White Collar Advice

Why Sean Combs Won't Get Time Served Without Effort Too many assume Sean Combs will get time served, but that's lazy thinking. As I explained on Law and Crime , federal judges don't just hand out leniency — they need proof. In Combs' case, the judge cited his past criminal history when denying release, showing skepticism already. A lawyer's polished statements won't cut it. What matters is what Co...

Summary: Define Success, Then Own It in Prison In federal prison, success doesn't look the same for everyone. Some people write books or prepare for release; others play pickleball or use an iPhone to stay connected. What matters is that you define your own goals and commit to them, without stalling or blaming others. As Michael Santos and I teach, no one else—not even your spouse—can carry that r...

Early Action Matters in Federal Cases Last week, I spoke with a pharmacist indicted for illegally distributing opioids—millions of pills. Back in February, he was scared but convinced the government lacked evidence. Now, months later, he's panicking. Why? Others cooperated early, gave information, and left him with nothing to offer. Here's the truth: DOJ prosecutors work full-time. Waiting only sh...

Sean "Diddy" Combs will be sentenced on October 3rd. In this video, I explain why it's a mistake to focus on predictions about whether he'll get time served. I served time in federal prison, and I've worked with hundreds of defendants preparing for sentencing.  Judges don't rely just on lawyers. They don't base their sentence on public statements or reputation. They read the probation report—and t...

In this episode, I reflect on a recent conversation with a father who waited too long to act during a federal investigation—and what Robert Greene's The 33 Strategies of War teaches us about timing, silence, and influence. We connect Greene's strategies to earlier themes from Montaigne, Seneca, Camus, and Ayn Rand, focusing on how people lose ground not through action, but through delay. This isn'...

Since 2009, 87 people in our community have gone to trial. Every one of them lost. It's not a statistic I share with pride, but it's the truth. We don't represent people at trial. We don't write motions. We're not defense attorneys. But we work with people who going to trial. And since odds are they lose, including the innocent, we encourage people to prepare. Let me say it again, something I tend...

Watching Isn't Enough—You Have to Do the Work If you're on this channel, you're likely under investigation—or love someone who is. Watching videos helps, but action matters more. Six weeks ago, I told a doctor to role-play sentencing with his lawyer, review the sentencing memo, and help shape his story. He didn't. The night before sentencing, he hadn't even read the memo. His lawyer's advice? "Do...

Why I Almost Wasted My Prison Term When I met Michael, he'd served 22 years. I had 18 months. He said, "I'll do every day with you," and he meant it. He became a mentor—but I resisted at first. One day he asked, "On a scale of 1–10, how hard are you preparing to go home?" I said, "One." His reply hit hard: own your choices or keep asking for favors when you get out. Most people inside didn't plan,...

When You Resign From a Brokerage: The Scramble for Control and Clients Leaving a brokerage isn't smooth—especially on a Friday. In this story, my resignation sparked panic. The branch manager tried to lock us in, knowing UBS would want our clients fast. The firm technically owns the accounts, so they handed them to top brokers who smeared us to keep assets in-house: "Justin's gone," "your account'...

Rebuilding Starts the Day You Plead Guilty Once you plead guilty, stop blaming others. You're not a victim—you're responsible for what comes next. I wasted my first few months in prison until I shared a cubicle with Michael. He helped me shift my mindset: create assets, take control, and provide value. That's how you rebuild. Write. Document your journey. Offer something useful to others. These st...

Don't Just Say You're Sorry—Show It Saying "I'm sorry" won't carry much weight with a judge. What does? Proof. Michael told me: create an asset. Write a book. Draft a reentry plan. Start a blog. I wrote a letter to my judge from prison—and that changed everything. These assets show effort. They give judges, case managers, and probation officers something real to read and consider. But here's the c...

How Cooperation Helped—And What Didn't For a year before sentencing, I worked with the SEC to explain how the fraud at UBS unfolded. That effort paid off. The SEC told the DOJ they didn't view UBS as a victim, which meant I didn't owe $8.5 million in restitution. Investors got their money back—thanks to UBS, not me—but it helped reduce the financial damage at sentencing. Still, the judge wasn't sw...

