Negotiating Tactics on the Buy Side

In this episode, Mark Podolsky, Scott Bossman, and Mike Zaino dive into the art of buy-side land negotiations in this entertaining and insight-packed episode of Nite Cap. The team revives a classic framework they created years ago, breaking down the different “types” of land deals investors encounter—from the easy “Humdinger” to the tricky “Retrader” and the infamous “One Dollar Skittle.” Tune in as the crew shares real-world negotiation tactics, mindset shifts, and creative ways to structure conversations with sellers while building rapport and solving problems. Along the way, they discuss why land investing helps people on both sides of the transaction, how beginners can start small, and why consistent action can create meaningful passive income over time.