The Man Who Had Everything
Richard wasn’t the kind of man who asked for help.
He told me that about four minutes into our first meeting — not to show off, more as a heads-up. He’d spent thirty-one years building a wealth management firm in Century City that, at its peak, oversaw just under two billion dollars. House in Bel Air, a weekend place in Montecito, Bel-Air Country Club where he played to a six handicap, a son at Dartmouth and a daughter finishing her MBA at Wharton. Black S-Class. A closet full of Zegna suits he called, without any irony, his armor.
He had also, for the better part of four years, been moving client funds through accounts his partners didn’t know about — fees he’d convinced himself were a rounding error, until a compliance audit turned them into a federal wire fraud indictment.
“I built all of it,” he said. “The firm. The relationships. The reputation. Thirty-one years. And now I don’t know who I am without it.”
That’s the part people don’t see in the DOJ press release. They see the government’s version of events about “greed” and “arrogance.” They don’t see the person sitting across from me in jeans and a fleece at nine in the morning because he couldn’t bring himself to put the suit on.
“I know I did it,” he said. “I’m not here to say otherwise. I mean I did it. I just don’t know what’s left, man.”
I knew that feeling.
He’d Done His Homework
Most people who sit down with me for the first time already know my story. Not because I handed them a bio, but because they watched a lot of my videos.
That started the night I got back from visiting Michael in San Francisco — the McDonald’s meeting I wrote about in Chapter 6. I stayed up until two in the morning and filmed a single video: Why I Went to Federal Prison. The editing was bad. The lighting was worse. I uploaded it and went to sleep.
Richard had watched several videos before we met. He told me upfront.
“I know your story,” he said. “Michael Santos, the blog, the cold walk, the halfway house. And I know at some point you’re going to introduce a philosopher I’ve never heard of.”
“How do you know you haven’t heard of him?”
“Because if it were Aristotle or Seneca you’d have led with it. You’re saving this one.”
I took a sip of coffee.
“Ever heard of Boethius?”
He shook his head.
“Good. I’ve got about ten minutes of material here.”
The Stockbroker and the Business Card
Before Boethius, I reminded him about parts of my story. When UBS fired me on January 15, 2005, I was thirty years old and had been a broker since I was twenty-three. For seven years, my identity was the business card. Justin Paperny, UBS Financial Services. I had a BMW and wore expensive shirts and had bought into the idea that I needed expensive things to look the part. I was becoming someone, I told myself.
When two security guards walked me out of UBS, I went home and sat there for three hours staring at a stack of my business cards.
I realized how much of my identity, self worth was on that card, the title.
I didn’t lose my licenses that day. That would come later. But I lost the thing the license had given me: a role, a rank, a spot in the order of things. Without it, I had no idea what was left.
I never really figured it out. I stalled through an investigation, showed up to sentencing in a suit with buttons popping off, and went to prison. I hid because I had no idea how to exist outside of what I’d been. Without the title, the income, the story I told, I thought I had nothing. And that is a strange and uncomfortable place to be.
“That’s why I kept watching the videos,” Richard said. “You kept describing something I couldn’t put a name to, but can relate to.”
“I couldn’t either, for a long time. I had a mentor in prison, Michael Santos, who introduced me to literature he had learned from other thinkers. He passed it along to me. He had a way of handing you exactly the right thing at the right moment. I was a loner, I used the time to read, and slowly, with his help, I began to get some of it. I figure if these ideas helped me make sense of what happened, they’re worth passing on.” I paused. “Which is where Boethius comes in.”
The Consolation Nobody Reads Until They Have To
“Anicius Manlius Severinus Boethius. Roman senator, consul, one of the most powerful men in the Western empire under King Theodoric. Scholar, philosopher, translator. By every measure the Romans used to keep score, the man had arrived.”
“And?”
“Arrested on treason charges he almost certainly didn’t deserve, thrown in a cell in Pavia, and executed around 524 A.D.”
Richard was intrigued by the story, I could tell.
“While he was waiting to die, he wrote one of the most widely read books of the Middle Ages. The Consolation of Philosophy. From a prison cell. Which tells you something about what’s possible from prison.
He almost smiled. “You’re going to tell me what I should do when I am in a prison cell?”
“I’m going to tell you what he figured out. You can decide what to do with it.”
Lady Philosophy and the Wheel
In the book, Lady Philosophy appears to Boethius in his cell — not a hallucination, a literary device — and he does what any of us would do. He complains. He’d done everything right. Been honorable. Served faithfully. How could Fortune do this to him?
And Philosophy asks him a simple question.
What exactly did Fortune take from you?
Boethius lists it. His rank. His wealth. His reputation. His power.
And she says: yes. She took all of that. But none of it was really yours. Fortune gave it to you. Her nature is to give and to take back. The wheel turns — it always has, it always will — and the only mistake is building everything on top of it and acting surprised when it moves.
“This is my art, this the game I never cease to play. I turn the wheel that spins. I delight to see the high come down and the low ascend.”
— Boethius, The Consolation of Philosophy
Fortune isn’t apologizing. She’s explaining the terms that were there from the start. Most people just don’t read them until the wheel has already moved.
“So the consolation is what?” Richard asked. “That I should’ve seen this coming?”
“The consolation is that the things Fortune can’t take are the ones worth having.”
He waited.
“Virtue. Character. The way you respond to what happens to you. She can take the house, the S-Class, the firm, the business cards. She has no jurisdiction over what you build inside yourself. That part doesn’t go on the wheel.”
