My Career Regret - The Money and Interestingness Trade

Ten years ago, I was an analyst for the General Motors pension fund, working on fund investments into leveraged buyout funds and venture capital deals.  I literally wrote the investment memo for GMs investment into Accel IX, otherwise known as the "Facebook Fund."  (I wasn't a lead on the deal team or anything--just a gruntworking analyst.)  Still, I came into contact with some of the largest names in the private equity world--partners from top PE firms like Blackstone, Carlyle, and TH Lee, top venture firms like Summit and Accel--and even debt/distressed funds like Cerberus and Apollo.  These folks were absolutely minting money--but because I didn't really know what I wanted to do with my career, I didn't spend any time building relationships with them.  In fact, the one area I was pretty set on eliminating from my consideration set--leveraged buyouts--was the area where partners seemed to make the most money.

Now that I'm gathering capital, that seems to have been a missed opportunity.  These folks were literally pitching my team, and because I didn't necessarily want to do the same thing as they did, I didn't care much to spend time with them.

And that's not to say that the only reason anyone should network with somebody is because of money--but the reality is that access to capital is an enabler.  You see, people doing interesting stuff often need capital to make that stuff sustainable.  That's the whole venture capital world in a nutshell--and it's crazy fascinating.  People are inventing stuff that sounds utterly ridiculous (a box that makes things!) and turning them into reality.  That chip that enabled the authorities to see that kid in the boat from a helicopter--someone invested in that.  Not only that, whoever invested in that chip is probably feeling like a pig in shit right now for being a tiny little part of that capture--and more for the experience, the meaningfulness, the pride--the overall interestingness of it all versus whatever money came out of it.

Because, venture isn't about the money.  I mean, sure it's an asset class and investors expect a return--but if you were really just going for trying to make the most amount of money possible, you'd go work for a private equity fund or a hedge fund.  Those places don't make chips that can see terrorists from the sky, though.  In fact, they don't make much of anything, other than money.  In fact, they make for pretty boring stories compared to saying that you backed the medical device company that will enable one of those bombing victims to run the marathon next year.  That's pretty damned interesting.

That's what I didn't realize--that I had something to offer.  My interest in tech and eventual move to venture capital, New York's growth as a venture capital community--it's all super interesting, and would have been to all the people I knew who had so much money that money didn't mean nearly as much as a good story.  That's why people buy pieces of sports teams.  It's not about the money--it's about interesting stories, access, and things that aren't buyable by just anyone.  

If I had to do it all over again, I should have realized that as a young, curious guy, I'd eventually get into stuff that would have been super interesting to an experienced private equity investor who had more money than they knew what to do with.  Just the other day, an entrepreneur came in who was working at one of those funds.  I told him, "So the partners are going to back you, right?"  He hadn't really considered pitching, because he figured that wasn't what they normally did.  I told him how what they "normally" do and have been doing for the last 20 years might not be as fun or as cool as what he was up to.

They're out there searching for interestingness and he had it in spades.   

If you're early on in your career, stick around people who have made it that you find likeable and of good character.  Even if you're not intending on following their footsteps, undoubtedly, you'll find yourself in a position to offer them the money for interestingness trade.  It's done all the time--and it will enable you to keep doing what you're passionate about, and you'll be able to share your passion and interestingness with someone who really doesn't need the money, but who loves and appreciates funding more interestingness.