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Inside the World of Prison Coaching

If you’re one of the few (inevitably white-collar) convicts who can afford the service, the lessons you learn can last a lifetime

It was the twilight hour, where nothing good comes of staring into the blue light of your phone. Jack, a pseudonymous 40-something finance worker, had just learned that a former colleague of his had been indicted for mortgage fraud. All signs seemed to suggest that he, too, would soon be the target of the same federal investigation (the details of which he’s asked be withheld, because his trial is still ongoing). “I had reached out to an attorney and started talking to them,” he tells me over the phone in a subdued, borderline strained tone. “I had never been in trouble in my life like this.” 

Sensing the very real possibility that sometime in the coming future, he would spend late nights like this one locked in a prison cell — a place he never imagined he’d be — Jack turned to YouTube, searching for answers to questions he couldn’t believe he was typing into a search bar. “I started to look up what it meant to be the target of a federal investigation. I wanted to see where the trail leads, and I stumbled onto one of [renowned prison consultant Justin M. Paperny’s] videos.”

An hour later, Jack sent Paperny a text. “He has his number on his YouTube channel,” Jack explains. “He just puts it out there and says, ‘Call or text me.’ I texted him and he asked, ‘Who’s this?’ I explained my situation to him and then he called me right away.” 

“He’s been a godsend,” Jack continues, the heaviness in his voice noticeably, even if only momentarily, lifted. “He’s really, really helped me. He’s been there. Obviously, it’s what he does for a living, but you get the sense that he cares about his clients and about me. Not many people understand what it’s like to go through this.”

If there was ever a stereotype of a white-collar criminal, Paperny fits that mold: He’s white, male, 45 years old, well-educated and of upper-middle-class pedigree. But unlike the arrogant, icy white-collar criminal personalities portrayed on TV (or, indeed, regularly seen on the news these days), Paperny comes across as genuine, sage and seemingly decent. When we meet outside of a coffee shop in the Californian city of Calabasas — an affluent suburban oasis, where the grass always appears to have been recently cut — Paperny greets me with a smile and offers to buy me a cup of coffee, ordering two cups of water with no ice for himself. He speaks in the staccato of a practiced inspirational speaker, but without the histrionics. Sitting across from him, I’m quickly put at ease by the wisp of wisdom in his voice.

When he talks about his work as a prison consultant, Paperny sounds less like a businessman and more like a sponsor, helping others to battle some terrible addiction. “To succeed as a convicted felon, you have to think differently,” he tells me. “You have to surrender yourself to the reality that you may be starting over from nothing. Surrendering means speaking openly and honestly about my past conduct, and about the shortsighted decisions made without thinking about my victims, without thinking how this would influence my family, how it would influence my unborn children. I want to embrace the reality that I was a greedy, entitled, white-collar defendant who put others before himself. I want to surrender myself to the reality that in my 20s I only worked with people who could advance my career and agenda, and if you couldn’t help me, I didn’t want you in my network.”

Paperny’s current network is made up of mostly men — eight out every ten clients, to be exact. “Now, granted, we’ve had more [female] clients now that our company has grown,” he tells me. “In the last three years, we’ve had more female clients than in the prior eight years combined.”

The company has not just grown but seemingly branched out — in addition to helping convicted felons prepare for prison, Paperny also doubles as an informal life coach. “A lot of the work that I do isn’t just prison related,” he says. “It’s answering questions like, ‘How does my wife not leave me? How do I get out of bed in the morning? How do I not kill myself?’ I’ve had people call me and say, ‘There’s a gun to my head. I’ve lost everything. My reputation is ruined. The government has destroyed my name. I’ve been fired. My kids won’t see me. My wife is divorcing me.’”

He also guides his clients through trial proceedings and helps them prepare to speak with the judge so that they might get a lesser sentence. “About a third of our business comes from referrals from white-collar defense attorneys across the country,” he says. “Our company trains lawyers on sentencing mitigation.”

When I talk about Paperny with two of his clients — one of whom, Jack, is facing the very real possibility of spending several months in prison, the other having already been sentenced to 26 months — I can’t help but notice the way they echo Paperny’s words as though they’re mantras. The second of these two men is Alec Burlakoff, the former head of sales at Insys Therapeutics Inc. who, as per Bloomberg News, “dressed as a giant bottle of the company’s addictive painkiller in an internal rap video,” and who was sentenced to over two years in prison for his role in a RICO conspiracy that helped provide incentives for doctors who prescribed more of the company’s opioid-based pain medicine. Burlakoff all but mimics Paperny’s conviction when he says, “You have to surrender before you can be in control of your own narrative.”

