Locked In with Ian Bick

Dillan Judkins grew up in Utah after being put up for adoption at birth by his mother, who was struggling with addiction, and raised by a loving Mormon family — but rebellion, alcohol, and trouble started early. In this episode, Dillan shares how a sexual assault charge stemming from a one-night stand at a party when he was 18 changed his life forever, leading to months in county jail awaiting trial, a probation deal, repeated violations, and ultimately spending nearly 15 years inside the Utah prison system. He explains how he survived prison with a stigmatizing charge, his side of the story, the realities of navigating the system, and the long-term impact incarceration has had on his life, identity, and future.

_____________________________________________ #UtahPrison #PrisonStories #TrueCrime #PrisonLife #HowISurvived #InmateStories #LockedIn #podcast

_____________________________________________ Connect with Dillan Judkins: Facebook & Instagram: InkkEnvyy Tiktok: inkk.envy

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 Arrested at Home: Waking Up to Police 00:34 Growing Up Adopted in Rural Utah 02:26 Finding My Biological Parents 03:34 Family Struggles & Feeling Like the Outsider 05:52 Rebellion, Church, and Early Violence 09:35 Losing Control 14:14 School Trouble & First Criminal Behavior 18:14 Dropping Out & Alternative School Life 21:12 The Night Everything Changed 29:14 Police Investigation & Interrogation 32:40 Charged With Serious Crimes & First Time in Jail 38:00 Jail Politics & Surviving Serious Charges 46:06 Trial Prep, Legal Mistakes & Taking a Plea Deal 52:35 Regret, Probation Violation & Sentenced to Prison 01:00:28 Living With a Life-Changing Sentence 01:06:07 County Jails, Prison Life & Treatment Programs 01:13:00 Inside the Sex Offender Program 01:24:09 Prison Reputation, Tattoos & Survival 01:32:00 Life After Prison: Stigma, Labels & Reality 01:40:13 Loss, Reflection & Lessons Learned

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Dillan Judkins grew up in Utah after being put up for adoption at birth by his mother, who was struggling with addiction, and raised by a loving Mormon family — but rebellion, alcohol, and trouble started early. In this episode, Dillan shares how a sexual assault charge stemming from a one-night stand at a party when he was 18 changed his life forever, leading to months in county jail awaiting trial, a probation deal, repeated violations, and ultimately spending nearly 15 years inside the Utah prison system. He explains how he survived prison with a stigmatizing charge, his side of the story, the realities of navigating the system, and the long-term impact incarceration has had on his life, identity, and future.

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Brian Watson spent over 20 years as a special agent in the IRS Criminal Investigation Division. In this episode, he explains how he got into the IRS, what the job is really like, and how criminal tax evasion cases are built from start to finish. Brian breaks down common myths about the IRS, how payroll tax cases work, what restitution actually means for defendants, and how investigations move from audits to criminal charges. This conversation offers a rare inside look at IRS criminal enforcement from someone who spent decades inside the system.

_____________________________________________ #IRS #TrueCrime #GovernmentSecrets #Whistleblower #InsideTheSystem #RealStories #LockedIn #podcast

_____________________________________________ Thank you to PRIZEPICKS for sponsoring this episode: Visit https://prizepicks.onelink.me/LME0/IANBICK and use code IANBICK and get $50 in lineups when you play your first $5 lineup!

_____________________________________________ Connect with Brian Watson: https://www.linkedin.com/in/brian-watson-625532179

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 How Major Tax Evasion Gets Flagged 00:57 Inside the IRS Criminal Investigation Division 02:57 What IRS Special Agents Actually Do 06:36 An Unlikely Path to Becoming an IRS Agent 12:13 IRS Special Agent Training & Academy Life 16:13 The Reality of Criminal Tax Cases 20:21 How Tax Evasion Cases Really Begin 23:43 Following the Money: Real Case Examples 29:09 Technology, Digital Payments & Modern Crime 31:58 Cash Businesses, Informants & Undercover Work 34:50 Money Laundering Explained Simply 36:33 Crypto, Digital Payments & Financial Trails 39:52 Building & Organizing Financial Crime Cases 43:00 Managing Multiple Investigations at Once 45:44 Payroll Fraud, Cash Wages & Tax Violations 49:47 The $10,000 Rule, Banks & Structuring Crimes 53:38 Casinos, Reporting Requirements & Paper Trails 56:17 Working Joint Cases With Other Federal Agencies 01:00:34 Celebrity Cases, Media Pressure & Reality 01:04:17 Financial Damage & Empathy for Defendants 01:07:39 Asset Seizures, Restitution & What Rarely Gets Recovered 01:10:12 Preventing Internal IRS Fraud & Embezzlement 01:15:04 When Managers or Accountants Commit Tax Crimes 01:18:48 IRS Myths vs. the Human Side of Investigations 01:21:51 Do the Wealthy Actually Pay Their Taxes? 01:24:13 State Tax Agencies & Federal Coordination 01:25:04 Reflections on the Criminal Justice System 01:29:00 Biggest Lessons & Advice for Students 01:31:13 Final Thoughts & Closing

