understanding…

If these topics are too serious, here’s a fun rec: Chibi Unity’s EPIC performance on AGT!

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

I went to watch Socially Inept: Tech Roast Show last night. They sold out the Palace of Fine Arts Theater! I know the guys and I remember when they were just getting started with this niche idea of roast comedy for techies almost three years ago…this is what can happen when you focus!

A thing on my mind:

Over the years, friends have asked me why I still work on startups. Some are more honest and point out that I haven’t had much to show for it. So what’s the point? It’s not an easy answer.

I heard “Happiness = Reality - Expectation” at some point. I did the “math,” thought it made sense, and didn’t think more about it. I believe I’m happy, but people close to me aren’t convinced because I’m always stressed and seemingly unhappy. There’s a way “happy” looks, I guess? I have very high expectations for myself, and I’m very open about it, so my happiness level according to the equation is negative.

I don’t remember the last time I had a “good day.” As I’ve gotten older, typical markers of a “good day” have gone away. It’s not enough to just get stuff done, if the things I did don’t matter, then it’s not a good day. It’s not enough to have customers write in about how life-changing Flow Club is, if it’s not followed by an increased in the growth rate, then it’s not a good day.

But I feel happy. You know they say to “enjoy the journey” and honestly what frightens me is that I may enjoy the journey too much that I’m not concerned enough about the destination. Do I not care about winning? Am I not pissed off for greatness? I think I am totally pissed, but the thought that I may not be haunts me.

I tell people that I like the stress, but they don’t believe me. Some of them have seen me when I’m really down or watched me cry. I tell people I’m happy because I get to play this really difficult game of my own choosing, and it’s endlessly challenging and stretching of my abilities. This game never lets me have a moment. I even chose a co-founder who is exactly like me, so we never let ourselves have a moment. It’s not easy to work with us. It’s not easy for us to work with each other. None of this looks happy.

I am very ambitious. I’ve always been that way. I don’t think I’ve ever felt good about myself or anything I’ve accomplished. Good things rarely register in my head, and I often need people to tell me what I did for me to think about it a little more. I remember finding out I got into Stanford. I was taking a nap because I had just come home from closing the cafe I worked at, and I still had a ton of homework to do. Admission results came out at 9pm, my dad woke me up to check. I told him which ones I got into, and went back to my nap. I didn’t really think much about it until later because while that was the goal at the time, I knew I wanted more. I wasn’t even sure what it is I wanted or even understood why I wanted it. I just knew there was more. Actually going to Stanford only raised my ambition because what I thought was my ceiling got pushed way up just from observing the brilliance of the other students. I got a glimpse of what it means to be “world class,” and I’ve stuck around the Bay Area because this is where there’s a high concentration of people who are world class at what they do.

Having a singular why for your ambition may even be dangerous. For the longest time, my why was my mom and my family. To “get out” and put everyone around me on a better path in life was my why. But over time, I discovered that it’s not my job. People I love will be happy or unhappy regardless of what I do for them. Once I realized that, I felt like a big part of my why got taken away. I wasn’t lost per se, but there was a sense of loss. David told me when we were 23 that the only kind of motivation that is sustainable is intrinsic because if you were in a long distance swim meet, at some point you look around and the only person left is you, there’s no one else to compete with except yourself, and you gotta keep going. David was wise beyond his years, but he sucks at swimming.

I’m reading PG’s essay on How to Do Great Work. I’m not done reading since this is like the longest thing PG has ever written. Still, quoting PG,

Ambition comes in two forms, one that precedes interest in the subject and one that grows out of it.

I think that makes sense. Some ambition is just who you are, your environment, upbringing, and the story you tell yourself as the result of all that, and the other part is just falling in love with the subject of your ambition. The subject of my ambition is building a startup, and seeing that this game is something I can and want to be ambitious about. Because it’s challenging. Because it’s fun. Because I get to work with brilliant people. Because it’s the most honest mirror to see who I am and what I’m made of, even if it’s a lot of (or mostly) luck.

I’m happy because I love learning to balance this ambition with living a good life. I’m often grumpy and frustrated about work, but I know it’s completely self-afflicted, my “predilection.” I hope people close to me can see that while I’m stressed all the time, it’s because I really want it. I also don’t let it take away from knowing how to live a life full of interests, curiosity, good people, and that I know how to be present, love, laugh, care, cry, and just be completely engaged with life.

🤷‍♂️

A piece of content I recommend:

The Inside Story of Nebula - Wendover Productions on YouTube

I’m deep in the edu-tainment corner of YouTube, and all the creators I love there promote a streaming service called Nebula. Here’s a story of how a bunch of people who make content for nerds like me on YouTube built a modern day Discovery Channel (with an assist from the founder of Discovery Channel).

