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Locked In with Ian Bick

I Was a Gay Inmate in Federal Prison — Here’s the Truth | Kyle Sandler

Locked In with Ian Bick

Ian Bick

Society & Culture

4.9606 Ratings

🗓️ 6 July 2025

⏱️ 108 minutes

🧾️ Download transcript

Summary

Kyle Sandler scammed 79 people out of $2.3 million, went on the run from the FBI, and ended up serving time in federal prison—twice. But his story doesn’t end there. In this interview, Kyle shares how he built a fake startup empire, what life was really like as an openly gay man in prison, and how he's now trying to make things right by helping others navigate the prison system through his consulting agency. #WhiteCollarCrime #FederalPrison #StartupScam #LGBTQInPrison #PrisonConsultant #FBIManhunt #ScamStory #lockedinpodcast Connect with Kyle Sandler: https://thekylesandler.com/ 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 Kyle Sandler's $2.3 Million Scam and Arrest 00:06:07 Perspective on Prison Experience 00:12:07 Unexpected Journey to a Prison Camp 00:18:58 Getting in Trouble on the Radio 00:25:45 Struggles and Mismanagement in Startup Incubation 00:32:48 Transforming Startups: Innovations and Challenges 00:39:31 Living a Lie: The Dual Life of a Fraudster 00:46:34 The FBI Target Letter and Life on the Run 00:54:00 Being Blackboxed in Transit 01:00:58 Emotional Impact of Leaving Family for Prison 01:07:17 Navigating the Prison Economy During Quarantine 01:14:00 Unspoken Rules in Prison Relationships 01:20:05 Personal Growth and Rehabilitation in Prison 01:27:00 Navigating Federal Prison Transfers 01:33:39 Personal Reflection and Change 01:40:32 Creating the Ultimate Podcast Guest Experience 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 megaphone.fm/adchoices

Transcript

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0:00.0

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0:29.7

I come through and these two big skinheads and little old gay me comes because I'm already

0:34.6

started to come out of the closet.

0:35.7

Comes through the door and they're like, hey, are you Sandler? to shit myself and I'm like yeah like come here oh my god this is all

0:43.3

the things I've been hearing about I'm about to get my to beat kyle sandler was adopted and raised in

0:48.0

maryland built a successful startup and moved to Alabama to expand his empire but behind the business

0:53.9

was a two point.3 million scam

0:56.4

that defrauded 79 investors. After going on the run from the FBI, Kyle was arrested and sent

1:02.9

to federal prison twice. In this episode, he opens up about his time behind bars, including what it

1:08.9

was like serving time as an openly gay man in prison

1:12.0

and how he's trying to rebuild his life by helping others through prison consulting and making

1:17.6

amends for the past.

1:23.2

Kyle, welcome to Lockton. We've been talking about doing this for a while now. But pleasure having you. I'm glad we could finally settle our beef for you to come on the show today. I just want to thank you for putting that behind it so we could actually do this. Yeah, there's a couple TikToks Kyle made shooting at me about how I operated my prison sentence that we'll get to later in this episode.

1:45.3

But it's all good, you know. I know how the business works. So I appreciate your open-mindedness

1:52.2

and letting me come on and being open-minded about it. We have so many mutual friends that it was

1:57.3

only natural to fix everything and do this. Of course. And we originally first met through Generation Hustle, which was a documentary that came out about us. You were one in the episodes. I was one in the episodes. Everyone always asked me about the series. It's not on HBO anymore ever since they merged with Discover. But you were one of the episodes on it. Yeah, I was episode nine. I think you were like episode number one or two.

2:19.2

Yeah, and then I think they switched up the order. Like, I don't know. I don't know why they canned it. I mean, some of the episodes were trash, but there were some really good ones, like the ones where they actually had the people. I heard that the produce, I heard that Alice Gimney got into some kind of beef with Discover.

2:15.0

Oh, that's what I heard.

2:16.6

I don't know if there's any truth to that, but that's what I heard.

2:19.4

Yeah, and I what I heard.

...

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