The Brutal Truth About Consistency in Land Deals with Jessey and Kevin of Pebble » 1428

There’s a brutal truth about land investing that most people don’t want to hear. The market is not dead. The deals are not gone. The opportunity is still massive. But the people who win are the ones who refuse to quit.

I brought Jessey and Kevin from Pebble on to talk about what they’re seeing behind the scenes. They have a front-row seat to thousands of land investors, and the pattern is clear. The hobbyists are dropping out fast. The consistent operators are doubling down and quietly stacking deals. The gap is widening.

We talked about what is actually working right now. Plain postcards. Simple letters. Real follow-up. Doing the boring work over and over again. No magic lists. No secret scripts. Just consistent marketing, smart targeting, and relentless follow-up. The gold is still in the mail, and even more in the follow-up.

We also dug into Pebble, what makes it different as a property-centric CRM built specifically for land investors, and how AI is starting to play a real role in intake, comping, and automation.

If you are serious about land, this conversation will either challenge you or confirm you are on the right track.

What’s Inside: 

—Why consistency and long-term follow-up create the majority of closed deals

—How postcards are outperforming letters and why simple mail works best

—Why following the money helps you choose the right counties and zip codes

—How Pebble and AI tools are helping investors streamline intake and operations