I Got Hired at Tommy Boy Records By Telling the CEO I Didn't Want the Job

In September 1995 I was 25 years old living in San Antonio, Texas.

I was going to Southwest Texas State University in San Marcos Monday through Thursday. I was mixing on KTFM radio Monday through Friday. I was doing a live broadcast Friday nights from Rock Island nightclub. I was driving to Houston on Saturdays to DJ a live broadcast from Club Shelter on 104 KRBE. I had a pre-recorded mixshow on KHFI in Austin airing on Saturdays. I was also DJing in Austin on Wednesday nights.

I was busy. I was making good money. I had a life I understood.

Then I got a call from Victor Lee — National Director of Video and Mixshow Promotions at Tommy Boy Records in New York City.

He asked if I'd be interested in interviewing to become his replacement as National Club and Mixshow Manager.

Tommy Boy Records. Home of Coolio. Naughty By Nature. De La Soul. One of the most influential independent labels in history.

I said yes mostly because — what could it hurt? Free trip to New York right?

They flew me out on a Thursday afternoon and put me up in a hotel in Times Square. It was my first time staying in a hotel in New York City.

The next morning I walked into the Tommy Boy offices and stood in the lobby staring at photos of Coolio, Naughty By Nature, and De La Soul surrounding the infamous Tommy Boy logo.

I was in awe.

They brought me into Tom Silverman's office — founder, CEO, and owner of Tommy Boy Records. Already in the room were Victor Lee, Mike Becce — a radio promotion legend from RCA Records — and Monica Lynch, the president of the label.

Four people. One interview. I was terrified.

They started asking me questions. I told them about growing up in Chicago, my dad being a concert promoter and manager of two cover bands, how I got into DJing, my radio work across Texas.

Then came the big question.

"Why do you want this job?"

I told them the truth.

"Honestly — I don't know if I want this job."

Tom Silverman — who had been half ignoring me the entire interview, going through his desk, looking like he was falling asleep — suddenly sat up and looked directly at me.

"Then why are you here?"

I started to panic. I thought I just blew it completely.

They asked where I saw myself in five to ten years. I told them if I didn't get this job I'd go back to Texas, finish nursing school, and become a nurse. But if given the opportunity I knew I'd work hard to be the best at this job and eventually I'd love to be in A&R.

Tom or Monica said that was a very ambitious goal. Not everyone gets to do A&R at Tommy Boy.

By the end of the interview I was convinced I was going home empty handed.

They deliberated. I waited.

Victor Lee came back.

"The job is yours if you want it."

I was in shock.

The offer was $28,000 a year. I was making nearly three times that DJing in Texas. No contract. Start immediately — even though I had six weeks left in my semester.

Every logical reason said don't take it.

My girlfriend. My friends. My family. My music director Charles Chavez at KTFM. Everyone said stay in Texas.

Monday morning Victor called for my answer. I looked at my girlfriend. I told her I was going to say no.

I picked up the phone.

And said yes.

My girlfriend started crying. I couldn't believe I said yes either.

Later they told me why I got the job over everyone else who wanted it.

"You weren't tainted."

Every other candidate came in with industry experience and industry thinking. Tommy Boy didn't want that. Tom Silverman was a deeply spiritual person — friends with Deepak Chopra, someone who believed in thinking completely outside the box. They needed someone who could learn the Tommy Boy way without unlearning someone else's first.

My honesty. My uncertainty. My clean slate. That's what got me the job.

And that was just the beginning.

The next chapter of this story involves driving from Houston to New York City, boxes of vinyl records on my first day, and getting screamed at by Everlast from House of Pain in a corporate apartment.

But that's a story for next week.

Sometimes the most powerful thing you can bring to the table is exactly who you are — unpolished, uncertain, and honest.

Bet on yourself. Even when the numbers don't make sense.

Have you ever gotten something by being completely honest when everyone else was performing? Leave a comment below.