Changing Times: Longer Federal Prison Sentences for Guilty Pleas
Release Date: 03/24/2025
White Collar Advice
A defendant called me—frustrated—because he didn’t agree with his plea deal. Turns out, his lawyer barely knew the facts. Didn’t understand how the business ran before things went wrong. Meanwhile, the U.S. Attorney saw him as a career criminal. Here’s the takeaway: You might not love your plea deal, but if your lawyer doesn’t fully understand your story, how can he negotiate the best sentence? Write out your full history. Make sure your lawyer knows it inside and out. every Monday at 1PM Pacific / 4PM Eastern.
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When I was a defendant, I made a mistake—I went silent for years, then called an old friend asking for a sentencing letter. He refused. He was disgusted that I only reached out when I needed something. I was embarrassed, but I learned a hard truth: relationships need nurturing. If you’re facing federal charges, don’t disappear. Stay in touch. Show people you’re worthy of their support. If you do that, they’ll be there when it matters. If you don’t, you’ll face sentencing alone. every Monday at 1PM Pacific / 4PM Eastern.
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A defendant expected probation. Instead, he got 120 days in federal prison. He cooperated, repaid the money, and took responsibility. But he failed to disclose unpaid employment taxes for his nanny. That one oversight made the judge question his honesty. The government assumed if he hid this, what else was he hiding? In federal cases, small mistakes have big consequences. The past can’t be changed, but you can prepare better. Assume every decision is under scrutiny. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern.
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A defendant just sentenced to a year and a day in prison called me to share his mistake: he took the easy way. He outsourced everything to his lawyer, did no real preparation, and expected probation. The right way is harder—it means owning your case, preparing daily, and proving through your own words and actions why you won’t reoffend. The government has unlimited resources. You don’t. But you do control your effort. Don’t leave your future to chance. every Monday at 1PM Pacific / 4PM Eastern.
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A lawyer told a prospective client it was "way too early" to prepare for sentencing. But was it too early for the government to arrest him? Too early for the DOJ to issue press releases? No. The FBI says by the time they knock on your door, 95% of their work is done. Judges want proof of what you’ve learned and how you’ll change—before sentencing. That record takes time to build. Waiting is a mistake. Start today. every Monday at 1PM Pacific / 4PM Eastern.
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Most people in prison read books to kill time. I did too—until my business partner, Michael Santos, asked me, “What did you learn?” I had no answer. I had read 20 books but couldn’t recall a single takeaway. That changed everything. From then on, I took clear notes: Why am I reading this? How will it help me? What can I use today? Reading became active, not passive. Whether you’re in prison or not, make every book work for you. Take notes. Apply lessons. Build a future. —Mondays at 1PM Pacific / 4PM Eastern.
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A former physician just out of prison told me he couldn’t find work—but after some digging, I learned he’d turned down jobs he felt were beneath him. One opportunity involved cold walking, selling solar panels door to door. I get it—cold walking is tough. But sitting at home complaining is worse. When I got out, I took a job as a receptionist at Sotheby’s. It wasn’t glamorous, but it was a start. Reality check: No one owes you your old life back. Work is work. Get moving. —Monday at 1PM PT / 4PM ET.
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If you’re facing a federal sentencing hearing, you need to hear about David Moulder—not because he got lucky, but because he took action when most defendants don’t. David was staring down a 48-60 month sentence in federal prison. The government labeled him as a kingpin in a conspiracy case. His lawyers told him what most lawyers say: “Let us handle it. Stay off the internet. There’s nothing you need to do.” But that advice didn’t sit right with him. "At the time, I felt overwhelmed and had no idea where to start," David said. "I began watching Justin's videos and Michael's...
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1. One Drink Can Cost Everything A DUI isn’t just a ticket—it can wreck your career, relationships, and freedom. I’ll never take that risk again. A rideshare is always cheaper than the consequences. 2. Felons and Firearms Don’t Mix Being near a gun after a felony conviction isn’t just illegal—it’s a fast track back to prison. I won’t make that mistake twice. 3. No More Jury Duty for Me I used to see jury duty as a hassle. Now, I’ve lost that right. It’s a reminder of what a felony conviction takes away. 4. I Won’t Judge Someone by Their Worst Day I met people in prison...
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Perspective Shift: At first, all I saw were my losses—career, reputation, freedom. But in prison, I met men who had served decades without bitterness. They weren’t wasting time feeling sorry for themselves. That made me rethink my own outlook. Lessons from Others: My business partner, Michael Santos, served 26 years. He introduced me to Viktor Frankl’s Man’s Search for Meaning, which helped me see that purpose isn’t about circumstances—it’s about mindset. What You Can Do: Focus on what remains, not what’s lost. Start planning now. at 1 PM PST / 4 PM EST.
info_outlineMany assume that pleading guilty and repaying restitution guarantees a lighter sentence. Not always. Federal prosecutors often argue that delays in taking responsibility justify harsher penalties—even if you never go to trial. Their reasoning? Wasted government resources.
Why Timing Matters
Waiting too long to plead guilty can be seen as a lack of true remorse. Prosecutors push for high-end sentences when they believe a defendant delayed accountability. Even restitution isn’t enough—if it’s paid too late, they’ll argue it was done out of obligation, not genuine responsibility.
What You Can Do
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Act Early: Delaying can backfire. Accepting responsibility sooner strengthens your position.
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Document Everything: Show why you repaid restitution and what steps you’ve taken to change.
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Control the Narrative: Proactively demonstrate your remorse, growth, and commitment to making things right.
Don’t wait until it’s too late. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern to learn how to prepare for sentencing the right way.