“When I sold Bizness Apps, I cared more about all cash at close and a 90 day transition than squeezing the last dollar, because I wanted to walk away clean and start the next thing. The person who cares the least wins the negotiation, so know what actually matters to you before you’re tired at the finish line.”
“I sold Kiko on eBay for $258k after it flopped, then Twitch to Amazon for $970m, and the thing nobody tells you is that both felt like a relief before they felt like a win. Deals fall through, the number is rarely the point, and the real work starts when you have to figure out who you are without the company.”
“I lost my first major acquisition because I let my investors overhype the company to a buyer who then had nowhere to go but disappointed. After that, I stopped treating an exit like a moment and started building it as a process from day one: know your acquirer's customer, prove the synergy, and never count the money until it is in the account.”
“I sold Nightingale to a client after the YC path, and the thing nobody tells you is that an acquisition is just another kind of financing event where the buyer writes the term sheet.”
“The weeks between signing the LOI and closing were the most emotionally turbulent moments of my life; you learn a lot at the final yard line, and most of it has nothing to do with the price.”
“I sold Cal AI after running a real process myself: I made a list of ten likely buyers, got most of them to undervalue us, and learned that you have to project that you are going somewhere with or without them. The negotiation felt like chess against people who played it every day, and I was 18 and doing it for the first time.”
“I wanted to sell Heyzap for years before it finally happened, and the process was worse than fundraising: your fate sits in someone else's hands for months. After the deal closed, I went from running everything to managing seven engineers who didn't need me, and the acquirer's adversarial approach made the earnout emotionally brutal.”
“I’ve been through close to 30 significant M&A transactions, and the ones that soured rarely failed over price. They failed because the acquirer promised everyone nothing will change, then changed everything.”