Same Game Different Turf

Confidence Within Myself: Herm Gebreab on Building Roadshow Through Persistence, Integrity, and Relationships

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This episode features Herm from Roadshow, one of the most trusted names in the high-end automotive world. From selling cars out of Cincinnati to building a globally recognized brand that works with athletes, entertainers, and top executives, Herm’s journey is built on persistence, relationships, and doing business the right way.

We get into how Roadshow was built from the ground up, what it actually takes to earn trust at the highest level, and why most people misunderstand success. This is not a story about overnight wins. It’s about years of consistency, learning on the fly, and staying in the game when most people quit.

We also break down the mindset behind building a brand that people trust, navigating NIL and young athletes with money for the first time, and why focusing on people over transactions is what creates real longevity.

Themes from this episode:

  • Building Roadshow from nothing to a global brand
  • Why persistence is the real separator in success
  • Learning business through experience, not a traditional path
  • The importance of relationships and referrals in scaling a business
  • Trust as the foundation of working with elite clients
  • Balancing risk, capital, and confidence in high-stakes deals
  • Why focusing on the client always wins long term
  • NIL, young athletes, and navigating money early
  • Authenticity and why being yourself scales further than trying to fit in
  • Turning clients into lifelong relationships, not transactions
  • The reality behind “overnight success” and the years it actually takes

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    Same Game Different TurfBy Mohamed Massaquoi