| I certainly wonder about the "do something else" in the sense of serial entrepreneurs. If I could cash in once I'd be done. If I had enough money to retire on, I would. Run a cat shelter or something. But the actual answer here is probably a combo of a few things: One, running a company is probably not as much fun as building a company. Much of my career has been "pioneer" roles where nobody else has done the job before. At a certain point, the foundation is laid and the problems to solve are different and often less interesting -- at least to me. It's the build vs. maintain thing. Two, they started with good and noble intentions. Money got involved. A lot of money got involved. The noble intentions were replaced with reality. Three, have you met users? As a site grows you have to deal with more and more people and people can be very demanding and not very appreciative. Coupled with the previous factors, I think original founders get burnt out and decide to take the cash and move on. The allure of building anew is too much, the grind of maintenance is too much, and the cash is too good to pass up. Also four... there's a peak for any site. You often don't know when or how, but you do now that someday your site's maximum value, interest, participation, and all that is going to peak and then decline. Sticking around to fight the good fight may just mean passing up a payday and being left with a declining property nobody wants anymore. |
And then one day, completely unexpectedly (to me) I read that they’ve been acquired by a private equity firm. I reached out to find out what happened and what changed. His answer was along the lines of “turns out everyone has an exit point after all. Priorities and motivations change and I’ve given this company everything I have to give it. It’s time to explore what’s next”
I think about it a lot. And I’ve witnessed it in various ways numerous time since. People that were hacking on a side project with the idea of “I just want this to be a fun passive income stream” seeing the adoption and love their work gets suddenly thinking “oh my, there’s potential here I didn’t see before! I could build a whole team and company around this… let’s go raise investment!”.
I think we’re just really bad predictors at how achieving the things we want will impact us emotionally. When we reach those milestones we react either more positive or more negatively than we could understand previously.