He thought about it. “I always assumed what I built was me.”
“Most people do. Nobody tells you otherwise until it’s gone.”
False Goods
Boethius had a name for what I’d been chasing — and what Richard had been chasing, and honestly what most people I work with have been chasing: false goods. Wealth, status, power, reputation — not evil, just borrowed. You can’t own them. You hold them for a while and Fortune takes them back.
True goods, by his accounting: wisdom, virtue, who you actually are. Can’t be seized. Can’t be suspended. No indictment touches them.
By the time I got to Taft, the BMW was gone. The expensive shirts were in a box at my mom’s house. The business cards were worthless. Everything I’d used to build the story of myself had been taken before I even got to prison.
What I found underneath wasn’t much. A scared kid from the San Fernando Valley who’d spent seven years mistaking a title for a personality. I wasn’t angry about it. I was embarrassed (no, ashamed) it took that long to see.
“The problem,” I told Richard, “is that nobody chases the true goods when the false ones are right there and visible. The S-Class is visible. The firm name on the door is visible. The Wharton MBA and the six handicap — visible. Virtue doesn’t show up in a Google search. Character doesn’t park in your driveway. So people don’t build toward them until they have nothing else left to build toward.”
“Until the visible things disappear,” he said.
“Until the visible things disappear,” I said.
He was quiet for a moment. “The videos are marketing, right? You’re not going to tell me they’re not.”
“Of course they are. I make them to help people and I make them so people find us and come into the community. Both are true. The content just has to be honest or nobody watches and nobody calls. When you find a video at two in the morning and it describes something you’re living — that’s the point.”
“And why I came in here already knowing your story,” he said.
“Which means we can get straight to you instead of spending an hour on me,” I said.
I’ll say this about the people I’ve worked with over the years: there is a connection that forms between people who’ve been through the federal system that doesn’t have much to do with where they started. I’ve sat across from people rebuilding from almost nothing and people with nine-figure net worth, and what I find is that the shared experience of enduring the consequences of a conviction instantly forms a connection. Some of my closest friends today came to me as clients first. There’s a mutual understanding within that group that doesn’t require much work or setup. We just sort of get each other.
Richard already had it. He wasn’t trying to manage the conversation or look good. He was just sitting there in a fleece trying to figure out what was left, what to do next.
I’d sat in that same place.
What the Wheel Actually Teaches
People sometimes hear the Fortune’s Wheel story and take away the wrong thing — that nothing matters, that life is random, that trying is pointless.
That’s not what Boethius is saying.
What he’s saying is more specific: put your foundation in the wrong place and you’ll always be at Fortune’s mercy. Build on what she can take, and she will take it. Build on what she can’t touch, and the wheel is something you can watch without it wrecking you.
The people I’ve seen rebuild after a conviction — and I’ve seen a lot of them over the years — almost always stop waiting for the wheel to turn back. They stop asking when the license or reputation comes back. They start asking what they have that’s actually theirs. What they can build that Fortune didn’t give them and can’t reclaim.
The people who don’t rebuild are usually still at the bottom of the wheel, waiting.
For me, in prison, it started with finding a guide, then making a daily commitment. A blog, a book, even when the only person reading was my mom typing envelopes at her kitchen table. Later, it was YouTube videos filmed in my kitchen. None of it was impressive by the standards I’d used before. But nobody could come in and take it. I learned to build what Fortune can’t confiscate. Do it before anyone asks you to. Keep doing it. White Collar Advice is just that idea on a longer timeline.
The Fleece
Before we wrapped up, Richard said something I’ve thought about since.
“I stood in my closet this morning for ten minutes. Couldn’t put the suit on. Grabbed this instead.” He pulled at the fleece. “I think it’s my brother’s. From a ski trip.”
“Hold on to one Zegna jacket,” I said. “You’ll want it eventually.”
He laughed.
“When do we start?” he asked.
“We already have!”
The Real Loss
On the drive home I kept coming back to the thing Boethius got right that most people in the middle of a case miss entirely.
The fall isn’t the worst part. The worst part is finding out that what you thought you were building was never really yours — that you were on the wheel the whole time and just didn’t know it.
The judge didn’t take Richard’s identity. Fortune did. The judge just put it in writing.
What I don’t say in a first meeting, because it tends to hit wrong before you know someone, is this: losing everything is one of the few ways most people ever get to find out what’s actually underneath. Most people spend their whole lives stacking false goods and never ask the question.
Richard at sixty-two, in a fleece, with a federal indictment, was being made to ask it.
Boethius asked it from a cell waiting to be executed. He wrote the answer in a book that outlasted the empire that killed him. I asked it on a track at Taft with a hundred index cards in my pocket, trying to memorize ideas I barely understood, with a man walking beside me who had been asking it for twenty-two years.
The wheel turns for everyone.
What you do next is yours.
Reflection Journal
Boethius asked Lady Philosophy: What did Fortune actually take from you?
Answer it honestly. Not the version for your lawyer. The real one.
- What specific thing — title, income, reputation, role — did you build your identity around? Name it.
- If that thing never comes back, who are you without it?
- What do you have right now that Fortune cannot put back on the wheel — and what would it look like to build toward that instead of waiting for it to turn?
Don’t answer the way you think you should. Answer the way Boethius would have wanted you to. In a cell, with nowhere left to hide.
