NASCAR driver Mason Maggio and his father, Tony Maggio, join Scott to revisit the journey that connected their family with Floridian Motorsports and helped shape Mason’s growing NASCAR career.

Mason shares the realities of competing with an underfunded team, from narrowly missing Daytona to qualifying against established names and surviving one of his hardest crashes at Talladega. They also revisit the Bristol fire that unexpectedly generated major attention for Mason and his sponsors.

The conversation explores the business behind racing, sponsorship challenges, family support, pit crew life, and Tony’s career in yacht brokerage. Above all, Mason and Tony share what it takes to keep creating opportunities in a sport where nothing is guaranteed.

Key Takeaways

• Floridian Motorsports went from a five-week-old team to competing across multiple NASCAR races.
• Mason narrowly missed Daytona qualifying by just eight hundredths of a second.
• Small NASCAR teams operate with significantly fewer resources than major organizations.
• Qualifying for races can feel like winning for underfunded teams.
• Mason survived a major Talladega impact and still finished the race.
• His Bristol engine fire became an unexpected opportunity for sponsor exposure.
• Drivers often spend significant time finding and maintaining their own sponsorships.
• Family support has played a major role throughout Mason’s racing career.
• Strong relationships can create opportunities across teams and seasons.
• Success in motorsports requires constant effort beyond race weekends.

Chapters

00:40 Welcome Mason and Tony Maggio

02:33 Building Floridian Motorsports from scratch

04:55 A last-minute opportunity at Atlanta

07:05 Nearly making the Daytona field

09:53 Qualifying against established NASCAR names

13:29 Mason’s unconventional start in racing

18:47 The realities of an underfunded team

21:50 Floridian Motorsports takes on Talladega

24:21 Surviving one of Mason’s hardest hits

25:51 Why NASCAR should tell more underdog stories

29:52 Taking the risk of starting a race team

32:52 Family support behind the racing journey

33:43 Moving from Trucks to the Xfinity level

38:10 Life behind the wall on pit road

46:33 The overlooked work of NASCAR pit crews

50:36 Competing while maintaining friendships

57:32 Mason’s 2026 season

58:11 The Bristol fire that went viral

1:02:05 Tony’s yacht brokerage career

1:09:40 Reaching 50 NASCAR starts

1:13:13 The challenge of finding sponsors

1:16:49 The grind behind racing and business

1:19:30 Why there is truly no off season

About the Guests

Mason Maggio & Tony Maggio

NASCAR Driver | Motorsports & Business Professionals

Mason Maggio is a NASCAR driver with experience across the Craftsman Truck Series and O'Reilly Auto Parts Series. His career has been built through persistence, sponsorship development, and opportunities with several independent teams.

Tony Maggio supports Mason’s racing career while working in yacht brokerage. Together, they manage the business, partnerships, and relationships required to keep building Mason’s career.

Keywords

PrimaryMason Maggio • Tony Maggio • NASCAR • Floridian Motorsports • NASCAR racing • motorsports • sponsorship

Secondary & Long-TailNASCAR driver • NASCAR Truck Series • NASCAR sponsorship • underfunded race teams • racing career • pit crew • motorsports business • yacht brokerage • racing partnerships

Tags

Mason Maggio, Tony Maggio, NASCAR, NASCAR Driver, Floridian Motorsports, Motorsports, NASCAR Racing, Truck Series, Racing Sponsorship, Pit Crew, Racing Business, Entrepreneurship

Disclaimer

This episode is intended for informational and educational purposes only. Any discussions regarding business, investing, entrepreneurship, or financial decisions reflect personal experiences and should not be considered financial, legal, or investment advice. Always consult qualified professionals before making financial or investment decisions.

Artist and entrepreneur Josh joins Scott to share his journey to becoming the internationally recognized “Transparent Artist.” He explains how business, relationships, and word of mouth brought his work to major names like Richard Petty, Jack Nicklaus, Guy Fieri, Bert Kreischer, and Metallica.

