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What it’s like to work for The Donald
September 8, 2006

Being on the reality-TV show The Apprentice was all my wife’s idea. Zahara downloaded the application for candidates from NBC’s website and put it on my desk. I put it on the pile of things I’m always meaning to get to. “No, really,” she said, as she rescued it from the pile. “Fill it out.”

Apprentice winner Randal Pinkett, SM ‘98, MBA ‘98, PhD ‘02, with his new boss, Donald Trump. (Credit: NBC Entertainment Photo:Virginia Sherwood)

After making it through an audition process that included on-camera interviews, physical and psychological tests (they said I have the personality of a Navy Seal), and a boardroom-style interview with Mr. Trump himself, I was told to pack my bags and head to New York City in mid-April 2005.

Having watched the show, I was surprised by how demanding our tasks turned out to be. It’s easy to be a couch-potato critic and say, “Oh, I could do that. That’s easy! What were you thinking??” Yet halfway through the first task (designing a fitness course for Bally Total Fitness), I was absolutely, positively drained. We were running nonstop, my brain hurt, my body was aching, and I simply wanted some rest. And that was only the first task; I had 12 more to go if I was fortunate enough to hang on.

A lot of the tasks were out of my area of expertise. I’d never done street marketing or sales, yet I found myself project manager for the task of getting people to call an 800 number to order samples of a new perfume. On another task, I made a simple mistake. Each team had to write a song, record it with an unsigned musician, and air it on satellite radio. The poster I produced promoting our team’s song had a typo­­­–the wrong channel number–for which I took some heat in the boardroom (where Mr. Trump reviews the contestants’ performances). I resolved to pay greater attention to details and started proofreading everything left and right.

A few tasks played directly into my MIT experiences. One week, we had to organize a tech expo for senior citizens–a task almost tailor-made for me. For my dissertation on the role of technology in underserved communities, I’d studied how people new to technology learn to apply it in their daily lives. And as a PhD candidate at the Media Lab, you always have to be prepared to sell, explain, or provide a quick demo of your work. My experience in Sloan’s Leaders for Manufacturing program helped, too, since that was very much about working in teams. Just being at MIT, surrounded by intelligent, accomplished people, was definitely great preparation for being on the show.

Between tasks, the contestants had a little time to relax in the suite we shared during the taping of the show and get to know each other. It was like a big slumber party at times. But we were all mindful of the fact that we were still adversaries: anything you say can and will be used against you in the boardroom. Also, the cameras were always on us, even while we were sleeping. At first it was a bit unnerving, and I played it a little safe; I wasn’t going to let my hair down with all of America watching. I just focused on meeting deadlines, and eventually I got comfortable with the cameras. In fact, when I got home, I had to remind myself there were no cameras anymore–I could do whatever I wanted.

We all reconvened for the final (live) episode in December. Mr. Trump hired me, but then asked whether I thought the other finalist should be a cowinner. That question had never been posed to a previous winner, so I suspect Mr. Trump was going for the water-cooler effect. But he picked the wrong person to try it on. The proposition of a tie was, to me, unacceptable. If our performances had warranted a tie, I’d certainly have been willing to consider it. And if he wanted to hire the other finalist the next day, he could. But as I told him on the air, the show is called “The Apprentice,” and I believe that I earned it. He agreed. As his apprentice, I’m now managing renovations of three properties in Atlantic City, overseeing an IT project, and helping with community relations for a development project in Philadelphia.

Mr. Trump is not that different as a real-world boss from the way he is on the show. He’s tough when he has to be tough, but he’s also got a witty side. It’s been fascinating to be at the table where million-dollar decisions are being made, and to see how particular he is about how he allocates his time. Watching him in action is a good lesson in how to set priorities and be realistic about what you can’t get done. If you’re not happy in life, you have nobody to blame but yourself.

Auditioning for “The Apprentice”

When I looked at the application for “The Apprentice” candidates that my wife, Zahara, had downloaded for me, I saw that it was short. I figured I had nothing to lose, so I filled it out and made a 10-minute audition video, rather than have to show up for a casting call. A month later, I got called to New York for an on-camera interview. They fired questions at me, but I handled it well since I’m a pretty collected guy; it takes a lot to really unravel me. After a background check, I was one of 50 people summoned to Los Angeles for a week to vie for 18 slots in the final round of casting.

In LA, we were subjected to a battery of physical and psychological tests, after which some people were sent home. I was told I had the personality of a Navy Seal: under pressure and very, very extreme conditions, I can remain focused and unrattled. (I’ve always been that way; as a kid with severe allergies, I didn’t flinch when I got upwards of 50 shots every other week.) After one-on-one, boardroom-style interviews with Donald Trump and the show’s producer, Mark Burnett, those of us who were cast were told to pack and report to New York City in two weeks.

Intellectually, the selection process to become a Rhodes Scholar was the most challenging thing I’ve ever done. But the combination of physical and intellectual demands of being on “The Apprentice”–no sleep, living (and competing) with hypercompetitive people, having the cameras rolling 24 x 7, running through New York City trying to finish tasks under incredibly tight deadlines–was uniquely stressful. But still, it was a lot of fun. I love challenges and this gave me plenty. In the process, I learned a lot about group dynamics and how much can really get accomplished in a short period of time.

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