Writing
Essays
Long essays on holding companies, selling businesses, money, marriage, and the things I got wrong.
Featured
Divorce is awesome
On unhappy marriages, the science of staying together for the kids, and why divorce is shameful when it shouldn't be.
I lit ten million dollars on fire trying to compete with Asana
How I burned $10 million bootstrapping a productivity app against a billionaire-backed competitor, the slow-motion train wreck of Flow, and the six lessons I bought at full price.
I got diagnosed with a brain disorder
After a neurologist flagged my working memory in the 20th percentile, I went down the ADHD rabbit hole, got formally diagnosed, started Vyvanse, and finally heard quiet for the first time.
She pushed the needle into my arm
What ketamine therapy actually feels like: an hour of dissolving into nothing, decades-old memories surfacing, and emotional wounds that 10 years of talk therapy couldn't touch.
All essays · 77
Have babies with the wrong person
On the birth of my daughter, why young people are obsessed with the prep work of dating but refuse to eat the meal, and why you should just have the freaking baby.
I gave $16 million dollars away
What I learned about giving money away—and why scientific research is the part of philanthropy that feels most like venture capital.
Rewriting fear
When you recall a fear and your body doesn't panic, your brain re-files the memory as 'not a big deal.' That's how I went from sweating through my shirt to cool as a cucumber.
I spent 25 years treating the wrong thing
On waking up in Maui certain I had cancer, the little pink pill that finally turned my brain into a library, and the prison most of us live in without realizing the door is unlocked.
Fight with a pulse oximeter
How John Gottman's Aftermath of a Fight conversation plus a $20 pulse-ox sensor turned our worst arguments into something productive.
Three cans before noon
How a Tiny acquisition of a tiny Montreal yerba mate company became an unlikely partnership with one of the world's most followed neuroscientists.
The misunderstood platypus
Chris and I built Tiny from a handshake in my apartment into a public holding company with 32 businesses, $250M+ in revenue, and no clean box to fit inside.
The buyer I wished existed
I almost sold my company to a PE firm for $50 million. The wire never came. Here's why I built a different kind of buyer for founders who want a permanent home for their business.
Start with the buyer
I've been on both sides of the table. Selling a company to the wrong person and buying 40+ businesses. Here's what I wish someone had told me before I signed.
Own the noun
From a $29 coffee maker to the world's biggest designer network. The pattern behind every business Tiny has acquired and the six things we look for.
Sixty percent of everything I touched failed
My success rate? About 40%. Here's what every failure taught me about finding businesses that actually work.
I accidentally bought a concrete company?
How Warren Buffett's '10% of a classmate' question and an unpaid speech at the University of Victoria turned into co-ownership of a precast architectural concrete business.
I asked ChatGPT to be my relationship coach
Zoe and I sat in our den with our jaws on the floor, reading a CIA-grade dossier on our marriage written by an AI that had never met us. Here's how that turned into Deep Personality.
From an 8 to a 1
How adding Guanfacine on top of Vyvanse and an SSRI gave me the persistent zen-like calm I'd never felt before.
The house is the patient
Mine was. Why airtight modern houses trap VOCs, mold, radon, and EMF—and what I found when I finally got a proper test done.
Divorce is awesome
On unhappy marriages, the science of staying together for the kids, and why divorce is shameful when it shouldn't be.
Oh, to be 86 again
What Charlie Munger taught me through dinners, divorce, the death of a 9-year-old son, a bear market and a hundred years of refusing to wallow.
I lit ten million dollars on fire trying to compete with Asana
How I burned $10 million bootstrapping a productivity app against a billionaire-backed competitor, the slow-motion train wreck of Flow, and the six lessons I bought at full price.
Start a group thread
Why I stopped trying to make friends by accident and started building deliberate rituals — forum, pickleball, lunch club, Camp Dad, and the group text that started it all.
Where are the protest songs
Every few decades, the pendulum swings and music answers. So why does this one feel quieter than the late '60s?
Letting people down
Why I started replying maybe to every commitment, set up an auto-responder telling people not to expect a reply, and discovered that letting people down is the secret to happiness.
How to succeed by failing (over and over again)
After 20+ companies and a 40% success rate, here are the six ingredients I keep coming back to: a simple model, low competition, an obvious need, the right co-founder, the visionary-integrator pair, and the right incentives.
