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Locked In with Ian Bick

Struggle Jennings: How I Survived Prison

Locked In with Ian Bick

Ian Bick

Society & Culture

4.8742 Ratings

🗓️ 17 March 2025

⏱️ 108 minutes

🧾️ Download transcript

Summary

Struggle Jennings talks about the life choices that landed him in prison, the drug empire he built, and how he broke into the music industry. #StruggleJennings #MusicIndustry #PrisonToSuccess #DrugEmpire #TrueCrime #CountryRap #SecondChances #realtalk Thank you to LUCY & FACTOR for sponsoring this episode: Lucy: Let’s level up your nicotine routine with Lucy.  Go to HTTP://LUCY.CO/IANBICK and use promo code (IANBICK) to get 20% off your first order. Lucy has a 30-day refund policy if you change your mind.  Factor: Head to http://FACTORMEALS.com/FACTORPODCAST and use code FACTORPODCAST for 50% off plus free shipping on your first box. Connect with Struggle Jennings: Instagram: https://www.instagram.com/iamstruggle/?hl=en Linktree: https://linktr.ee/IAMSTRUGGLE Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/ Presented by Tyson 2.0 & Wooooo Energy: https://tyson20.com/ https://woooooenergy.com/ Buy Merch: https://convictclothing.net/collections/convict-clothing-x-ian-bick Timestamps: 00:00:00 Serendipitous Meeting in Nashville 00:06:18 Influence of Childhood Experiences on Life Choices 00:13:12 Discovering a Lifelong Passion for Music 00:20:35 Navigating Childhood Without a Father Figure 00:27:14 Turning Point: Arrest and Intervention 00:34:18 The Search for a Father Figure and Vulnerability to Gangs 00:40:46 Reflecting on Life's Journey 00:47:26 Navigating Life's Challenges as a Single Parent 00:54:18 Legal Battles and Indictments 01:01:04 Journey of Music and Struggle 01:08:22 Overcoming Adversity: A Story of Family and Redemption 01:15:02 The Strength to Endure and Overcome 01:21:45 Transformative Moments at Riker's Island 01:28:32 Con Air Experience and Prison Transfers 01:34:42 Rebuilding Life After Prison 01:41:16 Understanding Empathy and Compassion in Difficult Times Powered by: Just Media House : https://www.justmediahouse.com/ Creative direction, design, assets, support by FWRD: https://www.fwrd.co Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

Struggle, welcome to Lockton, man.

0:01.8

I'm so glad we can make this happen.

0:03.7

Thanks for reaching out. And, you know, it's funny how we met. Like, I had DMD when we were just happened to be in Nashville. And then Clever introduces you to JD. And then we ended up seeing you like a couple weeks later. We came back and, you know, now here we are. Yeah, that's crazy. But, you know, there's no coincidence. Everything happens for a reason.

0:22.8

And then we had that other situation pop up and it was like, it just fell in the place, as it always does. It really is no coincidence in life. No, it worked out. I'm glad we got to enjoy a good dinner last night, have Brandon here. Yeah, man. You took me to an incredible spot, man. That place was great. Connecticut pizza. Let's go. We've got to give you a reason to come back, you know, show good hospitality. Yeah, no, I'm having to, I don't know if I can eat pizza anywhere else now. Is there good pizza in Nashville or no? Yeah, we got some good pizza spots, but that pizza last night was like, it was pizza. Yeah, you tried all the different flavors, too. You didn't have a normal cheese experience. Yeah, and you do it like I do. Whenever I take somebody to a restaurant I love, like for me, it's Jeff Ruby's in Nashville. I'll order every appetizer. You know, I want whoever's with me to try everything, and you did that. That was great. So I passed a struggle test. Yeah, man. Not bad for a, you know, scraughty white kid that went to prison, you know? When you first met me, did you think I went to prison? Well, no. But it doesn't surprise me.

1:28.6

You know, I've done enough time throughout my life that, you know, you realize that all walks

1:34.3

of life are subject to it.

1:35.9

Like, it's possible for anybody to go, you know.

1:42.0

It can be as easy.

1:43.5

Somebody can walk a straight line and have a bad week and end up in prison.

1:49.6

I've met guys that were super successful.

1:52.6

And, you know, I met judges that had too many drinks and drove home and got in a car wreck

1:59.1

and hurt somebody and ended up in prison with the same people

2:01.8

they had put in there.

2:02.6

So it's like, you know, I try not to ever judge when I see somebody at all.

2:08.5

Because I knew guys like you in prison, you know, that came in and just had that good, good old

2:14.3

boy, innocent look, you know, that you wouldn't, you knew they weren't out there

2:19.3

just, well, I can't even say that, because I've seen some guys that were like you that were stone

2:24.4

cold cowboys, you know. Yeah, that's how they say Ross Ulbate was in prison too. And he looked

2:31.7

younger than me and even skinnier and everything.

2:34.5

Yeah.

2:34.8

And he just got pardoned and got out too after 11 years. Are you familiar with his story? I'm not. Yeah, he just got pardoned by Trump. He was the one that did the Silk Road. Oh, yeah, yeah, yeah, yeah. Yeah, I'm very familiar with his story. Yeah, that's big. He was in the fence. Yeah, that's cool's cool. You know, I saw people kind of giving him shit about pardoning that guy, but like, you know,

2:58.6

there's a lot of time for, I don't need, I mean, I guess he pretty much just set up the website, right? Or was he dealing as well? No, he just set it up. And I guess he got that time because he was trying to orchestrate like a murder, but he wasn't, like it was more like threats and there was corrupt, like DEA agents. Like it was very intricate. But I don't think he deserved life. No one actually died or anything like that. And there's

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