I started a company with $400 and never figured out how to stop.

I was twenty-five and had $400 in the bank when I started Tiny. There was no plan. I’d been running a small design agency, MetaLab, out of a coffee-stained apartment in Victoria, and one day a friend asked if I wanted to buy his software business. I said yes before I worked out where the money would come from. That turned out to be a recurring pattern.

Twenty years later, Tiny owns Letterboxd, AeroPress, Serato, Dribbble, Creative Market, MetaLab, and a few dozen other businesses across software, consumer goods, and media. We model the structure on Berkshire Hathaway: buy great companies, leave the founders alone, hold forever. In 2023 we took it public on the Toronto Stock Exchange under the ticker TINY. For about eighteen months I was, on paper, a billionaire. The stock has since done what stocks do.

The outside got tidy. The inside didn’t. I got divorced. I got an ADHD diagnosis in my mid-thirties that explained roughly the previous fifteen years of my life. Somewhere along the way I got pretty sure most of what I’d been chasing wasn’t worth the chase.

That stretch is what the book is about. Never Enough is a memoir about getting what you wanted and finding out it was the next thing you had to defend. I wrote it because I’d spent twenty years performing a version of success I no longer believed in, and the only way out was to say so out loud.

The newsletter is the rolling, slightly-less-edited version. Every couple of weeks I send something to about thirty thousand people: a story, a mistake that cost me real money, a recommendation I actually use, an opinion I’m willing to defend. It’s the writing I wish someone had sent me at twenty-five — direct, occasionally embarrassing, free of the motivational-poster register that infects most business writing.

Outside Tiny, I run Tiny Foundation with my friends. It funds long-form journalism and open science. We’ve given away a little over $16 million so far. I also run Folly Partners, my personal holding company, and back a small number of founders I actually want to spend time with. The job has gotten quieter and weirder over the years, which is the right direction.

Long time horizons solve more problems than tactics. The best decision I ever made about Tiny was to never sell anything. The best decision I made about my own life was to stop measuring it in quarters. Almost every regret I have came from optimizing for the next eighteen months at the expense of the next thirty years.

Friendship beats networking by an embarrassing margin. The best deals I’ve done, the best partners I’ve found, the best advice I’ve gotten — all of it came from people I genuinely liked, talking about things that had nothing to do with work, often years before there was any deal to do. I’d rather have ten close friends in business than a thousand contacts.

Money is a tool with a strong opinion of itself. Used well it buys time, freedom, and the ability to pay other people’s hospital bills. Used badly it becomes the scoreboard, then the identity, then the prison. The trick — which I’m still practicing, badly — is to keep using the tool without letting the tool start using you.