Senior Broker Stole Books of Business. I Joined the Game.
Release Date: 01/14/2026
Don't Pack Anything You're Not Prepared to Lose
White Collar Advice
He called 90 minutes before surrendering to the camp at Fort Dix and wanted to know what to pack. I told him the longer you stay on the wrong train, the more expensive it is to get home. He said he didn't want to talk about the train, he wanted the packing list. So here's my story. Three days before I went to prison I looked at the Taft commissary list, saw white Reebok shoes and a Timex watch, drove to Big 5, bought them, and surrendered wearing them. They told me I could donate them or send them home. I think they went to the correctional officers trust fund. Don't pack anything you're not...
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How Do I Leave Prison Better Than I Went In
White Collar Advice
A crypto executive, married with two young children, emailed me. He's going to prison for 37 months for money laundering and mail fraud, and he asked how he can leave prison better than he went in. Four things. First, what is the next right thing for you to do? The consequences of a conviction are overwhelming, and plenty of people, including him until he went to jail, never start. Maybe you want to engineer an earlier release, so begin answering that. Second, why are you going to prison? There was a breakdown, a fracture, that compelled you to go rogue, to launder money, to break the law....
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My Son Asked If Prison Was Kind of Fun
White Collar Advice
My young son asked me if I'm happy I went to prison. I asked him why he would ask that. He said it seems like it was kind of fun. I told him I'm not happy I went, and I don't want him to go. I speak about it favorably because I learned so many valuable lessons. Here's a small one. I had a great trip in Billings, Montana, I'm flying home, and terrible weather in Denver has me delayed two hours, then another two. I'm not complaining. I'm sitting here alone listening to a Jim Rohn audiobook. I'm not standing for count. I'm not doing a fire drill at 2 a.m. When I share those details with my son...
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Start Thinking Like the Underdog You Are
White Collar Advice
About six months ago a former accountant who served 15 months for payroll protection fraud called me with one question: how do I disclose my felony conviction to potential employers. He didn't take the advice, because he called me today with the same problem while I'm in Montana still trying to get home. I reminded him that prison doesn't change the fact that he ran a successful business for more than 20 years and holds an undergraduate and a master's degree. He owned the conviction and accepted responsibility for it, but he isn't thinking like an underdog. Malcolm Gladwell wrote about that in...
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Matt Cox on the Fry Machine and Freedom
White Collar Advice
Matt Cox on the guys who won't take a job because it pays a hundred dollars a day instead of 300 or 400. Work five days at a hundred and you have 500 you didn't have before. He says they would rather stay in prison than do something beneath them, and he asks what's beneath you when prison is where you already are, at the bottom. If he's working the fry machine at a fast food place, he still gets to watch YouTube, watch Netflix, turn the channel, meet a girl, order his own food. All of that is an improvement. The worst day out here is better than the best day in prison. They don't see it that...
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He Told Me His Lawyer Wouldn't Let Him
White Collar Advice
A doctor back east called me. I spoke with him about nine months ago and he told me his lawyer wouldn't let him do the work. I said he could have a different conversation and try to engineer something different. He said no, he won't let me. So now he has a probation interview that isn't correct, a sentencing memorandum he never reviewed, and the longer sentence he absolutely knew was coming, and he's blaming everybody else. The lawyer is an opponent. The prosecutor is an opponent. The judge is an opponent. I told him how he gets back on track, and telling people what they don't want to hear...
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Instagram Followers Don't Make You a Lawyer
White Collar Advice
I'd rather be in prison than on a fast boat in the ocean, but my kids love it and I love my kids. When I got off the boat in the Bahamas I had a kind text from a guy who scheduled a call with me for Monday. He asked me to review his indictment and his potential plea agreement before we talk. I won't, and here's why. A consultant in Florida who has been to prison twice told someone he might as well go to trial, because if he loses the sentence is the same either way. That guy got nine or 10 years. Another guy, apparently because he has some followers on Instagram, told a doctor to take the deal...
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What Chipper Told My Best Friend Over a Drink
White Collar Advice
I saw Chipper Jones at dinner in the Bahamas and it took me back to 1999. I'm not comparing myself to a Hall of Famer, the second greatest switch hitter of all time behind Mickey Mantle, but it shows what one conversation can do. My best friend Brad Fulmer, who came to my sentencing hearing and visited me twice a month in prison, was in his second year with the Montreal Expos. He finished third or fourth in Rookie of the Year voting the year before, then got off to a bad start and felt the manager wasn't a fan and wouldn't play him against lefties. I was in Montreal watching the Braves play...
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Stop Playing Director in Your Own Mind
White Collar Advice
Back from the Bahamas, wrecked. I got a text that said please call me immediately, so I opened a Coke Zero and called. He told me I didn't know him, that he was on my live YouTube video two weeks ago and made a note of something I said, and that it proved why his judge gave him an extra two years. What I said was that a judge may give a longer sentence to account for the reductions: a year off from the First Step Act, another year to offset the drug program, and up to 12 months in the halfway house for good conduct. Three years with FSA, RDAP, and halfway house. He said that's exactly what...
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I Was Just Sentenced, What Should I Do Now
White Collar Advice
Someone left the courthouse and texted me: I was just sentenced, what should I do now? I don't know if he's married, if he has children, how old he is, or the length of the sentence, so I answered on a macro level for anyone who was just sentenced. Start with gratitude. You will serve time with men who were taken into custody at their guilty plea, remanded that day, and never saw freedom again. You're free, and that's your chance to prepare. Make sure your judgment and commitment order is correct. Did your lawyer ask for a specific prison, not the closest prison to your home, which could be...
info_outlineI remember standing in a brokerage HR room watching a senior broker brag about raising $15–$20 million in a day. The truth came out fast. Junior brokers washed out, and he absorbed their accounts—$3 million here, $5 million there. No mentoring. Just consolidation.
That moment showed me how growth really worked in that environment. Advancement wasn’t about teaching or ethics. It was about surviving long enough to take someone else’s book. That realization shaped the bad decisions that followed.
If you’re under investigation, understand the system you’re in—and how incentives work.
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