In this raw and inspiring episode of The Art of Rebounding, host Harold “Lefty” Williams sits down with Ocho, a personal trainer, entrepreneur, and founder of the Keep Winning brand, for a powerful conversation about discipline, faith, and what it really means to go all in. Ocho opens up about growing up in Baltimore, chasing his athletic dreams, transitioning from corporate life at Oracle into full-time personal training, and making the difficult choice to pursue purpose over comfort. Just as his life was gaining momentum in Los Angeles, an unexpected setback landed him in federal prison — forcing him to confront fear, uncertainty, and identity head-on. What followed was a mental and spiritual rebirth. While incarcerated, Ocho heard a message that would change everything: keep winning. That mindset became the foundation for his life, his training philosophy, and his now-thriving brand. Today, Ocho owns a private training gym in Los Angeles, works with high-profile clients, and leads with a philosophy rooted in discipline, sacrifice, and unwavering belief. This episode is a masterclass in rebounding — proving that your setback does not disqualify you, it can position you. Connect with Ocho: Instagram: https://www.instagram.com/ochotheceo/ Instagram: https://www.instagram.com/keepwinningla/ Connect with Harold "Lefty" Williams: The Art of Rebounding Book: https://www.theartofrebounding.com/landing Dare2Dream Website: https://dare2dream.xyz/ Instagram: https://www.instagram.com/theartofrebounding/ https://www.instagram.com/leftywilliams42/ X: https://x.com/leftywilliams42/ Facebook: https://www.facebook.com/leftywilliams42/ Executive Producers Harold “Lefty” Williams Shyneefa Williams Elisha “EJ” Williams WizKidFilms, Inc Production
In this raw and inspiring episode of The Art of Rebounding, host Harold “Lefty” Williams sits down with Ocho, a personal trainer, entrepreneur, and founder of the Keep Winning brand, for a powerful conversation about discipline, faith, and what it really means to go all in.
Ocho opens up about growing up in Baltimore, chasing his athletic dreams, transitioning from corporate life at Oracle into full-time personal training, and making the difficult choice to pursue purpose over comfort. Just as his life was gaining momentum in Los Angeles, an unexpected setback landed him in federal prison — forcing him to confront fear, uncertainty, and identity head-on.
What followed was a mental and spiritual rebirth.
While incarcerated, Ocho heard a message that would change everything: keep winning. That mindset became the foundation for his life, his training philosophy, and his now-thriving brand. Today, Ocho owns a private training gym in Los Angeles, works with high-profile clients, and leads with a philosophy rooted in discipline, sacrifice, and unwavering belief.
This episode is a masterclass in rebounding — proving that your setback does not disqualify you, it can position you.
Connect with Ocho:
Instagram: https://www.instagram.com/ochotheceo/
Instagram: https://www.instagram.com/keepwinningla/
Connect with Harold "Lefty" Williams:
The Art of Rebounding Book: https://www.theartofrebounding.com/landing
Dare2Dream Website: https://dare2dream.xyz/
Instagram: https://www.instagram.com/theartofrebounding/
https://www.instagram.com/leftywilliams42/
X: https://x.com/leftywilliams42/
Facebook: https://www.facebook.com/leftywilliams42/
Executive Producers
Harold “Lefty” Williams
Shyneefa Williams
Elisha “EJ” Williams
WizKidFilms, Inc Production