I found that having a failed startup was good resume fodder to some extent. I was worth more in the marketplace after my failed startup, since I was perceived as having a more versatile skill set.
(It helped that my failed startup, while financially a failure, was cool and helped me demo a lot of advanced coding skills. :)
But I did run into a personal problem: after being a startupper, I found it very hard to transition back into working for someone else. In the end I had to sit down and be honest with myself: did I want to start another startup right now or did I just want a paycheck? I decided-- for the time being-- on the latter. So I had to swallow a bit of the radical self-direction I'd become accustomed to and decide to work for my employer since that's the deal.
I remember one particular job I interviewed for after leaving a start-up, and got asked various questions like "why did you fail?" and "working for that little money? That's stupid!"
I always think of them as the perfect example of "the interview is for you to learn about the company and the company to learn about you."
So, if someone calls you stupid to your face in an interview, that's probably not a good place to work - so I'm guessing that was slightly a hyperbolic recollection.
That said, both questions can be turned around to your advantage: The first, show that you have learned from your mistakes and that's you're cool and focused in the face of adversity. The second, that you're not just a day labourer, but you're focused on and motivated by the long haul: "yes, it was a long shot, but if we'd succeeded, we'd change the way the world thinks about X".
No, they really said "stupid." I must have blanched -- I've worked with difficult people and can tolerate a lot -- because he immediately tried to back away from it.
But, yeah, bad place to work. They went bankrupt and got delisted from the exchange about 2 years later. I will admit to feeling some schadenfreude at that.
It's definitely about having the right attitude. I was able to find a job that gives me a lot of autonomy, but also direction. At the moment, I quite enjoy letting someone else make the big decisions for me!
There's always a freedom/stability trade-off. One thing I discovered with my own startup attempt, and also by watching others, is that being completely out there on your own can be a real pain in the butt. You have to hustle, and you have to spend a lot of time doing things you don't enjoy doing that are done for you in a larger employer.
I might do the independent thing again, but I'm going to be a lot more careful and deliberate about it. I've decided that the "throw yourself to the wind and then buckle down" model romanticized in startup cowboy culture is questionable. This time I'm being a spreadsheet nazi, and with my own finances as well as the venture's, and I'm making much more pessimistic assumptions about uptake. I'm also going for something where I can bill customers directly, not something that requires B2B selling. The latter is really hard to do for a little guy. B2B could come later if the product is successful in the open product market.
For years, I felt that my failed startup was exactly that. A failure, and an embarrassment. Recently, I took to writing about it, hoping that simply having it written down would change my perspective. It did.
I was looking for a job change, and I used this chance to add that failure to my resume. It is a part of my history, whether or not I personally felt that it was a failure. Surprisingly, the instant I sent out my new resume to companies (I previously left it out due to shame), I was invited for interviews with MUCH greater success, and got a few decent offers. Of course, the companies I applied to were different from the ones previously, so I cannot say for sure that putting the startup had a better result, but it seems to be true.
Even during interviews, employees at these companies seemed to light up when discussing my experience with my failed startup. It has allowed me to value those 3 years much more, and no longer look back on it and hide it in shame.
(It helped that my failed startup, while financially a failure, was cool and helped me demo a lot of advanced coding skills. :)
But I did run into a personal problem: after being a startupper, I found it very hard to transition back into working for someone else. In the end I had to sit down and be honest with myself: did I want to start another startup right now or did I just want a paycheck? I decided-- for the time being-- on the latter. So I had to swallow a bit of the radical self-direction I'd become accustomed to and decide to work for my employer since that's the deal.