“Is it going to be tough? Yes,” Burlakoff tells me over the phone from his home (he’s scheduled to report to prison sometime in April or May). He begins rattling off questions as though he’s the coach and I’m his client. “Is it going to be a major challenge in your life? Yes. But can it be something that can help you be successful further in life? Yes, if you make the most out of your time while you’re in there. So it’s also about, what are you going to do while you’re in there? Are you going to sleep all day, or are you going to be productive? Are you going to take the things that Justin taught you while you were sitting at home? Take those same skills and characteristics and bring those and transform those, translate those to what you’re doing when you’re sitting in a cell?” 

Burlakoff came to Paperny the same way Jack and most everyone else finds him — through YouTube. “My wife and I were doing extensive research on the internet,” he says. “Basically, I was in a state of panic. My life was spinning out-of-control, and I think that anyone who’s been in my shoes understands that you can’t get enough information and you don’t get enough answers.”

Paperny, of course, understands this predicament better than most. In 2004, when he was 28 and still, according to his own words, “a privileged, coddled kid from the hills of Encino,” he “made some bad choices.” These “bad choices” saw him convicted and sentenced by a federal judge to serve an 18-month prison term for one count of conspiracy to commit securities fraud — the total loss of his victims, most of whom had an average portfolio size of $500,000, was $9 milion, which he has since paid back in full through restitution. “I was exploited by everyone that said they could help me, and I was too quick to pull out the Citi Card and put it on there, 24 percent interest,” he tells me, referring to his personal court case. “If someone said they could help me, I’d give them money without evidence that they could actually do it.”  

And so, for the first few months in prison, Paperny tried to make it work the way most prisoners make it work: By staying physically active. “I adjusted in prison, like a lot of men do, which is just exercising all day,” he says. “I was reading 10 or 12 hours a day, but not a lot of writing.” 

That approach however, was before Paperny met Michael Santos, his current business partner and then-fellow inmate, who in 1987 was sentenced to 45 years behind bars, of which he would serve 26 consecutive years. “One day, I was in his cubicle and I’m like, ‘Man, I ran 10 miles today and did 12 pull-ups,’” Paperny tells me. “And he’s like, ‘Yeah, JP, let me ask you a question: How much are people going to pay you to do those pull-ups?’ I’m like, ‘What do you mean?’ He goes, ‘The pull-ups — how much are people going to pay you?’ And I’m like, ‘Nothing.’ And he says, ‘Well, maybe you should give more thought to how you spend your time in prison. Because you’re adjusting like every other guy in here who isn’t preparing to go home. You’ve lost your licenses. What are you going to do?’ And I’m like, ‘I don’t know.’ So that was the epiphany, or ‘aha’ moment, for me.”

After that, Paperny became more aware of the prisoners who were scared to go home. “I began to walk the track with some of these fellow prisoners, and listen to how they prepared for sentencing,” he says. “They didn’t prepare. They outsourced all the work to their lawyer. ‘My lawyer did this, my lawyer did that,’ and we work with great lawyers, but they’re paid to talk about why their clients are worthy of mercy. Defendants didn’t really know how to hold a lawyer accountable, how to hire a lawyer, how to prepare through their own efforts.”

That’s when Paperny began to sense an opportunity. “I was just like them,” he says of the prisoners around him. “With Michael’s help, we began to write a daily blog that I put on, just writing about my experiences in a minimum-security camp. What was I learning? What would I have done differently? What is life like in prison? And within a week of that first blog, no SEO, no Google marketing, I began to get letters in prison. From people saying, ‘Hey, I’m reading your blog, it’s so awesome. Thanks for providing a glimpse into prison.’”

A month later, Paperny had 100,000 unique visits on the website that he’d created in jail. “I’m like, ‘That’s crazy,’ he tells me. ‘Who’s reading this?’ Then again, I’m like, ‘I would have read this.’ An educated, white-collar defendant who prepared poorly for sentencing and prison — there’s a lot of people like me.”

Paperny’s instincts were right: In 2018 alone, it was anticipated that there were nearly 6,000 white-collar criminal prosecutions in the U.S., which doesn’t necessarily seem like a plentiful market, but according to a BBC report, the cost of hiring a prison coach like Paperny — of which there are only a few others — ranges “from a few hundred dollars to a few thousand to upwards of $100,000.” Paperny himself charges anywhere from $3,000 to $100,000 to engage with a client personally. 

