I am part of a group called Post Exit Founders. It is, functionally, an emotional support group, because every one of us is some degree of traumatized. That is not a joke I am dressing up for a headline. No matter how your deal went, selling your company is traumatic. Even the clean ones.
People assume the opposite. They picture you waking up one day, selling the company, and sailing off into the sunset. The reality is a lot of nos, a lot of things falling through, and a lot of nights wondering whether the whole thing is a referendum on you as a person. So let me tell you what actually happens, because I did not know any of it going in.
First, most companies are sold to someone who already knows you. The fantasy is that you build something, cold call a list of acquirers, and one of them says yes. That is not how it works. You sell to a partner who has been in your supply chain or your system long enough that you become more expensive to keep paying than to simply buy. Mattel had been one of our first content partners for years before they ever became our acquirer. Build those relationships from day one, because your eventual buyer is probably already in your contacts.
Second, you need a doppelganger on the inside. You are not going to call the M&A department and charm them into a deal. You have to find the one person who runs a P&L, who gets fired if they make a dumb bet and becomes employee of the month if they make a smart one, and who can pitch your company almost better than you can. At Mattel, that was a guy named Ron (a truly wonderful human). He could sell Caribu internally in rooms I would never be allowed into. Finding that person is like throwing a rock through the window of a speeding train. Precise, and mostly luck. But without them, the CFO and the CEO never get convinced, because it was never going to be you who convinced them.
Third, and this is the one I beg founders to internalize: you need runway, and you need two kinds of it.
Financial runway is leverage. Going through an exit is shockingly expensive, and the other side knows exactly how much cash you have. Here is the move they run. You get a letter of interest. You owe it to your investors to shop it, so you burn a month collecting others. Then due diligence takes 30 to 45 days. Now you are down to about six weeks of runway, and that is precisely when they come back and say, we said twenty million, but actually, we'll acquire you for five; will you take it? And what are you going to do? You can't raise in six weeks. Your team is depending on you. Your numbers have probably slipped because you have been buried in the deal. The more runway you have, the more you can say "that's a terrible offer, no thank you," and actually mean it.
Emotional runway is the other tank, and it empties quietly. You cannot start this process already burnt out, because throughout it you are still pitching. Still telling people how great your company is, why your team is worth keeping, why this is going to work. If you are running on empty, you cannot do that, and you will either give the company away or shut it down. Start way earlier than feels necessary, while you still have fuel in the tank.
One more thing, specifically for the women. The day the deal starts, you are negotiating with your future employer while still holding a fiduciary duty to your current investors. And an assertive woman doing exactly her job, fighting for her company, her team, and her investors, gets labeled difficult to work with. A man doing the identical thing is a strong negotiator. That dynamic is in the room with you whether you invited it or not. Name it to yourself so it doesn't catch you off guard.
Would I do it again? Unfortunately, yes. I would also tell my younger self the truth I am telling you: it is harder, lonelier, and more individual than anyone lets on. Find the people who have been through it, and let them be honest with you. That one conversation, founder to founder, is worth more than any playbook.
Next, the last piece in this series, and the one I think about most: why luck is really just preparation meeting opportunity.
A note on how this got written: I used AI to help me write this. The stories, the opinions, and the scars are all mine. I just have a very good robot assistant who helps me get them out of my head and onto the page. Which is more or less the whole point of what I do now.