Table of Contents
October 2008, Cheesecake, Root Beer, and a Terrible Idea
"Bud, are you serious? You're telling me you want to stay in prison longer?"
That was Sam Pompeo, across from me in the Taft visitation room, root beer resting on the table, cheesecake already half gone.
I told him, "Yeah, I'm totally serious. My mom will probably freak out. It would just be an extra three months or so. I would turn down the halfway house and stay here. I can do it. I'm making such progress. I have to seize the opportunity."
Sam wasn't just another visitor. He'd been one of my closest friends since 1998, when he sold me my first home in Studio City. We'd been through plenty of ups and downs together. The day I was fired from UBS in January 2005, he was the first person I called. His response wasn't hesitation; it was insistence: "You're joining me in real estate, starting now."
When agents in his office complained, directly and indirectly, about letting someone under investigation work there, Sam didn't flinch. His reply was simple: "Please mind your own business."
I've said it in interviews many times: all you need is one friend like Sam to get through a crisis. I was looking forward to this visit, even if it started with him telling me, "Bud, get it together. You need to get the hell out of here and come back and sell real estate with me."
I couldn't blame him for being confused (he literally thought I had lost it). From the day I got fired at UBS on January 15, 2005, to the day I surrendered to prison on April 28, 2008, he had watched me unravel in slow motion.
"Sam, you remember when I was lying on the floor in your office after I lied to the Feds? Then I left your office and went to Johnny Rockets for the double cheeseburger, chili cheese fries, and a shake while I chain-smoked outside. That wasn't normal or healthy. I was a disaster.
"Then I sat on your couch for a month before I went to prison, asking you to make me grilled cheese and chocolate shakes. It wasn't a good look."
That month summed up my crisis response: lie, hide, eat, stall.
"Sitting here now, I can't believe how naïve I was. I honestly thought doing nothing was some kind of strategy. The truth is, I just wanted this to go away.
"Since I've been here, listening to similar stories, I know I wasn't alone. Sam, it's the same story with most guys here. Different crimes, same regret. Most of them say some version of the same thing: I wish I had acted sooner. I wish I had prepared for sentencing, led better for my family, and learned how to hold those damn lawyers accountable. I wish I had done more to stress why I am different than my plea or DOJ press release.
"I was no different from the 15 fellow prisoners visiting with their families around us. Too many of us walk around the track saying, 'What I would do for a do-over.'"
The Suit Cost $1,500. The Lesson Was Priceless
"Remember my sentencing? I was still in fantasy land that perhaps through luck, not merit, I could avoid prison."
That changed in about four seconds when victims with rage in their eyes filled the front row, demanding I go to prison.
And what was going through my mind when I saw them?
First, what the hell are they doing here? They got all their money back. I see no value in having them there.
Second, this damn $1,500 suit I just bought is already too tight. The buttons were popping off.
Rather than show any empathy, I wondered if the suit was fixable. I also did my best to ignore my mom, who was there. I was grateful my dad didn't attend.
Judge Wilson didn't mince words. He looked right at me and said he was tired of salesmen turning the other way for money. Most don't get caught. I did. Then he said he was going to make an example out of me.
Victims in the front row practically started doing backflips, throwing high fives.
After sentencing, while I was in the bathroom trying to fix my suit, a victim's son told me, "Don't drop the soap in prison."
All I thought was, "A corny prison joke? That's what you've been waiting to tell me?"
In retrospect, I can't blame Judge Wilson. He did his job. I did nothing to influence his perception of me. I sat back and let the Department of Justice, with its unlimited resources, do my branding and marketing.
The Visiting Room: Boredom, Bad News, and Broken Plans
Sam looked around the visiting room and changed the conversation. It was a lot for him to take in.
"I'll give you this," Sam said. "It does look pretty laid-back here. Not a terrible place to serve time or visit, huh?"
"Yeah, it's terrific. Look, all things considered, it's an easy environment. Nothing like you see on television. The biggest problem here is boredom. There isn't much violence, but you do need to learn the unwritten prison rules."
The hard part for a lot of guys is visitation; visits aren't all they're cracked up to be. They get a lot of bad news from home. Children are struggling without their dad. Bills aren't being paid. Someone comes back and says his wife is leaving him.
I had it easier, I knew, without a wife or kids. Whenever I thought I had it bad, I looked around me.
By October 2008, I had been at Taft for five months. I had seen enough to know I wasn't unique in how poorly I prepared. Beyond the regret, I noticed something else: fear.
