The Land Investing Business Secrets

How I Handle Messy Property Titles (Podcast Ep#170)

Jessey catches up with Karl James, a familiar face on this show and someone who was there for a lot of his early days in land. Karl retired from a decades long career a f

Why We're Falling Back On Mailing for Land (Podcast Ep#169)

essey catches up with Dave Denniston, a returning guest last on the show back at episode 96, two years and a lot of changes ago. Dave has shifted his business toward subd

Winning Strategy to LandLocked Properties (Podcast Ep#168)

Jessey sits down with Travis King, a familiar face on this show and the host of The King Show, to talk about a strategy most land investors skip entirely: landlocked prop

The Data Mistakes Costing You Land Deals (Podcast Ep#167)

Jessey sits down with Courtney and Skyler, the team behind Terra Data Consulting, to break down what most land investors get wrong when it comes to their data. Courtney

He Made Every Land Mistake So You Don't Have To (Podcast Ep#166)

Jessey sits down with Joshua Kagan, a real estate veteran with 15 years of experience across fix and flips, commercial real estate and single family rentals who discovere

Behind the Scenes of a $3M Land Business (Podcast Ep#165)

Jessey sits down with Cameron Schulz, operations manager at Generation Family Properties, the land investing business founded by Dave Denniston. Cameron is 24 years old,

Why Land Deals Die on the Phone (Podcast Ep#164)

Jessey sits down with Sumner Healey, land investor, founder of LIA and co-founder of Land Insights, for a candid conversation about what it actually takes to scale a land

How To Follow The Market And Mail (Podcast Ep#163)

Jessey sits down with Joe McCall, a real estate investor who has been in the game since 2006 across houses, wholesaling and now land. Joe is seeing something a lot of p

Why Your Mailer Needs to Be an Interrupter (Podcast Ep#162)

Jessey sits down with Rhea Campbell, a land investor, lender, and full time entrepreneur who has built a portfolio spanning land, hotels, RV parks, restaurants and a bran

You’re Doing Due Diligence Wrong (Here’s Why) (Podcast Ep#161)

In this episode, Jessey sits down with Michael Robertson to break down how he’s getting more deals by going deeper on his list and doing something most investors complete

When You Know You Should Be Subdividing (Podcast Ep#160)

In this episode, Jessey talks with Casey Cavell about subdividin​g, bigger land deals, and how to think beyond just flipping one property at a time. ​ Casey shares how he

You're looking at doing land deals the wrong way. (Podcast Ep#159)

In this episode, Jessey sits down with Mason McDonald to talk about what’s actually working right now in the land business.Mason’s been deep in the land world for years n

Buyer’s Market: How Deals Still Sell (Podcast Ep#158)

n this episode of the Land Investing Business Secrets podcast, Jessey sits down with Chris Duff of Serious Land Capital to break down what’s really happening in today’s b

How I Consistently Close Land Deals (It’s Boring) (Podcast Ep#157)

In this episode, Andrew Baughan shares how he consistently closes land deals by focusing on follow-up, targeted mailing, and simple systems that work long-term. He explai

Boring but it works! (Podcast Ep#156)

Jessey sits down with investor and funder Drew Haney to talk about what’s really working in 2026—hint: it’s not the newest shiny strategy. Drew shares why boring system

Why I’m Done Flipping Infill Lots (Podcast Ep#155)

Dan Haberkost returns for a year-later update with Jessey to break down why he's pulling back from infill lots and going all in on large rural acreage deals. From process

It worked in 2025... Will it in 2026? (Podcast Ep#154)

What actually worked in 2025, and what is starting to fade in 2026?In this year-end panel, Jessey and Kevin sit down with Kay Walker, Josiah Ronco, and Scott Morongell to

Is mailing really working in 2026? (Podcast Ep#153)

Direct mail isn’t dead. It just needs better execution. Amber Freeman from PostcardMania joins Jessey to talk real numbers behind mail campaigns, what response rates to a

I mailed through the holidays - and got back 9 signed PA's in January (Podcast Ep# 152)

In this episode, Kay Walker returns to share what’s been working in her land business, including why she ignored conventional wisdom and mailed straight through the holid

Land Investors are Lazy (and that's good thing for you) (Podcast Ep#151)

Hunter and Kevin join Jessey to talk about what’s really working right now in land—from cold calling to custom mailers, market selection, follow-up, and why land investor