Bonus: This is Love and The Joe Pomp Show

Recommending two short podcasts that I listen to pretty regularly. This is Love features stories about different ways to define love. The Joe Pomp Show is daily bite-size breakdowns of the business of sports.

Finally, Flow Club was in the Wall Street Journal and Men’s Health UK! Men’s Health UK is print only, so I can only link you to the WSJ article.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Wrote something more personal today. Here’s a picture to go with it.

A thing on my mind:

My love for basketball started with baseball. My mom loves watching sports, especially baseball. As an only child, I remember watching a lot of baseball by myself growing up, pretending to be the play-by-play announcer while swinging a small baseball bat. Although I didn’t get to see my mom very often, when I did, baseball is all we’d talk about. That’s our love language.

The only birthday party I remember was at McDonalds. Probably because there’s a picture of it. My dad had just visited the US and brought back a basketball for me. I immediately went to the high school across the street to shoot with it. I later would discover that it’s actually oversized and non-regulation. My dad didn’t know any better, he didn’t care for sports.

I was raised by my dad. My mom didn’t want to be with him, so she’d only visit me occasionally. My dad felt some kind of way about it, and was constantly pitting me against her, telling me over and over that my mom didn’t want me. One time, in one of the countless fights I had with my dad he said, “Why are there always two ‘countries’ in this house? You’re always on your mom’s side, and I’m on the other side.” “Two countries” makes sense in Mandarin. “Two teams,” ironically, would probably make more sense in English. He went on to say, “You and your mom never talk about anything meaningful. All you talk about is sports and which team won. Who cares!”

I moved to the US for 6th grade. I didn’t speak English and kids can be pretty mean. I was scared, but I saw that the mean kids all played basketball! I started joining their games and would always just camp in the corner for the occasional three. My strategy mirrored my personality at the time - be quiet, blend in and try not to get bullied. I also played kickball, which reminded me of baseball. I made friends playing sports, and that’s how I felt safe.

At this time in LA, the Lakers were beginning their dynastic run with Kobe and Shaq. I watched all of the home games on KCAL-9. The Lakers were everyone’s favorite team and it was easy to like them because they were winners. I pretended to be a Lakers fan, but never felt a strong connection to the team. The spark came when I discovered the AND1 Mixtape and the streetball movement, which peaked when Nike made the most iconic basketball commercial of my generation. Whenever that commercial came on air, I’d go outside and start practicing the moves. I showed off the moves in school, which got me more friends and made me feel even safer. Streetball spoke to me, probably because it was about people who couldn’t succeed in the “basketball establishment,” reinvented what it means to play ball, and got everyone’s attention.

Every time I’d fight with my dad, usually about my mom, or just whenever I’m sad, I’d go to Petit Park with a basketball. I’ll join a game if there’s one, or I’d just dribble. Sometimes when I’m really sad, I’d just lay there in the middle of an empty basketball court like in some sad movie and just cry. The lights didn’t go out until midnight, so I was always there, sometimes even after lights out. Petit Park is where I went to cry.

Albert told me that the basketball team was having summer workouts for kids interested in trying out for the freshman team, so I went. I showed up every day that summer in the scorching LA heat. You can see smoke rising from the cement because it was so hot. The workout was entirely conditioning. We didn’t touch the basketball until the very last day. It was brutal and I stuck with it. When school started, I tried out and didn’t make the team. Albert did. Since that was the only thing I was interested in at the time, so I was completely devastated.

I was on the easy track in high school because of ESL and my low PSAT scores. When my hoop dreams ended, I was lost. Around the same time, something traumatic happened in my life. The morning after the traumatic event, I decided to stop being a victim and start taking control of my own life. I started trying harder in school and got a job. I remember that day very clearly because I felt like my whole outlook on life changed in one day. I was 14.

After graduating college, I started living and hanging with a group of friends who seemed to love basketball as much as I did. We all worked on startups. We’d coordinate to leave work at the same time and meet at the gym to ball. We’d get food after and talk shit about the douchebags we met on the court. One of the friends is no longer with us, and I still have his basketball shorts that I borrowed. I miss him everyday. He loved basketball. I remember one time, there was a loose ball followed by a fast break, and our team made 3 perfect passes with no dribble that led to a layup. He ran up to me screaming, “THAT WAS BEAUTIFUL!” If you think a random possession from a pickup basketball game can be beautiful, you are my kind of person. I miss you George.

