Looking for Love in All the Wrong Places | Ruben Santiago

In this episode of The Open Exchange, Paul sits down with Ruben Santiago for a raw conversation about identity, belonging, and the quiet reasons people make destructive choices.

Ruben opens up about growing up searching for acceptance, how hustling became a way to feel valued, and why selling drugs was never really about money. He walks through the consequences that followed, including prison, and the internal reckoning that forced him to confront who he was without the lifestyle that once defined him.

This isn’t a story about glorifying the past. It’s about understanding how unhealed wounds shape behavior, and what it takes to rebuild when everything familiar is stripped away.

If you’ve ever chased validation, identity, or love in places that left you emptier than before, this conversation will hit home.

Chapters:

00:00 — Meeting Ruben
Setting the tone, who he is today vs who he used to be.

04:12 — Growing Up Without Feeling Chosen
Early emotional gaps, environment, and the hunger for approval.

10:45 — When Hustling Beccomes Survival
How selling drugs wasn’t about money, but belonging.

18:30 — The Moment Everything Collapsed
Consequences, prison, and the cost of the lifestyle.

27:05 — Sitting With the Silence
What prison stripped away and what it forced him to face.

35:40 — Rebuilding Identity After Loss
Learning who you are when the hustle is gone.

45:10 — What Love Actually Looks Like Now
How Ruben defines love, purpose, and self-worth today.

54:30 — Advice to the Version of Himself Who Was Hurting
A message to anyone still chasing validation the wrong way.