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

I was eighteen and had $400 in the bank when I started a small design agency, MetaLab, out of my apartment in Victoria. There was no plan. My first paying client was a pulled-pork BBQ joint, and I taught myself web design one project at a time. That agency eventually became Tiny.

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 them alone, hold forever. In 2023 we took it public on the Toronto Stock Exchange under the ticker TINY.

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 a brain dump of whatever I’m thinking about in the particular moment I sit down to write it.

Outside Tiny, I run Tiny Foundation with my partner Zoe. It funds long-form journalism and science. We’ve given away a little over $16 million so far. I also run Folly Partners, my personal holding company, where I back a small number of founders doing amazing things and invest in boring, conventional things like stocks and real estate.