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Brian Watson spent over 20 years as a special agent in the IRS Criminal Investigation Division. In this episode, he explains how he got into the IRS, what the job is really like, and how criminal tax evasion cases are built from start to finish. Brian breaks down common myths about the IRS, how payroll tax cases work, what restitution actually means for defendants, and how investigations move from audits to criminal charges. This conversation offers a rare inside look at IRS criminal enforcement from someone who spent decades inside the system.

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Steven Johnson grew up in Connecticut surrounded by instability and a rough childhood that pushed him toward the streets at a young age. As a teenager, he joined the Latin Kings and quickly rose through the ranks, eventually becoming a chapter president before landing in Connecticut state prison. While serving time in the late 1990s and early 2000s, Steven made a decision that could have cost him his life — walking away from the gang while still incarcerated. In this episode, he shares what prison was really like during that era, how he survived the consequences of leaving the Kings behind bars, and how that choice completely changed the course of his life. After his release, Steven never looked back, building a new path rooted in discipline, accountability, and staying out of the system for good.

_____________________________________________ #LatinKings #PrisonStories #GangLife #LifeAfterPrison #TrueCrimePodcast #JusticeSystem #RedemptionStory #lockedin

_____________________________________________ Than you to AVA & LUCY for sponsoring this episode: AVA: Take control of your credit today. Download the Ava app and when you join using my promo code LOCKEDIN, you'll get 20% off your first year—monthly or annual, your choice.

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LUCY: Go to HTTP://LUCY.CO/IANBICK and use promo code IANBICK to get 20% off your first order. _____________________________________________

Connect with Steven Johnson: Facebook: https://www.facebook.com/steve.john.247800 YouTube: https://youtube.com/@newslifeandbeyond?si=9xofBYhgZMzYNf4b

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 Worst Jail Memory That Still Haunts Him 00:36 Meet Steven: Life, Background & Podcast Journey 03:20 Growing Up in New London, Connecticut 07:00 Family Life, Poverty & Early Struggles 13:41 Drugs, Trauma & Losing Stability at a Young Age 19:49 Teenage Hustles, Survival & Dropping Out of School 25:05 Entering Street Life & First Crimes 28:59 When Gang Culture Took Over Connecticut 32:32 Deeper Gang Involvement & Losing Control 36:04 Becoming a Latin King 40:03 Gang Leadership, Power & Expanding Influence 44:00 Trying to Change — Then Getting Arrested 54:05 County Jail Reality Check 01:03:33 Leaving the Gang While Locked Up 01:09:19 Transfer to Cheshire Prison & Daily Routine 01:14:02 Getting Sent to Virginia Prison 01:18:04 Prison Politics & Surviving Without Trouble 01:25:01 Life Lessons From Prison & Walking Away From the Gang 01:27:01 Life After Prison & Staying Clean 01:33:01 Rebuilding Family Relationships & Finding Purpose 01:40:11 Final Reflections & Advice to the Next Generation

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Michael Bishop grew up surrounded by emotional trauma, bullying, homelessness, and instability, moving in and out of the foster care system while dealing with serious issues at home. Fighting became a way to survive, and that anger eventually led to him being locked inside Massachusetts juvenile detention centers for nearly two years. In this episode, Michael shares a firsthand account of life inside youth detention, including physical abuse by guards and the long-term impact of being punished instead of protected. This conversation exposes the harsh realities of the juvenile justice system and how a broken upbringing and systemic failures shaped the course of his life.

_____________________________________________ #JuvenileDetention #PrisonStories #JusticeSystem #SurvivorStory #TrueCrimePodcast #Massachusetts #LifeBehindBars #lockedin

_____________________________________________ Thank you to PRIZEPICKS & GOLD DROP SELTZERS for sponsoring this episode: PRIZEPICKS: Visit https://prizepicks.onelink.me/LME0/IANBICK and use code IANBICK and get $50 in lineups when you play your first $5 lineup!

_____________________________________________ GOLD DROP: Head to https://www.thedryoak.com/ and use promo code LOCKEDIN at checkout for 10% off your order.

