White Collar Advice

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.

Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern to learn how to build real credibility.

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.

Take the lead. Build a life worth watching. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.

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.

Start building your own plan today. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.

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 those three points can increase a sentence by 12–18 months or more.

Don't wing it. Prepare. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.

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 judge, a loved one, or a future employer—they'll review what you create. So the question is: will you build your slate deliberately, or let someone else write it for you?

Due to budget cuts, the California Department of Corrections is eliminating funding for all reentry programs. That means fewer opportunities for people in prison to prepare for release—unless others step up. Our nonprofit partner, Prison Professors Charitable Corporation, led by Michael Santos, will keep running programs in every California prison. Why? Because White Collar Advice, with donors like Mossimo and Bill McGlashan, covers the cost.

Real-world impact: Over 100,000 people have used our courses—zero cost to the state.

Want to help others prepare? Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.

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 restitution—now he's putting in the work to protect his medical license.

Bottom line: Don't wing your probation interview. Build your case with facts, documents, and ownership.

Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.

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 consequences opens the door to personal growth. It's far healthier than deflecting, denying, or pretending nothing happened.

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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 just talk. Want a better outcome? Show your growth, don't just say it.

Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.

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 clear: I will be engaged. If they resist that, find someone else.

Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.