From Homeless to 9-Figure Empire w/ Stephen Scoggins | EP452

From sleeping in his car to selling a 400-person company, Stephen Scoggins’ story is nothing short of unbelievable. In this episode of the Awake & Winning Podcast, Kaylor sits down with Stephen for a raw, real, and radically honest conversation about men’s mental health, ego, hustle culture, and the hidden cost of chasing external success. Stephen opens up about the exact inner work that helped him break free from insecurity, addiction to approval, and the endless pursuit of worth.
Stephen is a serial 9-figure entrepreneur, author, and speaker who now mentors men on the path to true alignment and purpose. If you’re feeling stuck, burned out, or like something inside you is screaming for change, this episode will light a fire in your soul.

Episode Highlights: men’s mental health, rock bottom moments, shadow work, personal growth, divine masculinity, ego death, hustle culture, alignment, mentorship, community, emotional intelligence, freedom through self-discovery

Takeaways:
- The five enemies every man must confront: arrogance, ignorance, impatience, insecurity, fear
- Why external success won’t fix your internal emptiness
- How anger can be a catalyst—but not a sustainable strategy
- The power of mentorship and borrowing belief from others
- Redefining hustle: intensity vs. anxious aimless energy
- What it really means to “know thyself” and do the shadow work
- The path to divine masculinity and true freedom

If this episode lit a fire under you, don’t keep it to yourself. Screenshot it, throw it up on Instagram, and tag @thekaylorbetts or @awakeandwinning so we can share the love. And hey, if you’re vibing with the show, take 30 seconds to drop us a 5-star review, it helps us reach more freedom-loving legends like you.
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RESOURCES & LINKS MENTIONED IN THIS EPISODE:

Instagram | https://www.instagram.com/stephen_scoggins/
X | https://x.com/stephen_scoggin
YouTube | https://www.youtube.com/@stephenscoggins
Websites | https://stephenscoggins.com/
Podcast | https://open.spotify.com/show/0GS73Oo2UY9FcGvBS1ahm7
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SPONSORS:

Truly Tallow | https://www.trulytallow.com/ Use code “SUNNYBALLS10” at checkout for 10% off your order
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