“It’s important to battle the urge to do the whole lot the identical means you probably did it the primary time:” Execs and Cons of Being a Repeat Founder. Some steerage from an understudied section of the startup ecosystem.

Our trade talks about ‘repeat founders’ with plenty of reverence and for good motive given the dedication required to construct a startup. We additionally generally consider it as a single cohort, however there’s a in all probability extra nuance. The ‘first startup failed however she realized on another person’s dime and now could be a killer CEO’ expertise is likely to be completely different than the ‘first one was a large success and now the query is whether or not she will be able to high that’ when it comes to what’s being constructed, how she’s constructing it, and the strain she feels.

a really drained panda trying within the mirror, digital artwork [DALL-E]

I’m additionally guessing (does anybody have knowledge?) that the variety of repeat founders is growing non-linearly as increasingly more entrepreneurs begin earlier of their careers, so understanding patterns amongst this group has by no means been extra related. With this in thoughts I requested a couple of ‘repeaters’ about their very own experiences, largely to make use of as background to tell my very own opinions. One particular person was my pal Sean Byrnes is a a number of time founder and writes about his experiences + recommendation for CEOs/founders in a free weekly e-newsletter known as Breaking Level. His response to my query about professionals and cons of ‘the second time’ was so good that I’m going to share it in full.

You’ve hit on a subject I may speak about for hours! Be happy to attribute any of the next to me, however I’m undecided in the event that they match precisely what you’re searching for:

Execs of being a 2nd time founder:

1. You possibly can benefit from the experience much more. It’s like using a curler coaster: the primary time you experience a brand new coaster you’re scared the complete time since you don’t know what to anticipate at each flip. The second time you’ll be able to benefit from the experience, however when it’s time to be scared you’re MORE scared than you had been the primary time.

2. Due to #1 it’s lots simpler to take heed to everybody round you. Because you’re listening extra, everybody round you feels heard and consequently they respect your management extra. It creates a virtuous cycle of you because the “skilled founder” largely since you’re calm and assured whereas listening to them.

3. You know the way your selections as we speak are prone to play out over the approaching years so you’ll be able to have extra confidence in them. You can even coach your staff to assume long term for a similar motive, main to higher selections in every single place. That foresight once more reinforces the thought of the “skilled founder” because it feels like you may have a crystal ball.

Cons of being a 2nd time founder:

1. It’s important to battle the urge to do the whole lot the identical means you probably did it the primary time. Not solely is the world lots completely different than your first journey, it’s not completely clear if what you probably did the primary time was a reason for success or simply noise. Nonetheless, everybody round you WANTS you to do it the identical means you probably did it the primary time as a result of that’s your expertise. Because of this, you’re preventing plenty of forces to do issues in new methods and never be a prisoner of your historical past.

2. You’ve gotten extra to lose. As a primary time founder you don’t have anything however upside, no matter what occurs together with your firm, because it’s a resume and expertise builder. A 2nd time founder (particularly one who has seen success) dangers tarnishing their resume/fame with a failure. Which means you could be much less bold and never as prepared to take dangers. It’s a day by day wrestle.

3. Expectations are larger. Even when it’s not true, folks really feel that second-time founders must be extra profitable. Because of this, the folks round you’re much less forgiving of huge errors, large pivots and different course corrections which are mandatory on the startup path. Everybody begins out believing on this picture of a second time founder as having “the components” and the whole lot that cracks that picture wears away at their confidence.

You possibly can, in fact, overcome most of these Cons via transparency and honesty which is simpler due to the Execs. Oddly, I don’t see many second time founders take that route as they benefit from the feeling of being seen as having the solutions. It’s an addictive cocktail to have a better time elevating cash and hiring your staff, particularly for those who struggled in your first firm.

I’m nonetheless digesting a few of the different responses and attempting to get their permission to share like I did Sean’s. Hopefully extra to come back!

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