Sorry Brian, but it was my first reaction as well. I showed a friend the pic and asked "what do you think of this person?" and she said "he's evil and creepy" :(
If it were me, I would just take a quick snapshot right now and replace that photo temporarily, until you can get some better professional shots.
No really, open Photo Booth and take a brighter picture, right now.
Studies have shown that the first impression you get of a piece colors your perception even after you read the whole thing. Pictures have a stronger immediate emotional reaction than words do, and while the bolded "we will be implementing a $50,000 Airbnb Guarantee" definitely gives an immediate "wow, nice" feeling, it'd be even better if it wasn't dampened by the initial "uh, who's the Bond villain?"
For what it's worth I think that the photo looks perfectly fine. I'd be a very happy person if I could photograph that well. Customers don't care how professional the profile pictures look. They care about their experience using the service itself.
I hesitated to even bring it up because I didn't know how to say it without it sounding like a personal attack, but FWIW, I didn't mean it as one.
We all have photos taken of us that convey personalities that aren't really our own. I don't think you're a douche, but the photo gives that impression a bit.
Yo man: f these haters. Even the well meaning ones with their rubbernecking advice, even the fellow YC alums who don't understand that when a man has just been through hell and back that the last thing he needs is more people piling on with "constructive criticism" in an open forum. A lot of people tried to kill you just now, with a few like Melinda Byerley openly admitting that this was just an opportunity to express their envy and hatred.
For PR reasons you need to smile, even as JimmyL critiques the sincerity of your orthodontics. Smile on the outside and ask them in a chipper tone how you can be of service, but in the end, seriously, f* em. There's an insane amount of implementation work to do to get this 24/7 support and insurance program operational. F* em all and just plow. Pot of gold at the end of the rainbow. And your real customers and fans will thank you for it.
If it were me, I would just take a quick snapshot right now and replace that photo temporarily, until you can get some better professional shots.