By and large, these clients are businessmen, lawyers, doctors and executives — the sort of people whose crimes are nonviolent and financially motivated. According to a 2016 study, “a considerable percentage of white-collar offenders are gainfully employed middle-aged Caucasian men who usually commit their first white-collar offense sometime between their late 30s through their mid-40s and appear to have middle-class backgrounds. Most have some higher education, are married and have moderate to strong ties to community, family and religious organizations.” 

Which is to say that the majority of criminals who are able to hire Paperny for his services tend to come from privileged backgrounds. There’s pretty much no such thing as a prison coach for someone being put away for a drug-related offense. “We’ve had a number of clients in the Varsity Blues case,” Paperny admits, referring to last year’s college admission scandal, where 33 parents of college applicants were accused of paying upwards of $25 million between 2011 and 2018 to bribe college officials

This is precisely the crux of the prison-consulting business. On the one hand, it’s an undeniably vital resource for people with the means to afford it. On the other, eligibility for this service is relegated to the white and the rich. The systemic vulnerabilities that help prison consultants like Paperny game the system to mitigate lesser sentences are only ever truly available to this uniquely affluent subset of criminals, the ones that society deems as more deserving of mercy, and that can afford to hire the best people to protect their interests (think Michael Cohen, Bernie Madoff, and again, all the celebrities and rich suburban parents caught up in the college admissions scandal).

As my colleague Chris Bourn wrote in his article on white-collar prisons, one 2006 study that looked “into racial disparity in white-collar sentences found that despite standardized sentencing guidelines, ‘unexplained racial and ethnic differentials persist, even for non-violent and white-collar crimes.’” “According to the authors, one aspect of the puzzle that was easy to identify was wealth: ‘Paying fines reduces the prison time imposed, and thus, it seems that whites receive shorter sentences, in part, because they have a disproportionate ability to pay fines,” reports Bourn. 

When I ask him about this disparity, Paperny tells me that he prides himself on splitting up his business into three brands that offer a variety of different price points. “There’s ‘White Collar Advice,’ which is more the higher end, one-on-one consulting,” he says. Additionally, they have “Resilient Courses,” which is newer and he says inexpensively priced. For instance, he says, “There’s a Character Course for $97 that can help give a defendant guidance on how to compile character reference letters that portrays them differently than the government’s version of events. There’s also a Masters Course, which is a monthly program for $49 a month, where you get access to free, new content every day and the ability to ask us questions and engage.” Finally, there’s “Prison Professors,” which offers nearly 500 free videos on YouTube and upwards of a million words of free blog content to digest. “We understand that everyone’s not in a position to retain us, but we still want to help,” he says. “It’s why we give away so much free content.” 

In addition to free content, Paperny offers payment plans as well. “It’s a company policy,” he says. “But in some cases, when it can be a big deal for a family to hire us, when coming up with five, 10, 20, 30 or $50,000 is a lot of money, we’ll have that conversation and say, ‘Let’s reassess after 30 days.’” Paperny continues by claiming that every now and again, after 30 days, if a defendant has done no work, he’ll be the first to say, “Let’s pause [the classes].” “I can’t tell you it happens a lot, but sometimes it does,” he says. “And every time the client says, ‘You’re the only dude not grinding me right now for money. You’re the only one that wouldn’t take money.’” 

But no matter how much money a convicted felon may have, they’re still a convicted felon. As such, Paperny isn’t naive to the way in which the public views the indiscretions of the people he considers to be family. “This isn’t cancer, which elicits sympathy,” he says. “Who chooses to have cancer? We chose to do this. So, there’s an otherness that accompanies white-collar crime.”

While the money surely helps, Paperny’s empathy for people like Burlakoff, and other folks who have been convicted of committing heinous financial crimes, is cultivated from remembering his own prison experience. After all, when you’re forced to work in a prison kitchen with a guy who has SS Bolts tattoed on his arm and who questions the existence of the Holocaust, developing an ability to try and look past first impressions becomes vital. “I developed a sense of perspective and tried to understand where he came from and what his life may have been like,” says Paperny. “I learned his father was murdered and his mother was in prison and he was raised in foster care. I developed a sense of a perspective I would have not had, had I not gone to prison.”

While gaining perspective is a great deal of what Paperny coaches, he does also have answers for his white-collar clients who — a la the Hollywood movie Get Hard — are scared shitless about the physicality of prison. But his advice, again, isn’t what you’d expect. Unlike the movie, which features an obscenely rich hedge-fund manager played by Will Ferrell, who is coached by Kevin Hart’s character to survive a stint in San Quentin, Paperny isn’t teaching his clients how to fight. Quite the opposite: He’s teaching them how to walk away. “Whenever someone hires me, I ask him, ‘What’s your highest value?’” Paperny tells me. “They say, ‘My family, my kids. I want to get home.’ ‘So, you care about your prison reputation?’ ‘No.’ Do you care what the other prisoners think?’ ‘No.’ ‘Do you care if other prisoners think you’re too humble or deferential or weak?’ ‘No, I want to get home to my wife and kids.’ 

