“I sold Nira to Dropbox in 2024, and the part that kept me up wasn’t the valuation, it was knowing the team was taken care of. If this deal leaves your people with scraps while you cash out, that’s not a strategy problem; it’s a character problem, and it will follow you.”
“I sold Bizness Apps when I was mentally done with it, and the best thing I did was stop treating my own fatigue like a character flaw. If the offer is real, your team can be protected in the deal, and you’ve been flat for a year, holding is a bet that you have the energy left to make it grow again.”
“I sold EchoSign to Adobe when I was tired too, and the thing I underestimated was how much acquisitions mostly hurt your best, most driven employees. If the offer leaves your ten people with scraps after six years, that is not a win, it is a transfer of their work into your bank account.”
“I sold two companies for a little over $30 million, and both acquirers eventually drove them into the ground, so I know the exit can feel like the win right up until it isn't.”
“I would not start with whether to take this offer. I would start with what you are actually trying to accomplish, and what happens to your people, your product, and your own energy under each path.”
“I sold IT Glue in 2018, and the only way I could sleep through it was knowing the team and the product were landing somewhere that would keep building it. If this offer pays you out but strands the people who built it and the customers who rely on it, that is not a win, it is an exit with a body count.”
“I sold two profitable businesses not because I had to, but because I realized I was no longer the right owner for them. Flat revenue and exhaustion are real signals, not weakness. The question isn't whether you're giving up too early; it's whether the business has a better home than you can give it right now.”
“I sold Stayntouch after years of grind, and the thing that still sits with me is not the price, it is who walked away with what. If this offer pays you two and leaves ten people with scraps, that is not a victory, it is a liquidation with your names on it.”
“I have been the tired founder looking at an exit that solves my problem more than the company's, and the thing that cut through was asking whether the product still had a real next act or whether I was just done.”