White Collar Advice

Prison Holidays Hurt Families More Than You Think My first Mother's Day in federal prison hit harder than I expected. The visiting room was packed, the visit was cut short, and my mom was crushed. She wasn't just visiting her son—she was facing the reality of prison with me. Around the room, I saw the same pain on the faces of other families: crying kids, anxious spouses, pure exhaustion. That day...

Self-Reporting in Healthcare Fraud: One Doctor's Choice to Act Early When a physician noticed FBI activity on his LinkedIn profile, he didn't wait. He called us. Within days, we helped him create a full disclosure statement, documented his wrongdoing, and outlined the actions he was taking to make it right—including repayment. That gave his lawyer the leverage to self-report directly to the DOJ. T...

Start with Ownership: The Real First Step in Federal Prison The real work in federal prison begins when you stop blaming and start examining how you got there. That kind of introspection isn't easy—but it's necessary. Too many people avoid it and instead convince themselves someone will hand them a job later. Don't wait for a favor. Build something worth earning. I could've worked for my brother's...

The early days in federal prison can feel paralyzing—especially when the weight of lost reputation, uncertain career prospects, and family expectations hits all at once. Many people get stuck, believing the label "felon" means there's nothing left to fight for. That mindset kills momentum. The solution? Create a routine. Write daily—start with 10 minutes. Build a fitness habit you can sustain. Mos...

I discuss Adam Grant's book Give and Take and how it helped me better understand the difference between takers, matchers, and givers—especially the kind of giver who thrives without losing themselves. I reflect on how I used to only help people if it helped me, how prison forced me to rethink that, and how writing one blog post in 2008 changed everything. I also explore why giving without boundari...

A client in our community was given a rare second shot at a proffer session with the government. The first one? It nearly tanked—not because he lied, but because he left out details. Like saying you had a cheeseburger for lunch but "forgetting" the fries and Sprite. The government sees that as dishonesty. In a proffer, they already know the answers—they're testing if you're honest and thorough. Th...

Back in 2007, just after signing my plea agreement on my 32nd birthday, close friends invited me to Pebble Beach. I turned them down. My mindset? "What's the point? I'm going to prison." They went without me. Seventeen years later, I finally made that trip—with no sentence hanging over me, no guilt, just gratitude. I'm sharing this because I don't want you to make the same mistake. If you're not i...

After a hate-filled voicemail called me a "criminal" and questioned what kind of father I could be, I was reminded of a question I used to ask myself often in federal prison: Will my future kids forgive me for going to prison? Now, with two young children, I focus on showing them that a bad decision doesn't have to define your future—but it will follow you. People will judge you. They won't care a...

At sentencing, arguments based on personal hardship—like prison shortening your life expectancy—won't earn you credibility. One individual I spoke with planned to cite a study showing that two years in prison equals one year off a person's life. That kind of reasoning doesn't just fall flat—it can backfire. Judges want to see accountability, not self-pity. If you can't answer, "What would my victi...

A man recently called us, repeating Jordan Belfort's famous line from The Wolf of Wall Street : "I'm not leaving." He believed his conviction was unjust and refused to surrender to prison. I told him plainly: If you don't surrender, the marshals will come for you. You'll face arrest, lose any chance at a lower-security placement, and likely serve more time. Fighting the system emotionally instead...

If you're hiring a criminal defense attorney, don't just take their word for it—talk to former clients. If they claim attorney-client privilege prevents that, it's usually a red flag. The best lawyers have clients who will gladly vouch for them. One client I'm helping has a proffer session with the government tomorrow—a major step. Yet his lawyer spent only 20 minutes preparing him. No role-playin...

Just try.

A man once told me, "My lawyer knows the judge—we're good." A year later, he got six years in federal prison. Over dinner, he called me with regret: "Why didn't you push me harder?" The truth? I don't chase nonbelievers. If someone doesn't take sentencing preparation seriously, no legal relationship will save them. Judges don't hand out leniency based on who your lawyer golfs with—they respond to...

