We needed a name.
Chris and I were sitting in my apartment in Victoria, British Columbia, tossing ideas back and forth. We’d been at it for hours. Every private equity firm and holding company we could think of had one of those ridiculous, self-important names. BlackRock. Greywolf. Maverick. Cerberus. They all sounded like Bond villains or law firms that sue children. We wanted something different.
“What about Tiny?”
It felt down to earth. Friendly. And, frankly, kind of ironic and funny for a company whose entire plan was to buy as many businesses as possible. We went with it.
Chris put up 20% of the money. I put up 80%. We split the company 50/50. Equal partners. No partnership agreement. Just a handshake.
People think that’s insane. After what Chris and I had been through together — years of building MetaLab from a two-person web design shop into one of the most respected agencies in tech — we didn’t need one. I knew what kind of person he was when things got hard. That’s the only due diligence that matters with a partner.
Before Tiny existed, I was stuck.
MetaLab was printing money. We were designing apps for Slack, Uber, Google, and a long list of companies you’ve heard of. But I was burned out. I was 28, sitting on more cash than I knew what to do with, and the thought of starting another company from scratch made me want to crawl under my desk. I’d tried it with Flow, our project management tool, and watched $10 million evaporate over twelve years in a slow-motion fight with Asana. (Turns out, competing against a Facebook co-founder with unlimited venture capital when you’re bootstrapping from Victoria is like Fiji declaring war on the United States.)
I didn’t want to start more companies. I didn’t want to raise money. I didn’t know what I wanted.
One afternoon, I stopped at Bolen Books — the local bookshop on Fort Street that’s been around forever — and picked up a copy of The Warren Buffett Way by Robert Hagstrom. I’d heard of Buffett, obviously, but I’d never actually sat down and studied how he did what he did.
I stayed up until midnight reading.
The book hit me like a freight train. Here I was, spending years trying to build businesses from scratch — nailing boards together to build a handmade raft — when I could just buy a cruise ship. Buffett’s whole approach was elegant in its simplicity: find a high-quality business with a durable competitive advantage. Make sure it has an intelligent management team. Pay a fair price. Then leave them alone.
That was it. That was the whole thing.
I’d been doing entrepreneurship on hard mode my entire career. Starting from zero. Hiring from zero. Finding product-market fit from zero. Losing sleep. Losing money. Losing hair. When I could have been acquiring businesses that already worked, already had customers, already had revenue — and just making them a little better.
I went on a reading binge. Every Buffett biography. Every Munger speech. The Berkshire Hathaway shareholder letters going back decades. Charlie Munger had this line I kept coming back to: “It’s a lot easier to ride a horse in the direction it’s already going.” I had spent years trying to drag horses uphill.
Dribbble was the social network for designers. If you worked in design or tech, you knew it. Millions of designers used it to share their work, find jobs, and get inspired. It was the portfolio platform for the entire creative industry.
I loved the product. I also noticed something: the founders seemed tired.
Dan Cederholm had built Dribbble as a side project with Rich Thornett. It had grown into something massive, but they were running it with a tiny team, and the business side of things — ad sales, contracts, support tickets, hiring — was eating them alive. Dan was a designer and developer. He wanted to make things, not manage spreadsheets.
I cold-emailed him.
No response.
I emailed again a month later. “Hey Dan, just checking in. I know I’m being annoying.”
No response.
I kept emailing for almost a year. Not aggressively — just a brief, friendly note every few weeks. Eventually, Dan wrote back. He was curious. We got on a call. Things clicked.
I flew to Boston and rented a boardroom at the Four Seasons. (It felt very grown-up and serious, which was the point, because I was a 29-year-old from a small Canadian city trying to buy someone’s life’s work.) Chris came too. We sat down with Dan and Rich, and instead of launching into a pitch about how great we were, I tried something different.
I asked them to do an exercise I called Anti-Goals.
“Write down everything you hate about running Dribbble,” I said.
They looked at each other and started writing. The list was long. Cold-calling advertisers. Managing a growing support inbox. Legal contracts. Coordinating with a team spread across multiple time zones. Dealing with the business stuff that had nothing to do with building the product they loved.
When they were done, I took the list, circled every single item, and said: “We can handle all of this. Every one of these things. You just keep doing what you love.”
That was the pitch. Not “we’ll 10x your revenue” or “we’ll optimize your growth flywheel.” It was: we’ll take away the stuff that makes you miserable so you can focus on the stuff that makes you great.
Dan and Rich didn’t just want money. They wanted their company in the right hands. Someone who would take care of the community they’d built. We sent over a high seven-figure offer. It was the biggest check I had ever written.
