Never Enough — Andrew Wilkinson

On how money and success quietly wrecked my social life, and the rituals I built to become Friend Rich instead.

A few years ago I paid Jack Skeen to interview the people closest to me and write a 360 of my life.

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.

What ADHD treatment, $16M of philanthropy, beta blockers, and the right contact lenses taught me about not spending decades trying to fix the wrong problem.

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.

When you recall a fear and your body doesn't panic, your brain re-files the memory as 'not a big deal.'

What I learned about giving money away—and why scientific research is the part of philanthropy that feels most like venture capital.

How a Tiny acquisition of a tiny Montreal yerba mate company became an unlikely partnership with one of the world's most followed neuroscientists.

Why I built an anti-conference event that prioritizes warmth over status, plus Mateina with Andrew Huberman, new AeroPress products, and pulse sensors for fighting better.

How John Gottman's Aftermath of a Fight conversation plus a $20 pulse-ox sensor turned our worst arguments into something productive.

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.

I almost sold my company to a PE firm for $50 million.

I've been on both sides of the table.

From a $29 coffee maker to the world's biggest designer network.

My success rate?

A short ask: upvote Deep Personality on Product Hunt and complete the karmic cycle for years of free writing.

How a Twitter notification ended up in the Epstein files, plus the ChatGPT prompt that led to Deep Personality, an accidental concrete company, and the cure for not being able to burp.

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.

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.

On unhappy marriages, the science of staying together for the kids, and why divorce is shameful when it shouldn't be.

Mine was.

How adding Guanfacine on top of Vyvanse and an SSRI gave me the persistent zen-like calm I'd never felt before.

Life lessons from Charlie Munger, why public markets misunderstand Tiny, and a year-end roundup of favorite books, music, and movies.

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.

Every few decades, the pendulum swings and music answers.

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.

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.

The story of how I burned $10 million trying to compete with Asana, plus rituals for building friendships and the protest songs we're missing.

Hosting a small, family-friendly retreat in Maui for at-scale holdco operators—the rare role with its own set of headaches and almost no peer support.

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.

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.

My recipe for starting a profitable business: a simple model, low competition, an obvious need, the right co-founder, and aligned incentives.

If a godlike alien intelligence were arriving in 2030, you'd prep accordingly.

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.

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.

I ignored the box for three months.

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.

Mark Nichols had mopped floors at a Burlington Starbucks and that was about it.

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.

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.

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.

How I built an AI inbox triage that beats human assistants, plus Tiny's Q1 2025 results, the $150M fund explained, and finally good Canadian credit cards.

On hating conferences, an open invitation to the third annual Interesting People event in Victoria, and what it actually takes to make others feel warm and gooey inside.

Twenty quotes spanning 2,800 years of grown-ups being convinced civilization is doomed and the next generation is feral.

How a college student's elevator pitch turned into PressurePros, plus the inversion habit that calms my cortisol every morning.

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.

Why we bought a majority stake in Serato, the story of Norbauer & Co's luxury keyboards, and the visionary-integrator pattern behind every great company.

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.

How I went from a personal stylist to ChatGPT to a wardrobe app called Vibe—and why outfit beats abs every time.

I hate calling restaurants to book reservations.