Our business talks about ‘repeat founders’ with plenty of reverence and for good motive given the dedication required to construct a startup. We additionally typically 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 may be totally different than the ‘first one was a huge success and now the query is whether or not she will prime that’ by way of what’s being constructed, how she’s constructing it, and the stress she feels.
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 individual was my buddy Sean Byrnes is a a number of time founder and writes about his experiences + recommendation for CEOs/founders in a free weekly e-newsletter referred to 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 might 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:
Professionals of being a 2nd time founder:
1. You possibly can benefit from the trip much more. It’s like using a curler coaster: the primary time you trip a brand new coaster you’re scared your entire time since you don’t know what to anticipate at each flip. The second time you’ll be able to benefit from the trip, however when you understand it’s time to be scared you’re MORE scared than you have been the primary time.
2. Due to #1 it’s quite a bit simpler to take heed to everybody round you. Because you’re listening extra, everybody round you feels heard and consequently they recognize your management extra. It creates a virtuous cycle of you because the “skilled founder” principally 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 group to suppose long run for a similar motive, main to raised selections in all places. That foresight once more reinforces the concept of the “skilled founder” because it seems like you’ve got a crystal ball.
Cons of being a 2nd time founder:
1. It’s important to combat the urge to do every thing the identical approach you probably did it the primary time. Not solely is the world quite a bit totally different than your first journey, it’s not solely clear if what you probably did the primary time was a explanation for success or simply noise. Nonetheless, everybody round you WANTS you to do it the identical approach you probably did it the primary time as a result of that’s your expertise. Consequently, you’re preventing plenty of forces to do issues in new methods and never be a prisoner of your historical past.
2. You’ve got extra to lose. As a primary time founder you don’t have anything however upside, no matter what occurs along 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/repute with a failure. Which means you may be much less bold and never as prepared to take dangers. It’s a day by day battle.
3. Expectations are greater. Even when it’s not true, individuals really feel that second-time founders needs to be extra profitable. Consequently, the individuals round you’re much less forgiving of huge errors, huge pivots and different course corrections which might be crucial on the startup path. Everybody begins out believing on this picture of a second time founder as having “the system” and every thing 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 less complicated due to the Professionals. 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 group, particularly when you struggled in your first firm.
I’m nonetheless digesting a few of the different responses and making an attempt to get their permission to share like I did Sean’s. Hopefully extra to come back!