Chris and I personally guaranteed the bank loan. If Dribbble failed, the bank wouldn’t just take our company. They’d take our houses. Our cars. Everything. I remember Chris and I looking at each other after we signed the papers. Neither of us said anything, but the thought was obvious: this better work.
It worked.
A few years later, my colleague Ali Bosworth walked into the MetaLab office holding what looked like a PVC pipe.
“You need to try this,” she said.
I was a coffee snob. I had a $5,000 La Marzocco espresso machine at home. I’d spent years dialing in my grind, my water temperature, my extraction time. I had opinions about coffee that could fill a book (a very boring book, but still).
Ali poured hot water into this cheap plastic tube, stirred, and pushed down a plunger. It took about 90 seconds.
It was the best coffee I’d ever tasted.
The thing was called an AeroPress. It cost $29. And it made better coffee than my $5,000 machine.
I became obsessed. I dug into the company and discovered the inventor was a guy named Alan Adler — a Stanford mechanical engineering lecturer who also invented the Aerobie Flying Ring (the frisbee that set the Guinness World Record for farthest throw). He’d applied the same engineering obsessiveness to making the perfect cup of coffee.
I had to own this company.
I sent Alan a cold email. Three lines. Something like: “I love the AeroPress. I run a company that buys great businesses. Would you ever consider selling?”
No response.
I emailed again. And again. And again. For months.
Eventually, Alan wrote back. We set up a meeting in Palo Alto. He was in his eighties — sharp, warm, clearly brilliant. We talked about coffee, engineering, aerodynamics, and what he wanted for the future of his company.
Then he told me his price.
“Seventy million dollars.”
I paused for about half a second. “You’ve got a deal.”
When we bought AeroPress, only about 3% of its sales were happening online. The rest was pure word of mouth — coffee shops, specialty stores, die-hard fans telling their friends. It had this incredible underground following, almost cult-like, but there was no real e-commerce operation, no digital marketing, no social media presence to speak of.
We grew online sales over 500% in the first two years. The product was already perfect. Alan had spent decades engineering it. We just had to let more people find out about it.
After Dribbble and AeroPress, the flywheel started turning.
Deals came to us. The Serato acquisition — DJ software used by pretty much every professional DJ on the planet — started with a DM on Twitter. Someone just messaged me and said, “Hey, would you be interested in buying Serato?” (This is not the typical Morgan Stanley-mediated M&A process you read about in the Wall Street Journal. But it works.)
We bought Creative Market, the marketplace where designers buy and sell templates, fonts, and graphics. We bought Letterboxd, the social network for film lovers that went from a passion project in New Zealand to one of the most beloved apps on the internet. We bought MediaNet, a music licensing company. We acquired Meteor, an open-source JavaScript framework. We kept buying MetaLab’s cousin companies — eventually rebranding the digital services group as Beam.
Each deal followed the same playbook Buffett had laid out in those books I’d devoured at Bolen Books: find a great business with a moat, make sure the people running it are smart and passionate, pay a fair price, and get out of their way.
In April 2023, we took Tiny public on the TSX Venture Exchange under the ticker TINY. We filed a $150 million shelf prospectus that fall. We now have 32 companies in the portfolio doing over $250 million in combined revenue.
Not bad for two guys from Victoria who couldn’t agree on a name.
People ask me all the time: “How do you run 32 companies?”
I don’t.
Each company has its own CEO. Their own leadership team. Their own culture. Chris and I practice what I like to call “benign neglect,” which I stole from Buffett. (Steal from the best, I say.) We give our CEOs enormous freedom. We let them make decisions. We let them make mistakes.
This is the part that scares most investors and board members. You’re going to let them make mistakes? On purpose?
Yes. Because that’s how people learn.
We tell every new CEO the same thing: you’re going to make mistakes, and we’re fine with that. We just ask that they be flesh wounds, not mortal wounds. A million-dollar mistake that teaches you something valuable? We can absorb that. A bet-the-company decision made without telling us? That’s different.
Here’s what most people don’t understand about founders and CEOs. When you start a company, you’re chopping wood with your friends. Everyone’s in the same room. You’re all exhausted and excited and building something together. Then the company grows, and one day you look up and you’re alone in a glass office. Nobody tells you the truth anymore. Everyone’s performing for you. It’s isolating in a way that’s hard to describe unless you’ve lived it.
Tiny tries to prevent that. We connect our CEOs with each other. We host retreats. We create a peer group of people running businesses at similar stages who can be honest with each other because they don’t report to the same boss. (Chris and I are the boss, technically, but we try not to act like it.)
