I Had a $500-a-Day Drug Habit… Then I Ended Up in Prison | Derek Benson

Locked In with Ian Bick

Ian Bick

Society & Culture

4.8 • 745 Ratings

🗓️ 21 April 2026

⏱️ 147 minutes

🔗️ Recording | iTunes | RSS

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Summary

Derek Benson joins Locked In with Ian Bick to share his story of growing up between Connecticut and Florida, bouncing between private schools and military schools, and chasing a future as a student athlete before everything changed. After being introduced to drugs in high school, Derek’s life quickly spiraled into addiction, leading him down a path of arrests for burglary, theft, and other crimes as he struggled for over a decade. In this episode, he opens up about how addiction took over his life, the consequences that landed him in a Connecticut state prison for nearly two years, and the reality of hitting rock bottom. Derek also shares how he finally got sober, rebuilt his life, and the lessons he learned after more than 10 years of addiction. _____________________________________________ #AddictionRecovery #DrugAddiction #RockBottom #PrisonStory #ExInmate #TrueCrime #LifeStory #lockedinpodcast _____________________________________________ Connect with Derek Benson: https://www.investinginsobriety.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 Athlete to Addiction & Arrest (Full Story) 00:13 Early Life, Family & Upbringing 01:41 Moving, School Changes & Sports Background 05:06 Family Separation & Early Trauma 11:13 Living Between Parents & Confusion Growing Up 13:24 Hustler Mentality & Early Behavior 14:56 Military School & Boarding School Experience 19:09 High School Transitions & Identity Struggles 22:19 College Athlete Life & Substance Use Begins 25:12 Prescription Drugs & First Major Incident 29:24 Addiction Escalates in College 36:41 Trouble at Purdue & Entering Illegal Activity 41:49 Transfer to Hofstra & Drug Schemes 51:41 Post-College Struggles & Addiction Deepens 01:03:31 Living a Double Life: Crime & Addiction 01:13:47 Theft, Crime & Arrest 01:20:26 Jail, Withdrawal & Rock Bottom 01:27:27 Prison Life & Survival 01:35:00 Awaiting Trial & Legal Consequences 01:45:12 Release, Rehab & Recovery Journey 01:56:57 Reentry & Building a Support System 02:03:01 Work, Business & New Challenges 02:10:39 Sobriety, Reflection & Life Lessons 02:18:00 Giving Back & Final Thoughts _____________________________________________ To advertise on the show, contact sales@advertisecast.com or visit https://advertising.libsyn.com/LockedInWithIanBicka Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	All I could think about was going to my drug dealer.
0:04.0	And if we have a fucking field day, I'm going five, six, seven hundred bucks, right?
0:08.0	And one day you would spend on drugs?
0:10.0	500 plus dollars a day?
0:12.0	Easy.
0:13.0	My name is Derek Benson.
0:14.0	I was an active addict and alcoholic for 10 years.
0:18.0	I spent about 18 months incarcerated. I have been sober now for 11 years.
0:24.0	Derek Benson talked about growing up between Connecticut and Florida, chasing a future as a student
0:29.1	athlete, falling into a decade-long addiction, the crimes that led him to prison, and how he
0:34.9	eventually got sober and turned his life around.
0:37.5	Thank you. that led him to prison and how he eventually got sober and turned his life around.
0:43.6	I was born in Hartford, Connecticut.
0:45.1	What was your upbringing like?
0:48.3	You could say middle class, upper middle class.
0:53.1	Kind of a tumultuous childhood, relatively.
0:58.7	You know, my mom, the age difference between me and my mother is almost the age difference between my mother and my father.
1:00.8	So I think it's safe to say I might have been an accident.
1:05.2	What'd they do for work?
1:06.7	So my father had a sales distribution business.
1:09.4	At the time, I think my mom worked for United Technologies.
1:13.9	Yeah, I think my mom's job changed once she had me.
	...

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