White Collar Advice

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. Thanks to real prep this time, he gets another shot. Don't wing it. Prepare like your sentence depends on it—because it does.

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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 in prison yet, don't act like you already are. Spend time with people you love. Don't waste the days you still have.

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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 about your progress. Do the work anyway. That's the lesson.

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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 victim say to me?"—you're not ready. Real mitigation starts with acknowledging the harm you caused and building a plan that reflects that understanding.

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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 of strategically only makes things worse. If you've been sentenced, don't run—prepare, surrender, and serve your time with purpose.

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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-playing. No strategy. Just "tell the truth." That's not enough.

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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 clear, consistent mitigation efforts. If you're counting on connections instead of doing the work, you're setting yourself up to lose.

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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? Every word you say can be turned into leverage. Trust is earned, not assumed.

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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 White Collar Advice. Gratitude and perspective aren't buzzwords—they're survival tools. Learn how to build them into your own journey:

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