The best holding company operators in history — Buffett, Henry Singleton at Teledyne, the Markel guys — all figured out the same thing: hire great people, align incentives, then get out of the way. It sounds simple. It is, in theory. In practice, it requires an almost pathological willingness to sit on your hands and not meddle.
I’m naturally a meddler. ADHD brain. Always want to jump in and “help.” The hardest skill I’ve ever learned is doing nothing. Letting a CEO try something I think is wrong, watching it play out, and being genuinely okay with whatever happens. Because sometimes they’re right and I’m wrong. And even when they’re wrong, they learn more from the failure than they would from my interference.
I should be honest about the hard part.
Tiny’s stock dropped more than 80% from its peak. That’s not a typo. Eighty percent. For a while, the entire company was valued at under $200 million by the public markets — despite having over $200 million in revenue, $65 million in recurring revenue, $40 million in adjusted EBITDA, and a twenty-year track record of growth.
Our Q3 2025 results showed revenue up 16% year over year, recurring revenue up 72%, and adjusted EBITDA up 39%. The business was doing better than ever. The stock price didn’t care.
The problem is that Tiny is a platypus.
When European naturalists first encountered a platypus, they thought someone was playing a joke on them. A mammal that lays eggs, has a duck bill, a beaver tail, and venomous spurs? It didn’t fit in any known category. Some scientists thought it was a hoax — pieces of different animals stitched together.
That’s Tiny. We’re part holding company, part private equity firm, part conglomerate, part venture fund. We own DJ software and coffee makers and design marketplaces and film social networks. Nobody knows what box to put us in. Analysts don’t know which comparables to use. Index funds don’t know which bucket we belong in.
Being a platypus means embracing a certain amount of chaos. Some quarters, Letterboxd is crushing it while another company is struggling. Next quarter, the opposite. Over a long enough timeline, the winners more than compensate for the losers. That’s the whole bet. That’s always been the bet.
Ben Graham — Buffett’s mentor, the father of value investing — said that in the short term, the stock market is a voting machine. In the long term, it’s a weighing machine. Right now, the market is voting that they don’t understand us. That’s okay. Chris and I aren’t building Tiny for the next quarter. We’re building it for the next twenty years.
I look at the stock price roughly as often as I look at the weather forecast for next month. It’s interesting but not actionable. What I care about is whether our companies are getting stronger, whether our CEOs are happy and growing, and whether we’re making smart capital allocation decisions. If we get those things right, the stock price will eventually catch up.
Or it won’t, and we’ll buy back shares at a discount. Either way, I’m fine.
We’ve been doing this for almost two decades now. Some things I’ve figured out, some things I’m still figuring out.
I know that the best deals come from relationships, not investment banks. Dan Cederholm sold to us because we spent a year building trust, not because we had the highest bid. The Serato deal came from a Twitter DM. The best acquisitions we’ve ever made happened because someone knew someone who knew us and thought, “Those guys would be a good fit.”
I know that culture is the moat. Not technology, not IP, not market share. Culture. A company with a great culture and a mediocre product will outperform a company with a great product and a toxic culture every single time. We’ve seen it over and over.
I know that I’m a visionary, not an integrator. (I didn’t figure this out until I was diagnosed with ADHD in my thirties, which explained a lot about why I was great at starting things and terrible at finishing them.) Chris is the integrator. He’s the one who makes sure the trains run on time while I’m out looking for new trains to buy. We need each other. A visionary without an integrator is just a guy with ideas. An integrator without a visionary is just a manager.
And I know that enough is a moving target. That’s what the book is about, really. The feeling that no matter how much you have, no matter how many companies you buy, no matter how big the portfolio gets — it’s never enough. The hedonic treadmill keeps spinning. The goalpost keeps moving. Learning to notice that, to catch yourself in the loop, is probably the most important skill I’ve ever developed. More important than reading a balance sheet or structuring a deal.
If you want the whole thing — the barista days, the panic attacks, the $10 million I lit on fire with Flow, the time I accidentally ended up in the Epstein files (long story, I promise it’s not what you think), the divorce, the ADHD diagnosis, all of it — I wrote a book about it. It’s called Never Enough. James Clear said it was “like going to business school and therapy all in one book,” which is probably the most accurate description of anything I’ve ever produced.
And if you’re running a company and any of this resonates — if you’re a founder who’s tired of the parts of the job you hate, or you’ve built something great and you’re thinking about what comes next — I’d love to hear from you. No pitch, no pressure. Just a conversation.
