The Land Investing Business Secrets

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 people are missing right now: direct mail response rates are actually going up, not down. And he has the data to prove it.

In this episode Joe breaks down his exact process for finding where the money is moving, drilling down to the right zip codes, and sending...

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 brand new golf course. But before any of that, she had to figure out how to get sellers to actually respond.

In this episode Rhea breaks down why most land mailers are completely forgettable and what she does differently to make sellers stop, read and pick up the phone....

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 completely ignore.

Michael focuses on the bottom of the funnel, people who actually need to sell, and instead of just doing due diligence on the property, he goes deep on the seller.

They get into how he builds his lists, what he looks for before making an offer, and how he ...

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.
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Casey shares how he got into real estate, why he moved into land, and how he approaches subdividing with a focus on higher-value deals. They get into what to look for in a property, how to think about highest and best use, and why having a clear niche makes everything easier.

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 now, and since the last time he was on the show a lot has changed. He’s still flipping land, but he’s also become a licensed broker, stepped into a VP role sourcing large ranch deals, and is working on subdivisions across Colorado and Wyoming.They get into how Mason...

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 buyer’s market and how experienced operators are still closing profitable deals.Chris shares why his team shifted toward higher-value properties, how underwriting has changed in tougher markets, and what it really takes to succeed when volume is down and competition...

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 explains why boring, repeatable processes beat chasing new strategies and how consistency has helped him stay profitable in competitive markets.We also cover postcards vs letters, cold calling ROI, tightening your lists, tracking KPIs, and how Andrew structures his busin...

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 systems still outperform trends, how he vets operators, why volume and consistency matter more than ever, and what he's seeing across hundreds of land deals funded.

What you’ll learn:

• Why boring businesses win
• How Drew vets the person behind the deal
• What tr...

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 servers to subdivides to legal access headaches, Dan shares how he's navigating longer deal cycles, smarter dispo, and growing his rental portfolio with less chaos and better margins. This isn’t about hype. It’s about adapting to what works now.📌 What you...

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 break down what's still working, what has slowed down, and how each investor is adjusting to new market realities. Direct mail is still strong. Infill lots are more competitive. Creative financing is helping close deals. This is a real look at how investors ar...

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 actually expect, and how to improve deliverability with smarter targeting.They also dig into what makes a postcard actually convert, why land investors often get lazy with data hygiene, and the biggest mistakes to avoid when mailing cold. Amber shares her take on A2...

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 holidays.

The result?

Nine signed purchase agreements in January.

Kay breaks down the emotional roller coaster of running a lean solo operation, how she experiments with mail, and what’s helped her stay consistent and profitable.

What you’ll learn:

• Why K...

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 investors’ "laziness" is your biggest competitive advantage.Both run separate land businesses but teamed up to create a community-focused course aimed at helping people scale smarter. In this episode, they break down the tools, tactics, and realities of growing a...

College dorm to full-time investor. Owen Scott shares how he built a lean virtual wholesaling business with consistent deal flow and low overhead. In this episode, he breaks down his cold calling process, AI trends, direct mail strategy, and how he’s stacking lists for high-response marketing while staying efficient with a small team.What you’ll learn:• How Owen closed 6 deals in 6 months, starting from his dorm room• Why he switch...

Young entrepreneur Vikram joins Jessey to share how he hit over $150K in land profit in just 7 months.

From hiring early to dialing in high-volume texting and direct mail, Vikram breaks down his biggest wins, lessons, and the systems he’s building to scale his business the right way.

What you’ll learn:

• How Vikram hit 5 deals and $150K profit in under a year

• Why he hired a full-time texter early (and how they qualify leads)

...

Scott Morongell returns for a candid look at what's really going on in the land space. From rising marketing costs to builder relationships and tighter deal margins, Scott breaks down how he’s adjusting in a market that rewards precision, not guesswork.

This episode covers how to build trust with sellers, the risks of retrading contracts, and why working closely with buyers upfront matters more than ever. Scott also shares why h...

Clay Hepler joins Jessey for a raw, no-fluff conversation about what land investors really need to scale. From knowing when (and who) to hire, to being brutally honest about what’s actually holding you back, Clay shares what it takes to stop building yourself a business prison and start building something that works.He also breaks down how to think about marketing ROI, what kind of return you should expect from direct mail, texting...

Air Force pilot turned land investor Josh Travis joins Jessey to talk about what it really takes to move from just doing deals to actually building a business that runs on its own. They dig into direct mail that feels human, why honesty in copy works, and how the Traction framework helped Josh scale his land business while still flying jets.

What you’ll learn:

• Doing the business vs building the business (and why most people mix t...

Brandon Cobb started out flipping houses, but a few key deals shifted his focus toward land development. Now he spends his time on horizontal projects, getting lots approved, engineered, and pre-sold to national builders before a shovel ever hits the dirt. In this episode, Brandon shares how he reduces risk, manages timelines, and turns raw land into builder-ready communities.What you’ll learn:- Why pre-selling to national builders...