Episode 54: Land Investing Stories: When Real Deals Get Messy (and Profitable)
Oct 9, 2025
Dive into the messy world of land investing as the hosts share real-life stories of challenges and triumphs. From firing an underperforming transaction coordinator to navigating disputes in Florida subdivisions, they highlight the importance of accountability and communication. Experience the drama of a deal nearly derailed by a seller's erratic behavior, showcasing persistence that led to profit. Learn about scaling operations, securing financing, and building strong team dynamics—all while keeping humor intact!
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volunteer_activism ADVICE
Fix Performance With KPIs Or Transition Fast
Hold underperforming staff accountable with coaching and clear KPIs before transitioning them out.
Provide generous offboarding but prepare backups and expect some to ghost during transition.
insights INSIGHT
Transaction Coordination Is A Scalability Bottleneck
Transaction coordination becomes mission-critical as volume grows and small failures cascade.
Automations and stage-triggered task lists beat manual follow-ups when scaling.
volunteer_activism ADVICE
Get Buyer Signoff Before Delivering Materials
Always confirm buyers know your development plan before doing onsite work or delivering materials.
Require written buyer permission for work on a lot after contract to avoid disputes and remediation costs.
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🎙️ Welcome to The Ground Game Podcast! 🎙️ Join hosts Clay Hepler and Justin Piche in this exciting episode of The Ground Game Podcast, your ultimate guide to mastering the art of land investing, team building, and land development. If you're interested in a raw, transparent look into what it takes to build a seven-figure land investment business, this podcast is for you! In this episode, Clay and Justin dive deep into:
Real-Time Land Investing Stories: Clay shares a recent experience with an underperforming transaction coordinator, discussing the tough decisions that come with leadership and the importance of accountability in a growing business. Justin reflects on a challenging deal in Florida, highlighting the critical need for clear communication and effective processes in land development.
Navigating Team Dynamics: The hosts discuss the complexities of managing a growing team and the challenges that arise when transaction volumes increase. They emphasize the importance of having robust systems in place to ensure nothing falls through the cracks.
Lessons Learned from the Field: Clay and Justin share valuable insights from their experiences, including the necessity of proactive problem-solving and the importance of maintaining strong relationships with buyers and realtors to avoid misunderstandings.
Persistence in Closing Deals: Clay recounts a dramatic story of a deal that almost fell through due to a seller's erratic behavior, illustrating the importance of not giving up when there’s a significant opportunity on the line. Justin adds his perspective on the emotional rollercoaster of navigating complex deals and the lessons learned along the way.
Building a Sustainable Business: The episode wraps up with a discussion on the importance of creating a business that supports your lifestyle, not the other way around, and how effective leadership and team building can drive success in the land investing space.
This episode is packed with valuable insights and actionable advice that you won't find anywhere else. So, if you're ready to take your land investing game to the next level, hit play and join us on this exciting journey!
Hosts:
Clay Hepler: A seasoned real estate entrepreneur driven to build an eight-figure land flipping and development business.
The Ground Game Podcast