Love and Startups: What I learned from my best friend's wedding


This past weekend, I attended the wedding of a guy I played t-ball with in the summer of 1985.  That fall, we were seated across from each other in first grade.  A year ago, I went with him to pick up the ring and two days ago, I was in his wedding party.

Their relationship and the event made me think a lot about partnership and building something special--topics that are  top of mind in my day to day job as a venture investor. 

It's one thing to build something meant to be a quick flip, but if you're going to build a gamechanging business, I think there are a lot of lessons you can learn from marriage and finding that special someone that can be applied here.  Granted, I've never actually gotten to that point, but I've tried to do a lot of observing of great couples like this one--in hopes that I'll have just as successful a start as they did.

1) "A" Talent attracts other "A" talent. 

My friend has been best man to something like 5 or 6 guys already, and when/if I ever get there, will undoubtedly be mine.  It's funny to think of him as the groom, because he is definitely the "best man".  That's how he got such a great girl.  So, when you're putting together your team, don't settle--and keep in mind that you are setting the tone for the rest of the hires.  If you aren't at the top of your field, you're going to have trouble attracting other high quality hires to come work for you. 

2) Be patient before diving into something.

His brother described this as "worth waiting for" and, at 32, he was one of the last of his group of friends from Brooklyn to marry.  I'm idealistic and I think that if you're going to go all in on something, it should be something amazing.  If that takes some time to come along, just wait for it.  We have a very aspirational startup culture now where doing your own thing is cool--and there's plenty of money to support lots of people starting companies.  Unfortunately, I feel like half the people starting companies now would be best suited to be great CTOs or VPs of Marketing at someone else's startup.  I feel similarly to a lot of the couples I meet.  *That's* the person you went all in on?  Really?  The right relationship and the right startup idea should pull you in and take off like a rocketship, not feel like something that requires a monumental effort to achieve a modicum of success with. 

3) Plans will go awry.

I've always thought that the person I wind up with is going to be someone who understands that the best laid plans will get diverted in a hurry--and that we're really signing up to face the unknown together rather than knowing exactly how things are going to wind up.  Those are the kinds of people you need to recruit in your startup--people who can react, improvise, and generally roll with the punches.

4) The relationship and the company is bigger than you.

It seems that to have a successful marriage, you have to build up the relationship to be more than just the sum of the parts--that there's more going on than just you getting what you need and the other person getting out of if what they need.  You should make each other better, and work as a team amazingly together.

That's why, when big companies do acqui-hires, they want to buy whole teams.  It's hard enough to find great talent, but to build them into your culture and get them working together is even harder.  So, when you find a team that comes together, you've got more than just the sum of the parts.  Everyone feeds off of and learns off of each other when it's working. 

5) Product note: Grouping your friends is unnatural, stressful, and doesn't reflect reality

I'm pretty sure I don't want a bridal party--mostly because I can't even think of five or six guys that would really be appropriate for it.  Out of my five closest friends, four of them are women, and any attempt at grouping all of them up would, at least in my life, create an awkward amalgamation of people that doesn't reflect my real life.  They wouldn't all be friends with each other, and I feel like it just represents a weird mix of a snapshot of you you're closest to right now combined with some additional consideration for historical relationships--the Veteran's Committee vote, if you will.  That's why I have a lot of concerns about services like Google+ where usage of the site requires some kind of "management" of your social network.  You're bound to forget people, or not be using the same services as others.