Our trade talks about ‘repeat founders’ with quite a lot of reverence and for good cause 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 realized on another person’s dime and now’s a killer CEO’ expertise may be completely different than the ‘first one was a massive success and now the query is whether or not she will prime that’ when it comes to what’s being constructed, how she’s constructing it, and the strain she feels.
I’m additionally guessing (does anybody have information?) that the variety of repeat founders is rising 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 just a few ‘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 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 may 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 on the lookout for:
Execs of being a 2nd time founder:
1. You’ll be able to benefit from the journey much more. It’s like using a curler coaster: the primary time you journey a brand new coaster you might be scared the whole time since you don’t know what to anticipate at each flip. The second time you possibly can benefit from the journey, however when you realize it’s time to be scared you might be MORE scared than you have been the primary time.
2. Due to #1 it’s loads simpler to take heed to everybody round you. Because you’re listening extra, everybody round you feels heard and because of this 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 understand how your selections right now are more likely to play out over the approaching years so you possibly can have extra confidence in them. It’s also possible to coach your crew to suppose long term for a similar cause, main to raised selections in all places. That foresight once more reinforces the thought of the “skilled founder” because it appears like you’ve gotten a crystal ball.
Cons of being a 2nd time founder:
1. You must struggle the urge to do all the things the identical means you probably did it the primary time. Not solely is the world loads completely different than your first journey, it’s not completely 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 means you probably did it the primary time as a result of that’s your expertise. In consequence, you’re preventing quite a lot 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. Meaning you could be much less bold and never as keen to take dangers. It’s a every day wrestle.
3. Expectations are increased. Even when it’s not true, folks really feel that second-time founders must be extra profitable. In consequence, the folks round you might be much less forgiving of large errors, massive pivots and different course corrections which can be mandatory on the startup path. Everybody begins out believing on this picture of a second time founder as having “the method” and all the things that cracks that picture wears away at their confidence.
You’ll be able to, after all, 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 crew, particularly in the event you 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 return!
