Ending Your Startup Journey

A founder who took his company public describes the emotional crash after success, the board's advice to plan his exit, and how he realized it was time to step down. The turning point came while traveling, when he stopped feeling the adrenaline that had driven him for years.
Chapters
Final days. So this is not. This is a story shared to me by a friend. It's really, really personable, and I feel really, really honored to have it. And I asked him. He was this CEO. He was a startup, and he was a founder and CEO of a public company. And after they IPO'd, he ended up stepping down. And now he does investing. He does lots of great things. But I was just like, tell me about how you knew it was time. And so he said, you know, like, when you're doing a startup and you've been there from the very, very, very, very beginning, you are always trying to get to the point where you have a successful and you have a sustainable company. And we have worked for years and years to get there. And this moment when we finally achieved it, and I could feel it, he's like, it was like an adrenaline high like no other I've ever experienced. And when he was at that peak, he's just like, we did it. I can't imagine ever leaving this organization. This is where I'm going to be for my entire life. There was no world in which he could ever imagine himself not being part of, of this team. Fast forward a little bit. One of the things with the CEO is you always are working on things that your team doesn't have time for. And so it first started off where he's working on some HR tasks, then he's trying to work with his CFO to be able to build a dashboard that captures some random finance thing. And he said it wasn't something where being in a startup has tons of highs and tons of lows. But he got to a point where he realized that he had a lot of blah phases. And specifically after all of this, he woke up and he was in his hotel room. He had been traveling, doing all these conferences, speaking things, meeting with partners, and he realized that he hadn't left his hotel room in four to five days. And he just suddenly looked at all the papers around him and he was just like, is this really what I want to be doing? And all the things that he really enjoyed doing, like working on the product and working on the engineering, those things still existed, but it wasn't under his purview anymore. And he realized, hey, listen, I'm not sure. It was just the inkling of maybe this isn't actually where I want to be long term. So he went to his board and he said, listen, not doing anything right now, but I just want to ask you, Just trying to figure out how I feel. And the nice thing about his position is that all of his board members have been previous CEOs, and they got it, and they said, perfect. They delivered the perfect response, which is like, I hear you. I know this is hard. Really appreciate where you've been from. I've been there, too. And there have been times where I thought, you know what? Maybe this is the beginning of the end, And I've been wrong. And there have been times where I thought, maybe this is the beginning of the end, and I've been right. And what I want you to do is I want you to, in your head, start imagining a future in which you stay and start imagining a future in which you go. And I want you to start thinking about who your successor would be, how you would get there, and start planning for it, and then in six months, see which future feels better for you. And so he did, and he originally thought, hey, listen, my COO is definitely going to be my number two successor. I'm so excited. And he realized, actually, maybe not. And he got really, really lucky. He said that was his biggest mistake. He got really, really lucky where he was able to find a number two, but it was just a fluke, and he just got super, super lucky. And so then that was it. And so he left, and that was the end of his starter journey.
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