Neither Rich or a King

Makes you think:

There’s a saying: “You can be rich or be king.” You can sell your company for as much as possible, or you can be in charge. Though maybe neither is entirely possible. When I founded my second company, we had seven people, and we still argued over what to do and how to do it. I was CEO and I still didn’t get my way. was founded in 2003 and Yahoo!, just two years later, bought the site and then promptly ground it into pieces. Joshua Schachter, the founder, shared some of his reflections in NYMag.


I’ve since become an angel investor, and I’ve done just shy of 200 investments. And when founders sell, they wanna go out and celebrate. As often as not, they’re weird and awkward anyway, so it’s not like … I think a lot of time that selling is not the victory it seems. It takes away all of your forward momentum. Do you take building a product and being vibrant and known and trade that for cash? It may be the intellectually correct thing to do, to ensure your financial stability going onward, but it’s not emotionally rewarding in the same way.

I know that feel bro. I had to laugh-out-loud at this:

… Leadership had no vision or mission, so they couldn’t evaluate any decision. Upper management wasn’t taking risks, and everyone else was just optimizing to not get yelled at or stay at work late. My contract was that I had to stay for two-and-a-half years. At the end of my time at Yahoo, I woke up screaming a few times. It was a grind and super demoralizing.

This is why I decided to bail immediately after I sold my last company and not stick around for any earn-out or retention package. I know what it’s like to “wake up screaming” – it’s the worst.

I don’t want to be rich nor a king – those aren’t goals of mind (and never have been). Instead, I want to work with good people on a product that I believe in for as long as I possibly can. It’s not too much to ask for, right?

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