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 Brutal Beginnings Inside Juvenile Detention 00:40 Childhood Trauma, Homelessness & Foster Care 01:05 Meet Mike: His Story Begins 02:24 Growing Up With Instability & Family Struggles 05:04 Homelessness, Loss & a Broken Family System 08:26 Bullying, New Schools & Feeling Like an Outsider 13:13 Gifted Programs, Mental Health & Acting Out 16:32 Rebellion, Police Encounters & the CHINS Program 23:00 School Fights, Suspensions & Falling Behind 27:27 DSS Group Homes & Foster Care 33:02 Foster Homes, School Incidents & Authority Clashes 40:54 Probation, Drug Tests & Escalating Legal Trouble 46:26 Alternative School, Metal Detectors & Physical Restraints 53:46 Probation Chaos, Failed Drug Tests & Court Dates 56:14 Sentenced to Juvenile Detention 01:01:14 Intake & Assessment Unit: Fear, Isolation & First Restraints 01:11:51 Westborough Secure Unit: Abuse, Trauma & Turning 18 01:20:05 Staff Abuse, Manipulation & Surviving the System 01:31:01 Developing Narcolepsy While Locked Up 01:39:27 Violence, Corruption & Hard Lessons Learned 01:46:03 Other Kids' Stories: System Failure on Repeat 01:53:37 The Final Straw: Restraint, Investigation & Consequences 02:02:02 Transferred to a New Facility: A Glimmer of Hope 02:08:11 Release From Juvie, Recovery & Life After Lockup 02:13:29 Mental Health, Healing & Breaking the Cycle 02:16:49 Final Thoughts: Advice for At-Risk Youth

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Michael Bishop grew up surrounded by emotional trauma, bullying, homelessness, and instability, moving in and out of the foster care system while dealing with serious issues at home. Fighting became a way to survive, and that anger eventually led to him being locked inside Massachusetts juvenile detention centers for nearly two years. In this episode, Michael shares a firsthand account of life inside youth detention, including physical abuse by guards and the long-term impact of being punished instead of protected. This conversation exposes the harsh realities of the juvenile justice system and how a broken upbringing and systemic failures shaped the course of his life.

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Matt Frey spent seven years working as a therapist inside Rikers Island from 2011 to 2018, a job he never imagined taking growing up in the suburbs of New York. In this episode, Matt gives a rare inside look at day-to-day life at Rikers from the inmate perspective, breaking down what really happens in both General Population and Mental Observation housing. He shares firsthand experiences with extreme violence, inmate suicides, unprovoked attacks on staff, and the psychological toll of working inside one of America's most notorious jail systems. Matt also explains how inmates sometimes manipulate mental health services for protection or legal advantage, what it's like hearing confessions protected by confidentiality, and the surreal reality of assessing people just hours after seeing their alleged crimes on the news. Now running his own psychotherapy practice after leaving Rikers, Matt reflects on boundaries, trauma, and how working inside the jail changed him forever.

_____________________________________________ #RikersIsland #PrisonStories #TrueCrimePodcast #JusticeSystem #PrisonLife #MentalHealthInPrison #LifeBehindBars #lockedin

_____________________________________________ Thank you to AVA for sponsoring this episode: Take control of your credit today. Download the Ava app and when you join using my promo code LOCKEDIN, you'll get 20% off your first year—monthly or annual, your choice.

_____________________________________________ Connect with Matt Frey: Instagram: @freymentalfitness @outliftathletics @mcfrey27 Facebook: https://www.facebook.com/profile.php?id=61585253558683

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 Life Inside Rikers Island (What No One Sees) 01:14 Meet Matt: A Therapist Inside Rikers Island 03:00 From Rikers Island to Private Practice 07:12 Matt's Early Life & Why He Chose Mental Health 13:55 First Jobs in Mental Health & Prison Work 18:43 First Day Working at Rikers Island (Shock & Reality) 20:44 How Therapy Works Inside a Jail 23:10 Violence, Suicides & Mental Health at Rikers 27:29 Solitary Confinement & Its Psychological Damage 32:58 Daily Life at Rikers: Safety, Filth & Neglect 37:06 Confidentiality, Courts & Ethical Dilemmas in Jail 45:01 The Human Side of Rikers: Trauma & Inmate Stories 53:34 Why He Left Rikers Island 01:00:26 Lessons Learned About Justice, Mental Health & Reform

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Dylan Syer speaks publicly for the first time about the high-profile accusations that upended his life, including allegations of fraud, identity theft, and grand larceny stemming from his work as a celebrity personal shopper. Prosecutors claimed Dylan used access to clients' finances to make unauthorized luxury purchases, accusations he firmly denies. In this episode, Dylan explains what he says really happened, how the charges caused his business to collapse overnight, and what it was like being sent to Rikers Island while fighting to clear his name. He also opens up about the emotional toll of the case, navigating the criminal justice system, and ultimately being sentenced to one year of weekends at Rikers — a punishment that kept him trapped between freedom and incarceration.

