Writing From The Inside: Gambling, Addiction, Prison, and Starting Over podcast artwork
Society & Culture

Writing From The Inside: Gambling, Addiction, Prison, and Starting Over

by Chris Swett
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Latest episodes

  • How to Tell Your Spouse

    October 21, 2026 · 14 min

    There is a number in your head that your spouse does not know. You have rehearsed telling them in the car and at the kitchen table, but every time you found a reason to wait. I waited too. I hid a gambling addiction for years. Then, one…

  • Read the Fine Print

    October 14, 2026 · 13 min

    FanDuel’s terms of use run almost 12,000 words. I read corporate documents for a living, and I never read this one. This week I put it on the witness stand and asked it five questions. One side of this relationship studies the other side…

  • Relapse, Recovery, and What’s Coming Up

    October 7, 2026 · 13 min

    Earlier this year I relapsed. I turned $100 into $6,000 and lost every dollar of it. Then, I did one thing I had never done before. This episode is about what I did different, what I learned about why I gambled to begin with, and what I’m…

  • From Federal Clerkship to Guilty Plea

    September 30, 2026 · 12 min

    Right out of law school, I clerked for a federal judge in the District of South Carolina. One of the cases that moved through chambers that year was built on invoices for hauling that never happened, trucks that never moved, loads that…

  • Why Sports Betting Apps are Harder to Quit than Casinos

    September 23, 2026 · 15 min

    This week's episode is about what the phone changed. A casino required my body to be somewhere else, and an absence is a thing a wife notices and can ask about in the morning. The phone required only my attention. It took that without…

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  • $100,000 Three Nights in a Row

    September 16, 2026 · 12 min

    On a weeknight in late January, I picked Malcolm Brogdon at $5,400 because most of the field looked at that price and moved on. He finished with thirty-six points, seven rebounds, and nine assists. I won a hundred thousand dollars. I won…

  • Loving Someone Who Is Addicted and Still Functioning

    September 9, 2026 · 14 min

    Last week I gave you the conversation. This week is about what happens when it does not work, which is where most of you actually are. You said it. He denied it or he admitted a smaller version and told you it was handled. A week went by…

  • How to Actually Have the Conversation with an Addict

    September 2, 2026 · 19 min

    The first four episodes of this show were about me. What I lost, what I did to my wife, what the numbers on my account statement looked like at the end of two years. This one turns around and faces the other direction. This episode is not…

  • What FanDuel Knew about Me- Sports Betting Addiction and the Data

    August 25, 2026 · 11 min

    Ninety-five percent of the losses in the sports betting industry come from five percent of the people betting. The apps know exactly who that five percent is, in real time, the same way a casino used to need hours to spot a player in…

  • What I Did to My Wife's Name- When Wire Fraud Reaches Your Family

    August 19, 2026 · 13 min

    I put my wife's name on a company that was committing fraud, and she had no idea it existed. She never saw an invoice, never touched a check, never signed a single document. Her name was on the formation paperwork because I put it there…

  • Writing From The Inside- The Podcast

    August 11, 2026 · 11 min

    I spent over a decade as a trial lawyer, negotiating settlements worth more than a hundred million dollars for people who'd been hurt by companies that should have known better. I also gambled away everything I built, wagering over eleven…

Full episode archive on Apple Podcasts →

About the show

A former trial lawyer who negotiated over $100 million in settlements pleads guilty to wire fraud and money laundering tied to a gambling addiction that ran undetected for over two decades. Follow his journey through sentencing, prison, and ultimately reentry and redemption. Writing From The Inside is the honest account of how it happened and what it teaches about addiction, accountability, and what comes after for anyone carrying something they haven’t said out loud. writingfromtheinside.substack.com