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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At sentencing, vague claims like "I tried my best" fall flat. Judges expect clear proof of remorse, accountability, and an action plan—not excuses. George Santos’ 87-month sentence is a reminder: empty words don’t move the needle. In prison, most people work hard to rebuild their lives. But a few cling to a victim mindset, which only prolongs failure. If you pled guilty, remember: you are not the victim. Own your choices, show real change, and earn back trust.

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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 yet—but your second chance already has.

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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 telling.

Reminder: Rebuilding character isn't a tabloid headline. It's a daily choice.

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