10/6/25

Ep. 65 | James Fiore | Real Estate Investor

In this episode of the Realistic CEO Podcast, the host sits down with seasoned entrepreneur and real estate expert James Fiore. James shares his incredible journey of owning and flipping over 300 properties and multiple businesses, including retail stores and insurance companies. Despite starting small, he managed to build a significant portfolio worth millions. He discusses his experiences in real estate, his strategies for buying and selling businesses, the importance of education and work ethic, and the value of integrity in business. This episode is packed with insights for aspiring entrepreneurs and real estate investors looking to learn from a true industry veteran.

00:00 Introduction: The Dream of Becoming a CEO

00:29 Meet James Fiore: A Journey Through Various Careers

02:01 Real Estate Success: Building Wealth Through Property

04:02 The 2008 Real Estate Bust: Opportunities and Challenges

08:52 Financing and Lending: Helping the Next Generation

17:26 Early Ventures: From Paper Routes to Nightclubs

20:11 Early Business Ventures and Successes

20:28 Building and Selling Liquor Stores

21:42 Navigating the 2008 Economic Collapse

22:07 Lessons Learned and Business Philosophy

24:44 Innovations in the Liquor Store Industry

29:28 Transition to Real Estate Investments

32:19 Advice for Aspiring Entrepreneurs

32:45 The Importance of Work Ethic

35:37 Final Thoughts and Reflections

36:57 Conclusion and Gratitude

Next

Ep. 64 | Tucker Bartone | Playa Bowls & Crumble | Franchise owner