October 30, 2025
Recently I had a long call with an old friend who was facing an age-old predicament that I’ve been seeing more and more these days:
Lucked out, worked hard, employer is crushing it, and now she’s sitting on a large amount of paper money gains at her startup
Company does a tender offer, either buying their stock back or allowing a third party to come in and buy shares
Employees might be allowed to sell, say, 10% (or whatever) of their equity
So here’s the question: do you sell, or do you roll the dice and risk it longer?
I took a tender offer on my early GitHub shares, and it comes up a lot in emails and conversations with others I run across in the startup world. It’s a decision can be annoyingly agonizing. And there’s a lot of conflicting advice out there, each with different motivations behind it. I’ve added to that, too, with lots of advice over the years of “look at all the alternatives in front of you and make an even-headed decision”.
Anyway, fuck it, here’s the bottom line: take that money, queen.
Gambling with your life
I’ve found it helpful to look at your life as a gamble: a set of probabilities that add up to whether or not you should make a decision a certain way. Assuming you’re in this situation, you might be looking at a windfall of, say, half a million to tens of millions of dollars. That’s wildly lucky, and can be life-changing money.
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