I've started, co-founded, or invested in over forty businesses. My success rate? About 40 percent.
Some made millions. Some lost millions. Most just kind of fizzled out like a damp firework on a rainy Victoria evening — a burst of excitement, a long hiss, and then nothing. The successes include MetaLab, Pixel Union, WeCommerce, and a handful of others you'd recognize. The failures include a designer cat furniture company, an online DJ school, a project management app that bled over ten million dollars, and a few ventures so bad I'm embarrassed to type their names.
I used to hide this. When you're trying to look like you know what you're doing, admitting that six out of ten things you touched didn't work feels like career suicide. But here's the thing I've learned after twenty years of building, buying, and occasionally burning down businesses from my home base in Victoria, BC: the failures were the education. The successes were the payoff. And neither would exist without the other.
Let me walk you through the highlight reel of my worst ideas.
In my early twenties, my buddy Chris and I started a designer cat furniture company called H.J. Mews. I had adopted a kitten, looked at the hideous cat trees available, and thought, "We can do better." We could not. Or rather, we could make beautiful cat furniture — we just couldn't sell it profitably. Online retail is a low-margin, capital-intensive, logistically nightmarish business, and we learned that the hard way. Every sale lost money. We shut it down after a year, several thousand dollars poorer and significantly humbler.
Around the same time, I was moonlighting as a DJ. I'd bought turntables, landed a regular spot at a club in Victoria, and decided the logical next step was to launch an online DJ school. My DJ name was DJFKFC — which should tell you everything about my judgment at the time. The school flopped. Maybe it was ahead of its time, before online courses were a thing. Or maybe — and I think this is more likely — it was just a terrible idea executed by a twenty-something who thought owning turntables qualified him to teach.
The real damage came later, when MetaLab was making good money and I started treating it like an ATM. I'd wake up with an idea in the shower, hire a team by lunch, and be bored with it by Friday. At one point I was running a handful of startup businesses simultaneously, each in a state of disarray, all of them burning cash at a rate that would make a venture capitalist blush. My CFO Chris kept waving spreadsheets at me like a man trying to flag down a plane. I kept telling him we were going to make millions. Maybe billions.
We were not.
Of all my failures, Flow is the one that still stings.
In 2010, I built a project management app out of MetaLab. It was beautiful. It was fast. Within 24 hours of launch, thousands of people signed up. I thought we'd built the next Basecamp. Revenue grew quickly — we hit millions in annual recurring revenue, all bootstrapped, all profitable. I was convinced we were going to own the productivity space.
Then Dustin Moskovitz showed up.
The Facebook co-founder had started Asana, a direct competitor. He reached out and suggested a merger. I looked at his product, decided ours was better designed, and said no. I thought we'd outrun them on taste.
This was the single dumbest business decision I've ever made.
Moskovitz didn't need my permission. He poured hundreds of millions of venture capital dollars into Asana. Then Monday.com raised hundreds of millions more. Then Wrike. Then ClickUp. We watched from the sidelines as competitors rolled out mobile apps on every platform, bought billboards, ran Super Bowl-adjacent ads, hired enterprise sales teams, and redesigned their products until they looked just as good as ours.
We were the patsies at the poker table, stubbornly refusing to raise money. We told ourselves we were disciplined. We told ourselves we were principled. We were lambs to the slaughter.
Our monthly burn climbed: $20,000, then $40,000, then $60,000, then $80,000, then $150,000. At one point, Chris had to inject personal funds to make payroll. We were like Fiji trying to invade the United States — speedboats and AK-47s versus aircraft carriers and artillery. We got obliterated.
By the end, we'd lost over ten million dollars. I kept the thing on life support with a skeleton crew in India for years before finally pulling the plug in 2025. If I'd put that ten million into an S&P 500 index fund instead, it would've grown to over thirty million dollars by now, kicking off roughly $300,000 a year in passive income.
Six lessons I took from Flow:
After enough failures, I started asking a different question. Not "what should I build?" but "why am I building at all?"
My approach had been like hand-crafting a raft using logs I 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.
Meanwhile, Warren Buffett — the laziest, most successful person in the world — had figured out a better system. He found a cruise ship with an expert captain who had already mapped out the course. Then he bought a ticket, boarded, lay on the sun deck, and read annual reports all the way to Hawaii.
That metaphor changed my life. Not because I'm lazy (though I am, a bit). But because it forced me to confront something uncomfortable: I'd been confusing effort with results. I'd been confusing the thrill of starting something with the discipline of finding something that already works.
Building from scratch feels heroic. You're the founder. You're the visionary. You're pulling all-nighters and living on ramen and feeling like you're in the trenches. But in my experience, starting a company usually fails. And when it does work, it works despite the chaos, not because of it. The survival rate is brutal, the capital requirements are unpredictable, and you spend years solving problems that an existing business already figured out.
