Dear Startup Boys: Tuck in Your Shirts for the Media

Say that Peter DaSilva is coming over to take your photograph. The San Francisco-based photographer has shot them all, from Ev Williams to Mark Hurd to Hunter Walk to Carol Bartz to, now, Mike Krieger and Kevin Systrom, the Instagram darlings of the moment, to accompany the front-page New York Times story about their sale to Facebook (for a billion in cash and stock, basically about a week after Instagram raised $50 million, at a $500 million valuation). And Peter’s done it all without kicky filters! Tee hee! Anyway so of course maybe this photograph will end up on the front page of the New York Times and you didn’t tuck in your shirt while Peter was there, and now you look unkempt, schlubby and not good in general. Even if you are a very handsome person, you will look that way!

I know that it feels square. I know that it feels like your dad’s way to wear shirts. Maybe it’s old thinking. Maybe it’s inside the box, not even near the outside of the infamous box? And I know that sometimes you even forget a belt because you are so very busy! But before a photographer comes over, why don’t you stop, look down and check yourself. Just say “Hey, give me five minutes.” Maybe have one of the three women who work at Instagram come over and give you an honest opinion, if the culture there allows that? (Too scared to ask them? Then just ask Instagram engineer Philip McAllister, he’s super-pretty.) Also, if you need a gay to take you shopping, lemme know.

It’s okay, this isn’t a big deal! People will take your photograph again later and you can correct this minor oversight in your business model.