"I see guys scared to go home," I told Sam. "They don't know how they'll support themselves without a medical, law or accounting license.
"My friend Alex, who I wash pots and pans with, says, 'All I think about is the money I made, legally, before I broke the law. Now I start over with nothing. I almost wish I never made it since I know what it is like to have it. What the hell do I do now?'
"Men are turning down visits, turning down the halfway house, and a few have actually gotten disciplinary infractions on purpose to lose some of their good-time credits."
"It is sad to hear so many of these stories. I don't understand some things you said. What is good time?" Sam asked.
"Good time is 15 percent they give us off our sentence for essentially not doing anything wrong. At 18 months, I got two months and 21 days."
"How do you lose good time or get in trouble?"
"Oh no, here come the prison questions. We need to focus on the big stuff. We both know my mom is going to call you the second you leave this visit with a hundred questions about what I will do when I leave. Last week, she asked how quickly after prison I would get married. We need to plan!"
Sam laughed. "Fair enough. This prison stuff is interesting, though. I sell real estate all day; give me a break. I reserve the right to ask more questions!"
"So You Are Scared and Want to Stay in Prison?"
"I am not scared. Anxiety, yes. But we both know I have it better than most: my youth, a home to return to, some resources left, someone like you to work with. What I have to solve is this miserable situation I created. I think I know how. Can I tell you?"
"Yes. Can I get some more cheesecake first?"
Five minutes later.
"What happened?" I asked.
"Long line at the vending machine. And it was hard to get the money in," Sam said.
"You ready?"
"Yes."
"You see that person over there in the corner?"
"Yes."
"That's Michael Santos. We're in the same dorm. No joke, he's been inside for 22 years."
Sam shook his head. "How can he even be in a camp? I thought camps were for people with short sentences."
"Good God, more prison questions! Let's keep going. This guy gets up at 1 a.m., writes until 7 a.m., runs 10 to 15 miles, then teaches classes every day at the warehouse behind the commissary. He's constantly producing. He gets invited to contribute to books from Stanford Law School and Princeton. He's written more books than I can count. He has more discipline than any athlete I've seen. And he's mentoring me.
"He asks me questions I can't answer, and that's bad. 'What is success for you? What outcome are you trying to engineer?'
"When I couldn't answer, he encouraged me to start reading. A passage in one of the books helped me recognize the opportunity I had to learn from him."
Machiavelli wrote in The Prince: "A prudent man will always try to follow in the footsteps of great men and imitate those who have been truly outstanding, so that, if he is not quite as skillful as they, at least some of their ability may rub off on him."
"Michael is that great man for me. As Machiavelli would put it, he's the one I'm following. I'm not him, but if I imitate him, maybe some of it rubs off. Maybe I can find a path on the other side of these prison boundaries to help others and myself."
"Who's Machiavelli?" Sam asked.
"You're Italian. You should know Machiavelli. Someday I'll go see his tomb in Florence."
Sam grinned. "Bud, did you just read me an exact quote from this Prince Machiavelli character?"
"No; the book is The Prince, written by Machiavelli. And yes, that's the exact quote. I'm reading, learning quotes and trying to understand them. Most of them I don't. The ones I do, I build into my vocabulary. So I'm going to start using some words that might sound out of place. By using them, I learn. I'm striving to become more insouciant in prison."
"Do you even know what that means?" Sam asked. "Bud, you've used six words in this visit that I do not understand."
"This is the feedback I need. I may be overdoing it."
The Stoic in the Quiet Room
My rant continued.
On the track the week before, Michael handed me Epictetus. Naturally, I didn't understand most of it, but I did understand this line: "We cannot choose our external circumstances, but we can always choose how we respond."
"I couldn't control the press release. I couldn't control the victims in the front row. But I can control what I do now. For three and a half years, I did nothing. Now I want to follow Michael's lead. I want to build an online record that shows how I'm owning this mess I created. I want to help others who are drowning the way I was. I want to give rather than take. I want to be useful.
"I'm not naïve. Some people hated the writing idea immediately. A few guys clearly resent the time I spend with Michael. But I don't care. At 4 a.m., I join him in the quiet room and work. This isn't about them. It's about making sure my 18 months don't become a life sentence. I have to keep writing and keep trying."
Sam said, "Wow, this has been quite an experience so far."
