How not to dress like a VC

I’m in shorts today.  Why?  One, because it’s hot out.

Two, also because I attended the Startup Waffles breakfast at Dogpatch. 

Also, I kind of hate pants.  Once, in college, I wore shorts until December—until single digit temps.  It was my personal protest against the cold weather.  Yes, I was that guy.

When you’ve got waffles, syrup, and vegan chocolate chips being doled out to 150 local entrepreneurs at 8 in the morning, you don’t exactly want to be the guy in the khaki pants and blue shirt dressed up like the only obvious VC in the room.  In fact, by my count, only one other VC was there.  I also spotted an angel.  Sometimes, I wonder how other investors get deals.  You don’t have to be out at all of the entrepreneur events—but at least show up to *some* of the ones not involving pitching.

I feel like there are two types of deals.  One deal is the kind of deal that everyone is going to see.  It’s going to make the rounds and you’re going to see it.  You should probably wear your khakis for that meeting, especially since there’s a good chance the entrepreneurs will be wearing theirs.  

Then there are the deals that you meet because someone struck up a conversation with you on a waffle line, on a Brooklyn kayaking tour, or in a blog comment.  It’s pretty easy to get yourself on the list of commodity money that you should approach, but much harder to become someone that entrepreneurs feel genuinely interested and comfortable talking with about what is undoubtedly the most important and scariest thing they’ve ever done.

I try to be all about the friendly, casual approach.  Entrepreneurs have enough things to be stressed out about—they don’t need to get freaked out over getting coffee with me.  I aim for people to spend time with me because they feel like it’s time well spent and enjoyed—not just because they could wind up with a check at the end.  I don’t wear what I wear, talk how I talk, or do what I do to “appear” friendly…  I don’t think you can fake that kind of thing.  I’m just a casual guy in situations where I don’t see a reason for unnecessary formality. 

I skipped three powerpoints in the last two days and got called the funniest VC this company had met with (probably a low bar, though).  Just talk to me about your company, and more importantly, about yourself. 

Is it possible that I come off as too friendly or too casual… bordering on unprofessional?  If you judge people’s professionalism and competency based on whether or not they’re wearing shorts in the hottest NYC on record, then I think you’re going to have a tough time in the startup world.  Angels, biz dev opportunities, and certainly technical talent comes in all shapes, sizes, and forms of fashion.  Assume they call come in one flavor and you’re going to miss out—although I might even go as far as to say that khakis should probably negatively influence your thinking on a dev hire.  :)

At the same time, if we do decide to work together, we’re probably going to wind up seeing each other at our worst anyway.  If you wind up with a board member, it’s like getting married.  Imagine marrying someone based on a bunch of dinners at fancy restaurants where everyone was dressed to the nines. 

Personally, I’d rather make sure I get that post-run sweatpants look under my belt first before I go buying rings.