Your business shouldn't do good
Why charging less might be the most selfish thing you can do—a counterintuitive case for separating profit-maximization from philanthropy, and the math behind why a struggling do-good business helps nobody.
Pascal's wager for AI
If a godlike alien intelligence were arriving in 2030, you'd prep accordingly. AI is that alien. Here's how I'm hedging—through power infrastructure and digital employees.
Do you want people to like you?
After two hours of monologue at lunch, I was reminded why the Harvard research is so simple: ask follow-up questions, and watch people light up.
The snoring score
I ignored the box for three months. Then Zoe's sleep got better, then mine did, then I cut my snoring by 70% and she stopped elbowing me at 3am.
I want you to hate me
On the courage to be disliked, escaping the prison of reputation, and why having 2% of people hate you is the price of an authentic life.
30,000 views for a paper store
How two University of Victoria business school students with great taste, fast pace, and a viral reel about a stationery store became my newest co-founders.
She pushed the needle into my arm
What ketamine therapy actually feels like: an hour of dissolving into nothing, decades-old memories surfacing, and emotional wounds that 10 years of talk therapy couldn't touch.
The Starbucks floor mopper
Mark Nichols had mopped floors at a Burlington Starbucks and that was about it. I gave him my agency anyway. He turned out to be the man for the job.
Humans can't sort email
Why human assistants couldn't keep my inbox clean—and how an AI agent built in Lindy now triages 80% of my email before I ever see it.
2,800 years of the kids aren't okay
Twenty quotes spanning 2,800 years of grown-ups being convinced civilization is doomed and the next generation is feral.
I solve every business problem by firing myself
How an old friend's $3,600 luxury keyboard atelier taught me the visionary-integrator pattern that runs through every great company—and why most founders don't need money, they need someone to do the parts they hate.
Men: no offense, but you dress like shit
How I went from a personal stylist to ChatGPT to a wardrobe app called Vibe—and why outfit beats abs every time.
I got diagnosed with a brain disorder
After a neurologist flagged my working memory in the 20th percentile, I went down the ADHD rabbit hole, got formally diagnosed, started Vyvanse, and finally heard quiet for the first time.
Never call a restaurant again
I hate calling restaurants to book reservations. Ten minutes in Lindy and I had a Claude-powered voice agent that does it for me—handles allergies, alternate times, and calendar invites.
Sleep like Dracula
Huberman scared me into dimming every light after sunset—and to my surprise, it dramatically improved my sleep.
The tail end
Tim Urban's tail-end essay haunted me for years. The realization it triggered: I hadn't danced in over a decade. So I found a sober Sunday-morning rave and started again.
I hate wealth managers
Most wealth managers add zero value and charge a fortune for something you could do yourself for free. But if you really want a guy, here's the one I trust.
Parent lazier, not harder
Modern parenting is a stress-induced crisis because we've abandoned how humans actually raise kids. The fix isn't more effort. It's alloparenting, free-range play, and trusting your kids to entertain themselves.
Therapy for nerds
Why Dialectical Behavior Therapy clicked for me where talk therapy had limits—and the two principles I use to snap myself out of unproductive moments.
How business made me twenty best friends
I joined a forum fifteen years ago to swap business advice. I ended up with twenty of my deepest friendships—and a model for how to build real community as an adult.
Magic becomes Tuesday
How quickly an iPhone-like miracle becomes background noise—and why we shouldn't forget how insanely amazing the modern world actually is.
Six Porsches worth of SaaS savings
Why every dollar you save on SaaS goes straight to the bottom line, why most companies stop negotiating once they get big, and what we did about it.
Slow down time
Your brain is a prediction engine. If everything matches its model, it stops forming memories. The fix is one new route per day.
Miss kicking the ball
The thing that brought you joy in the first place is the first thing you stop doing as your business grows. Writing a book reminded me what kicking the ball feels like.
Alone in my living room
Spatial FaceTime is the first time I've felt the future come into focus through Apple's headset—and a glimpse of what social hangouts will look like in a few years.
Sell to people who don't care what it costs
Why software for teachers is a nightmare and software for hedge fund employees is easy mode—the underrated power of selling to people who don't pay out of pocket.
I hired a shrink to 360-review my life
Mohnish Pabrai told me about a psychologist who'd done a deep audit of his entire life. I hired the guy. Six weeks later I had a shit-sandwich report that ended my marriage and changed everything.
