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. 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 looked nice. The inside wasn’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 realized most of what I’d been chasing was hollow.

That stretch is what my book is about.

My Friends Newsletter is the rolling, slightly-less-edited version. Usually once a month, I send something to about thirty thousand people: a story, a mistake, a random recommendation. 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.