Josh discusses his transparent currency and commodity art, Bitcoin, philanthropy, hospitality investments, and balancing career with family. He also shares how 11 of his artworks traveled to the moon aboard the Odysseus lunar mission and the meaning behind his “Love Is in Our Genes” series, centered on humanity, unity, and love.

Key Takeaways

• Josh turned a lifelong passion for art into an international career through business experience, relationships, and word of mouth.
• His work combines currency, commodities, symbolism, and personal stories, with Bitcoin and blockchain reflecting his focus on transparency.
• His art has reached major figures in sports and entertainment, including Richard Petty, Jack Nicklaus, Guy Fieri, and Metallica.
• He created four customized pieces for Metallica and sent 11 artworks to the moon.
• Philanthropy remains central to his career.
• Building a team helped him expand internationally.
• He invests art income into hospitality and other assets.
• Family is reshaping how he approaches travel and work.
• “Love Is in Our Genes” represents humanity, unity, and love.

Chapters

00:00 Art on the moon and a billion-year legacy

00:42 Welcome to No Off Season

01:30 Josh’s NASCAR connections

04:40 Creating artwork for Richard Petty

06:30 Meeting Jack Nicklaus

09:52 Sports-inspired artwork

10:48 Transparent currency and commodity art

14:28 Turning business experience into an art career

16:51 Building a celebrity collector network

18:43 Friendship with Guy Fieri

21:34 Meeting Bert Kreischer

25:30 Investing in Bahamas hotels

27:22 Creating art for Bert Kreischer

30:09 Creating artwork for Metallica

34:00 Sending artwork to the moon

35:39 Art and philanthropy

37:00 Building a team and expanding globally

39:12 Family life and future travel

40:19 New athlete commissions

41:17 Fernando Mendoza and sports art

46:00 Challenges behind the art career

48:25 Bitcoin, transparency, and currency art

53:35 Investing and long-term wealth

54:46 A billion-year lunar legacy

56:18 “Love Is in Our Genes”

59:10 Closing thoughts

About the Guest

Josh Leidolf

Artist | Entrepreneur | Investor

Josh is an artist and entrepreneur known for transparent currency and commodity art. His work combines financial imagery, personal symbolism, and customized elements.

His network spans sports, entertainment, business, and philanthropy. His work has involved Richard Petty, Jack Nicklaus, Guy Fieri, Bert Kreischer, Metallica, and other prominent figures.

Beyond art, Josh invests in hospitality and other ventures. Eleven pieces of his artwork were also sent to the moon aboard the Odysseus lunar mission.

Keywords

Primary: Josh • Transparent Artist • Currency Art • Contemporary Art • Celebrity Art • Art Business • Metallica • Art on the Moon • Entrepreneurship • Investing

Secondary: Richard Petty • Jack Nicklaus • Guy Fieri • Bert Kreischer • NASCAR • Bitcoin • Blockchain • NASA • SpaceX • Odysseus • Moon Art • Love Is in Our Genes • Philanthropy • Hospitality • Wealth Building • Art Investing

Tags

Transparent Artist, Currency Art, Contemporary Art, Art Business, Entrepreneurship, Metallica, Richard Petty, Jack Nicklaus, Guy Fieri, Bert Kreischer, NASCAR, Bitcoin, Blockchain, NASA, SpaceX, Odysseus, Moon Art, Investing, Philanthropy, Hospitality, Wealth Building, Legacy

Disclaimer

This episode is for informational and educational purposes only. Discussions regarding business, cryptocurrency, Bitcoin, investing, art valuation, real estate, or financial decisions reflect personal experiences and opinions. They should not be considered financial, legal, tax, or investment advice. Consult qualified professionals before making financial or investment decisions.

Former NASCAR Cup Series driver Matt DiBenedetto joins Scott to share the remarkable journey that took him from a young racing fan in California to competing at NASCAR's highest level. Matt reflects on his unconventional path into professional racing, the sacrifices his family made, and the defining moments that shaped his career.

