I’ve started, co-founded, or invested in over forty businesses. My success rate? About 40 percent.
That means most of the things I’ve tried have failed. Some spectacularly. Some quietly. A few made millions. A few lost millions. Most just kind of fizzled out, like a campfire nobody bothered to tend.
People hear “forty companies” and assume I’m some kind of serial genius. I’m not. I’m a serial experimenter who got lucky enough times to cover the losses.
Let me walk you through some of the lowlights.
There was the cat furniture company. Chris and I were convinced we could build luxury furniture for cats. We spent months on it. It went nowhere.
There was my brief career as a DJ. My DJ name was DJFKFC. That’s all you need to know about how seriously I should have been taken.
There were the startups I funded while running MetaLab — a handful of businesses, each in a state of disarray, continuing to burn unholy amounts of cash. I was spreading myself so thin that none of them got the attention they needed.
The biggest failure was Flow.
In 2010, Chris and I built a project management app. It was beautifully designed, thoughtfully built, and we grew it to millions of dollars in revenue. We were proud of it.
Then Asana came along. Founded by a Facebook co-founder with unlimited venture capital. Then Monday.com. Then Wrike. Venture capitalists poured hundreds of millions of dollars into competitors and we, being the patsies at the poker table, stubbornly refused to raise money. We kept thinking we could beat them on merit. That our software was better designed, more thoughtful, technologically superior.
We couldn’t have been more wrong. We were lambs to the slaughter. It was like Fiji trying to invade the United States. We didn’t stand a chance.
Over twelve years, we lost more than ten million dollars on Flow. Ten million dollars. I could have bought a very nice house. Several very nice houses, actually. Instead I bought a front-row seat to watching venture-backed competitors crush a bootstrapped product in slow motion.
Six lessons I took from the wreckage:
1. Don’t fight a war you can’t win. If your competitors have unlimited capital and you don’t, you’re not being scrappy. You’re being delusional.
2. The market doesn’t care about your craftsmanship. Users want the product that’s good enough and everywhere, not the product that’s perfect and nowhere.
3. Sunk costs are real. We held on for years because we’d already invested so much. That’s not strategy. That’s the gambler’s fallacy.
4. Ego kills companies. We refused to raise money because we didn’t want to give up control. Pride is expensive.
5. Timing matters as much as execution. We were early to project management software and late to understanding what the market actually wanted.
6. Sometimes the best move is to quit. We should have shut it down years earlier and redirected that energy into businesses that were actually working.
After enough failures, patterns start to emerge. Not just in what goes wrong, but in what goes right.
Every successful business I’ve been involved with shares four ingredients:
A simple, easily understood model. If you can’t explain it to your parents over dinner, it’s too complicated.
Low competition or an overlooked niche. The best businesses operate in spaces nobody’s paying attention to. Not the hot new thing — the boring old thing that’s been quietly printing cash while everyone chases the next AI startup.
An obvious, painful need. Not a nice-to-have. A must-have. Something people are already paying for, badly, and you can do better.
A great co-founder. Specifically, a visionary paired with an integrator. Someone who sees the future and someone who builds the road to get there. I’m the visionary. Chris is the integrator. Without him, I’m just a guy with ideas and no follow-through.
The stuff that works is almost always boring. I made $20,303 power washing driveways with a college student. No venture capital required. No pitch deck. No board meetings. Just a pressure washer, some elbow grease, and a willingness to get dirty.
Here’s a metaphor I keep coming back to.
Imagine you want to travel from Seattle to Hawaii by sea. My approach to entrepreneurship had been akin to hand-crafting a boat using logs I’d found on the beach, with a few buddies who had never built a boat in their lives. Sure, it was possible we’d make it to Hawaii, but it would be a miserable, white-knuckle journey, and we’d probably drown.
Buffett, meanwhile, had found a cruise ship with an expert captain who had already mapped out the ship’s course and was ready to set sail. All he had to do was buy a ticket, relax on the sun deck, and enjoy the ride.
It quickly became clear who was winning.
Building from scratch means finding product-market fit from zero, hiring from zero, finding customers from zero. Every day is a new crisis. Every month is a question of survival. And even if you succeed, the emotional toll is enormous.
Buying a business that already works — that already has customers, revenue, a team, a product people love — and making it a little better? That’s a fundamentally different game.
Every fuckup now pays me back in spades.
The Brian disaster at MetaLab taught me to never trust charisma over character, and to install financial controls from day one. The Flow catastrophe taught me to never fight VC-funded competitors without VC money. The cat furniture debacle taught me that just because you can build something doesn’t mean you should.
Learning from failure now came with a multiplier, as I could leverage my education across companies. Every painful lesson from my twenties made me a better buyer in my thirties.
You didn’t need to come up with a brilliant startup idea to get rich. You didn’t need to buy a broken business and rack your brain for how to fix it. All you needed to do was find something that you believed in, and loved, and then see where you could make it just a tiny bit better.
Most of my companies failed. The ones that succeeded more than covered the losses. And every one of them — success or failure — made me better at the job I do now.
The full story is in my book, Never Enough.
