ELLIOTT CALDWELL PODCAST
ON SUCCESSFUL DNAA
Conversations with founders, operators and CEOs across every industry. Elliott explores how entrepreneurs build companies, grow businesses and create lasting financial independence, drawing from his own experience building The Rise Collective and investing in short-term real estate. Topics cover entrepreneurship, leadership, business strategy, investing and the mindset it takes to win.
The goal of this channel is simple:
to understand how successful people think, how they build businesses, and how entrepreneurship creates wealth and opportunity.
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Latest Episodes
Catch up on the latest episodes for expert insights on social media, investment strategies, and financial freedom—straight from industry leaders and top influencers!
Season 2
May 29, 2026 (Ep. 26)
The Truth About Pressure, Mistakes, And Redemption: Stephen Garcia
Stephen Garcia is a Tampa native, former University of South Carolina quarterback, and one of the most recognizable players in Gamecock football history. In this episode, Stephen opens up about his journey from highly recruited high school quarterback to leading South Carolina during one of the most important eras in the program’s history.
May 22, 2026 (Ep. 25)
How To Build A Life That Actually Impresses People: Tony Salazar
Tony Salazar is the founder of Eight Limbs Creative, a full-service advertising agency he built after starting his career at 30. After spending most of his 20s immersed in Brazilian jiu-jitsu, competing, bartending, and chasing the fighter lifestyle, Tony found content creation through a sponsorship requirement that pushed him to start making videos.
May 15, 2026 (Ep. 24)
How To Build A Sales Team That Prints Money: Jonah Lewis
Jonah Lewis is the founder of Prosper, a life insurance sales organization with offices in Tampa, Chicago, Scottsdale, and South Dakota. In this episode, Jonah shares how he overcame childhood struggles, losing his mom at 14, getting kicked out at 17, and hitting rock bottom, to building a sales organization with nearly 500 agents and $4.6 million in commissions.
May 8, 2026 (Ep. 23)
Why Your Calling Is Bigger Than Your Plan: Pastor Tommy Kyllonen
Pastor Tommy “Urban D.” Kyllonen is the lead pastor of Crossover Church, as well as an author, hip-hop artist, speaker, & entrep. In this episode, Tommy shares his journey from growing up as a pastor’s kid and living a double life as a teen, to rediscovering his faith at 19 & stepping into urban ministry. Basketball leagues and hip-hop concerts helped grow Crossover Church into a community.
May 1, 2026 (Ep. 22)
How One Bad Practice Changed Everything: Jonathan Odom
Jonathan Odom shares his journey from top high school football recruit to University of Florida tight end, then pivoting into content creation, podcasting, and pursuing Olympic handball. He reflects on a memorable recruiting moment, his initial hesitation about Florida, experiences under different coaches, and how injuries ultimately pushed him to redefine his path after football.
April 24, 2026 (Ep. 21)
How to Build a Business Without Missing Your Kids Grow Up: Tony Berardo
Tony Berardo shares his journey from leaving corporate America to launching his content agency during COVID, highlighting the risks of betting on yourself in uncertain times. He explains how building his brand, Human Dad, allowed him to create a business centered not just on financial success, but on freedom, giving him more control over his time, family life, and overall lifestyle.
April 17, 2026 (Ep. 20)
How to Find Your Purpose Before Hitting Rock Bottom: Mitch Hetrick
Mitch Hetrick is an entrepreneur and founder of Change The Culture, a nonprofit focused on mobilizing young adults to create real impact in their communities. In this episode, he shares his raw and unfiltered journey from chasing clout and partying with influencers in LA to hitting rock bottom and rebuilding his life from scratch.
April 10, 2026 (Ep. 19)
Why College Is Failing Entrepreneurs Today: Simon Lerner
Simon is a real estate developer, day trader, and co-founder of Tampa Entrepreneurs, one of the fastest-growing entrepreneurial communities in Florida. In this episode, he breaks down how he went from immigrating to the United States at 13 years old to building businesses across real estate, trading, and community.
April 3, 2026 (Ep. 18)
Why Exotic Cars Are the Ultimate Cash Flow Business: Gilberto Luigi Leon
Gilberto Luigi Leon, founder of PG Lux in Florida, scaled his luxury concierge and exotic car rental business to six figures in under two years. He shares how he turned a passion for exotic cars, yachts, and private jets into a thriving cash-flow business, growing from two cars to a fleet of 20+ while riding booming demand.
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New episodes are released regularly covering entrepreneurship, short-term rental investing, and business growth strategies.
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