Table of Contents
The Transparency Offense
"Remove it or we'll delete you."
That was support at JDate, the Jewish online dating site. My offense this time? Transparency.
"Look, I don't know about you," I wrote back, "but I'm trying to be transparent. I think women on this site should know I went to federal prison before they start sending me messages, no?"
"This is our final message. Remove the reference or we delete the account."
I stared at the screen.
They must think I'm bragging. Who brags about going to prison?
That month, I was living out of a suitcase: Chicago, New York, Atlanta, Quantico. I called it the Why I Went to Federal Prison Tour.
After one talk to a room of new FBI agents, a female FBI agent caught me afterward and said, "That was surprisingly refreshing."
Then she asked if I wanted to grab coffee. Smart, confident, direct.
All I could think was: you train these people; you don't date them.
The idea of a long-term relationship, with an FBI agent or anyone, wasn't appealing. I needed to stay local, in the 818.
Back in my New York hotel room, which was more halfway house than hotel and had a sign in the lobby about a "bed bug issue," I gave in.
"Fine," I typed. "I'll remove it. I enjoyed our conversation."
Seconds later, the chat closed. A window popped up asking me to rate the experience.
As soon as I deleted "I went to federal prison" from my profile, I started giving myself a hard time.
"And there it is, JP. You talk to students about ethics, honesty and transparency, then delete the one fact you always promised to disclose. You went to the big house for 18 months!"
Then I stopped.
I realized how ridiculous I sounded, quoting myself like some moral authority over a dating profile.
Camus wrote about absurdity. He could have been talking about me that night, turning a JDate chat into a seminar on integrity.
"Dude, get it together. Lighten up. Relax. All is fine," I told myself. "You don't have to turn every moment into a story about prison or a quote from a dead philosopher."
I poured a glass of wine and wondered why I had chosen that hotel.
"Alright, enough. Some battles just aren't worth fighting. And as Eazy-E said, 'Eazier Said Than Dunn.'"
During my sentence, I promised myself I'd be perfect afterward. Flawless. Never abandoning my values, no matter what.
There are just two big problems: I'm flawed and human.
I laughed, took another sip and shrugged.
"I'll figure it out. Not everything's an ethics quiz."
Once I moved on from my biggest post-camp betrayal, deleting four words from a dating profile, I had another problem.
How was I going to tell a woman I actually went?
I noticed the book in my hand, From Socrates to Sartre: The Philosophic Quest, which I had picked up after running ten miles through New York City.
"Ah, this is the problem," I said. "I read too damn much. It's all I think about."
I put the book down, watched television for a few minutes and passed out.
Hold the Line
The next morning, while I was getting dressed for a lecture at NYU, an email arrived that wasn't meant for me.
By then, speaking had become my new career. I had recently closed the ACFE conference in Washington, D.C., in front of 15,000 people. That talk made me the highest-rated speaker at the event.
When another business school booked me that fall, the professor running the program said, "You'll be our top-paid speaker."
Then I received this:
"He's a fraudster out of jail. Yeah, he might be the highest-rated speaker, but that doesn't mean we should pay him more. Plus, it would be hard to pay him more than a Forbes journalist who's coming in to speak. Offer him less. I'm sure he'll take it."
The email wasn't from NYU. It came from another business school. The professor who invited me and offered the higher rate didn't write it; one of the event organizers did.
Now I was a discount.
Before my conviction, I might have thought the same way. Not that the person was evil or undeserving. Just that he had fewer options and would probably take less.
He's been to prison. He needs the opportunity. He'll say yes.
I understood the reasoning because I had spent years rationalizing my own decisions.
My phone rang. The organizer.
"Justin, that email was, well, it came out wrong. We value your work. You have to understand the budget pressures."
"Stop," I said. "You wrote what you meant. You think because I'm a fraudster out of prison and probably broke, I'll take less money. Right?"
There was a pause.
"Yes," he said. "I'm ashamed I sent it."
"I appreciate the honesty. I'll still come. But the higher rate stays. You don't get a discount because someone paid their debt."
Another pause.
"Understood."
That was it. No yelling. No follow-up emails.
I needed the money. I still wasn't taking less for that reason.
It reminded me of a story Al Pacino told about filming The Godfather in Italy. There was an extra on the set, poor and exhausted, who was mocked brutally by a director. In the middle of the scene, the man removed his costume, walked away and gave up the pay he needed.
Pacino said, "I loved him. I admired him. But I could never be him."
I understood why he admired the man.
I wasn't going to the business school to prove I wasn't a criminal. I was going there to do my job and help students understand why people who know right from wrong still commit white-collar crimes.
