The Land Investing Business Secrets

Courtney and Skylar from Terra Data Consulting discuss how data science and strategic list segmentation are critical for land investors to reduce marketing costs and improve deal outcomes. They emphasize that most deals now come from multiple touches and follow-ups rather than single mailers, and that understanding end-goal strategies (flipping, subdividing, etc.) should drive both data filtering and marketing messaging.

Joshua Kagan, author of 'The Smart Land Investor,' discusses his two-year journey in land investing, including market shifts, competition increases, and costly mistakes he made along the way. He shares his methodology for evaluating markets using three key metrics and describes a recent successful subdivision deal in Northern Arizona. The episode also touches on macroeconomic concerns affecting the land market in mid-2026.

Jesse interviews Cameron Schultz, a 24-year-old operations manager at Granite Family Properties (GFP), a $3M land investing business owned by Dave Denniston. Cameron discusses his role managing a 13-person remote team, the company's operations, core values culture, and the challenges of running a land business without being the owner.

Sumner Healy, a seven-year land investing veteran and founder of LEAH coaching community, returns to the Pebble podcast to discuss how he rebuilt his land business after a period of coasting, achieving 17 acquisitions and $2.6M in sales value in a single month. He covers sales training methodologies, pre-qualification frameworks, and the importance of walking sellers through contracts live on the phone. He also shares updates on LEAH 2.0, his revamped coaching subscription program.