“It takes humor, humility, and balls.” —Alan Grubman
What was your first job?
When I was 11, I was a singer for two years on an NBC show called The Horn and Hardart Children’s Hour. NBC would send a limo to pick me up in Brooklyn. This was mind-blowing, because nobody was dead; the only time you ever saw a limousine in Brooklyn was when it was part of a funeral procession.
Did you set out to make a fortune?
When I was eight years old I said I wanted to be a millionaire. But in those days a Jewish millionaire was something like $10,000.
How did you decide to become an entertainment lawyer?
I knew everybody in the entertainment business drove in limousines and went to good restaurants, and during my first year in law school I said to myself, “If you represent someone who’s rich they’ll pay you more than somebody that’s poor.”
What’s the best deal you ever did?
Selling the independent record companies—Geffen, Chrysalis, Island—to the majors, in the late ’80s.
What’s the best negotiating tactic?
Humor, humility, and balls.
You’ve said that success is 25 percent brains and 75 percent luck. What was your luckiest moment in business?
Being on The Horn and Hardart Children’s Hour. To realize that the entertainment industry was where I wanted to spend my life. If my mother hadn’t pushed me to go on that show I’d probably be a negligence lawyer in Brooklyn right now, giving you my card and saying, “If anybody spits on the sidewalk, give me a call.”
How did your parents react when you started doing so well?
My father was in the garment business. After about a year or so [as a lawyer] I started doing better than he had done at the height of his career. And I remember him saying, “Alan, can I ask you a question?” I said, “What’s that, Dad?” “What you’re doing, is it legal?” I said, “Pop, trust me. Neither you nor I is going to go to jail.”
What’s the secret to success as an entertainment lawyer?
I’ve always made it clear, whether it was to Bruce Springsteen or Madonna or U2 or Rod Stewart or Shania Twain, that I’m on the business side, not the music side. Very often businesspeople want to hang out at studios and concerts with their artist clients. I never do that. My role is not to shmooze. I’m there to protect them.
Do you always think you have to pick up the check?
Yes. I always like people to feel obligated to me—whether it’s my clients or the people I’m dealing with. Obligation usually makes for a better deal.
So what’s better, power or money? If you had to choose one?
Often they’re intertwined, but I’d say money. Power without money is usually fleeting. Bill Clinton has enormous power right now. In January his power will be gone.
What’s the most self-indulgent thing you’ve ever bought?
In 1981 I bought a Rolls-Royce. I wanted the world to know I was successful. Then in 1990 my very dear friend David Geffen said, “You know, Alan, it is not necessary for you to drive in a Rolls-Royce anymore. Will you please get rid of that car?” It was like I had a blinking neon sign on my forehead: NOUVEAU RICHE. The NOU went on, then the VEAU went off.
How is your business changing?
I am now being forced to develop an understanding of the Internet and the computer world. I do it with great pain and angst.
What do you consider “fuck you” money?
Five years ago it was $50 million. Ten years ago it was $25 million. Now it appears to be $100 million.
Are you afraid of failing?
Petrified. The way I analogize failure is going back to the old days in Brooklyn. Once you taste a better way of living and then are forced to go back to that inferior way of living—it’s a terrible, terrible thought. Frightening. I must continue to work hard, I must continue to do what I’m doing because I don’t want all this to disappear all of a sudden.
If you lost it all, what would you miss the most?
Everything.