In federal prison camps—while violence is rare—gossip can be just as dangerous. One man was pulled out of the camp at 5 a.m. and never came back. Six months later, others learned why: another prisoner, pretending to be a friend, used a private conversation about hidden assets to cut a deal with the government. That conversation led to an indictment—and freedom for the informant. The takeaway? Ever...

Seventeen years ago, I self-surrendered to federal prison thinking 18 months felt like a lifetime. But after meeting men serving 6, 10, 15 years for tax fraud and marijuana charges, I quickly gained perspective—and gratitude. As tough as it felt, I realized others had it far worse. That shift in mindset changed everything for me, not just during prison, but even now, raising my kids and running Wh...

I'm in Dana Point celebrating Matt Boyer's 50th. Matt's the bookmaker tied to the Shohei Ohtani case. When we first spoke, he told me, "I did it. I'm pleading guilty. I want to lead—for my wife and five kids." That mindset matters. He may go to prison, but he's not living like he already has. Too many people do. I did—for three and a half years. Waste of time. Truth: Your sentence hasn't started y...

Someone offered to sell me details about Elizabeth Holmes' daily routine in prison—what she eats, how often she showers, and when she calls home—for $5,000. I passed. Why? Because none of that helps someone build a life after prison. What matters isn't her hygiene—it's whether she's using her time to grow, to rebuild trust, to prove she's worthy of her family's support. That's the only story worth...

Seventeen years after surrendering to federal prison, I got a call that reminded me how easy it is to screw this up. A defendant had his acceptance of responsibility stripped—three points gone—because he told his probation officer it was just "a business deal gone bad." The officer questioned if he even thought he committed a crime. That mistake? It could mean years more in prison. Fact: Loss of t...

In this week's newsletter, I revisit a 5 a.m. conversation in prison that introduced me to Tabula Rasa —John Locke's idea of the clean slate. I reflect on how I tried to fake it after prison, how that approach failed, and what it took to start building authentically. I challenge you to do the same: document your progress, build in public, and let the world hold you accountable. Whether it's a judg...

A doctor who pled guilty to tax charges reached out, worried about his upcoming probation interview. His lawyer said it was no big deal—just a short background talk. But that's wrong. We've interviewed federal judges and people like Chris Maloney, former Chief of U.S. Probation, who said the interview can shape the judge's final decision. Real prep matters. This doctor took responsibility and paid...

While golfing with an old friend, a former professional baseball player, he shared how taking steroids shaped his career. Though many players dodged accountability, he owned his mistake, recognizing it as part of his journey. He acknowledged the harm he caused but also the catharsis of owning it and rebuilding his life. As a convicted criminal, I can relate—admitting mistakes and accepting consequ...

While connecting in Dallas, I spoke with a federal judge at a work event. I asked, "What's a red flag you see at sentencing?" Her answer was simple but powerful: "When a defendant reads a polished statement, but I have no evidence they actually mean it." Judges only see you once, maybe twice. If you don't build a track record before that day—letters, personal narrative, routine—they assume it's ju...

This week, a family drove from Miami to Tampa to meet with me—nervous and frustrated. Sentencing is close, but their lawyer shut them out. When they asked how to help with the sentencing memo, the lawyer replied, "What makes you think I need your help?" That's a red flag. No one knows your life better than you. You're not a bystander—you're the CEO of your future. Before you hire a lawyer, make it...

After prison, I spent time in Los Angeles courtrooms, studying how judges sentence people. One moment stuck with me: a defendant praised his education and community service, urging the judge not to send him to prison. But he ignored the victims. The judge cut him off— "I'm not sentencing your résumé. I'm sentencing you." The lesson? Judges care about accountability, not just accomplishments. Let y...

In this episode, I talk about Plato's Allegory of the Cave—and how it helped me stop lying to myself in prison. I was waiting for things to magically get better, instead of facing what was real. I also share a story about Kodak and a man in Florida who finally took the lead in his case. This episode is for anyone stuck, pretending it'll work out, hoping the judge will just understand. I've been th...