I Got a Second Chance—But Only Because My Co-Defendant Blew His Six months after I pled guilty, I got a call: my co-defendant Keith had been indicted again, this time for hiding assets through a straw buyer. That move tanked his credibility—and opened the door for me. The government wasn't going to use most of what he said against me. Instead, I got a shot to cooperate with the SEC. They wanted de...

I Lost My Chance to Cooperate—And Paid the Price By the time the government came to me, they already had their case—thanks to my client, who got ahead of it and cooperated. I didn't. I lied. That lie cost me the chance to earn credit for cooperation. When my lawyer told me I could either plead or go to trial and lose, the plea deal on the table was five years. That phone call came 10 months after...

How I Went from Witness to Target in One Meeting I walked into the meeting thinking I was just a witness. But seven minutes in, the FBI asked if I remembered a press release claiming my client's hedge fund returned 27% annually. I said no—twice. Then they showed me proof: an email I had written mocking that very claim. My lawyer ended the meeting on the spot. I wasn't under oath, but I had just ob...

The Day the FBI Knocked—and I Blew My Chance to Mitigate On April 28, 2005, the FBI showed up at my door. I wasn't prepared. I had already left UBS, but they were investigating my past role in the GLT Fund. Instead of hiring a criminal defense attorney, I hired a civil lawyer. I walked into that FBI meeting with zero preparation—blaming others, denying responsibility, and lying to my lawyer. What...

When Denial Ends and the Paper Trail Starts On June 16, 2002, I took a client's money knowing deep down it would end badly. By December 15, 2004, it did. A forged letter—on UBS letterhead—claimed investors would be made whole if the hedge fund collapsed, with my name signed at the bottom. Only, I never signed it. My branch manager had me write my signature eight times. It didn't match. That's when...

Covering Yourself Doesn't Erase Complicity At a meeting, an elderly investor believed he had $3 million. The truth? Less than $1 million remained—and the rest had been gone for years. That moment forced a decision. Instead of reporting the hedge fund manager's fraud, the brokers created a disclosure form to shield themselves. The commissions—$100K to $200K per month—kept coming. UBS compliance sig...

In 1997, I was a new broker at Merrill Lynch with $10–15 million raised, but management pressured me to join a team. I watched how that model worked: junior brokers gave up their books and ended up doing all the work while senior partners took the credit—and the commissions. They stopped prospecting, stopped growing, and eventually got pushed out. I saw a system that rewarded the wrong things and...

When Commissions Blind You to Consequences In this story, $6 million was lost due to reckless trading. The broker wasn't managing the money—just executing the trades—but the commissions kept flowing: $100K to $200K per month. Compliance knew. So did the broker. Then came another $6 million, raised under false pretenses. That's when denial turned into criminal conduct. Even without speaking to inve...

When the FBI knocked on my door in 2005, I thought I could manage the situation. I was wrong. In this episode of The Presumption of Innocence , I sit down with defense attorney Matt Adams to unpack the moment everything changed—how I hired a lawyer, ignored his advice, lied to federal agents, and turned what might have been a civil case into an 18-month federal prison sentence. We talk about what...

When You Know It's Wrong—But Do It Anyway On June 16, 2002, I took a $6 million hedge fund transfer from a manager I knew had a shady history. I knew it would go bad—and I took the money anyway. Why? Because I needed to hit my numbers. That's how many white-collar crimes start: not with some grand plan, but with a moment of pressure and a willingness to ignore the red flags. I had grown up with op...

What I Learned About Status in Federal Prison When I arrived in federal prison, I thought people would judge me based on my white collar conviction or my 18-month sentence. I was wrong. No one cared about my crime or background—what mattered was how I behaved. I learned fast: don't brag, don't complain, and don't act like you're better than anyone else. A felony levels everything. Whether you did...

How Ego and Entitlement Led Me to Federal Prison I thought I deserved a raise. I was bringing in big commissions and figured I'd earned more. When my senior partner laughed me off, I didn't just get mad—I got even. I found a loophole in Bear Stearns' accounting system and used it to steal what I thought I was "owed." That decision—rooted in entitlement—started a slow slide: I ignored my clients, s...

Entitlement Will Keep You in Federal Prison Longer In federal prison camps, you can act entitled—but it will cost you. One white-collar defendant mocked the drug program on a recorded call. Another inmate tipped off staff. Result? He was kicked out and lost a year off his sentence. Programs like RDAP and home confinement under the new BOP directive reward preparation and follow-through—not arrogan...