“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.

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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.

a very tired panda looking in the mirror, digital art [DALL-E]

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.

3. You know how your decisions today are likely to play out over the coming years so you can have more confidence in them. You can also coach your team to think longer term for the same reason, leading to better decisions everywhere. That foresight again reinforces the idea of the “experienced founder” since it sounds like you have a crystal ball.

Cons of being a 2nd time founder:

1. You have to fight the urge to do everything the same way you did it the first time. Not only is the world a lot different than your first trip, it’s not entirely clear if what you did the first time was a cause of success or just noise. However, everyone around you WANTS you to do it the same way you did it the first time because that’s your experience. As a result, you’re fighting a lot of forces to do things in new ways and not be a prisoner of your history.

2. You have more to lose. As a first time founder you have nothing but upside, regardless of what happens with your company, since it’s a resume and experience builder. A 2nd time founder (especially one who has seen success) risks tarnishing their resume/reputation with a failure. That means you can be less ambitious and not as willing to take risks. It’s a daily struggle.

3. Expectations are higher. Even if it’s not true, people feel that second-time founders should be more successful. As a result, the people around you are less forgiving of massive mistakes, big pivots and other course corrections that are necessary on the startup path. Everyone starts out believing in this image of a second time founder as having “the formula” and everything that cracks that image wears away at their confidence.

You can, of course, overcome most of those Cons through transparency and honesty which is easier because of the Pros. Oddly, I don’t see many second time founders take that route as they enjoy the feeling of being seen as having the answers. It’s an addictive cocktail to have an easier time raising money and hiring your team, especially if you struggled in your first company.

I’m still digesting some of the other responses and trying to get their permission to share like I did Sean’s. Hopefully more to come!