Things I Got Wrong
The $10M I lost on Flow, the agencies I burned, the deals I blew, and what each of them actually cost me to learn.
I lost ten million dollars on a project-management app called Flow because I thought we could out-build Asana with a smaller team and a prettier UI. We could not. The post-mortem is somewhere in this section if you want the play-by-play of how a smart group of people set ten million dollars on fire over four years while telling each other things were almost about to turn around.
I write about my mistakes more than my wins because the wins mostly happened by accident and the mistakes are where the actual lessons live. Most business writing inverts this — you get a clean retroactive narrative where the founder always knew, the strategy was always coherent, and luck never gets a credit. That's not how any of it actually went for me, and pretending otherwise is how you end up with a generation of operators who think they're broken because their real life doesn't match the case study.
Read the $10M Flow story for the full anatomy of a slow-motion disaster. Read how I succeed by starting companies that mostly fail for the framing that lets me keep doing this without quitting in shame every eighteen months.
If you find any of this useful, the money and ambition pieces and marriage and family cover the personal-life version of the same lessons.
More on things i got wrong
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.
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.
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 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.
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.
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.
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.
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.
Sleep like Dracula
Huberman scared me into dimming every light after sunset—and to my surprise, it dramatically improved my sleep.
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.
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.
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.
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.
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.
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.
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.