What happens when purpose matters more than fame?
In this powerful and deeply human conversation, Caitlin Crosby — founder of The Giving Keys — shares her journey from growing up in Hollywood and working in acting and music, to building a global pay-it-forward movement that has employed over 150 people transitioning out of homelessness.
Caitlin opens up about body image pressures in the entertainment industry, the moment a homeless couple became her first business partners, and why words like hope, strength, and worthy can literally save lives. She also speaks candidly about single motherhood, resisting victim mentality, navigating trauma, redefining “happy endings,” and why service is often born from struggle.
This episode is a raw, honest exploration of meaning, resilience, faith, and what it truly means to give back — especially when life doesn’t go as planned.
Whether you’re an entrepreneur, parent, creative, or someone searching for deeper purpose, this conversation will move you.
Follow Caitlin: https://www.instagram.com/caitlincrosby/
Follow The Giving Keys: https://www.instagram.com/thegivingkeys/
Follow Keesha: https://www.instagram.com/keeshawscott
Learn More About Keesha: https://keeshascott.com/
00:00 – Introduction
01:00 – Who Is Caitlin Crosby? Growing Up in Hollywood
02:30 – The Birth of The Giving Keys & the Pay-It-Forward Model
03:30 – Acting, Music & Why Fame Was Never the Goal
05:45 – Body Image, Photoshop & the “Love Your Flaws” Movement
08:00 – Why Human Connection Matters More Than Performance
10:15 – The Homeless Couple That Changed Everything
12:30 – Employing People Transitioning Out of Homelessness
13:15 – Single Motherhood, Hustle & Resisting Victim Mentality
16:10 – Trauma, Compassion & Being ‘Chosen’ for Hard Things
19:00 – Daily Practices for Breaking Out of Victim Mentality
22:00 – What Is a “Happy Ending,” Really?
25:10 – Gratitude, Perspective & Defining Yourself Beyond Lack
26:10 – Launching The Giving Keys Foundation (501c3)
27:40 – Mental Health, Suicide Prevention & Giving Keys Away
30:40 – What’s Next: Speaking, Coaching, Music & Trauma Counseling
32:25 – Final Reflections on Service, Faith & Legacy
