In December 2022, I signed the papers that sold SA Capital to OptionsSwing. I was 24. That transaction was then followed by a second acquisition, then a third, a compounding chain of deals that most founders never experience once, let alone three times in two years.
I didn't plan any of it. But looking back, I can see the logic running through all three. And I think that logic is the most useful thing I've ever learned about building companies.
Here's the story, and the four things I wish someone had told me before any of it happened.
One: The exit is not the destination. It's the beginning.
When founders talk about exits, they talk about them as endpoints. The thing you're building toward. The number that validates the decision to quit your job, burn the bridges, take the risk.
That framing is wrong, and it will cost you.
The exit is not an ending. It's an integration, the beginning of a new phase where you're working inside the structure of the company that bought you, with obligations you didn't have before, operating in a culture you didn't build. The deal closes, and the real test starts the next morning.
When we sold SA Capital, I became Head of Strategy, Operations, and Partnerships at OptionsSwing. I also took a seat on the Board of Directors. Those are good outcomes, but they came with expectations. The team that acquired us bought us because of our marketing, our operational infrastructure, and our business acumen. We had to deliver on that. Immediately. With no runway period, no grace quarter, no "we're still learning the business."
"The founders who treat the close as the finish line discover quickly that the real test starts the day after."
I've seen founders negotiate hard for the headline number and pay no attention to their role, their vesting terms, or their operational obligations post-close. Then they wonder why they're miserable six months in.
The headline is the least important part of the deal for your life after it closes.
Two: Your acquirer's thesis matters more than your pitch.
We got the OptionsSwing deal done because Jason Lee, their CEO, saw something specific in what we'd built: operational capability that would help them scale. Not our technology. Not our brand. Not our community size. Our operational infrastructure and the team behind it.
If we'd pitched on community size, we would have been benchmarked against every other financial education platform with more followers. If we'd pitched on technology, we would have lost to companies with better products. If we'd pitched on revenue, we would have lost to companies that had been operating longer.
We won the deal by understanding what the acquirer needed to be true about us, and then demonstrating that it was already true.
That sounds simple. It isn't. Most founders pitch their company as they see it. They tell the story they've been telling investors, advisors, and employees for two years. They've refined that story to perfection, and then they walk into an acquisition conversation and tell exactly the wrong version of it to exactly the wrong audience.
"Study your acquirer the way you studied your first investor. Know their thesis. Know their gaps. Know what problem you solve for them. Then tell the version of your story that answers those questions, and only those questions."
Acquisition conversations are not investor pitches. Investors are buying your future. Acquirers are buying your present, specifically, the parts of your present that solve something they need right now. The pitch has to be built around that gap, not around your vision.
Three: Distribution is the asset that survives every transaction.
SA Capital was, on paper, a financial education platform. But the real asset wasn't the curriculum. It wasn't the technology. It wasn't even the students, as much as we cared about them.
The real asset was distribution, the channels, the content systems, the community, and the trust we'd built with an audience of retail investors who paid attention to what we said.
That distribution transferred. It became valuable to OptionsSwing. And it became one of the key reasons the SA Capital founding team was retained in leadership positions, rather than thanked and shown the door, which is what happens to most founders post-acquisition when their company's value was purely technical.
I've watched a lot of acquisitions since then, from the inside and from the outside. The founders who retain equity, influence, and operational roles post-close are almost always the ones who own something that's hard to replicate independently. And in a world where AI is collapsing the cost of building software, where you can spin up a functional product in weeks for almost nothing, the hardest thing to replicate is an audience that trusts you.
Technology is being commoditized. Distribution is not.
"Build distribution like it's the product. Because at exit, it might be the only asset the acquirer genuinely cannot rebuild on their own."
This is why Iron Key Capital, the fund I now manage, evaluates distribution before product in every deal we look at. I've seen too many technically excellent companies sell for disappointing multiples because they were solving a problem the acquirer could have solved themselves if they'd just spent six more months on it. I've seen simpler companies sell for extraordinary multiples because they had an audience, a community, or a distribution channel the acquirer needed and couldn't replicate.
Four: The third exit teaches you what the first two can't.
The Strive Asset Management acquisition of Asset Entities, the third transaction in this chain, happened without my active involvement in the deal. By that point, I was building Iron Key Capital and scaling SA Media. I was watching from the outside.
But I learned something from the outside that I couldn't have learned from the inside: exits compound when you build something that a larger entity needs in order to be bigger than they could be without you.
SA Capital needed OptionsSwing to scale. OptionsSwing needed Asset Entities to access public markets. Asset Entities needed Strive to access a distribution and credibility stack they couldn't build alone. Every transaction in the chain followed the same logic: someone needed what the company below them had built, and it was cheaper and faster to acquire than to build.
That logic is not accidental. It's engineered, or it should be, from the day you start the company.
The founders who engineer compounding exits don't do it by being lucky. They do it by understanding, from the beginning, what the chain of value above them looks like. Who are the five companies that could logically acquire you? What does each of them need? What would they be willing to pay for it? And how do you build the version of your company that answers those questions specifically, not hypothetically?
"Build what someone above you in the value chain can't build without you. That's not a pitch. That's a strategy, and the difference between founders who exit once and those who exit again and again."
The One Thing That
Runs Through All of It.
If I reduce everything to a single idea, it's this:
The companies worth acquiring are not the biggest or the most technically impressive. They are the ones that solve a specific problem for a specific acquirer at the right moment in that acquirer's growth trajectory.
Building a great company means building toward an exit thesis, not just a product thesis. Those are different things. A product thesis tells you what to build and who it's for. An exit thesis tells you what the company needs to be worth to someone else, and how to make it unmistakably that thing.
Most founders never ask that second question. They build the best version of their vision, pitch that vision to investors, scale it as far as their capital allows, and then hope that some acquirer shows up and sees what they see. Sometimes they do. More often they don't, not because the company wasn't good, but because it wasn't specifically what the acquirer needed at that specific moment.
I started SA Capital in December 2020. I was 22 years old, fresh off a capital markets trading floor, building in a pandemic, with three co-founders I trusted completely and a theory about what retail investors needed. Three exits later, I've deployed over $25 million in capital through Iron Key, helped build one of Canada's Top 5 Startups, and scaled a media company to 250 million content views across platforms.
None of it was planned. But all of it followed the same underlying logic: understand what others need before they ask for it, build it better than they can build it themselves, and be willing to sell when the moment is right, not when it's comfortable.
That's the lesson. Three exits. Two years. One lesson.
The rest, as it turns out, takes care of itself.