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How High-Profile CEOs Prep for Jail Time

It’s no easy task to go from life behind a desk to life behind bars, but a good prison coach can make all the difference

For plenty of C-suite executives, having a consigliere—whether to assist in greasing wheels in Washington or counsel on the intricacies of international expansion—is a necessity. So, when Masters of the Universe find themselves facing time behind bars, many of them hire a prison coach. 

Los Angeles–based consultant Larry Levine, who has been doing the job for eight years, says the skills he learned during a 10-year sentence for drug trafficking, securities fraud and racketeering are what make him a successful coach. “I helped out so many people while I was inside—with medical assistance, early release, transfers—I thought, I could turn this into a business,” he says. He wasn’t the only one. 

The field, which has blossomed in recent years, includes coaches coming out of careers within the prison system as well as ex-convicts who can offer critical insight. And while some coaches specialize in shortening sentences—consultant Herb Hoelter cited community service to help Beanie Baby billionaire Ty Warner avoid jail time in a tax evasion case—others help prepare clients for life on the inside. 

Bruce Cameron, a Dallas-based counselor, advises clients on what they can bring to jail, options for managing finances from behind bars and which fellow inmates to socialize with. Other advisers focus on helping relatives cope with the change. “People watch The Shawshank Redemption, and they’ve got a perception of prison,” says Levine, “but it’s not necessarily like that.”

For criminals at minimum-security camps, life isn’t much like a prison movie. “It’s people just like them who made some poor decisions and ended up convicted,” Levine says. “The important thing is everybody there is getting out one day and they don’t want to get into trouble.” In fact, Hoelter claims the atmosphere can be downright friendly. “It’s almost like a fraternity,” he says. 

For some of the better-connected prisoners, there’s even a buddy system. The breadth of Hoelter’s practice allows him to offer a “big brother” program for new clients. “If somebody’s going to Schuylkill in Pennsylvania, we’ll call another guy’s wife and say, ‘Hey, we’ve got this rookie coming in. Can your husband just look after him?’ ” he explains.

That sort of connection can be a lifesaver, since what truly ends up plaguing inmates is the boredom. “You’re going from an environment where you had control over thousands of people to an environment where they say, ‘Hey, this is when we have breakfast,’ ” says Hoelter.

So, how does the deposed head of a Fortune 500 company make the best of his powerless life? “The question we pose to guys is, ‘What are the things you’ve always wanted to do?’ ” Hoelter says. He encourages reading a book a week, learning a language or finding a prison job that utilizes the inmate’s skills. Legal skills, that is. He mentions a client doing time for tax fraud who offered a course in personal finance: “I never wanted to know what he taught them,” he says.

One thing that can make a prison stay more difficult? A high profile. Hoelter, who worked with Bernie Madoff, Martha Stewart and Michael Vick, tells famous clients the most important thing to do is blend in. “We tell them to act like everybody else,” he says. Some inmates do this better than others.

“Leona Helmsley, rest her soul, was a tough case,” Hoelter admits. “She thought she should be treated as a queen. It didn’t work out.” Easier to acclimate was Stewart, who was photographed upon her release wearing a poncho crocheted for her by an inmate pal with yarn from the commissary. 

Hoelter also spoke with Madoff before he entered a Butner, North Carolina, prison in 2009 to serve a 150-year sentence. “We knew he was going to go in for the rest of his life,” he recalls. “He asked me, ‘What can I do with myself?’ And I said, ‘You can make life better for all the people around you in there.’ I think that was good advice.”