Buying & Selling
M&A, exits, earnouts, and the wire that didn't come on the day it was supposed to.
I once sat at my kitchen table refreshing my online banking for nine hours waiting for a wire that was supposed to land at 9am. It came in at 4:47pm. I had aged about a decade by then and decided I should probably write down everything I'd learned about selling a business so other people didn't have to do that alone.
I've now been on both sides of the table maybe a hundred times. I've sold companies for life-changing money. I've bought companies at 3x earnings and watched them quintuple. I've also blown deals over things that, in hindsight, were embarrassingly small — a working-capital adjustment, a sentence in a non-compete, an ego flare from a founder who couldn't stomach a single line of due diligence.
Most M&A advice is written by people who get paid on close. Mine isn't. The pieces here cover what actually happens — the taxonomy of buyers and what they really want, the companies we admire and why, and the case for selling to a holding company instead of a PE firm that will gut your team to hit a model.
If you're thinking about selling, or thinking about buying, the holding-companies pieces are the natural next stop.
Start here
Start with the buyer
I've been on both sides of the table. Selling a company to the wrong person and buying 40+ businesses. Here's what I wish someone had told me before I signed.
The buyer I wished existed
I almost sold my company to a PE firm for $50 million. The wire never came. Here's why I built a different kind of buyer for founders who want a permanent home for their business.
Own the noun
From a $29 coffee maker to the world's biggest designer network. The pattern behind every business Tiny has acquired and the six things we look for.
More on buying & selling
Three cans before noon
How a Tiny acquisition of a tiny Montreal yerba mate company became an unlikely partnership with one of the world's most followed neuroscientists.
The misunderstood platypus
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.
Sixty percent of everything I touched failed
My success rate? About 40%. Here's what every failure taught me about finding businesses that actually work.
I accidentally bought a concrete company?
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.
I lit ten million dollars on fire trying to compete with Asana
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.
How to succeed by failing (over and over again)
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.
Your business shouldn't do good
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.
Pascal's wager for AI
If a godlike alien intelligence were arriving in 2030, you'd prep accordingly. AI is that alien. Here's how I'm hedging—through power infrastructure and digital employees.
30,000 views for a paper store
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.
I solve every business problem by firing myself
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.
Sell to people who don't care what it costs
Why software for teachers is a nightmare and software for hedge fund employees is easy mode—the underrated power of selling to people who don't pay out of pocket.
Howard Stern is Getting Ripped Off
Howard Stern looked wildly overpaid until I ran the numbers. Then he looked underpaid, trapped inside Sirius while subscription podcasting became a monster business.
Slack’s $2.8 Billion Dollar Secret Sauce
How Slack stole a multi-billion dollar market by becoming everyone’s favorite sassy robot sidekick.
Fire in a Crowded Forest
In 2008, I was buying bulk potatoes to make rent while clients stopped paying. That fear permanently changed how I run every business.
Growth Shouldn’t Hurt
I used to think headcount meant misery. Then I realized growth only hurt because I had built the wrong systems and insisted on doing the wrong jobs.
The Berkshire Hathaway of The Internet
Buffett made buying a business look almost absurdly simple. I wanted Tiny to be that kind of buyer for internet companies: fast, fair, and allergic to deal theater.
Dribbble 2.0
Dan Cederholm was my web design hero. Years later, I annoyed him into letting Tiny buy most of Dribbble without wrecking what made it special.
Skateboard, Bike, Car
MetaLab once refunded a $100,000 strategy project because we forgot what we were good at. The fix was simple: stop making decks and start making things people can use.
Business Kryptonite
A cupcake shop on reality TV explained why Instacart scared me: when every order loses money, scaling just makes the hole deeper.
We need to talk about startups…
The 2015 startup market felt like 1999 with better hoodies. This was my warning that cheap money and big valuations do not repeal gravity.
Designer News 2.0
LayerVault was shutting down, Designer News was at risk, and I could not resist buying the design community I had been reading since the beginning.
Unicorns vs. Horses
A VC told me I was stupid for bootstrapping Flow. I wanted to be In-N-Out, not McDonald's: slower, profitable, independent, and still standing decades later.
Ballpark Has a New Home
We finally found Ballpark a new home after realizing Flow had swallowed all of our attention and our first SaaS product deserved better parents.
The Fallacy of Hoop Jumping
The design industry loves telling people to pay their dues. I think that is mostly a trap. Start where you want to end up and let the work do the selling.
We’re Selling Ballpark
Ballpark was our firstborn SaaS product, then Flow grew five times bigger and stole the oxygen. Selling it felt like the responsible thing to do.