My hands were shaking.
I was sitting in a lawyer's office in Victoria, BC, signing what felt like four phone books of documents. Stacks of paper with yellow "sign here" tabs. My business partner Chris was next to me, scribbling his name on an identical pile. We were selling Pixel Union, our Shopify theme company, for $7 million.
A few months earlier, we'd been offered $2 million. We almost took it. Then the buyer, Richard, came back at $7 million after some back-and-forth that I still don't fully understand. I remember thinking: this cannot be real. I was 27. I'd been making good money, but I'd never had a number with that many zeros attached to my name at once.
I walked out of that office and did the math in my head. I could invest the millions I had left after taxes, earn about 8 percent on my money, and live a comfortable life without lifting a finger. No clients. No deadlines. No stressing about payroll. I was free.
That feeling lasted about three months.
Richard brought in a guy named Brian to help run things. Brian was older, charismatic, and carried himself like someone who'd done this a hundred times. He wore nice suits. He had a firm handshake. He told great stories about deals he'd done. I trusted him immediately, which turned out to be one of the most expensive mistakes of my life.
Brian was a grifter.
It didn't surface all at once. It never does with people like that. First there were small things — expenses that didn't add up, trips that seemed unnecessary. Then bigger things. He was approaching our clients behind our back, building a competing agency using our resources. He'd deleted email threads to cover his tracks. Hundreds of thousands of dollars in unauthorized spending. He'd been stealing from us to fund his own venture while collecting a salary to run ours.
The firing required lawyers. The cleanup took years. The legal battle that followed was one of the most stressful experiences of my life, and I've had a few.
Here's what killed me: we had sold to the wrong person, and by extension, we'd let the wrong person into our company. The number on the check didn't matter. The person writing it did.
I think about that a lot. Founders obsess over valuation — the multiple, the earnout structure, the tax treatment. I get it. But the single most important variable in any acquisition is who is buying your company and what they plan to do with it after you hand over the keys.
A couple years later, I was sitting in Chris's fishbowl office at MetaLab, our design agency. We'd just gotten off a terrible conference call. I don't even remember what it was about — some client issue, some HR fire, some vendor problem. It all blurred together.
I looked at Chris. "How is it that we have millions of dollars in the bank and yet here we are, dealing with the same stressful crap as before?"
Chris leaned back in his chair. "I'm done."
He wasn't being dramatic. He meant it. And I felt the same way.
I tried to explain the feeling to a friend later that week, and I came up with this metaphor that I've been using ever since.
Imagine you love chopping wood. It's your happy place. You're out in the yard, the sun is shining, you've got your axe, and there's a satisfying crack every time you split a log. Pure bliss.
Then your neighbor walks over and says, "Hey, I'll pay you $20 to chop some wood for me." Great. You're doing what you love and getting paid for it. Then another neighbor wants in. Then you hire a friend to help. Then you buy a bigger lot. Then you need a foreman and an accountant and an HR department.
Fast forward fifteen years and you own a sawmill. You're sitting alone in a glass office at the top of the building, wearing a suit, doing paperwork. The air conditioning is blowing a chill down your back. No axe. No fresh air. No friendly coworkers splitting logs beside you.
That is what it feels like to build a business past a certain size. And it's the reason most founders start thinking about selling.
When you decide to sell, you'll meet three types of buyers. I've dealt with all of them, from both sides of the table.
Private equity firms. These are spreadsheet people. They operate by committee. They'll spend four to six months running due diligence, request every financial document you've produced since birth, and then — right before closing — renegotiate the terms. I've seen it happen to friends. I've had it happen to me.
We once had a deal for MetaLab that was supposed to close at $50 million. The PE firm had a committee that kept adding conditions, changing terms, sending back redlines. The process dragged on for months. My team was distracted, morale dropped, and the wire never came. The deal fell through.
PE firms buy your company, load it with debt, cut costs to juice margins, and flip it in five years. They'll tell you about "operational excellence" and "value creation." What they mean is: they're going to fire people and raise prices until they can sell it to the next PE firm at a higher multiple. If you care about your team and your product, this should terrify you.
Strategic acquirers. These are big companies that want your product, your technology, or your customer base. Google, Salesforce, Adobe — that crowd. The pitch sounds great: "We'll give you resources. You'll have distribution. Think of what we can build together."
What actually happens: your team gets absorbed into a 50,000-person company. Your product becomes a feature. Your culture dissolves. Your best people leave within eighteen months because they didn't sign up to work at a corporation. The founders get a nice payout and a two-year earn-out that feels like a prison sentence.
Some strategic acquisitions work beautifully. Most don't. If you go this route, be honest with yourself about whether you can thrive inside someone else's machine.
Permanent capital / holding companies. This is what Tiny is — what Chris and I built after living through the first two options. We buy companies and hold them forever. No fund lifecycle. No pressure to flip in five years. No committee approving a wire transfer.
The idea is simple: we find businesses with great teams and strong economics, and we leave them alone. We take away the stuff the founders hate — the HR headaches, the legal paperwork, the board meetings — and let them keep doing the work they love.
I'm biased, obviously. But I built Tiny because I wished someone like us had existed when I was selling Pixel Union.
Founders always ask me, "What do you look for when you're buying a company?" They expect me to say something about TAM or competitive moats or technology defensibility. Those things matter, but they're not what we check first.
Here's what we actually look at:
Bank statements. We check bank statements rather than running months of accounting minutiae. If the cash is coming in and the numbers roughly match what the seller told us, that's 80 percent of due diligence right there. We're not going to spend four months auditing your QuickBooks. If you're lying about your revenue, it shows up in the bank account pretty fast.