Basketball showed me that I can improve. The only thing I was good at was dribbling the ball. I couldn’t shoot. I had an ugly shot with my (non-dominant) left hand for whatever reason because that’s just how I was able to get the ball to the basket. I spent a lot of time trying to change my shot to a right-handed shot. No one showed me how to do it, but I’ve watched enough basketball to know what a standard (2-motion) shot should look like. So I just kept working on it. One time, I heard someone explain why you need “backspin” on the ball, and that gave me an idea of what the ball’s rotation should look like if you’re shooting correctly. I got mostly there, and I’m still working on it.

I used to play basketball with a huge chip on my shoulder that made me a selfish player. Partially this is due to really hating being the Asian kid that no one thinks can play, and I’m probably still bitter about not being picked in high school. I even remember losing a 1v1 game to this guy who played on my high school team, and the smug look he gave me afterwards. Eventually, I realized that’s a losing mentality, and tried to change my habits. Since I’m usually the guy bringing the ball up, I decided to only look for a shot every 3rd possession. So if you were smart, you’d pick up the pattern that I’d pass up the ball twice before I decide to attack. I thought I was being a better teammate, but then I started to hear people tell me to shoot the ball because I’m sometimes the best option. I started learning to read the situation to understand who I am and what my role should be in relation to the game and to the other players. I started making the game less about me and what I can do, and more about winning and having the most fun together.

In the last few years, I’ve lost a step on the court. Loving basketball now means focusing on my health. I want to play as much as I can for as long as I can, and that means I have to improve my flexibility, watch my diet, sleep better, etc. There’s a group of old guys that play Sunday mornings at USF, the oldest is 81. I asked him for his secret, and he said to “never stop playing.” “Even when you go on vacation, find a basketball court.” The idea is that your body will keep letting you do the things you regularly do, but as soon as you stop, your body stops, potentially forever.

I started re-connecting with my mom as an adult. Our conversation is now mostly about basketball instead of baseball because it’s the more interesting one to watch these days. I have a much richer life now with a career I deeply care about. Yet, I don’t seem to be able to talk to my mom about all the other wonderful things in my life. She didn’t go to college, she doesn’t know what startups are, and honestly she’s not that interested. That made me a little sad at one point because I wanted to share with her all the other wonderful things I got into and who I turned out to be. I remember thinking maybe my dad was right—talking about sports is meaningless. I told my therapist this, and she said, “If sports is how you connect, then connect over sports. As long as you are connected, there will be opportunities to share more of your life with my mom in the future.” Maybe. I think I’m okay though even if that day never comes. Because my dad is wrong. Loving basketball and sharing that with the people love is the most meaningful thing in the world. Like George said, it’s BEAUTIFUL!

A piece of content I recommend:

“Baseball is who I am.” The Unforgettable Story of Sarah Langs on ESPN Daily.

I was inspired to write about basketball after hearing this story about Sarah Langs and her love for baseball. It was relatable because like her, I’m also not an athlete. There are plenty of heart-warming stories out there about athletes, but not so much about fans and their connection to the game.

Bonus Rec #1: Secrets Of The Great Families - Scott Alexander

Bonus Rec #2: Entire Comedy Show of ONLY Crowd Work - Akaash Singh Comedy

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Went to the mountains by Los Gatos last weekend for a retreat with my co-founder David. I had such a good time! We’re close like brothers, but as we’ve gotten older and life’s gotten busier, we don’t really get to connect much anymore. Our conversations are usually all business and to the point so we can get to our lives. Highly recommend just disconnecting (slow wi-fi) in order to connect.

A thing on my mind:

I was re-reading Sam Altman’s “How To Be Successful,” which is great but this tiny part caught my attention (emphasis mine):

Self-belief must be balanced with self-awareness. I used to hate criticism of any sort and actively avoided it. Now I try to always listen to it with the assumption that it’s true, and then decide if I want to act on it or not. Truth-seeking is hard and often painful, but it is what separates self-belief from self-delusion.

Hate criticism? Actively avoid them? I might’ve been a masochist for too long because I was surprised to read that.

I remember in college meeting a lot of brilliant, confident and often delusional characters. One time, one of them had a big public fall from grace. My friends and I were talking about it (admittedly in a moment of schadenfreude) and we made up this idea of the “bullshit-to-substance ratio.” Basically, you gotta walk the walk, otherwise at some point the BS-to-substance ratio becomes too high that it becomes plenty obvious to everyone you are full of it. The person who fell from grace seemed to have tripped over the line and got burned for it. But it was interesting to me how someone’s BS-to-substance ratio can even get that high to begin with? Then I got into the startup game, and this story seems to be playing out all the time. See SBF and Liz Holmes for the most prominent examples.

