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“You have to fight the urge to do everything the same way you did it the first time:” Pros and Cons of Being a Repeat Founder
Some guidance from an understudied segment of the startup ecosystem
Our industry talks about ‘repeat founders’ with a lot of reverence and for good reason given the commitment required to build a startup. We also sometimes think of it as a single cohort, but there’s a probably more nuance. The ‘first startup failed but she learned on someone else’s dime and now is a killer CEO’ experience might be different than the ‘first one was a big success and now the question is whether she can top that’ in terms of what’s being built, how she’s building it, and the pressure she feels.
I’m also guessing (does anyone have data?) that the number of repeat founders is increasing non-linearly as more and more entrepreneurs start earlier in their careers, so understanding patterns among this group has never been more relevant. With this in mind I asked a few ‘repeaters’ about their own experiences, largely to use as background to inform my own opinions. One person was my friend Sean Byrnes is a multiple time founder and writes about his experiences + advice for CEOs/founders in a free weekly newsletter called Breaking Point. His response to my question about pros and cons of ‘the second time’ was so good that I’m going to share it in full.
You’ve hit on a topic I could talk about for hours! Feel free to attribute any of the following to me, but I’m not sure if they fit exactly what you’re looking for:
Pros of being a 2nd time founder:
1. You can enjoy the ride a lot more. It’s like riding a roller coaster: the first time you ride a new coaster you are scared the entire time because you don’t know what to expect at every turn. The second time you can enjoy the ride, but when you know it’s time to be scared you are MORE scared than you were the first time.
2. Because of #1 it’s a lot easier to listen to everyone around you. Since you’re listening more, everyone around you feels heard and as a result they appreciate your leadership more. It creates a virtuous cycle of you as the “experienced founder” mostly because you’re calm and confident while listening to them.
