Key Takeaways
- The LOI is not the finish line. It is the starting pistol for the real negotiation.
- Clean books, simple cap tables, and no undisclosed liabilities close deals. Messy ones do not.
- Emotional attachment to a deal gets you bad terms. Know your walk-away number before you walk in.
- Distribution is what acquirers buy. Revenue is the evidence. Distribution is the asset.
Nobody tells you what an exit actually feels like. The courses talk about valuation multiples. The podcasts talk about building toward a strategic outcome. But when you're sitting across the table from an acquirer, reviewing a term sheet at midnight, nothing you've read prepares you for what happens next.
I've been through it three times. SA Capital. OptionsSwing. A third that never made the headlines but changed how I think about everything. Each one was different. Each one taught me something the previous exit didn't.
"The exit isn't the end of the story. It's the beginning of the accountability."
Exit One: SA Capital
SA Capital was a financial education company I co-founded in 2020. We grew fast, built a real community, and within two years had something real on our hands. We weren't looking to sell. The deal came to us.
What I got wrong: I treated the LOI like it was the finish line. It's not. It's the starting pistol for the real negotiation. The 90 days between the LOI and close were the hardest of the process, and I wasn't prepared for the operational intensity required to keep the business performing while simultaneously running due diligence.
What I got right: We had clean books. Simple cap table. No undisclosed liabilities. Clean data rooms close fast. Messy ones don't close at all. That lesson has shaped how I build every company since.
Exit Two: OptionsSwing
After the SA Capital acquisition, I joined OptionsSwing as VP of Operations and Sales. The company then went through its own acquisition by Asset Entities, a NASDAQ-listed firm. This time I was on the inside of a sale I didn't initiate.
What this taught me: Your leverage in a deal is almost entirely determined before the conversation starts. The founders who get the best terms are the ones who weren't desperate, who had runway, and who had built something where the acquirer needed them more than they needed the acquirer.
We had that. Asset Entities needed what OptionsSwing had built. The community, the methodology, the brand trust. That dynamic meant we could be patient. And patience in deal negotiations is everything.
Exit Three: The One Nobody Saw
I'm deliberately not naming this one. But the lesson is the most important: not every exit is a win, even when the numbers look right.
There was a deal where the headline number was strong, but the structure meant my real return was a fraction of what it appeared. Earnouts that never triggered. Representations and warranties that ate into proceeds. A timeline that dragged long enough for key team members to leave.
By the time the deal closed, it was a muted celebration. The money was fine. The experience cost more than it should have.
What I Would Tell Every Founder
1. Hire an M&A advisor before you think you need one. Not a broker. An advisor. Someone who has sat in these rooms and can tell you when the deal is being structured to your disadvantage.
2. Build your business for optionality, not for exit. The companies that get the best exits are almost always the ones that weren't trying to exit. They were building something that worked.
3. Know your walk-away number before you walk in. Once you're emotionally attached to a deal happening, you will accept terms you shouldn't. Define your minimum before the first meeting.
The exit nobody teaches you is the one that actually happens. Not the ideal case. The real one, with real ambiguity, real counterparties, and real consequences. I've been there three times now. The fourth will be different. It always is.