“I sold Nira to Dropbox in 2024, and the thing that made the decision clear was not the price. It was whether the next chapter of the business was more exciting to me than the check.”
“Forget what you raised or what you think it's worth; ask whether the path you're on leads somewhere meaningful. If it doesn't, take the offer or find the best home for the company. If it does, the real question is whether this buyer is your best path to that future.”
“I sold Bizness Apps when I was ready to move on, not when it peaked, and that question, would I still do this if I didn't have to? mattered more than the number. If the offer lets you walk away excited about what's next, that's usually the signal.”
“A check on the table has a way of turning every long-term question into an immediate transaction question, but the offer someone put in front of you isn't always the decision you actually need to make. I'd step back and ask what you're trying to accomplish: liquidity, a partner, a successor, or just the option to keep building.”
“I wouldn't decide on the offer itself until I know what I actually want the next five years to look like. Most buyers want the owner around for two to five years, so the real question is whether you built this thing to keep running it or to get out.”
“I’d look hard at what changes about your life and role after closing, not just the price. I’ve seen owners take a number that felt good and still feel trapped because they never defined what they were exiting to.”
“When we sold 91% of Buscapé for $342 million, I had to separate the price from the real question: am I selling because I’m exhausted or because this is the best next chapter for the mission?”
“I once turned down an acquisition offer during a brutal stretch because I believed we were building something worth more than the safety of selling in a panic. A year after any sale, the price stops mattering; what haunts you is whether your customers, employees, and values came out better.”
“I sold a private currency company for $64 million, and the best exits happen when the buyer wants you gone, not when you’re trapped needing the deal. If your business still needs you every day, the offer is probably lower than it should be, and you’re selling from weakness. Build it so you don’t need to sell, then decide from a place of power.”