What to Expect When You're Going to Jail

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Justin Sullivan / Getty

Inmates at the Mule Creek State Prison exercise in the yard in Ione, Calif.

Plaxico Burress couldn't wriggle out of jail time for accidentally shooting himself in the leg with an unlicensed handgun in a New York City nightclub last November. But the former New York Giants wide receiver's personal fortune will help him on one score. Burress has retained the services of a "prisoner consultant" to advise him on "what to expect while incarcerated, and how to use his period of confinement as productively as possible," as his attorney, Benjamin Brafman, told the New York Post. To get a sense of what Burress's counseling sessions might be like, TIME caught up with Steven Oberfest, a personal trainer and martial-arts expert who bills himself as the industry's creator. The founder of Prison Coach, Oberfest — whose background includes a 15-month stint in a New York prison on racketeering charges — has been preparing wealthy convicts for their incarceration since 2002. He talked to TIME about the business of prison prep and the dos and don'ts of inmate etiquette.

How did you get into the business?
I was training clients in physical defense, and one of them mentioned she knew a socialite who did something stupid and had to go to prison. She didn't know anything about it, and she was scared. She wanted to prepare for it, to learn how to defend herself.

A light came on in my head. I've been incarcerated and this experience, [coupled] with the physical element, sparked me to think about what it would take to help someone who had never experienced violence transfer into a whole new society. Many of these guys are fat cats who never had to worry about anything. They really have to adapt quickly, because there are so many people to piss off and so many things you can do wrong. If you wind up doing something on the "No" list, it can make your time — whether it's 16 months or 16 days — a living hell.

How many people have you counseled?
Right now we counsel four to six people a month. These can range from a 100-hour course for $20,000 to $100-an-hour phone consultations or $150-an-hour webinars.

How many prison consultants are there?
New guys pop up all the time. But I'd say there are three to five who do it right and have been in the ballgame for years.

So what's the first thing you do with clients?
First I want to find out what their life is like. I want to know about their personality, whether they have any addictions to gambling, sex, drugs, cigarettes. The goal is to get someone to go in addiction-free, where they don't need anything from anybody. You don't want to put yourself in debt.

The other thing is basic prison etiquette. A lot of people don't know how to be respectful — period. They're cocky and they walk around with a chip on their shoulder. Now they don't even have a name; they have a number. They have to follow rules. And they have to make sure they don't do stupid things.

Like what?
Like locking eyes with inmates. Looking into other people's cells, bunks or lockers. There are simple things, like where you sit when you go for chow. You need to sit with your own race, or your own kind. You can be a white dude without any racist issues at all, but if you sit down at a table with five African Americans, you have the potential to really piss them off — and at the same time, white guys will wonder why you're not sitting with them. If you start talking to a correctional officer, people are going to start labeling you as a rat, even if you are just asking an innocent question. They won't look at you as one of them. They'll look at you as a threat.

You want to be invisible. You need to mind your own business. While you're incarcerated, the only thing you have is respect. If you disrespect someone, you'll pay a price for it.

Popular culture and movies would have you believe that to survive in prison, you're supposed to pick a fight right away.
That's just movies. You don't want to pick a fight with anyone. If you follow directions, you can go in and come out with no problems whatsoever. I'm thinking of a guy who was well known and came out with no problems, and he was 5 ft. 2 in., 130 lb. If you start being a whiny bitch, people will take advantage of it. You start crying about your sentence and your innocence, people are going to make fun of you.

If you were counseling someone with a lot of media exposure, like Burress or Bernie Madoff [who also employed a prison consultant], what would you tell them?
If you're being followed in the media, well, these correctional facilities have TVs. Once they find out where you're going, they're waiting for you. You're going to be scrutinized by everyone. It's like your first day of school. Take Madoff, for example: there's a bounty on this guy. He's ruined so many lives, screwed so many people over. If he has no fear, he's more psychotic than I would've thought.