Building Tiny
Holding companies, capital allocation, and the Berkshire-of-the-internet thing I keep getting asked about.
The first time someone called Tiny a "holding company," I had to look up what that actually meant. We were just buying internet businesses we liked and leaving the founders alone. Turns out there's a name for it, and Warren Buffett spent sixty years writing about it.
I started Tiny because I was bad at running a single company. Every time I got a business past a certain size, I'd lose interest, hire a CEO, and go start something else. After about the fifth time, I noticed the pattern was the business model. We now own forty-something companies, and my actual job is mostly reading P&Ls, sending Loom videos, and trying not to break things.
I write about this stuff because the playbook is weird and most of the existing literature is either Buffett worship or M&A-banker boilerplate. Neither is useful when you're trying to decide whether to buy a Shopify app at 4x earnings on a Tuesday afternoon. The pieces in this section are the operating manual I wish I'd had at twenty-eight, including the alternative-to-private-equity argument for founders who don't want to fire their team in year two, and the writeup on Tiny itself — what we actually do, how we underwrite, why we hold forever.
If any of this lands, you'll probably also like the pieces on selling companies and the things I got wrong along the way.
Start here
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.
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.
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.
More on building tiny
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.
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.
The Starbucks floor mopper
Mark Nichols had mopped floors at a Burlington Starbucks and that was about it. I gave him my agency anyway. He turned out to be the man for the job.
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.
Six Porsches worth of SaaS savings
Why every dollar you save on SaaS goes straight to the bottom line, why most companies stop negotiating once they get big, and what we did about it.
Miss kicking the ball
The thing that brought you joy in the first place is the first thing you stop doing as your business grows. Writing a book reminded me what kicking the ball feels like.
Why I stopped hiring myself
Why I changed my mind on $60,000 recruiter fees—and the three reasons hiring one usually saves a busy CEO money rather than costing them.
The Psychology of Human Misjudgement
The Munger talk I come back to whenever I need a reminder that most bad decisions come from predictable human wiring, not mysterious personal failure.
Joe Rogan Got Ripped Off by Spotify
Spotify's Joe Rogan deal looked enormous. I thought it was cheap, because the biggest podcast in the world was probably worth far more than the headline number.
The Power of Anti-Goals
How I designed my perfect day by fixating on what I hate
The Daily Podcast Revolution
I had spent hundreds of hours with Brian McCullough in my ears before we ever met. Then he pitched me on daily podcasts for every niche, and Tiny wrote the first check.
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.
Just Start
I did not really read The Now Habit. The title was enough. The useful part is embarrassingly simple: take one step before the idea curdles into procrastination.
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.
The Rockstar Myth
The lone-genius designer myth is a burnout machine. Hiring scared me, then it became the thing that let me keep doing the work I actually loved.
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.
Getting Zapped
Business teaches through pain. You hire badly, launch badly, get zapped, and then decide whether the scar becomes a lesson or a cage.
Build The Rocket First
We built Flow with three people, no venture money, and client work paying the bills. A year later it was doing $500K in recurring revenue.
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.
Introducing Flow
Before Flow became my $10 million lesson, it was a simple idea: one place for work tasks, home tasks, delegation, and the grocery list I kept forgetting.
The Little Things
Two tiny Flow changes, annual billing and one green upgrade button, did more for revenue than months of big product work.
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.