I spent last weekend at my 10th law school reunion. About 125 of my 500 or so classmates came back to Cambridge to reconnect with others who had suffered together through torts and civil procedure, through law firm interviews and the law review competition, through moot court and ultimately the bar. It was easy to pick out my classmates from the crowd — we were the young ones (relatively speaking). The other reunion classes were the 25th, 30th, 40th and 50th. While I'm impressed that so many folks came back for their 50th reunion, they did tend to blend together — the men all looked an awful lot like the portrait of the grey and distinguished Archibald Cox that hung in the law school halls and the women pretty much looked like Sandra Day O'Connor.

I was struck at the reunion by how many people I met who were no longer practicing law. In a crowd that ostensibly went to law school to learn how to be lawyers, there were professors, CEO’s, Congresspeople, SEC Commissioners, Consultants, Investors, Bankers, Entrepreneurs, among many other professions. During a session with my classmates, someone asked how many of us were no longer practicing law 10 years out. About half of the people in the room raised their hands. Those people were then asked if they used what they learned in law school in their jobs today, and every one of them, including me, raised their hands. Legal training is incredibly versatile in some respects. You learn to think and analyze and apply precedent to new fact patterns. When you think about it, that is no different from what one of my colleagues describes as the principle skill of a Venture Capitalist — pattern matching. Picking successful companies is about recognizing startups with similar characteristics (similar entrepreneurs, similar business models, similar sales channels, etc.) to those companies that have been successful in the past. Which is a relief, because I would hate to think that I suffered through 3 years of the socratic method for nothing.

On an unrelated note, I have a cautionary tale for entrepreneurs seeking funding. During a nighttime reception at the reunion, I was chatting with one of my classmates and told him that I was now a Venture Capitalist. He quickly grabbed another one of our classmates who had recently started a software company. The entrepreneur was a smart guy who had relevant domain experience and the software he pitched me on made some sense. The only problem is that he was quite drunk and proceeded to get drunker as the night went on. And as he got drunker, he grew more offensive. I’ll spare you his less-than-enlightened political and social commentary but suffice it to say that it would be hard not to interpret it as racist. By the end of the evening there was no chance that I would fund his company, at least not so long as he was running it. While he is certainly entitled to his opinions (I do not have a political litmus test for folks seeking my funding), I can not imagine investing in anyone who shows such incredibly bad judgment. What will he say when he takes a customer out to dinner? What will he say when he’s wining and dining a CEO candidate? So much of the success and failure of a startup depends upon the good judgment of its management that it would be foolhardy to invest behind someone you know to have shown poor judgment. And I would not.

Despite being accosted by an intoxicated rube, it was great to catch up with my law school classmates. Ten years out of law school, they have found themselves in all sorts of interesting positions across business, government, entertainment, academia and, of course, law. I look forward to hearing what everyone is doing fifteen years from now at our twenty-fifth. When that time comes, I am going to try my hardest not to look like Archibald Cox.