"And think about it, I've only been gone five months. I wasted the first two just exercising all day. Imagine if I had started preparing the first day in prison. Or better yet, on April 28, 2005, the day the FBI showed up at my front door."
October 12, 2008: The First Blog
A week after that visit, Michael and I sat in the quiet room and got to work on my first blog.
When it was done, I folded it into an envelope addressed to my mom.
Michael stopped me before I dropped it in the box.
"The end of this blog says you will write daily. Is that a commitment you can fulfill?"
"Yes," I said.
The Mockery: Tourist, Fraud, or Writer?
While I imitated Michael, my writing had to take a slightly different approach. He had been writing on MichaelSantos.net for years, teaching people how to succeed in prison.
One year in a minimum-security camp didn't make me an authority on overcoming adversity. I was timing laps on a dirt track. What I could do was share prison from my perspective: a former stockbroker who had blown it in spectacular fashion and now had to live with the consequences.
I didn't know what would come from the blog. I committed to writing daily, even if the only people who read it were members of my family who wanted to know I wasn't wasting the time.
Some mocked me. Staff said I hadn't been in long enough to write about prison. A few prisoners rolled their eyes.
"Tourist. You're in for a year. You don't know what real time is."
Others resented that their spouses were reading my blog and asking, "Why aren't you doing something like this guy?"
That didn't always make me popular. My aloofness didn't help me make friends either.
My family pushed back too. They wanted me to serve the time, come home and move on. They didn't understand why I wanted to keep writing about the worst period of my life.
Writing helped me make sense of how I got there. Maybe it could also reach the guy who, like me, drowned his stress at Johnny Rockets, or the father hiding in his man cave and avoiding his kid's Little League game.
Some people loved it. About a month in, letters came back during mail call. Too many, in fact. A guard would call my name, and I'd walk back with a stack. Men saw it and hated me for it. I understood. I had lived with that same envy as a defendant, watching other people move forward while I spiraled.
I didn't complain about the mockery to Michael. He had been inside for decades, serving a 45-year sentence he received at 23 years old. Complaining to him about someone calling me a tourist would have been ridiculous.
Something had changed since I was a defendant. Back then, I overreacted to everything: every email from a lawyer, every legal bill, every phone call, every headline. Now I was almost numb.
By then, my old decisions had already failed me. My reputation, my career and my freedom were gone. What was left to protect?
The mockery didn't bother me as much as I expected. Oddly enough, the more pushback I got, the more certain I became that I should continue. I liked it.
February 2009: 100 More Days Until My Release From Prison
By February 2009, with Michael's help, I had been writing daily for months. Every night, another envelope slid into the mailbox. My mom typed them all. Some people didn't buy it, but the blogs kept going out. Lessons From Prison was nearly complete.
Sam made the drive back to Taft. Same plastic chairs, same cheesecake. This time, his tone was different.
"Hey, man, you've made a lot of progress since October. I read most of your blogs."
"Not all of them?" I shot back.
"Bud, the real estate market is crashing. Pretty clear you chose to sit out this recession in prison! I read most, and I share them with people in the office. I didn't fully get what you were planning in October, but it's clear now. You want to help people the way you wish someone had helped you when you were so off your game."
He paused.
"I'm proud of you. You've done so much since you've been in prison. You were right; you were fortunate to meet Michael and learn from him."
I was ready to change the conversation.
"Hey, some good news. I'm taking the halfway house. I'm ready to come home. There'll be ups and downs, but I'm ready. I'll see you on May 20."
Sam shook his head. "Bud, you're something else. I believe in you. I will always be here to help."
"I know. To that end, I need a job when I get out of here. I've already written the draft employment letter. It's in the mail to you. Please approve it, put it on your company letterhead, sign it and send it back. I want to send it to my probation officer."
"Done," he said.
That was Sam. He didn't need time to think about it. The same friend who gave me a desk when people complained about me was giving me a job before I came home.
Back in October, he thought I was out of my mind for wanting to remain at Taft. By February, I wasn't asking to stay anymore. I was ready to come home.
Chapter 1 Reflection Journal
Machiavelli advised following someone whose conduct you admire. Who are you following, and what are you doing that resembles the person rather than merely quoting him?
What have you neglected that was still yours to control?
When Michael asked whether I could fulfill my promise to write every day, the question forced me to make the promise specific. What promise have you made that sounds impressive but is too vague to test?
Written by
Justin Paperny
Founder White Collar Advice
