DiscoverThe Gratitudeology™ Podcast with Jamie HessCaitlin Crosby | How Hiring a Homeless Couple Changed Everything… and Led Her to Oprah
Caitlin Crosby | How Hiring a Homeless Couple Changed Everything… and Led Her to Oprah

Caitlin Crosby | How Hiring a Homeless Couple Changed Everything… and Led Her to Oprah

Update: 2025-06-18
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Caitlin Crosby started life in the spotlight, right out of the gate. Her parents met in “the industry” in Hollywood, and she grew up in front of the camera. In her teens, she began writing songs with Babyface and subsequently signed to his label, Arista Records.


But once she was out on tour… Caitlin realized she was destined for more. She didn’t care about the same things as other “normal” Hollywood girls. While they were focused on getting into the hottest club, she was dreaming about ending homelessness, participating in her church youth group, and helping people feel secure in their bodies by celebrating their flaws.


It all led to one fateful day, when a chance meeting with a young homeless couple would change everything… and lead her to start a spiritual enterprise business called The Giving Keys that would come to touch hearts across Los Angeles, and eventually the world…


… including the ultimate heart to be moved, that of Oprah Winfrey’s (!), naming Caitlin to her coveted list, her “Super Soul 100.”


Tune in for a dose of inspiration and a reminder that a life lived in service tends to be the happiest life of all.


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Show Notes:

A big thank you to Caitlin Crosby for joining us and sharing your inspiring story. Follow her on Instagram @caitlincrosby, and for more on her business, visit @thegivingkeys.

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Make sure to follow Jamie @jamiehess on Instagram for news & updates, and visit our companion Instagram account @gratitudeology for a sneak peek into the personal moments discussed on the show.


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The Gratitudeology Podcast theme music is by HYLLS, performed by Nadia Ali @thenadiaali




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Caitlin Crosby | How Hiring a Homeless Couple Changed Everything… and Led Her to Oprah

Caitlin Crosby | How Hiring a Homeless Couple Changed Everything… and Led Her to Oprah

Jamie Hess