The conversation explores his rise through Joe Gibbs Racing, the financial realities of motorsports, racing for legendary teams like Wood Brothers Racing, and the challenges that ultimately shifted his focus beyond the racetrack. Matt also discusses his growing passion for real estate development, entrepreneurship, faith, investing, and building a meaningful future after full-time racing.

Whether you're a NASCAR fan, entrepreneur, investor, or someone navigating life's next chapter, this episode offers valuable lessons on perseverance, relationships, leadership, and embracing new opportunities.

Key Takeaways

• Passion often begins with unexpected moments and grows through consistent effort.
• Matt's NASCAR journey started without any family racing background.
• Success came through perseverance, hard work, and taking calculated risks.
• Financial challenges nearly ended his racing career before breakthrough opportunities arrived.
• Relationships and reputation opened many doors throughout Matt's career.
• Joe Gibbs Racing became Matt's first major opportunity after years of grassroots racing.
• The business side of NASCAR has shifted significantly toward sponsorship-driven opportunities.
• Maintaining strong relationships with former teams has created lasting opportunities beyond racing.
• Real estate investing became Matt's long-term focus while still competing professionally.
• Faith, personal growth, and surrounding yourself with the right people have shaped Matt's life beyond motorsports.

Chapters

01:10 Welcome to the No Off Season Podcast

01:35 Growing up with no racing background

04:05 Discovering NASCAR and getting his first go-kart

09:25 Racing through the outlaw kart ranks

11:20 Moving across the country to chase NASCAR

12:30 Joe Gibbs Racing opportunity

15:00 When Matt's family sold everything

16:05 The driver combine that changed everything

17:10 NASCAR during the financial crisis

19:10 Climbing through NASCAR's national series

24:05 Breaking into the NASCAR Cup Series

26:10 Racing for Wood Brothers Racing

28:20 Support from fellow NASCAR drivers

31:05 Transitioning to the Truck Series

35:05 Meeting Scott and building a friendship

37:40 From racing to real estate investing

42:50 Building Green Gates development

46:30 Faith, business, and personal growth

49:20 Future racing opportunities

54:40 Closing thoughts

About the Guest

Matt DiBenedetto

Former NASCAR Cup Series Driver | Entrepreneur | Real Estate Developer

Matt DiBenedetto is a former NASCAR Cup Series and Truck Series driver known for his perseverance, humility, and strong relationships throughout the motorsports industry. After competing for organizations including Joe Gibbs Racing, Leavine Family Racing, Wood Brothers Racing, Go Fas Racing, and Rackley WAR, Matt has expanded his focus into real estate development, business investing, and entrepreneurship. Today, he combines his competitive mindset with a passion for leadership, faith, and creating long-term opportunities beyond racing.

Keywords

Primary

Matt DiBenedetto • NASCAR • NASCAR Cup Series • Wood Brothers Racing • Joe Gibbs Racing • entrepreneurship • real estate investing • motorsports • business • faith

Secondary & Long-Tail

NASCAR career journey • professional race car driver • real estate development • investing after sports • racing sponsorships • NASCAR business • Truck Series • Xfinity Series • Joe Gibbs Racing development driver • Wood Brothers Racing history • Green Gates development • entrepreneurship after professional sports • leadership • Christian faith • business partnerships

Tags

Matt DiBenedetto, NASCAR, NASCAR Cup Series, NASCAR Podcast, Motorsports, Race Car Driver, Wood Brothers Racing, Joe Gibbs Racing, Entrepreneurship, Real Estate, Investing, Business, Leadership, Faith, Personal Development

Disclaimer

This episode is intended for informational and educational purposes only. Any discussions regarding business, investing, entrepreneurship, or financial decisions reflect personal experiences and should not be considered financial, legal, or investment advice. Always consult qualified professionals before making financial or investment decisions.