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In this powerful episode of Look At Me Now, Alexis sits down with survivor, storyteller, and author Cleo Young for a raw, unflinching conversation about life in — and beyond — the cycle of incarceration. From a childhood shaped by instability to decades spent navigating state and federal prison systems, Cleo shares the pivotal moments that pushed him toward change, the lessons he learned in the most unlikely places, and how he ultimately found freedom on the open road as a long-haul trucker.

00:00 – A somber opening: Alexis meets Cleo

00:41 – “Survivor scholar of life”: A different kind of introduction

02:03 – The poem that made a psychologist cry

04:03 – “The gangster”: A lyrical truth from inside the system

05:09 – Ten years for survival: Life in the SHU

06:39 – Forgiving everyone — including himself

08:51 – Coming home, going back: Why change is so hard

10:10 – Pride, provision, and the pull of the streets

11:21 – From tiptoeing to knee-deep in the game

12:34 – Breaking into school for a VCR: Early survival tactics

13:28 – Boys Ranch revelations: Poverty has many faces

15:26 – Team-building, manners, and what the hood can’t teach you

16:21 – Thriving in structure, drowning in chaos

17:43 – Running away, returning home

18:51 – Knowing right from wrong, but feeling out of options

20:29 – The urgency of survival in the ’90s

21:02 – An aunt’s lifeline and a high school graduation

22:44 – Gangs as family and safety net

23:00 – First prison sentence at 18: A family reunion behind bars

24:33 – Denied the chance to learn a trade

26:11 – Smuggling runs with his mother

27:02 – Telemarketing, renovation, and a glimpse at stability

29:22 – The job he loved — and the parole violation that ended it

31:49 – Starting over again and again

34:09 – General Relief and the temptation next door

35:45 – Selling drugs — and the raid that changed everything

37:33 – It’s not about knowing right from wrong

39:37 – Growing up without choice or autonomy

40:47 – The urgency that erases patience

41:46 – Losing friends to drugs, violence, and prison

42:09 – Why this incarceration felt different

43:27 – Filling time with jobs and hustles

44:49 – Thinking he could “beat the system” — and losing again

45:57 – Federal time: 20 years for marijuana

47:20 – Fighting his case from the law library

48:51 – Learning from unexpected mentors in prison

49:49 – Winning an appeal and walking free

50:26 – Cancer, loss, and the system of “Why?”

53:04 – Radical self-accountability

54:24 – Early release, hard lessons, and leaving gang life behind

56:23 – Choosing trucking: Covid-proof, recession-proof, felony-friendly

58:00 – Starting from zero and loving life without fences

59:49 – From hopelessness to hope: What he tells others

01:01:06 – Know where you’re going — and do the research

01:02:18 – Choosing the high road when the low road calls

01:03:05 – Surviving the minute, the hour, the day

01:05:10 – The pride barrier: Why asking for help is so hard

01:07:21 – Being present and recognizing your worth

01:09:09 – Freedom, beauty, and the power of possibility

01:10:04 – Writing books and living fully

01:12:21 – Making the most of every moment

01:13:21 – “You’re worth it and you deserve it”

01:14:09 – First podcast appearance — and where to find Cleo

Connect with Cleo:

• Book: How to Start an LLC by Olivia J. Young
• Instagram: @cleo_young (if applicable)

Follow Alexis @alexis_artin

Learn more at AlexisArtin.com

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This is an Operation Podcast production