When I met the organizer at the event, I shook his hand. He apologized again, and I told him it wasn't necessary.
Who am I to ask for forgiveness if I won't give it?
"Don't worry," I said. "I'll wake these college kids up after your Forbes speaker puts them to sleep."
Katsuya, Studio City
Back home from another long trip, I was ready for a different experience.
Not a conference. Dinner.
My first JDate.
I was meeting a Merck pharmaceutical sales representative at Katsuya in Studio City, a place I'd visited plenty of times before prison. Familiar sushi. Unfamiliar situation.
I had decided not to tell her by text or email. In person felt right until I was sitting across from her.
It came out faster than I expected, right after she asked about the travel.
"So you were traveling for work?"
"Yes," I said. "Talking to business students about ethics, white-collar crime and prison."
The server set down crispy-rice spicy tuna and a baked crab roll.
"Why? Do you work in prisons, or are you a lawyer or something?"
"No," I said. "I went to federal prison."
"What do you mean?"
She wasn't really confused. She heard me. The words were sitting there between us.
"It's a lot to take in. I went to federal prison for 18 months. Now I use that experience to help good people who never imagined they'd be in the system prepare properly."
"Oh," she said. "I see."
Neither of us spoke for a few seconds.
I could stand in front of 15,000 people and talk about prison, yet I was uncomfortable telling one person over dinner.
On stage, the introduction already existed. USC athlete. Author. The guy who went to prison and came back to talk about ethics. The audience knew why I was there. NBC and ABC had covered some of my speaking visits. Eastern Illinois University once shut down the town so I could lecture. People came for the story.
A blind date doesn't come with a trailer.
At dinner, I was a guy telling a woman I met online that I had been in prison. No introduction or helpful context. Just the word prison landing somewhere between the spicy tuna and baked crab.
"I was not expecting that," she said.
While she searched for her next question, I remembered a line attributed to Montaigne:
"If I speak the truth, it is not to convince others, but to free myself."
I first read it while standing in line for the chow hall. Now I had to use it.
We didn't see each other again. I have no idea what she thought on the drive home.
Maybe she appreciated the honesty. Maybe she called a friend and said, "You will not believe who I had dinner with."
Either one was possible.
For me, the dinner was useful. I had disclosed my conviction to a woman over a glass of wine for the first time. I knew I could do it again.
Driving home, I thought about the philosophers whose quotes continued circling through my mind. Sometimes I imagined them watching me, which wasn't that different from being a kid and imagining Wade Boggs or Bo Jackson watching me take batting practice.
Dead philosophers and baseball players. Apparently, I need an audience even when I'm alone.
The Work of Remembering
As I write this in September 2025, I think about why I'm sharing these stories.
Someone once wrote this under one of my first YouTube videos in 2014:
"Random, useless stories from a crook who served 18 measly months in a camp and used the time to steal all of Santos's ideas."
I responded, "I agree with the 18 months and Santos criticism."
He wrote back, "Not sure how to react to that. Wasn't expecting it."
Why share a dating story, an event organizer's accidental email or a random YouTube comment from December 2014?
Because I don't want to forget them.
Lessons From Prison had a chapter called "Writing to Connect." Back then, I wrote so other people could understand what I was experiencing. Now I also write because I wish more people in my family had done it.
When Jason and Alyssa ask about my grandparents, I tell them the stories I know.
One grandfather left Chicago in the 1930s, bought a building and started a business. Over dinner once, he told me, "I always root for the underdog."
I wish I had asked him why.
My other grandfather was a dentist who went to war when my mom was born. He was gone for two years. He missed her first words and first steps.
My grandmother lost her daughter at 33 to brain cancer. The pain nearly broke her. Somehow, she continued.
I wish I knew more about how.
They never wrote it down.
That's why I do.
In Ethics in Motion, I foolishly wrote that I thought I had arrived. I know better now. I still contradict myself, make promises I don't keep and turn dating profiles into ethics examinations.
I can also be a moralizing, pompous ass. Sometimes writing keeps me accountable. Sometimes I overdo it and annoy everyone in my house.
Jason and Alyssa already know both versions.
I want them, and their children someday, to know where I've been, what I got wrong and who helped me. They won't have to wonder the way I still wonder about my grandparents.
Chapter 3 Reflection Journal
The event organizer assumed you'd take less money because you'd been to prison. Where have you let someone discount you, and did you correct them the way you corrected him?
Montaigne wrote that speaking the truth is not to convince others but to free yourself. What truth are you still managing instead of simply stating it?
Your grandparents never wrote down their stories, and you still wonder about the things you never asked them. What do you know that you haven't written down yet?
Written by
Justin Paperny
Founder White Collar Advice




