Sad Boy Radio

Sad Boy Radio A new podcast that discusses everyday problems through the universal language of music. Viewers are
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Sad Boy Radio CC###IX: Overcoming What Shaped Me? Owner, , slides to to discuss creating Smash Jibarito, vending at &...
12/12/2025

Sad Boy Radio CC###IX: Overcoming What Shaped Me?

Owner, , slides to to discuss creating Smash Jibarito, vending at & , overcoming struggles from childhood, and finding his confidence as he continues to grow.

In the song, “Autumn Drive,” Bryson Tiller says, “Cause I miss the basics / rolling up two swishers in my A6 / kick it, watch a flick in my basement,” Tiller reflects on the times when life was simple. When the responsibility of others lives weren’t places on his shoulders, and the only thing he had to worry about was the simple things in life. Josean & I take a trip down memory lane. We reflect on the moments when life was simple, and we were being shaped by life unknowingly.

Also discussed: Embracing role as a leader, overcoming ego, and learning to let go of relationships that don’t serve you.

Sad Boy Radio CC###VII: Paradise Don’t Last Forever? Chicago Rapper, , slides to to discuss his new album “Paradise Do...
12/05/2025

Sad Boy Radio CC###VII: Paradise Don’t Last Forever?

Chicago Rapper, , slides to to discuss his new album “Paradise Don’t Last Forever,” and the moments that led to its creation. Jay Wood talks about unintentionally hurting people in relationships, losing close family, and navigating “paradise” while dealing with heavy circumstances.

In the song, “Landline Three,” Wood says, “For my homie in the grave that ain’t here no more / this is for the hoes I never call / in a room full of applause / I still feel alone I’m trynna get back to me,” Wood uses this song to reflect on his journey & the relationships that are not available anymore. However through it all, he leaves the “landline” available for anyone who may need it... even if they don’t want to use it.

Also discussed: being okay with being the “villain” in someone’s story, watching parents age, and “Freesole Collective”



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Sad Boy Radio CC###VII: Paradise Don’t Last Forever? Chicago Rapper, , slides to to discuss his new album “Paradise Do...
12/05/2025

Sad Boy Radio CC###VII: Paradise Don’t Last Forever?

Chicago Rapper, , slides to to discuss his new album “Paradise Don’t Last Forever,” and the moments that led to its creation. Jay Wood talks about unintentionally hurting people in relationships, losing close family, and navigating “paradise” while dealing with heavy circumstances.

In the song, “Landline Three,” Wood says, “For my homie in the grave that ain’t here no more / this is for the hoes I never call / in a room full of applause / I still feel alone I’m trynna get back to me,” Wood uses this song to reflect on his journey & the relationships that are not available anymore. However through it all, he leaves the “landline” available for anyone who may need it... even if they don’t want to use it.

Also discussed: being okay with being the “villain” in someone’s story, watching parents age, and “Freesole Collective”

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