Show notes
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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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