_____________________________________________ #RikersIsland #PrisonStories #TrueCrimePodcast #CelebrityLifestyle #LifeAfterPrison #JusticeSystem #RedemptionStory #lockedin

_____________________________________________ Thank you to AVA & GOLD DROP SELTZERS for sponsoring this episode: AVA: Take control of your credit today. Download the Ava app and when you join using my promo code LOCKEDIN, you'll get 20% off your first year—monthly or annual, your choice.

_____________________________________________ GOLD DROP SELTZERS: Head to https://www.thedryoak.com/ and use promo code LOCKEDIN at checkout for 10% off your order.

_____________________________________________ Connect with Dylan Syer: Instagram: @SireConsultant TikTok: @SireConsultant

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 Police Raid, Fraud Charges, and Everything Falling Apart 01:55 Dylan Sire's Case: The Allegations and Why This Story Matters 02:59 Childhood, Family Values, and Early Influences 05:53 Discovering Luxury Fashion and the High-End World 09:47 Breaking Into High-End Sales and Designer Retail 14:12 Launching His Own Boutique and Becoming an Entrepreneur 22:14 Building a Celebrity Personal Shopper Business 27:47 Industry Shifts, Competition, and Cracks in the Model 33:53 Big Clients, Luxury Spending, and How the Business Worked 38:18 Financial Pressure, Business Trouble, and Legal Red Flags 42:38 Account Freezes, Chargebacks, and Sudden Collapse 47:17 Arrest, Booking, and Arrival at Rikers Island 54:00 Inside Rikers Island: Survival, Fear, and Reality 01:01:56 Bail, Media Attention, and Public Fallout 01:09:01 Court Proceedings, Charges, and Legal Strategy 01:16:20 Sentenced to Weekends at Rikers: How It Worked 01:23:30 Relationships, Trust, and Personal Consequences 01:32:00 Rebuilding After the Case: Frugality, Growth, and Lessons Learned 01:36:00 Final Reflections, Accountability, and Moving Forward

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Andrew Gautreau grew up in a good family in Louisiana, but addiction took hold in his teenage years and quickly sent his life off the rails. After finishing trade school, he began getting arrested for drug offenses — yet somehow still landed a job as a prison guard, training for a month at Angola, one of the most notorious prisons in America. His time on the job lasted just six months before he quit right before being fired, all while being arrested twice for drug charges outside the prison. As his addiction spiraled further, Andrew ended up cycling through local jails and a correctional work facility, where he spent nearly two years behind bars. In this episode, he opens up about addiction, hypocrisy inside the justice system, life on both sides of the bars, and how he ultimately turned everything around and got sober.

_____________________________________________ #PrisonStories #AddictionRecovery #CorruptPrisonGuard #LifeAfterPrison #TrueCrimePodcast #AngolaPrison #FormerInmate #redemptionstory

_____________________________________________ Thank you to PRIZEPICKS & LUCY for sponsoring this episode:

LUCY: Go to HTTP://LUCY.CO/IANBICK and use promo code IANBICK to get 20% off your first order.

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PRIZEPICKS: Visit https://prizepicks.onelink.me/LME0/IANBICK and use code IANBICK and get $50 in lineups when you play your first $5 lineup!

_____________________________________________ Connect with Andrew Gautreau: https://tattedbadclothing.myshopify.com/

_____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/

_____________________________________________ Shop Locked In Merch: http://www.ianbick.com/shop

_____________________________________________ Timestamps: 00:00 From Addiction to Prison Guard: A Life on the Edge 01:00 Growing Up in Louisiana and Early Influences 08:00 Family Values, Childhood Trauma, and Identity 13:00 First Drugs, Addiction, and Losing Control 18:00 First Arrests, Criminal Charges, and Consequences 24:00 Escalation: Jail Time, Probation, and Repeat Mistakes 31:00 Becoming a Correctional Officer Against the Odds 36:00 Inside Angola Prison: Training, Reality, and Moral Conflict 42:00 Daily Life as a Prison Guard Behind the Walls 47:00 Drugs, Arrests, and Walking Away from the Job 52:00 Addiction Spirals: Crime, Chaos, and Self-Destruction 58:00 Rock Bottom: Overdoses, Homelessness, and Survival 01:03:00 Getting Sober and Rebuilding From Nothing 01:09:00 Life After Addiction: Giving Back and Helping Others 01:13:00 Lessons Learned, Redemption, and Final Reflections

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