I used to be kind of judge-y about this, but over the years I’ve come to see that maybe it’s necessary, and a lot more necessary for some? Believing in yourself is hard and just like everything it takes practice and looking for positive feedback loops. Obviously, we all should strive for healthier confidence that incorporates criticism, but criticism is not easily digested as part of a positive feedback loop. Also, the more ambitious you are, the more confidence you need. The Miami Heat is playing out of their minds right now, and they talk about how Jimmy Butler is fully trusting role players like Gabe Vincent and Caleb Martin to make them feel like they’re the best in the world. I’m guessing there’s not a lot of criticism going on in that locker room right now.

I’ve met people over the years who are very good at protecting their egos for whatever reason. I know this guy who is great at noticing whenever he feels even slightly bad, and would make it a point to do self-care or take time off to restore the ego. I used to think that’s low pain tolerance or a lack of courage, but now I think I can see the wisdom in it. If you know you need your confidence to be at a certain level in order to operate, you need to actively shield yourself from being derailed. I can’t imagine there weren’t people around SBF telling him he’s flying too close to the sun, but I think I can understand why he’d want to tune that out and only look for positive reinforcement. I’ve written in the past about how I want to run my startup like I play basketball, and it’s the same idea of doing everything you can to feel like you’re the best when you step on the court.

Obviously this is a very generous take, and I’m not saying I’m gonna go delude myself. I’m too grounded for that. I’m just saying maybe all of this is a lot more deliberate and necessary if you are Gabe Vincent and you have to think that you are the best option on your team in order to make the game-sealing shot.

A piece of content I recommend:

Staring into the abyss as a core life skill - Ben Kuhn

If you read what I wrote and you’re like wtf Ricky 🙄, then go read Ben Kuhn for an actual smart take. I think it’s a much more grounded perspective. He says to be successful is to have no delusions and ample amount of courage to stare into the abyss, face the music, or whatever you want to call it, and then make bold changes on schedule that are not delayed by your ego.

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

Great job planning a surprise birthday dinner for me. I was surprised! Thanks to all the friends who showed up and hope to see the rest of you soon.

A thing on my mind:

Every time I come back to writing after a long time away, it’s hard to start. I want to let you in on all the things I’ve been thinking about, but I know that’d be too much.

I visited Taiwan in February for the first time in four years because of Covid. I’ve been visiting every year since I was 18, so the four-year gap was the longest I’ve experienced as an adult, which made it less routine and more eye-opening for me. Without going into details, the short of it is that I realized I’ve never felt like I had a “home,” defined as a place where I know I have people who love and support me unconditionally. The good news is that there is a place like that in Taiwan, IF I choose to let it be home for me. I’ve spent roughly a third of my life in Taiwan, Los Angeles, and the Bay Area, and there are relationships and places that can be markers of “home” in each of these places, but when it comes to a grounded, secured feeling of unconditional love, I think the closest is in Taiwan, followed by the Bay, then LA.

My Taiwan trip triggered a lot of feelings that resulted in recurring nightmares about my childhood, which led me to try to address them more proactively. I’ve never used words like “trauma” and “abuse” when talking about my story, but it’s interesting to hear my therapists (old and new) use these words back at me. Perhaps I can benefit if I lean into those concepts more explicitly in my therapy. I read (listened) to a book called Adult Children of Emotionally Immature Parents, and while the book title is great (90% of the value) and some of the stories are validating, the recommendations on what to do were underwhelming for me. I’ve developed all the coping techniques on my own the hard way in order to get to where I am today.

From talking to my therapist, I’m realizing I need to understand better what makes me happy outside of work, do more of it, communicate my boundaries, and ask for what I want. It’s really hard for me. One thing I know that makes me happy is being with my friends because they are the main reason why the Bay Area feels like home #2 for me, but it’s getting much harder to see each other at this age. Since Covid I’ve been slowly mourning the death of some of my friendships, and each person leaves a big gaping hole in my heart. The reason why I love writing this newsletter is because it’s a way for me to reach out and connect with friends I don’t get to see often. If you’re reading this, know that I’m sending you LOL (Lots of Love)!

A piece of content I recommend:

Andrew Schulz - INFAMOUS on YouTube

This is probably the best special I’ve seen. Andrew dances on the line between offensive and funny like his name is Dave Chappelle, and I think he’s way funnier than Chappelle. I think he might be controversial? I’m not sure but wouldn’t surprise me.

Bonus: Staring into the abyss as a core life skill - Ben Kuhn

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.