After two decades of pattern-matching across dozens of businesses, I've found four ingredients that every one of my successes has in common.
Simple, easily understood model. The business has to be explainable in one sentence. "We pressure wash driveways" or "We sell themes for Shopify stores." If the pitch takes thirty minutes, walk away. If there's a complicated technology moat you need to explain with a whiteboard, run.
Low competition or overlooked niche. The sexier the industry, the more crowded it is. I've lost money in restaurants, productivity software, and social media. I've made money in design services, e-commerce tools, and pressure washing. The best businesses are in categories that bore most people to tears.
Obvious, painful need. Your customer should be in pain right now, looking for a solution. Not "we need to educate the market" pain — real, physical, can't-ignore-it pain. A homeowner staring at their green, mossy driveway. A Shopify merchant who needs a theme by Friday.
A great co-founder who operates. A business cannot live off the side of my desk. I learned this the hard way, many times. After getting diagnosed with ADHD, I finally understood the pattern: I'm good at the vision. I'm terrible at the follow-through. Every business I've succeeded in had a co-founder or operator who was the opposite — methodical, detail-oriented, relentless about execution. The Visionary and Integrator model from the Entrepreneurial Operating System describes this pairing perfectly, and recognizing it changed my work life beyond recognition.
Here's the other thing: the stuff that works is almost always boring.
Last year, I partnered with a college student named Andan to start a pressure washing company in Victoria. I know. Pressure washing. My MetaLab colleagues probably thought I'd lost my mind. But in the first month, that company made $20,303 in revenue. No venture capital. No pitch decks. No Series A. Just a motivated kid, a power washer, and dirty driveways.
I'm targeting $203,030 a month within twelve months. And honestly? I think we'll get there. Because the business is simple, the competition is local and sleepy, the need is obvious, and my partner is hungry.
Here's where the story gets good.
Every fuckup now began to pay me back in spades. And not in some vague, "I learned about myself" way. In a direct, practical, dollars-and-cents way.
The cat furniture disaster taught me that just because you can build something beautiful doesn't mean you should. Online retail is a grind even for people who've spent decades in it. A design agency guy and his buddy have no business thinking they'll crack it on their first try.
Flow taught me to never fight a war against an army that's been handed unlimited ammunition. If the category has venture-backed competitors burning hundreds of millions, either raise your own war chest or find a different battle.
The simultaneous-startup chaos taught me the most important lesson of all: you can't run five companies off the side of your desk. You need operators. You need financial controls. You need someone whose full-time job is worrying about the thing you started in the shower.
MetaLab taught me to install trust slowly. I gave too much authority too fast to people who talked a great game. Charismatic strangers are the most expensive thing in business. Now I verify before I trust.
The power of this education is that it compounds. Learning from failure came with a multiplier, because I could leverage every lesson across the next company, and the one after that. Each scar made me faster at pattern recognition, quicker to spot the warning signs, more ruthless about cutting losses.
I went from someone who threw money at shower ideas to someone who could evaluate a business in an afternoon and know — in my bones — whether it was a winner or a trap.
So I stopped building. Started buying.
Every painful lesson became a filter. When someone brought me a deal, I could pattern-match instantly against twenty years of failure. Too competitive? Pass. No clear operator? Pass. Requires market education? Pass. Complicated technology play? Pass.
What was left were simple, profitable, well-run businesses in overlooked niches. Boring stuff that printed cash.
Dribbble. Creative Market. AeroPress. Letterboxd. Serato. Businesses that didn't need to be reinvented. They needed to be found, supported, and made a tiny bit better.
That became Tiny — a publicly traded holding company on the Toronto Stock Exchange. Over forty companies under one roof. Hundreds of millions in annual revenue. Over a thousand employees. Not because I'm smarter than other entrepreneurs, but because I failed enough times to know what works and what doesn't.
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.
That philosophy came from two decades of doing it the hard way first.
Most of my companies failed. I'm not being modest — the math is the math. Sixty percent of everything I touched didn't work out.
But the 40 percent that succeeded more than covered the losses. Way more. And every one of those failures — the cat furniture, the DJ school, the ten million dollar project management app — made me better at the job I do now: finding great businesses and helping them grow.
If you're sitting there with a failed startup, or a business that's bleeding money, or an idea that turned out to be stupid, I want you to know something. That failure is not wasted. It's tuition. Expensive tuition, sure. But the education is real, and the returns come later, in ways you can't predict.
I went from a barista making $6.50 an hour to building a billion-dollar holding company. The path between those two points is littered with wreckage. I wouldn't change a single piece of it.
Read more about how we built Tiny or what we look for in businesses.
That's all for now…
-Andrew
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The full story — the wins, the losses, the disasters, and everything in between — is in my book, Never Enough.
