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“I stalked him. Found out where he parked his car and waited.”

Title and Employer?

Partner, Endeavor Talent Agency.

Okay, but what do you really do?

I represent writers and directors. My primary responsibility is to find them interesting creative and financial opportunities in television and film.

Law school, class rank?

Chicago–Kent College of Law. Top 10%.

What firms did you work at?

Cook County Public Defender. Pat Boyle and Associates. And for a year of so, I had my own firm. Represented restaurant and nightclub owners—probably because I worked nights as a bartender to make extra money.

Practice area?

Criminal, Personal Injury and some transactional stuff (relating to bars and restaurants).

Worst memory of being a lawyer?

Pleadings and discovery.

Best memory of being a lawyer?

Being a public defender. I loved it. It was exciting and fun and I felt like I was actually doing something real. The only drawback was the money. I made about $27,500 a year, which didn’t go too far in Chicago. So I supplemented my income by bartending, drafting appeals for private criminal attorneys and handling “pain in the ass” transactions for friends. Truth is, when I added everything up, I actually made more money than most of my friends at the big firms—and unlike them, I actually had some fun.

Describe your “I have to get the f*** out of here” epiphany.

There wasn’t really one specific moment. Like I said, I actually liked being a lawyer. So it wasn’t really some major, earth-shattering epiphany. It was more of a gradual thing.

So how does a former Public Defender from Chicago hit it big in Hollywood?

After being a lawyer for seven years or so, I started asking myself those early-thirties “meaning of life” questions, like “Was I really meant to be a lawyer?” “Is it wrong to crave a more exciting job?” I was working for a civil litigation firm at the time and I was bored. I wanted a more fast-paced, exciting challenge. For some reason, I picked LA and the entertainment business. Not really sure why. It just sounded fun. So I sold my loft and decided to move west.

You just moved to LA and said “Here I am?”

Kind of. But nobody cared. I was 32, didn’t know anyone—and didn’t even know what kind of job I wanted. But that was irrelevant. Or just stupid. Anyway, call it fate or serendipidity, but just prior to moving, I met a few guys who were making a movie in Chicago. They’d come into the bar where I was working and get drunk and have a wild time. They were quickly dubbed the “cool movie guys in town for the summer.” Long story short, one of them offered me his apartment for a week to get settled—and I ended up living there for four years. The “cool guys” became my LA family.

So you get to LA, then what??

I landed a part-time job at New World Television. Sounds sort of sexy, but it wasn’t. They were going out of business and needed some hack attorney—like me—to help with remaining production issues. The only thing I did during those three months was concentrate on finding a new job. I called every person listed on the New World phone sheet and took anyone and everyone out for drinks, breakfasts, coffees...Whatever, wherever, so long as they knew more than me...which included every person in LA.

Shortly thereafter, I landed a job in the legal affairs department at ABC. I think the head of the department felt sorry for me. Honest. He was from Chicago, went to a no-name law school like me… So he gave me a job drafting licensee agreements. Problem was, I’d never really drafted a contract. So I sucked at it. Each day I would walk into my bosses’ respective offices to discover that I was an even bigger moron than I was the day before. And trust me, the job wasn’t glamorous. But for seeing Drew Carey in the cafeteria once, I was completely disconnected from “Hollywood.” I might as well have been working at some mid-size firm in Akron. It was right around then that I decided to become an agent. They seemed to have the best job in Hollywood. They made deals, but didn’t have to worry about minute details. But being a loser licensee lawyer isn’t exactly the fast track to agent superstardom. So I had to start my job search all over again.

How did you transition from “loser licensee lawyer” to agent?

It wasn’t easy, trust me. The first thing I did was call up some agents I knew and offer to work for free—but they all said no. In fact, they thought I was insane. So I started looking for people with similar backgrounds to me who might give me a break—or like the guy at ABC, feel sorry for me. When I discovered that one of the top literary agents in town was a former public defender, I made a beeline for his office. But the receptionist wouldn’t let me in the door. I tried calling him a bunch of times, but his assistant wouldn’t put me through. So I basically stalked him. Found out where he parked his car and waited for him. Unfortunately, when he saw me standing by his car, he was terrified. I quickly explained who I was and what I wanted, and he was kind enough to let me take him out for a drink later in the week. Though he didn’t offer me a job, he did give me some great advice: Get a job as a business affairs executive. Learn how to negotiate deals on behalf studios or networks. After a few years, you’ll have something (deal making experience) to offer agencies.

After about a month, I got an entry-level job at Fox Television Studios as a business affairs executive. I negotiated actor, writer and director deals for about a year, established more relationships and felt like I was finally ready to become an agent. Again, I went around and offered my services for free to the major agencies—and again, they all said no (and continued to think I was some annoying, freakish pest).

A month later, I got an offer to work as a business affairs executive at a new management/production firm founded by Michael Ovitz, who was, at that point in time, the most powerful man in Hollywood. So I said yes. I immediately began to harass the various managers, asking them how to break into the talent-representation side of the biz. (Agents and managers basically do the same thing. The main difference is that agents are more heavily regulated under state law and can’t “produce.”) But no one was interested in helping. After about seven months, I got a meeting with Ovitz. Like I said, back then, this guy was God. The most influential man in show business. My heart was thumping. I told him I wanted to “represent talent” and that I would work for free. Unlike everyone else, he didn’t look at me like I was out of my mind. All he said was “I’m not sure how something like that would work…and there might be legal complications if we don’t pay you.” Right then, I knew I had a shot. So I told him he could pay me whatever he wanted. That he could keep a tab, so to speak, and if he wasn’t happy after six months, I’d write him a check for whatever I cost the firm. A week later I was a manager working for Mike Ovitz.

Unfortunately, about a year later, the company began to fall apart. Executives and clients (such as Leo DiCaprio, Cameron Diaz, Robin Williams) were leaving the firm. It was time for me to jump ship too. The good news was, I finally had enough street cred to get a job at major agency now.

I started my career at United Talent Agency, then moved to Endeavor. We represent lots of amazing, talented people, including Matt Damon, Ben Stiller, Adam Sandler, Martin Scorcese, Mark Walhberg, Steve Carrell, Jack Black and David E. Kelley (another ex-lawyer).

Any advice for bitter lawyers out there looking to change careers?

Follow your dream—and don’t be afraid to suck it up and make a fool out of yourself.

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“I stalked him. Found out where he parked his car and waited.”