At the AOL/SeedStart event last week at the Bowery Hotel, I got in a conversation about hugging.  I’m more apt to hug female friends of mine from the startup world than I am in any other industry.  That also goes for NoNeck.  I don’t usually hug other dudes (except for my high school buddies… but all boys Jesuit prep schools are kind of like that), but NoNeck is well worth a squeeze.  Hugging or not, it’s also a pretty blurry line when I’m working and when I’m playing.  I do a lot more recreational things with people I know in the tech scene than I ever did in finance.  We play on sports teams together, hangout late.  Am I working or am I just hanging out with friends at a bar?  What actually counts as a friend?   The other day, I noticed that someone who works in digital media who was following me on Twitter was checking in to the McBurney YMCA  on Foursquare.  I immediately followed them back and asked them if they swim—inviting them to swim with me the next time I was there.   

It’s all part of a culture of, for lack of a better word, intimacy, that happens in the innovation and startup world.  When you are your company and you own the outcome of your career, because you’re building it like an entrepreneur, you’re just going to sink more of yourself into it.  I can’t get to know your company without getting to know you as a person.  I can’t recommend you to be employee number four or five for the company that I just joined the board of unless I’m pretty sure you fit within the culture and have the same values as the founding team.  It’s incredibly hard to network in this industry without sharing yourself.

That also lends itself to some difficulties and some awkwardness.  Guy/girl professional acquaintances can run into awkward situations and different expectations—not out of any bad intent, but that’s just the nature of the kind of thing that happens when you’re getting to know what drives someone to leave a stable job to do a startup and what drives them to work as hard as they do.  It also means I have to walk a careful line when turning an investment opportunity down and maintaining a professional relationship—because it’s hard for an entrepreneur not to feel like you dissed them personally.  I’m not using your competitors product because I have an issue with you or your business—it’s purely based on the feature set—but I understand why you might think that way.  I’d feel the same way when I could get people to check out or pass around my startup.

It’s also not a bad litmus test, though.  If you can’t fully throw yourself in to a startup—to dive into the deep end—then I think you’re going to find the pervasive nature of the work, how it takes over your life, very difficult to handle.  It may take some getting used to, but ultimately, we all open up the kimono somewhat on our way to driving our businesses and our careers forward in this industry.

How not to dress like a VC

Should every startup get funded?