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.

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Entrepreneurs struggle to scale because they rely on tactics, funnels, and closers instead of systems and human connection. Many feel like sales just “isn’t them.”

Imagine having a sales machine that works whether you’re online or not. Imagine building a team that sells with heart. Imagine finally getting back your time—and your confidence.

This episode delivers the blueprint. Jim Padilla unpacks how to stop selling and start solving—and how doing so can change your business and legacy. Stick around—this one will shift your sales paradigm.

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Guest Bio:

Jim Padilla is a renowned sales strategist and founder of Gain the Edge, known for generating over $500 million in client revenue through high-performance sales teams and systems. His expertise in influence stems from a rough early life—foster care, street life, and jail—where reading people became a survival skill. Jim transformed that skill into a calling, helping mission-driven entrepreneurs scale ethically and sustainably. He’s also on a bigger mission: building “opportunity cities” to empower ex-cons and aged-out foster youth with purpose, training, and employment.

Link: https://gtenow.com/salescallaudit-diy

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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

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Atiba De Souza is your secret weapon when your team is underperforming. 

As a CEO strategist and team productivity expert, Atiba transforms struggling organizations into high-performing machines using AI-powered systems and proven leadership frameworks. 

In this electrifying episode, Atiba breaks down the difference between AI tools, agents, and employees—and why every business leader needs to rethink their org chart NOW. 

From his 1996 basement-built search engine to today’s AI employee revolution, Atiba’s journey is packed with eye-opening insights, practical steps, and a few headsmack moments that just might change the way you lead.

GUEST BIO: 

Atiba De Souza is a CEO strategist, team productivity expert, and AI innovation pioneer. With a background in software engineering dating back to the 1990s—when he built and sold a search engine from his mom’s basement—Atiba has spent decades optimizing performance in both government and private sectors. Today, he helps businesses build AI-powered systems that enhance productivity, improve decision-making, and bridge the gap between human leadership and digital execution. He’s also the author of The Delegation Trap, and a dynamic voice on the intersection of leadership and technology.

Link: clientattractionpros.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

“They told me to go home and die. Instead, I built a business and beat cancer—twice.”

Globally recognized YouTube strategist and high-performance coach Owen Hemsath joins The Headsmack Podcast to share how stage 4 cancer, twice diagnosed, didn’t stop his mission—it reshaped it. 

From building 6- and 7-figure YouTube channels to abandoning chemotherapy for a holistic path, Owen reveals the real ROI of purpose, presence, and priorities. 

If you’re navigating hustle, health, or the hunger for impact, this episode is a game-changer.

Key Takeaways:

• Business growth doesn’t require burnout
• YouTube channels need siloed content strategy
• Holistic healing starts with radical food and lifestyle shifts
• AI can scale your marketing, but it can’t replace humanity
• Faith is a competitive advantage—if you let it be

Guest Bio:

Owen Hemsath, better known as Owen Video, is a globally renowned YouTube Growth Strategist and High-Performance Coach. With a client roster spanning top influencers and brands, Owen has pioneered media strategies that transform online presence into high-converting thought leadership. A two-time cancer survivor, Owen’s approach blends tactical brilliance with profound personal growth. His holistic health advocacy and unfiltered authenticity make him a transformative voice in both media and mindset.

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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

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Henry Kaminski Jr. is a force in hospitality branding, with 16+ years in the creative industry and a story that reads like a movie script. 

After losing $300K overnight when Hurricane Sandy wiped out his top clients, Henry reinvented himself—landing Russell Brunson as a branding client, helping launch ClickFunnels, and becoming a thought leader in personal branding. 

As former CMO for celebrity chef Fabio Viviani’s hospitality group, he doubled locations nationwide and implemented cutting-edge marketing tools in a traditionally outdated industry.

Now with his new venture, Brand to Table, Henry is fusing digital innovation with high-touch hospitality. 

In this episode, he shares the real stories behind the rise, the falls, and the reinventions. 

From SMS marketing that drove $1.3M in restaurant revenue to GPT-powered menu generators and brand strategy breakthroughs—this is a masterclass in modern branding.

Guest Bio: 

Henry Kaminski Jr. is a branding expert with over 16 years in the creative industry, specializing in restaurant and hospitality marketing. Known for launching the Brand Doctor and helping personal brands thrive, Henry has worked with major names like Russell Brunson and served as Chief Marketing Officer for a national hospitality group, doubling their locations in under three years. Today, he runs Brand to Table, a firm blending deep hospitality insight with cutting-edge tech like AI, SMS, and GPT-powered marketing to transform how restaurants scale and connect with customers.

Link: https://www.brandtotable.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

Jamie Rowe, lead vocalist of Nashville-based hard rock band Kalamity Kills, joins Paul to talk about breaking molds, surviving dark nights, and launching one of the most important rock songs of the year—“Starry Skies (988).” 

