When I'm hiring I absolutely love to see founder experience as it teaches so many valuable lessons and is usually a sign of an independent, self-starter personality. I do try to watch out for this "founder damage" (great term!) – some founders get to the point where they simply can't work for someone else ever again. Once I'm over that hurdle I consider it a major positive sign.
Congrats to the OP on their success so far as well!
Unless I expect that it'll be an extremely sore topic, I will typically also just ask them why they want to work with us. I think that some people are shy about the questions you can ask in all sorts of situations. If you ask people they'll often tell you.
From what I've seen, having investors that the founder is answerable to can also help to mitigate this effect, although investors will sometimes pump you up + stroke your ego which can have the opposite effect.
For example, a software license email to one of them didn't arrive. That person started being passive aggressive as if I had done them wrong. Then later, they used the lack of that license as an excuse for unrelated problems. I would have expected a senior developer to be adept enough at problem solving to just ask why they didn't get that license that I had promised.
But it appears they were mentally still stuck at being a tiny cog in a huge machine.
I've hired lots of people like this who tended to leave or be managed out after 3-6 months.
That person didn't say they'd leave, they said they want to learn something, you took it as they'd want to leave which says more about you and your interpretation of it than anything else.
To be precise it is more in the context of founders and this text from the message above "see how a successful company operates". Basically if you go there and say "hey I am a founder and I need to learn how X works in a successful company"
Anyway I definitely extrapolated this, I doubt anyone would say it this blatantly. Just --if--.
The company I'm currently at even knows about the work I'm doing outside the company and supported me as I was working through the latest YC application rounds.
You want good people to join your company, it provides brand recognition if they then go on to found or do amazing things even better. You should never assume when hiring someone they'll stay for any length of time, obviously you want to try and create and environment where they want to stay but if you got a year or more out of the arrangement I consider that successful. That's why you need strong documenting and knowledge transfer policies.
The days of staying at companies long term (>3 years for senior people and >1.5ish years for regular folks) really isn't a thing any more at least in tech and startups.
There are no structures in place that make it advantageous to stay and 10s of thousands of dollars on the table as a worker that make it advantageous to shop around.
Plan accordingly as a manager and things will be a lot easier instead of losing talent because your worried they'll want to do other work at some point which is pretty much a given for most people.
"I have a lot left to learn. I know this because I saw room for improvement at X, Y, Z. I'm looking forward to working with experts/professionals/etc more senior than I am to learn from them, etc."
I was referring to 'room for improvement at marketing, time management, etc'. Skills, not locations.
I was mostly reacting against the phrasing describing yourself like a child compared to someone.