Backseat Ballers

Real Stories from the Trenches of Business

Backseat Ballers isn’t a financial show — it’s a raw, unfiltered look into the lives of entrepreneurs who've battled setbacks, built from nothing, and kept pushing when the world told them to quit. Created for founders, grinders, and business builders in Lenexa and nationwide, this show highlights the real stories behind success: the adversity, the turning points, and the personal growth that define every entrepreneurial journey.


Each episode takes you behind the curtain of business ownership, uncovering the moments that nearly broke today’s leaders and the grit that carried them through. Guests include entrepreneurs, investors, and subject-matter experts who speak openly about failure, resilience, reinvention, and the winding path toward building something meaningful. Their insights aren’t polished or sugar-coated — they’re earned.

Man in black cowboy hat and vest, holding cigar and whiskey glass, wearing sunglasses. Dark background.
Gold text reads

Where Real Entrepreneurs Share the Wins, the Wounds, and the Work

While these conversations often touch on money, tax decisions, business exits, and wealth-building, the goal is not to give financial advice. Instead, Backseat Ballers showcases the real human stories behind those decisions: how entrepreneurs think, how they recover, and how they grow through challenge after challenge. OWLFI produces the show to elevate those stories, amplify authentic leadership, and inspire listeners with experiences you won’t find in conventional business shows.


This is content built on truth, not theory — a place where candid conversations replace clichés and where lessons come from people who’ve lived them.


The show covers topics that matter most to business owners preparing for their next chapter, including practical strategies for wealth-building and tax-efficient planning. OWLFI produces this content to build credibility and trust through authentic education rather than generic financial advice. Weekly episodes are available on Apple Podcasts, Spotify, Youtube, Facebook, Instagram, and Owlfi.com, making it easy to access insights whenever your schedule allows.


Check Out Our Latest Episode: 

Man in cowboy hat and sunglasses leaning on car.

What You’ll Hear:

This isn't your typical financial show filled with theory and textbook scenarios.


  • Real entrepreneurs sharing real adversity — the failures, pivots, and breakthroughs that shaped them
  • Raw, personal stories instead of generic business advice
  • Behind-the-scenes moments that define a founder’s mindset
  • Deep conversations about growth, resilience, and reinvention
  • Practical takeaways rooted in lived experience, not textbooks


Episodes are released weekly on Youtube, Apple Podcasts, Spotify, and Owlfi.com, making it easy to tap into powerful entrepreneurial wisdom anytime.