Headsmack: Conversations with Misfits Damion Lupo / CEO. Entrepreneur. Author
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
Paul Povolni, the founder of Voppa Creative, has been a creative leader for over 30 years, with clients around the world. He’s led teams in creating award-winning branding and design as well as equipping his clients to lead with Clarity, Creativity and Culture.
Headsmack Website