From Homeless to Nine Figures: What Damion Lupo Learned the Hard Way

Damion Lupo isn’t your average entrepreneur. With over 70 companies under his belt and multiple 9-figure ventures, he’s built wealth, lost it all, and built again—stronger.

In this episode, Damion dives deep into what makes or breaks a business. He shares how chasing money nearly destroyed him, why trust is the fastest path to scale, and how embracing failure is the secret to reinvention. 

His framework? 

Solve real problems, hire the best, focus obsessively, and never stop learning.

Whether you’re in your first year of business or bouncing back from burnout, Damion’s story proves that reinvention isn’t just possible—it’s powerful.

Guest Bio:

Damion Lupo is a lifelong entrepreneur who has founded over 70 businesses across multiple industries, from real estate and finance to construction and retirement planning. A bestselling author of 12 books, he is the creator of the EQRP®—an innovative self-directed retirement solution—and the co-founder of FrameTec, a tech-driven company revolutionizing home construction. After losing a $25M portfolio and experiencing homelessness, Damion rebuilt his life with a mission-driven mindset, helping others break free from financial slavery and build lasting freedom.

Link: turnkeyretirement.com

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Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture.

Headsmack Website

Voppa Creative Website