What’s the Biggest Mistake People Make Before Surrendering to Federal Prison—And How Do You Avoid It?
Release Date: 09/08/2025
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...
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The FBI Showed Up. I Lied to My Lawyers. Then I Waited.
White Collar Advice
In this episode, I share what I wish someone had told me when the FBI knocked on my door back in 2005. I didn’t handle it well. I stayed silent, told half-truths, and thought expensive lawyers and keeping busy would protect me. It didn’t. By the time the plea came, the government had already built the case and written the narrative. The DOJ press release branded me a criminal, and I had nothing in my file to counter it. In prison, I met Michael Santos, who pushed me to stop staring at shadows and start creating proof of who I was becoming. That first blog I wrote in 2008 changed...
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Going to Federal Prison? Don’t Issue Clichés—Do This Instead
White Collar Advice
Stop Wasting Time—Start Proving You Deserve Leniency A defendant facing sentencing told me, “I wish I knew then what I know now.” But wishing doesn’t move the needle. His probation officer already sees him as “trash.” That perception won’t change with excuses. In the next two weeks, he needs to document growth—something that proves he’s more than a case number. Judges and probation officers don’t reward regret. They respond to action. Start showing—not just saying—what you’ve learned, what you’re doing, and how you’ll rebuild. Join our every Tuesday at 11AM...
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George Santos Fears Prison—My CNN Breakdown on What He’ll Really Face
White Collar Advice
George Santos told Tucker Carlson, "I don’t think I survive this." CNN asked me if that fear was justified. I’ve served time in federal prison, and over the last 15 years, our team has worked with thousands of people getting ready to surrender—people from all backgrounds, including high-profile defendants like Santos. He’s reporting to a minimum-security camp, not a violent facility. But fear isn’t unusual. What’s unusual is how public he’s been about it—and how little he’s done to prepare. In this segment, I break down: – Why fear isn’t the problem—lack of preparation...
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Steal This Idea In Federal Prison
White Collar Advice
Share the Progress—Don’t Just Ask for Leniency Judges hear promises at sentencing all the time—but most defendants don’t follow through. One member of our community did. He documented his daily prison routine, reported what he was learning, and shared how he was preparing to live responsibly and repay victims. His consistency paid off: a judge resentenced him to time served under the First Step Act. The takeaway? Don’t wait until you want something. Build a record. Share it. Show it. That’s how you earn trust—and liberty. Join our every Tuesday at 11AM Pacific / 2PM Eastern to...
info_outlineIn 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 about abstract ideas—it’s about the record you build, the actions you take, and the plan you bring in with you. Judges, prosecutors, and case managers are skeptical, but actions carry weight. For more detail, you can listen to the full podcast or read the blog version on White Collar Advice.