I'm a product guy. Successful, good at what i do, and looking for a change. Came across an opportunity which (at first blush, so to speak) matches what I'm looking for -- the team, the company stage, growth potential, etc. The catch is that it's a well-known gay "dating" site. And more in the "looking for mr. right now" sense of dating than "looking for mr. right".
Career killer?
Would a background like that hurt my chances of a successful exit if I ever started something on my own?
I probably wouldn't think twice about hiring someone who worked there (speaking as both startup junkie and a gay guy), but I've been through acquisitions and know those HR girls in Fortune 500 companies might think twice if they're doing a background check.
1) Eliminate the word career from your vocabulary. It's something invented by beaurocrats as a rationalization for being timid.
2) Ask your self "can I identify with this product?" Or, more importantly, are you OK with other people making the connection that you are about "Y"? Can you say: I am X and I built Y" with a resounding sense of pride. Would you feel comfortable being introduced on CNBC as Mr. "Y". If the answer is not "Yes!" with an exlamation point, then don't take the job.
What you should never do, however, is base your life decisions on your opinions on what an investment banker might think.
That's not only a bad way to live, but also a bad way to run a business. Be your own compass!