I treat myself like a drug addict
Anything that stimulates dopamine can hook you—including your phone. Here's the self-binding protocol I now use to keep mine inert.
Your new house is gassing you
When David Heinemeier Hansson's energy-efficient dream house started making his wife collapse, the culprit was formaldehyde and not enough airflow. Here's what I changed in my own home after I heard the story.
Why I stopped hiring myself
Why I changed my mind on $60,000 recruiter fees—and the three reasons hiring one usually saves a busy CEO money rather than costing them.
The Psychology of Human Misjudgement
The Munger talk I come back to whenever I need a reminder that most bad decisions come from predictable human wiring, not mysterious personal failure.
Joe Rogan Got Ripped Off by Spotify
Spotify's Joe Rogan deal looked enormous. I thought it was cheap, because the biggest podcast in the world was probably worth far more than the headline number.
The Power of Anti-Goals
How I designed my perfect day by fixating on what I hate
The Daily Podcast Revolution
I had spent hundreds of hours with Brian McCullough in my ears before we ever met. Then he pitched me on daily podcasts for every niche, and Tiny wrote the first check.
Howard Stern is Getting Ripped Off
Howard Stern looked wildly overpaid until I ran the numbers. Then he looked underpaid, trapped inside Sirius while subscription podcasting became a monster business.
Slack’s $2.8 Billion Dollar Secret Sauce
How Slack stole a multi-billion dollar market by becoming everyone’s favorite sassy robot sidekick.
Fire in a Crowded Forest
In 2008, I was buying bulk potatoes to make rent while clients stopped paying. That fear permanently changed how I run every business.
Growth Shouldn’t Hurt
I used to think headcount meant misery. Then I realized growth only hurt because I had built the wrong systems and insisted on doing the wrong jobs.
The Berkshire Hathaway of The Internet
Buffett made buying a business look almost absurdly simple. I wanted Tiny to be that kind of buyer for internet companies: fast, fair, and allergic to deal theater.
Dribbble 2.0
Dan Cederholm was my web design hero. Years later, I annoyed him into letting Tiny buy most of Dribbble without wrecking what made it special.
Skateboard, Bike, Car
MetaLab once refunded a $100,000 strategy project because we forgot what we were good at. The fix was simple: stop making decks and start making things people can use.
Just Start
I did not really read The Now Habit. The title was enough. The useful part is embarrassingly simple: take one step before the idea curdles into procrastination.
Geoff Bozos
For every Jeff Bezos, there are 99 Geoff Bozos. This is the math that kept me bootstrapped when everyone else was chasing unicorn odds.
Business Kryptonite
A cupcake shop on reality TV explained why Instacart scared me: when every order loses money, scaling just makes the hole deeper.
We need to talk about startups…
The 2015 startup market felt like 1999 with better hoodies. This was my warning that cheap money and big valuations do not repeal gravity.
Designer News 2.0
LayerVault was shutting down, Designer News was at risk, and I could not resist buying the design community I had been reading since the beginning.
The Rockstar Myth
The lone-genius designer myth is a burnout machine. Hiring scared me, then it became the thing that let me keep doing the work I actually loved.
Unicorns vs. Horses
A VC told me I was stupid for bootstrapping Flow. I wanted to be In-N-Out, not McDonald's: slower, profitable, independent, and still standing decades later.
Ballpark Has a New Home
We finally found Ballpark a new home after realizing Flow had swallowed all of our attention and our first SaaS product deserved better parents.
Getting Zapped
Business teaches through pain. You hire badly, launch badly, get zapped, and then decide whether the scar becomes a lesson or a cage.
Build The Rocket First
We built Flow with three people, no venture money, and client work paying the bills. A year later it was doing $500K in recurring revenue.
The Fallacy of Hoop Jumping
The design industry loves telling people to pay their dues. I think that is mostly a trap. Start where you want to end up and let the work do the selling.
Introducing Flow
Before Flow became my $10 million lesson, it was a simple idea: one place for work tasks, home tasks, delegation, and the grocery list I kept forgetting.
The Little Things
Two tiny Flow changes, annual billing and one green upgrade button, did more for revenue than months of big product work.
We’re Selling Ballpark
Ballpark was our firstborn SaaS product, then Flow grew five times bigger and stole the oxygen. Selling it felt like the responsible thing to do.
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