Our trade talks about ‘repeat founders’ with a whole lot 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 most likely extra nuance. The ‘first startup failed however she discovered on another person’s dime and now could be a killer CEO’ expertise may be totally different than the ‘first one was a massive success and now the query is whether or not she will high that’ when it comes to 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 rising non-linearly as increasingly 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 number of ‘repeaters’ about their very own experiences, largely to make use of as background to tell my very own opinions. One individual was my good friend 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 execs 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 discuss 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 may benefit from the experience much more. It’s like driving a curler coaster: the primary time you experience a brand new coaster you might be scared your complete time since you don’t know what to anticipate at each flip. The second time you possibly can benefit from the experience, however when you understand it’s time to be scared you might be MORE scared than you had been the primary time.
2. Due to #1 it’s loads simpler to hearken to everybody round you. Because you’re listening extra, everybody round you feels heard and because of this they admire 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 understand how your selections right this moment are prone to play out over the approaching years so you possibly can have extra confidence in them. It’s also possible to coach your workforce to assume long term for a similar motive, main to higher selections all over the place. That foresight once more reinforces the thought of the “skilled founder” because it seems like you could have a crystal ball.
Cons of being a 2nd time founder:
1. It’s a must to combat the urge to do every thing the identical manner you probably did it the primary time. Not solely is the world loads totally different than your first journey, it’s not solely clear if what you probably did the primary time was a reason behind success or simply noise. Nonetheless, everybody round you WANTS you to do it the identical manner you probably did it the primary time as a result of that’s your expertise. Consequently, you’re preventing a whole lot of forces to do issues in new methods and never be a prisoner of your historical past.
2. You might have 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/popularity with a failure. Meaning you could be much less bold and never as keen to take dangers. It’s a every day battle.
3. Expectations are increased. Even when it’s not true, individuals really feel that second-time founders must be extra profitable. Consequently, the individuals round you might be much less forgiving of large errors, massive pivots and different course corrections which might be mandatory on the startup path. Everybody begins out believing on this picture of a second time founder as having “the method” and every thing that cracks that picture wears away at their confidence.
You may, after all, overcome most of these Cons by means of 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 neater time elevating cash and hiring your workforce, particularly when you struggled in your first firm.
I’m nonetheless digesting a number of the different responses and making an attempt to get their permission to share like I did Sean’s. Hopefully extra to return!
