Why do case managers sometimes dismiss your plan on day one—and why is that a test?
White Collar Advice
In this episode, I share what I learned about prison friendships, documentation, and credibility. Some people surrender with a plan, only to have a case manager dismiss it. That can be a test. They’re watching how you respond. I tell the story of a physician who quietly earned extra time in the community just by living consistently and productively. And I also share my own mistake—aligning with the wrong friend, Arthur. At first he encouraged me to exercise, but soon I saw the mockery, the judgment, and the hypocrisy I was enabling. Breaking away freed me to spend time with men who built...
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What is the U-shaped Curve of Prison—And Why Does It Trap So Many People?
White Collar Advice
In this episode, I share what I learned inside federal prison about how people adjust, why so many regret their time, and how the U-shaped curve explains it. Early on, I spent my days exercising until Michael Santos asked me how much I’d earn for doing pull ups. That question, along with watching friends panic as release drew near, pushed me to shift. I cut down exercise, started writing, lined up work opportunities, and built something I could show to probation and future employers. Too many people coast at the bottom of the U and then face release with no plan, full of anxiety and regret....
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Why Do So Many Defendants Treat Their Lawyer Like a Nanny—And Stay Quiet Even When It Hurts Them?
White Collar Advice
A year ago, we spoke with an executive whose lawyer told him to “get off the internet and wait.” No plan. No preparation. Just bills piling up. Meanwhile, the government was working full-time to build its case. This defendant finally realized silence wasn’t a strategy, fired that lawyer, and began creating proof of who he really was. In this episode, I walk through the email Michael Santos sent him—a framework built around values, history, and action. Judges don’t care about polished excuses; they care about evidence of growth and contribution. Family responsibilities, work history,...
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What Does the Prosecutor’s Playbook Actually Look Like Behind the Scenes?
White Collar Advice
I had to be blunt with someone in our community this week. He’d proffered, cooperated, paid restitution, hired good lawyers—and still thought that meant prosecutors were his friends. They’re not. Their job is to convict, and they’ll use every resource to do it. Probation officers aren’t neutral either. They see themselves as protecting society, and unless you influence the report, it usually mirrors the government’s version of events. Judges? Most came from prosecution. They review hundreds of cases and usually align with what’s in front of them: prosecutor, probation, defense...
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What’s the Biggest Mistake People Make Before Surrendering to Federal Prison—And How Do You Avoid It?
White Collar Advice
In this episode, I move beyond the story of surrendering to prison lost and confused, and focus instead on how to prepare for a successful journey before you even walk through the gates. I cover practical steps like designating a primary point of contact, understanding the Financial Responsibility Program, limiting how much cash you surrender with, and preparing for health and medication challenges. I also talk about building deliberate reading lists, documenting your progress, and using what we call the quadrant theory to evaluate prison decisions as high or low risk and reward. This isn’t...
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Why Did I Eat Like It Was My Last Meal on Earth the Day I Surrendered to Prison?
White Collar Advice
On April 28th, 2008, I surrendered to the Taft federal prison camp, three years to the day after the FBI came to my door. I wasn’t ready. I stuffed myself at Carl’s Jr., lied to my family, and walked in with no real plan other than to exercise and keep my head down. In this episode, I talk about what it felt like to go in lost, the lessons I learned from my mentor Michael Santos, and how creating something tangible—a handwritten blog—became the turning point for my time inside. I share how reading with purpose, writing daily, and documenting progress changed not only my prison...
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What Hidden Excuses Creep Into Letters, Even When You Think You’re Accepting Responsibility?
White Collar Advice
I admire when people try to create assets—letters, statements, narratives—for sentencing. But if you send the wrong message, it can backfire. In this episode, I walk through a real example of what not to do. The letter sounded polished, but the message was all wrong: I’m not like other criminals. Everyone in my industry did it. Prison isn’t necessary for me. Judges don’t hear remorse in that—they hear arrogance, excuses, and zero empathy for victims. Judge Bennett once told us a good allocution can reduce a sentence if it shows responsibility, a plan, and real change. The opposite...
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Why Will a Federal Judge Be More Inclined to Listen If They See Their Own Values in You?
White Collar Advice
When I stood in front of Judge Steven Wilson, I never thought about his values—or how mine compared. Looking back, I should have. Judges, prosecutors, probation officers—they all form opinions about you, and if you don’t create a record, the only version they see is the government’s. In this episode, I walk through an exercise I wish I had done as a defendant: list your judge’s values and ask how yours align. Discipline, accountability, public service—are you showing those in your life right now? I also share ten questions every defendant should answer, from how prosecutors see...
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What Do Judges Mean When They Say, “Show Me How You’re Fixing It, Not That You’re Sorry”?
White Collar Advice
We can’t change the past. But if you’re under investigation, you can absolutely influence what happens next. Too many defendants keep their heads down, pay back some money, plead guilty, and think that’s enough. It isn’t. Judges expect more than compliance or boilerplate apologies. I’ve been to sentencing hearings where defendants beg for mercy with the same lines: “I’m sorry. I’ll never do it again. I cooperated.” Judges see through it. They want proof you’re different from the government’s version of events. That means showing—early and often—what you’ve learned,...
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How Can One Page, Written Early, Influence a Judge More Than Any Courtroom Apology?
White Collar Advice
When UBS fired me in 2005, I wasn’t thinking about a government investigation. I was worried about my job, my clients, and how to spin a story. Three months later the FBI knocked, and I lied. Then I went dark for a year, convinced they’d forgotten about me. They hadn’t. During that time, I should have been building a record that countered the government’s version of events. Instead, I left the field wide open, and the government set the tone with their press release. In this episode, I talk about why silence makes you weaker, why judges do read everything, and what former judges have...
info_outlineThe Real Cost of a Conviction
When people think about the biggest consequence of a criminal conviction, they often focus on prison, DOJ press releases, or the guilty plea itself. But as Justin Paperny shares, the deeper cost comes later: isolation. After prison, even success draws skepticism — online hate, accusations, even extortion attempts. Justin’s viral video brought both praise and attacks, but years after prison, he’s learned to feel indifferent. That indifference, though, comes with loneliness few understand.
Takeaway: The emotional aftermath of conviction lingers long after release.
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