A former frontman of Guardian, Rowe shares his powerful journey from Christian rock stardom to forming a band that blends modern energy with authentic heart. 

This episode dives into the struggles behind the scenes, the raw moments of suicidal ideation that inspired their Billboard Top 40 hit, and how music can save more than just a soul—it can save a life.

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Guest Bio: Jamie Rowe is a veteran rock vocalist with a global legacy and a freshly ignited mission. Best known as the former frontman of Christian hard rock band Guardian—with 13 #1 radio hits and performances in over 35 countries—Rowe now leads Kalamity Kills, a modern hard rock band redefining impact and authenticity. Co-founded with producer/guitarist Jamey Perrenot (Taylor Swift, LeAnn Rimes), the band has charted with emotionally charged singles like “The Chemistry of Meant to Be” and the suicide prevention anthem “Starry Skies (988),” featuring Aaron Gillespie of Underøath. Rowe’s voice, both musically and personally, continues to be one of raw power, gritty hope, and deep purpose.

LINK: https://www.kalamitykills.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

James Barnard knows logos—and how to turn design into a powerful business.

As an award-winning logo and visual identity designer, James went from burnout to booked out by mastering not just the craft, but the business of design. 

With over a million followers and a global client base, James is one of the most trusted voices in branding today. 

In this episode, we dive into the biggest mistake that nearly ended his business, the viral video that changed his life, and how he uses smart strategy (like the “brand noun” process) to create logos that actually work. 

Whether you’re a designer or a business owner, this one’s packed with insights you can use immediately.

Guest Bio:

James Barnard is an award-winning logo and visual identity designer, educator, and international speaker. Originally from the UK and now based in Australia, James is the founder of Barnard Co., a design studio focused exclusively on brand identity. With over 1 million social media followers, James is a leading voice in the design community, known for his teaching style, practical insights, and humorous yet insightful content that resonates with both designers and business owners. His work has been published in LogoLounge and featured in Adobe’s global programming. He also offers courses in Illustrator, Photoshop, and brand development, helping the next generation of designers level up their skills and businesses.

Link: https://barnard.co/

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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

Brian Dixon is a bestselling author, publisher, and online business strategist helping everyday messengers write their book and grow their business.

In this episode of the Head Smack Podcast, Brian shares his unexpected path from aspiring rockstar to middle school teacher, to charter school founder, and ultimately to co-founder of Hope Writers. 

He walks us through the 5 essential steps to building—not just writing—a transformational book, revealing how your hardest moments can become your most powerful message. 

Learn how to avoid the biggest mistakes first-time authors make, what publishers won’t do for you, and why skill stacking could be the missing link in your business success story.

Link: Hopewriters

Guest Bio:
Brian Dixon is a bestselling author, publisher, and online business strategist passionate about helping aspiring writers turn their experiences into impactful books. A former charter school founder and teacher, Brian co-founded Hope Writers—a thriving community of over 1,900 members—and has worked with well-known figures like Michael Hyatt and top mom bloggers to launch life-changing books. He combines a heart for teaching with tactical strategy to empower everyday messengers to write, publish, and promote with purpose.

Send a text

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

From Pajama Jeans to Pagewheel: What Holly Homer Can Teach Us About DIY Entrepreneurship

Holly Homer didn’t plan to start a business—she just needed an outlet from the chaos of motherhood. Her journey from sending long Saturday morning emails to a friend to building KidsActivities.com and Pagewheel is proof that success starts with showing up.

She used her life as content, leaned into her mess, and built one of the most beloved parenting brands online. When tech became her bottleneck, she didn’t outsource—she co-invented a platform to make funnels easy. Holly’s story is a masterclass in turning real-life chaos into creative currency—and building the tools to do it again and again.

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Holly Homer is a pioneering content creator who stumbled into entrepreneurship over two decades ago when she launched one of the earliest mom blogs, June Cleaver Nirvana. Today, she’s the founder of the wildly popular KidsActivities.com and co-creator of Pagewheel, a no-tech funnel-building platform designed for creators who’d rather focus on content than code. Based in Dallas, Holly’s journey from overwhelmed mom to digital powerhouse is marked by scrappy innovation, heartfelt storytelling, and a passion for making online business more accessible.

Pagewheel.com 

For those with kids: KidsActivities.com

Send a text

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

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Nikhil Sai went from broke dropout to marketing phenom, generating over $500 million in client results and interviewing more than 100 millionaires on The Nikhil Sai Show. 

In this electrifying episode of The Headsmack Podcast, Nikhil shares how he built a global business from scratch, why pricing is everything, and the “inversion funnel” strategy that turns cold leads into five-figure clients. 

If you’re an entrepreneur, coach, or agency owner tired of being overlooked, this is your wake-up call. Learn how to work less, earn more, and only serve clients who value what you do.

Link: https://funnelingmedia.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