If that’s the case, Paperny advises his clients to avoid “high-risk behavior.” “I tell my clients, don’t change the channel in the TV room, even if no one’s in there,” he says. “You have to avoid complaining and bitching, informing on other prisoners. You have to learn to be deferential and create a routine. If that means you gotta get up at 3 a.m. and spend three hours alone? Great. If that means you have to go to bed at 6 p.m. and avoid the TV room or the hustling and the gangs and the fighting and the iPhones and the vaping and the marijuana and the drugs? Go to bed at 6 p.m.”

But once more, the focus of Paperny’s consulting advice is less to do with the physical dangers of prison than it is the mental preparation it takes to have a life after prison. “We’re proponents of creating first-person content,” Paperny tells me. For example, when one of his clients wanted to read in prison, he advised that same client to write a book report on every book he read, why he read it and how it would help him prepare for his inevitable release. “My client asked, ‘What, are we in third grade?’ I said, ‘Well, maybe, because if not, you’re going to read a hundred books. You won’t be able to tell me what you learned from them.’ You’ve got to become a content producer — you’ve got to begin to develop content that you could disseminate and share with a case manager in prison or your probation officer to try to get off probation early. Or a potential employer when he says, ‘You have a prison record.’ ‘Yes, Mr. Employer. This is what I learned from prison. This is how I documented my journey. This is how I become better and identified with my values.’”

All of which becomes easier if, according to Burlakoff, “You come to the understanding, deep down inside your soul, that you are guilty.” “You’re ready to take responsibility for your actions; you’re ready to reconcile, you’re ready to make amends and you’re ready to do the work to move forward,” he says.  

While it may be easy to shrug off the reconciliation efforts of a guy who got caught for profiting off of an already severe drug epidemic, taking ownership isn’t exactly common behavior amongst criminals convicted of white-collar crimes. In fact, it goes against their very psychology. “The perpetrators of white-collar crimes are physically, psychologically and even temporally distant from their victims,” Eugene Soltes, a researcher who had conversations with 50 convicted executives, writes in her article on the topic in The Atlantic. “An embezzler doesn’t have to get close to victims, touch them or see their reactions. As a consequence, embezzling doesn’t motivate the same visceral senses as robbery.” 

In other words, Burlakoff, having already been sentenced, and therefore, having little to nothing to gain by posturing a faux affirmation of guilt, still clings to the steps of Paperny’s how-to-survive-as-a-convicted-felon program as though they’re scripture.  

And it really is a program. “He has a program that he sends to you,” says Jack, who expects to serve somewhere between 30 and 37 months in federal prison. “It’s step-by-step and a lot of it is about starting to accept responsibility for your actions and your bad choices. Pleading guilty and understanding your tendencies. To try to say, ‘Hey, I’m a person who made bad decisions and I’m not sorry for them because I got caught, I’m sorry for them because I have caused people harm and I have created these victims out of my poor decisions.’”

It’s that sort of introspection which, while even Paperny admits can be “somewhat selfish because it’s very cleansing and cathartic,” helps a convicted criminal get through their prison sentence. It’s also what prevents Jack from falling into a depression. “Those feelings are definitely very prevalent,” he tells me, referring to the anxiety he feels on a daily basis as he awaits sentencing. “One of the things that you get from [Justin’s] videos and speaking to him is, he tells you, your life isn’t over. This isn’t the end. Can you take this situation and use it and turn it around and turn it into a positive? I’ll never feel relieved, but I find comfort in speaking to Justin about rewriting my story.”

 Jack’s testimonial really gets to the heart of Paperny’s most important service to the convicted criminals who hire him — providing them with the tools to reclaim their personal stories. “Some defendants can’t do it,” he says. “Some would rather sit at home and lament all day over the unfairness of their life, how they got screwed, how the government is ruining their life. And when that happens, you should know it amounts to a life sentence, because they may only get a year or two in jail, but when they come home, they haven’t developed new skills to work. They haven’t developed any way to tell their story. They haven’t yet humbled themselves to fully accept responsibility and to acknowledge the fact that they created victims.”

But as Paperny knows all too well, it’s never too late.