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Learn to Read the Damn Room show art Learn to Read the Damn Room

White Collar Advice

A guy on his second day at Montgomery federal prison camp stood in the chow hall and complained. The judge said at his sentencing it was clear he would never return to another courtroom. He paid his lawyer around $800,000, a former prosecutor who ran the fraud division and knows the judge and the prosecutor. His guidelines were 41 to 51 months and he got 18. He wanted to know why he wasn't home working and paying taxes, why he was in prison at all. He said all of it in front of men who had been in there five, 10, 15, 20 years for nonviolent drug crimes. A buddy called me from Montgomery to...

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Before Prison I Said Lock Them All Up show art Before Prison I Said Lock Them All Up

White Collar Advice

Before I went to prison, if you had asked me about people in prison I would have said they're all bad, lock them up, they're felons, they're criminals. Then I went, and I saw guys working hard who never had the opportunities I had and squandered. Prison Professors gives you a way to help people going to prison and to document your own journey. More than 9,000 people have done it, and there are more than 14 million words on the website. You can share that work with your judge, with probation officers, and with the halfway house when you need a job approved, whether it's KFC or something else,...

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Three Mistakes in Seven Pages of Undisputed Truth show art Three Mistakes in Seven Pages of Undisputed Truth

White Collar Advice

Three takeaways from the first seven pages of Mike Tyson's autobiography, Undisputed Truth. One, he wrote that from his character reference letters you would have thought he came up with a cure for cancer, had a plan for peace in the Middle East, and nursed sick kittens back to health. He knew the letters were a lie and said nothing about his character. Two, he wrote that he was so arrogant in the courtroom during the trial that there was no way they were going to give him a break. He knew it was off putting to the judge and he couldn't help it. Three, he told Don King, his former promoter, at...

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At Least Skeletor Tells You He Cheats show art At Least Skeletor Tells You He Cheats

White Collar Advice

I read something this morning, then wasted time watching Masters of the Universe, and Skeletor's line at the end took me right back to what I read. Someone home from prison, prosecuted under the Biden DOJ, asked for my thoughts on his indictment. I told him I'm not a lawyer but I would read it. What I read made me sick. The DOJ convicts most people. They have endless resources. Your name versus the United States of America, and people thin slice it, they form a snap judgment, that's a wrap. So why lie? In this indictment a cooperating informant got the executive to say he would help raise...

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Why He Asks for More Time Than the Judge Wants show art Why He Asks for More Time Than the Judge Wants

White Collar Advice

I had dinner with a prosecutor tonight. I wasn't expecting it. I was at my club working on our legal directory, which will have about a hundred lawyers in it soon, and a friend who golfed with him brought him in. Two things stuck with me. He admitted he may ask for a longer sentence when he knows the judge is inclined to give a shorter one, to balance it out. And he talked about the lawyer, and how credible the lawyer is. He studies the defendant, the background, who they are, the offense, how they got into it, whether it was a one-time crime or something that went on a long time, and the...

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The Judge Asked If He'd Ever Earned a Living Lawfully show art The Judge Asked If He'd Ever Earned a Living Lawfully

White Collar Advice

I've attended more than 1,500 sentencing hearings. This one was a guy who graduated college, went straight for an MBA, and built a business raising money to make investments. Three good quarters, then a bad quarter. Instead of telling his investors he lost money, he covered it up and told himself he would make it back. It became a Ponzi scheme, about $7 million, friends and family. I spoke with him 17 months ago and asked what he thought his judge would want to see. He told me he had an MBA, that he got it. I have a degree from USC. So what. That was me at 26, a broker at Bear Stearns thinking...

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Thank You, Have a Great Vacation show art Thank You, Have a Great Vacation

White Collar Advice

Someone stopped me at the water park in the Bahamas today while I was with my family. It happens about once a month. He was complimentary about the videos, then said we've got to acknowledge I only served 18 months, that it was nothing. He said it kindly. It took me back to 2008, when I got bad news in prison, started complaining to Michael, then apologized because he was serving a quarter century. Michael told me he was my friend and he was there to listen. He said my 18 months was traumatic for me and I should not compare it to him. So I told the man thank you, have a great vacation. Whether...

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Freedom Doesn't Prove You Changed, Conduct Does show art Freedom Doesn't Prove You Changed, Conduct Does

White Collar Advice

Freedom doesn't prove you've changed. Your conduct does. George Santos was sentenced to 78 or 87 months for fraud and identity theft, went to prison, complained, got clemency, came home, and then bet in the prediction markets that he would be somewhere. He made $35,000. He got caught. He settled with a civil agency, and his lawyer proudly said he doesn't admit or deny liability. In 17 years I've watched people go to prison for embezzling $35,000. If you get a pardon or clemency, you should be above reproach. You should set the standard for how to behave. Santos doubled down instead, and he...

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Study Your Judge, Then Mirror Those Values show art Study Your Judge, Then Mirror Those Values

White Collar Advice

I had an early Zoom call with a doctor indicted in Florida and his lawyer. The doctor couldn't reconcile two things: the FBI agent told him at his arrest that they were in the bottom of the eighth inning, and his lawyer told him to sit back, relax, and wait for discovery. So I brought up Judge Carlos Mendoza, who isn't even his judge. Mendoza enlisted in the Marine Corps out of high school, served in Desert Shield and Desert Storm, came home, went to junior college, college, and law school, and Obama appointed him in 2014. Then I asked the doctor why he became a physician. To help people, he...

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Nobody Can Take This Investment From You show art Nobody Can Take This Investment From You

White Collar Advice

I read a quote from Warren Buffett. He wrote that the best investment you'll ever make is in yourself. Learn to communicate on paper and in person. If you can't get your idea across, it's like winking at a girl in the dark. Nothing happens. Get good at it, raise your own value 50%, and nobody can take it from you.

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More Episodes

This episode was recorded on the way into sentencing, after a long night and with real life still moving in the background. The government is asking for three years in prison. There’s no dramatic speech here and no last-minute plea for mercy.

I talk through what actually matters at this stage. Not promises. Not saying you’ll never do it again. Judges hear that every day. What stands out is a record.

I reflect on someone in the community who didn’t ask for forgiveness. I just did the work. Daily meetings. Volunteering hundreds of hours and documenting it. Working, saving, and paying money back. No shortcuts. No big moment where everything suddenly changes.

I call it boring because it is. Real change doesn’t feel exciting. It’s repetitive. It’s quiet. It’s showing up when no one is watching and doing the same thing again tomorrow.

If you’re facing sentencing and wondering what redemption actually looks like, this episode explains it plainly. You don’t argue your way out of prison. You build a record and hope the judge sees it.

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Justin Paperny