z on life

Doing a startup and dating are similar in lots of ways, so it felt right to share a few thoughts on that. It should be noted that this is a guy’s perspective on dating girls and being that I have no other perspective to pull from, it will inherently be a bit biased. That said, I’d love to hear a girl chime in on this one.

Okay here we go:

Startups and girls can both cause you to think irrationally and can lead to bad decisions. When you get really involved in either, you stop thinking about what is right and just about what you want. It’s almost never good to make emotional decisions in startups, but it happens all the time. This is how founders stay with a sinking ship for way too long, sell out way too early, or tear a company apart due to irreconcilable differences. It goes without saying that the dating metaphors of those things in the last sentence should be crystal clear.

In either case leaving them is really, really hard and there are lots of variables in the decision. In both contexts, you can definitely ruin your future, credibility, career, and even friendships. Worse yet, the more money involved, the wilder the severance will be. On the other hand, leaving can be the best thing you’ve ever done, depending on the situation. In either context, it’s hard to make the right choice.

Getting girls, like raising venture funding, is easiest when you have someone on board and can be terribly difficult when you don’t. Psychologists and pickup artists alike would agree that the social proof of having a girlfriend makes it enormously easier to meet girls. Likewise, getting the first term sheet is much harder to achieve than the cascade of attention and interest that will automatically follow with VCs once there is someone leading the round. You get the most, when you need the least.

Everyone wants a Cinderella story whether it is the story-book romance of meant-to-be high school sweethearts or becoming the next Mark Zuckerberg. The truth is, very few will end up like this in either context, but everyone wants it nonetheless.

It’s important to know what the goal of the commitment is and that expectations are set early. If one co-founder wants to go all the way and make a billion-dollar business and the other wants a flip, there will be some intense arguments along the way and things probably won’t work out. Likewise, mismatch in relationship commitment and goals is just brutal, and leads to nothing other than vicious breakup or complete entrapment. Both cases sound pretty sub-optimal.

Marriage is the IPO of life, unfortunately most are left wanting more. Marriage is one of the biggest life goals for many (sorry to those who would argue), but less than half of marriages keep people happy enough not to have another one later. Serial entrepreneurs with 9-figure exits and enough accomplishment and money to keep most normal people happy for multiple lifetimes continue to get back in the game over and over again. I guess the best entrepreneurs love to trade up?

There’s always anxiety on the launch pad whether its picking up a girl in a bar or launching a product. Neil Strauss in “The Game” argues that guys need to pick up a girl within the first three seconds of seeing her or it is a blown chance. You’ll just keep waiting for the perfect moment or convincing yourself something better is coming but you’ll never jump. This is so true in startups too. If you get close to a product launch and keep pushing out one more feature, one more detail, one more design, you’ll never launch. It’s always one more day, or three more seconds.

Girls, like VCs, are looking for a track record and will want to know a relationship history. It’s among the first thing girls ask, often indirectly, and its also why sites like DontDateHimGirl.com exist in the first place. Likewise in venture, referrals and personal references for a core team will make or break the diligence process. The question is, should there be a DontFundThem.com variant, or conversely, should guys go on dates with a relationship resume?

Fail fast and iterate definitely applies to both domains. You only have so much time to start successful companies. So, you need to start that career progression early and grow yourself with the steepest possible trajectory without the fear of the failure that is inevitable. Analogously, meeting girls is exactly the same in that failure is inevitable but the learning process tied with failure is crucial. The more girls you meet and interact with, the better you will be at seeming interesting to future ones. You only have so much time. The clock is ticking. And one of those future ones will be ‘the one’ so you better not blow it. Are you ready?

- - -

So, since dating and startups have been proven to be basically equivalent, the key questions still remain. Was Silicon Valley built by great ladies men? Are charming guys better than most at building billion dollar businesses? Or are my only-half-serious theories completely off-target? At the very least, hopefully they were entertaining :).

This entry was posted on Tuesday, March 25th, 2008 at 10:51 pm and is filed under Main, My Favorite Posts. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.