The Toughest Sell A Founder's Guide to Startup Exits
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Part I: Before You Begin

Chapter 6Know Thyself

When it comes to selling your company in a buyer’s market, everything becomes negotiable—your valuation, your role, your product roadmap, even your identity. In the middle of an acquisition, there are moments when you’ll say yes to anything just to keep the deal alive. Be warned, these are times when your values either save you or sell you out.

I learned that early on in the process. During one of our early acquisition talks that resulted in a term sheet, the CEO of the potential acquirer looked Borui and I in the eye and said, “We love what you guys are working on and will take good care of you two and the key employees.” What he didn’t say was that the terms that he wanted us to sign would lay off a number of our employees and be a terrible deal for all our investors. After months of rejections and half-promises, part of me just wanted the pain to end and sign the deal. But then I thought about the people who built that product—the engineers who poured weekends into it, the users who had grown with us, and the investors who had believed in us when everyone else said no. That was the moment I realized: if you don’t know what you stand for before you start an M&A process, you may fall for anything in order to close the deal.

Values aren’t an accessory to M&A—they’re the only compass that works when you’re lost in the fog. So from that moment on, I forced myself to write down the three things that mattered most to me: take care of our people, make a bigger impact, and be a good husband and father. Everything else—valuation, timing, prestige—was noise.

The first line came easy. I kept seeing the faces of the people who had taken a bet on us when we were nothing but two grad students with a barely working demo. Some had joined fresh out of school, others left big-name jobs to chase a dream with us. During the pandemic, when the world shut down, I had to make two rounds of layoffs that cut our headcount from sixty to seventeen. To this day, I can still remember every name I let go. Each conversation felt like a personal failure. I promised myself that if I ever had to make another big decision—whether to sell, pivot, or keep going—it would start from the question: will this take care of our team?

The same applied to our investors. I often joke that I still don’t know what convinced people to write million-dollar checks to two twenty-somethings with no track record, but they did. They showed up for us through every high and low, joined late-night calls about strategy, and never once pushed for an outcome that wasn’t in the company’s best interest. They believed before anyone else did. The least I could do was make sure they didn’t lose their money—or at least not a big chunk of it. The decision to pursue an acquisition wasn’t just business pragmatism; it was an act of stewardship. When someone bets on you, you owe it to them to try to return the chips.

The second line—make a bigger impact—was born out of frustration. After years of growth, our consumer photo apps had plateaued. Meetings became exercises in squeezing another dollar from ads and paywalls. We were optimizing ourselves into irrelevance. I remember looking at our dashboards one day and thinking, “We’re trying to squeeze blood out of rocks.” The only way forward was to bet big again, to either pivot into something new or join forces with someone who could take what we’d built and amplify it. You don’t win by cutting costs; you win by finding purpose. M&A wasn’t about survival anymore—it was about impact.

The third line was the hardest one to write because it had nothing to do with business. I started Polarr the same year I got married. For years even after we got married, Charis and I shared our home with a roommate to save on rent. Every anniversary trip turned into a “maybe next year.” I was constantly traveling pre-pandemic. Typically flying out of SFO on a red eye on Saturday night to go to Korea to work with our partners as soon as I landed and returning on Friday after work so I could spend a couple days at home before grinding it out in the office the following week. We lost our first child in 2018 through a miscarriage, and when our son was finally born in 2020 after a complicated pregnancy, something in me shifted. I realized I’d been building a company to prove something to the world, but the world didn’t need another photo editing app—it needed me to be present for my wife and kid. When we found out we were expecting again in late 2021, I made a promise: I needed to be there for my family no matter how crazy work got.

Those three lines guided every conversation that followed. They made hard decisions a lot easier. When an offer came in from our eventual acquirer, I didn’t run the spreadsheet; I read the values. Would our team be taken care of? Yes. Would our technology and products reach a bigger audience? Absolutely. Would I be able to spend more time with my family? For once, yes. The deal made sense because it was aligned with my values.

Selling a company will test everything you believe in. When the money, ego, and pressure swirl together, the only thing that keeps you grounded is knowing why you’re doing it. For me, that “why” wasn’t freedom or fame—it was faithfulness to the people who believed in me, the mission we built, and the family waiting on the other side of the door.

Writing down my values didn’t make the decision easier—it made it clearer. It reminded me that exits are never purely financial; they’re moral, emotional, and deeply personal. The numbers only make sense when they serve the story you want to live.

In the next chapter, I will talk about what happens when that clarity meets opportunity—how to know when selling is the right move. Because not every offer deserves a yes, and not every exit is a victory. Sometimes the hardest—and wisest—choice is to sell for the right reasons.

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