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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Sean Gibbons shares the rollercoaster of his real estate career—from acquisitions to complex, sideways deals—highlighting how creativity, resilience, and relationships carry you when plans implode.
• House-hacked a duplex after reading Rich Dad, Poor Dad
• Cut his teeth in acquisitions at Wisconsin Discount Properties before going solo
• Survived a $3.5M greenhouse foreclosure that ultimately settled for $20,000
• Partnered in an indoor shooting range that shifted from acquisition to full-on startup
• Juggles multiple flips under hard-money deadlines and rehab curveballs
• Turned a stalled cabin sale into a win with a creative land contract
• Practices radical transparency with lenders when defaults loom
• Preaches flexible exit strategies and “being like water”—flowing around obstacles
• Stays locked on the destination (financial freedom) while adapting the route
Chapters
1. Introduction and Sean's Background (00:00:00)
2. The Greenhouse Disaster (00:11:20)
3. Shooting Range Business Venture (00:18:57)
4. Flipping Challenges and Hard Money Issues (00:27:08)
5. Creative Land Contract Solutions (00:36:00)
6. Communicating with Lenders and Pivoting (00:45:15)
7. Key Lessons and Final Thoughts (00:53:38)
60 episodes
