Current title and employer?
Chairman and Chief Executive Officer, Conversive, Inc.
Sounds fancy, but what do you really do?
I run a software company. Most of the time, that means I’m the den mother for a bunch of people trying to accomplish a bunch of different tasks at the same time without screwing each other up. My job is to keep them all running in the same direction. In a really good week, they not only move in the same direction, their movements mutually reinforce one another and the company takes another step forward. In a great week, I have enough time left over to actually promote the company’s message, build our visibility and talk with our clients.
Does anyone care where you went to law school or what your class rank was?
No one cares about any of that stuff in my business. Or in the real world, for that matter. It’s not as though I work with dumb people who don’t appreciate academic accomplishments. It’s just that where I am now those achievements have very little applicability. The law is unique in many ways. It really is a continuation of academia by other means. Resumes count. Your “brand” as a lawyer builds on a foundation of your law school, journals, clerkships, etc. But you’re not going to be a better manager than the next guy because you were on Law Review. Those things just don’t matter. Where I am, it’s more like my tribe of software geeks and I are trying to cross the Sinai and get to the land of sustainable revenues before hostile tribes eat our lunch or possibly even us. You’re either doing it or you’re not. Your ideas live and die on a day-to-day basis, and your credibility lives or dies with them. If you’re not getting there, no one’s going to feel any better about you just because you graduated in the top 5% of your class.
What firms did you work at?
Graham & James
Then Riordan & McKinzie
Both have been scooped up by mega-firms.
Corporate. I started out buying America for the Japanese at Graham & James. Then I worked in corporate finance at Riordan & McKinzie. Our principal clients were VCs, LBO funds and their portfolio companies. So we did everything—private financings, M&A, IPOs, etc.
Worst memory of being a lawyer?
Probably looking at my one-year-old son sleeping. I had been working on a deal, and I realized that I hadn’t seen him awake in two weeks and hadn’t seen him in the daylight in over a month.
Best memory of being a lawyer?
I did a deal with one of the partners at Riordan, who was actually a great guy. We finalized negotiations in New York and then closed the deal in Bermuda. I spent all night getting the docs ready for the closing. We closed in the morning surrounded by all these bankers wearing cranberry shorts, black shoes and socks. I had a couple of hours to go riding around the island on a moped looking for pink sand beaches before the closing dinner at a picturesque restaurant. It in no way resembled any other deal that I’ve ever worked on.
Describe your “I have to get the f*** out of here” epiphany?
There were many. I came out of law school straight into a recession. I learned very quickly to be concerned about the capabilities and priorities of law firm management. Like someone who knows their marriage won’t last right after they walk down the aisle, there were many, many moments of clarity while I was looking for the exit. I was shocked, overall, by what poor businesspeople most lawyers are. I also started to look at the telephone very differently. I realized that after 4:00 in the afternoon, and especially on Fridays, the telephone had a right end and a wrong end. Like a gun. And I was on the wrong end.
However, there was one moment of confirmation that was a real biggie. There was an associate a couple of years ahead of me, who I worked with a lot. Columbia Law school, Harlan Fiske Stone Scholar, brilliant, blah, blah, blah. But even more than that, this guy pulled insane hours. He was like Superman. When we did a securities filing, we wouldn’t just send it in electronically—this guy would get on the redeye and file the damn hard copy in person at the SEC the next morning. Then he’d fly home in time to bill some more hours that afternoon. He was the guy who always remembered obscure regulations at opportune moments, had perfect analysis, was an absurdly efficient worker and the clients loved his guts.
And he got passed over for partner.
I took one look at that scenario, and I knew that I was screwed. Not just a little screwed—completely dead. It was obvious that even if your performance was outstanding, the law firm remained a rigid hierarchy where you had to have sponsorship. Doing great work is not enough. I knew that to thrive in that environment I would have to kiss up in a very serious way to some people that I deeply detested. And let’s face it. There aren’t that many people that you are really, sincerely going to like after spending more than 2,000 hours a year in their company. The notion of pulling big hours and then electively spending extra time at work sucking up was just a non-starter for me. It became very clear that I wasn’t going to be able to make a life out of that.
Any advice for bitter lawyers out there looking to change careers?
First, take a personal inventory of what kind of non-lawyer qualities you have. In other words, what do you really want to do, and what are you good at? Is it really the practice of law that you dislike, or just practicing law in a firm? For many attorneys, the big company in-house counsel route can be very appealing. It does put you on the right side of the telephone on Friday afternoons. If you decide that you really don’t want to practice law, then you’d better figure out what else you’re good at and how can you make a living at it.
Second, realize it’s going to take a lot of time. That means both that it is probably a process of years and that you have to devote time to it constantly. Stop schmoozing partners and start networking with people in your areas of interest.
Finally, you should realize that you are going to be taking on more risk. A lot more risk. Financial risk, reputational risk, social risk. Just to be clear here, we are not talking about market risk, secular risk or anything else that is abstract, or that can be diversified away with good portfolio management. We are talking about the very, very real probability that you personally will fail. If you learn to accept that risk is inevitable, you may also find that sometimes the best exit is the most audacious one. Write a bestseller, or start a new political party, or become the world’s best wine critic. Lawyers have done all of those things, and let me tell you, they didn’t care what their partners said about them after they were gone. It’s a big world out there and no one cares if you made Law Review.