EPISODE · Jan 4, 2026 · 2H 7M
I Drank Myself To The Edge Of Death — Then Went to Prison | Joseph De Gregorio
from Locked In with Ian Bick · host Ian Bick
Joseph De Gregorio was raised in a good family and built a successful career on Wall Street, but the 2008 market crash derailed everything. After losing his footing, he started his own business, which eventually turned into a fraud scheme—a decision he ultimately took responsibility for by coming clean and turning himself in to authorities. At the same time, Joseph was battling a severe alcohol addiction, drinking himself to the point of needing a liver transplant. He was later sentenced to federal prison, where he faced harsh conditions and medical challenges while serving time in a federal medical center prison. After his release, Joseph reinvented his life, dedicating himself to helping others navigate the justice system through prison consulting and sentence mitigation work, turning his darkest chapter into a mission to help people avoid the same mistakes. _____________________________________________ #IAlmostDied #PrisonSurvival #AddictionRecovery #TrueCrimeStories #LifeAfterPrison #RedemptionStory #PrisonLife #survivorstory _____________________________________________ Thank you to FRONTLINE HEALING FOUNDATION for sponsoring this episode: Visit https://frontlinehealingfoundation.org/ to donate or share their mission. _____________________________________________ Connect with Joseph De Gregorio: Website: https://www.jnadvisor.com/ LinkedIn: https://www.linkedin.com/in/jnadvisor-joseph/ 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 Wall Street Success to Federal Prison 02:40 Who He Was Before Everything Fell Apart 11:10 Childhood, Ambition & the Drive to Win 19:16 Inside Wall Street: Money, Power & Pressure 30:08 The 2008 Financial Crash That Changed Everything 39:47 Addiction, Burnout & Losing Control 47:32 Liver Failure, Transplant & Near-Death Hospital Battle 01:03:53 Getting Sober: AA, Accountability & Truth 01:11:20 Turning Himself In to Federal Authorities 01:22:13 Federal Prison While Medically Compromised 01:35:48 Release, Home Confinement & Supervised Release Reality 01:40:58 Life After Prison: Education, Purpose & Reinvention 01:52:00 Beating the System: Mitigation Strategy Explained 02:01:53 Legal Tech, Consulting & The Future of Defense 02:09:40 Final Lessons, Advice & How to Contact Him Learn more about your ad choices. Visit podcastchoices.com/adchoices
What this episode covers
Joseph De Gregorio was raised in a good family and built a successful career on Wall Street, but the 2008 market crash derailed everything. After losing his footing, he started his own business, which eventually turned into a fraud scheme—a decision he ultimately took responsibility for by coming clean and turning himself in to authorities. At the same time, Joseph was battling a severe alcohol addiction, drinking himself to the point of needing a liver transplant. He was later sentenced to federal prison, where he faced harsh conditions and medical challenges while serving time in a federal medical center prison. After his release, Joseph reinvented his life, dedicating himself to helping others navigate the justice system through prison consulting and sentence mitigation work, turning his darkest chapter into a mission to help people avoid the same mistakes. _____________________________________________ #IAlmostDied #PrisonSurvival #AddictionRecovery #TrueCrimeStories #LifeAfterPrison #RedemptionStory #PrisonLife #survivorstory _____________________________________________ Thank you to FRONTLINE HEALING FOUNDATION for sponsoring this episode: Visit https://frontlinehealingfoundation.org/ to donate or share their mission. _____________________________________________ Connect with Joseph De Gregorio: Website: https://www.jnadvisor.com/ LinkedIn: https://www.linkedin.com/in/jnadvisor-joseph/ 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 Wall Street Success to Federal Prison 02:40 Who He Was Before Everything Fell Apart 11:10 Childhood, Ambition & the Drive to Win 19:16 Inside Wall Street: Money, Power & Pressure 30:08 The 2008 Financial Crash That Changed Everything 39:47 Addiction, Burnout & Losing Control 47:32 Liver Failure, Transplant & Near-Death Hospital Battle 01:03:53 Getting Sober: AA, Accountability & Truth 01:11:20 Turning Himself In to Federal Authorities 01:22:13 Federal Prison While Medically Compromised 01:35:48 Release, Home Confinement & Supervised Release Reality 01:40:58 Life After Prison: Education, Purpose & Reinvention 01:52:00 Beating the System: Mitigation Strategy Explained 02:01:53 Legal Tech, Consulting & The Future of Defense 02:09:40 Final Lessons, Advice & How to Contact Him Learn more about your ad choices. Visit podcastchoices.com/adchoices
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I Drank Myself To The Edge Of Death — Then Went to Prison | Joseph De Gregorio
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