meta_pixel
Tapesearch Logo
Log in
Real Estate Investing Mastery Podcast

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

Real Estate Investing Mastery Podcast

Joe McCall

Business, Entrepreneurship, Investing, Management

4.8551 Ratings

🗓️ 25 February 2026

⏱️ 50 minutes

🧾️ Download transcript

Summary

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

Transcript

Click on a timestamp to play from that location

0:00.0

Welcome. This is the Real Estate Investing Mastery Podcast.

0:24.7

Jesse and Kevin from Pebble. What's going on, guys? How are you?

0:26.2

Hey, hey, we're doing well.

0:28.2

Nice. Joe, good to see you again.

0:34.2

Good to see you, too. You know, I love your podcast, Jesse. I've listened to tons and tons of episodes, and it's, you always got good things on there. You're interviewing people that are doing deals. You're, you're involved with the business and the, of land investing. You've got a great software called Pebble. So I wanted, I asked if I could get you guys on to talk about a few things. I wanted to talk with you guys about where do you see the land investing market going right now? About, I don't know, six months ago, you had an interview with somebody talking about how many people are dropping out of land investing, but the people that are staying in are actually doing really well. And I'm personally seeing better numbers than I have in years in terms of response rates on our direct mail and deals and stuff like that. But I wanted to talk to you guys about what you're seeing on your side, you know, and then let's talk about Pebble. What are some of the things that Pebble do? Because, you know, I use Freedom Soft, but it's not for everybody. I get that. No software is perfect and every software has a learning curve and some people like things better than other things. So like, I wanted to talk about what you guys are doing at Pebble.

1:27.7

And, but yeah, welcome to my show. Glad you guys are here. Yeah, thanks. Thanks for having it, John. All right. So let's, let's talk about first, uh, where you see the market going right now. Like, what's going on? You guys have a lot of people that are using your software. You also talk to a lot of people that are doing land. You know, it's early

1:42.7

2026 right now. What have you guys

1:44.8

seen the last six months or so?

1:46.7

Yeah, it's early 2026 right now. What have you guys

1:44.8

seen the last six months or so? Yeah, it's, it's been a, it's been a wild ride. You know,

1:49.5

we've, we've sort of seen the whole COVID era, zero interest rates bubble, whatever you want

1:56.3

to call that. And then we've seen the reverse of interest rates going up and seeing the real estate

2:02.6

market as a whole kind of go through this wild gyration over the past few years. And land,

2:08.2

you know, is a subset of it. It's somewhat, it's somewhat insulated, but not, not 100%. So we see

2:14.6

what we're seeing, you know, is deals are harder to come by just because there are,

2:20.1

when somebody looks at their assessed values or whatever and they see that their properties are going

2:25.0

up so much, it's harder to sell, right? It's going to be a more difficult thing to get somebody

2:31.3

to sell if they've seen that their property values have gone up so much.

2:34.2

We've generally not seen any sort of recession things going on that have made the kind of

2:40.5

push people into that selling scenario. So yeah, it has been, it has been harder for, I think,

2:47.3

for a cohort of land investors who are not, maybe are not focused on certain types of deals

2:55.1

or maybe they're just sort of at a surface level. But on the flip side, we've also seen the

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Joe McCall, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Joe McCall and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.