“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 well-nigh ‘repeat founders’ with a lot of reverence and for good reason given the transferral required to build a startup. We moreover 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’ wits might be variegated than the ‘first one was a big success and now the question is whether she can top that’ in terms of what’s stuff built, how she’s towers it, and the pressure she feels.

I’m moreover guessing (does anyone have data?) that the number of repeat founders is increasing non-linearly as increasingly and increasingly entrepreneurs start older in their careers, so understanding patterns among this group has never been increasingly relevant. With this in mind I asked a few ‘repeaters’ well-nigh their own experiences, largely to use as preliminaries to inform my own opinions. One person was my friend Sean Byrnes is a multiple time founder and writes well-nigh his experiences translating for CEOs/founders in a self-ruling weekly newsletter called Breaking Point. His response to my question well-nigh 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 well-nigh for hours! Finger self-ruling to symbol any of the pursuit to me, but I’m not sure if they fit exactly what you’re looking for:

Pros of stuff 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 unshortened time considering 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. Considering of #1 it’s a lot easier to listen to everyone virtually you. Since you’re listening more, everyone virtually you feels heard and as a result they fathom your leadership more. It creates a virtuous trundling of you as the “experienced founder” mostly considering you’re wifely 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 increasingly conviction in them. You can moreover mentor your team to think longer term for the same reason, leading to largest decisions everywhere. That foresight then reinforces the idea of the “experienced founder” since it sounds like you have a crystal ball.

Cons of stuff 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 variegated than your first trip, it’s not entirely well-spoken if what you did the first time was a rationalization of success or just noise. However, everyone virtually you WANTS you to do it the same way you did it the first time considering 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 increasingly 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 wits builder. A 2nd time founder (especially one who has seen success) risks tarnishing their resume/reputation with a failure. That ways you can be less would-be and not as willing to take risks. It’s a daily struggle.

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

You can, of course, overcome most of those Cons through transparency and honesty which is easier considering of the Pros. Oddly, I don’t see many second time founders take that route as they enjoy the feeling of stuff seen as having the answers. It’s an haunting cocktail to have an easier time raising money and hiring your team, expressly 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 increasingly to come!