Hello,
friend.
I’m Andrew. I’m the co-founder of Tiny (we’re the owners of Letterboxd, AeroPress, Serato, and many others).
In my spare time, I fund science and journalism and invest in incredible entrepreneurs.
Over the years, I’ve…
- Had a short stint as a barista
- Started dozens of businesses (most of them failed)
- Gotten divorced
- Invested in 150+ startups (and regretted it)
- Lit $10 million on fire building a to-do app
- Bought dozens of wonderful businesses
- Written a memoir about why none of it made me happy
- Been a billionaire on paper...then watched my stock drop 80%
- Gotten diagnosed with a brain disorder
I write a Friends Newsletterto about 30,000 people — a brain dump of recommendations, stories, and things I’m thinking about, once or twice a month.
Recent issues
See all issuesWhat I write about
Building Tiny
Holding companies, capital allocation, the Berkshire-of-the-internet thing.
Buying & selling companies
M&A, exits, earnouts, the wire that didn't come.
Money & happiness
The hedonic treadmill, the Munger lunch, why a billion on paper didn't fix me.
Things I got wrong
The $10M I lost on Flow, the agencies I burned, the deals I blew.
Marriage & family
Divorce, dad trips, parenting two boys, the stuff nobody warns you about.
ADHD & anxiety
Vyvanse, Guanfacine, SSRIs, and what actually quiets the brain.
Friendships & forums
Interesting People, Camp Dad, the rituals that keep my friends close.
Victoria & recommendations
Restaurants, books, gadgets, podcasts, things I'm using.
Never Enough
A memoir about getting everything you wanted — and still wanting more.
“Like going to business school and therapy all in one book.”
“A massively important topic written by a guy with firsthand experience. Everyone should read this.”
A conversation
See all 87 interviewsBuilding The Berkshire Hathaway of Tech with Harry Stebbings
Harry Stebbings on Tiny's anti-VC thesis — sustainable vs unsustainable growth and the relationship between money and freedom.
Hi, I’m Andrew.
I dropped out of college, made coffee for $6.50 an hour, and started a design agency from my parents’ basement called MetaLab. I taught myself web design from a book by Dan Cederholm and won my first client by faking that I had a team.
That turned into Tiny — a Canadian holding company that now owns 40-plus businesses, including Dribbble, AeroPress, Letterboxd, and Mateina. We took it public in 2023.
I wrote Never Enough because the inside of all that didn’t match the outside, and I’d rather be honest about it than keep pretending. The newsletter is the ongoing version of that — recommendations, mistakes, and a few things I’m thinking about. Twice a month.
I write smaller things on X — and post the occasional photo elsewhere.
The occasional long-form post — usually a hard-won lesson dressed up in business clothes.
Still here?
Drop your email. I’ll send something every couple of weeks. Unsubscribe whenever — I won’t take it personally.
(I will take it personally.)