Culture. Is the team happy? Do people seem engaged? Is there weird tension in the office? You can feel it in a thirty-minute visit. We've walked away from deals where the numbers looked perfect but something felt off with the people.
The founder's energy. This is the big one. Is the CEO burned out or energized? Because if they're burned out, we need to understand whether there's a team that can run the business without them. And if they're energized, we need to understand why they're selling.
When someone emails me about selling their company, I ask three questions: What's your annual revenue and profit? Is there a team that can run the business day to day? What are your valuation expectations?
That's it. If those three answers make sense, we'll have a conversation. If they don't, I'll tell you straight. I'm not going to string you along for six months.
This is the part most founders don't think about until it's too late. You've built something. People depend on it — not just your customers, but your employees. Their mortgages, their kids' schools, their sense of purpose. When you sell, you're making a decision that affects all of them.
When we bought Dribbble, I'd been emailing the founders — Dan Cederholm and Rich Thornett — for almost a year. Monthly. "Hey, just checking in. Still interested whenever you're ready." Eventually they agreed to meet in a rented boardroom.
I could tell within five minutes they were exhausted. They loved the community they'd built, but they hated everything that came with running it at scale. So Chris and I did something we'd started doing with every acquisition: we asked them to make a list of Anti-Goals.
"Write down everything you hate about your job," I said. "Every meeting, every task, every obligation that makes you miserable."
Dan and Rich looked at each other. Then they started writing. Ad sales calls. HR issues. Managing a team that had gotten too big. Dealing with investors. Legal paperwork. The list was long.
For each item on that list, we built a plan to take it off their plate. We'd handle hiring. We'd deal with the advertisers. We'd manage the business side. Dan and Rich could go back to doing what they'd always loved — building the product and caring for the community.
Then we recruited Zack Onisko as CEO. Zack understood the design community. He wasn't some MBA parachuted in from a PE firm. He was a designer himself, someone who got what Dribbble meant to its users. Dan and Rich stayed involved in the ways they wanted to, and handed off everything they didn't.
We were trying to be the buyer we wish we could have sold to.
After buying more than forty companies, I've seen every kind of deal process. Here's what should make you nervous:
Committees. If your buyer needs approval from a committee, a board, a fund manager, and an advisory panel before they can make a decision, run. Every additional approval layer adds months and increases the chance the deal dies. The best buyers can make decisions fast because the person you're talking to actually has the authority to write the check.
Late-stage renegotiation. You've agreed on terms. You've spent two months in due diligence. Your lawyers have run up $200,000 in fees. And then the buyer comes back and says, "We've found some things in diligence and we need to adjust the price." This is not a bug. It's a feature of how certain buyers operate. They lowball you after you're already emotionally committed and financially exhausted.
Anyone who calls your team "human capital." If the people buying your company refer to your employees as resources to be optimized, they will treat them that way. Words matter. Listen carefully to how buyers talk about your people.
The "Put Grandma on the Roof" move. This is something Brian taught me, and I wish I'd never learned it. The idea is that if you want to get rid of someone, you don't fire them outright. You slowly gain their trust, then engineer a situation where they feel like leaving was their own idea. Brian used this exact playbook on one of our key people — he spent weeks building a mentorship relationship, taking the guy to lunch, listening to his frustrations. Then he suggested they recruit an executive to "help" him. That executive was actually the replacement. By the time our guy figured out what had happened, he was already on his way out.
It's sociopathic. And it happens in acquisitions more often than you'd think. If a buyer's representative starts befriending your team members one by one, asking about their frustrations, pay attention.
Founders think the hard part is the sale itself. It's not. The hard part is what comes next.
I've seen every version of the "after."
Some founders stay. Dan and Rich stayed involved with Dribbble. They got to do the creative work they loved without the management burden they hated. It worked because we designed it to work — we asked them what they wanted and built the structure around their answer.
Some founders leave. When we acquired AeroPress for $70 million, Alan Adler — the inventor, who holds forty patents and had been tinkering with coffee makers and sport toys for decades — was ready to step back. He retained an ownership stake and kept inventing, but the day-to-day operations passed to our team. We grew online sales by 500 percent in two years. Alan got to focus on what he'd always cared about: designing things.
Some founders come back. We bought Pixel Union back. The company I'd sold years earlier for $7 million, the one that had gone sideways after Brian got involved — we acquired it again in 2019 and committed $25 million to build out the Shopify ecosystem around it. It felt like coming home.
Every one of those outcomes is valid. The important thing is that it was the founder's choice. Not the buyer's. Not the PE firm's. Not some committee's.
I've been on both sides of this.
I sold a business to the wrong person and lived with the consequences. I watched a grifter tear apart something I'd built. I sat in a lawyer's office at 3 AM during a legal battle I never should have had to fight. I learned that the number on a term sheet means nothing if the person behind it can't be trusted.
And then I spent the next decade buying businesses and trying to be the person I wish had bought mine. Sometimes we got it right. Sometimes we didn't. But we always started from the same place: what does the founder actually want, and how do we build around that?
If you're thinking about selling your company, here's my advice: don't start with the valuation. Start with the buyer. Talk to the founders of other companies they've bought. Ask those founders what happened after the check cleared. Ask about the people who left and why.
The number matters. But it's the fourth or fifth most important thing. The first is whether you'll be able to sleep at night six months after you sign those phone books of documents.
Read more about the Tiny story or why I built an alternative to PE.
That's all for now…
-Andrew
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Follow me on Twitter/X: @awilkinson
If you want to talk, my email is andrew@tiny.com. I wrote a lot more about all of this in Never Enough. Some of it was hard to put on paper. But I figured if I was going to tell the story, I should tell the real one.
