The Land Investing Business Secrets

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's background in data science led her into land investing years ago, and now she and Skyler help other investors clean up their lists, choose smarter markets, and stop wasting money on properties that were never going to work. They...

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 discovered land investing just two years ago and has not looked back since. Joshua recently published The Smart Land Investor, an Amazon number one new release in real estate, and every lesson in it came from a mistake he made himself. In...

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, two years into his role, and responsible for keeping a 14 person remote team running smoothly while Dave splits his time between land and his financial planning business. This episode is a rare look inside the day to day of a scal...

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 business in today's market. Sumner pulled back from his land business for two years, kept it on maintenance mode, and still did $500,000 in profit annually. Then in 2025 he went all in and everything exploded. In this episode...

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...

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 selle...

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 fo...

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 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 nic...

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...

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...

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,...

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 pe...

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 ada...

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...

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 maili...

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...

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,...

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, starti...

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 earl...

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 mor...

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 sho...

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 bu...

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:-...

What if the fastest way to bigger land profits was learning density, not swinging hammers? In this episode, Jessey sits down with Ricardo “Revenue Rick” Giles to unpack how he finds value in the dirt, not the structure. From zoning and residential density to when he chops a parcel and when he develops, Rick shares a clear playbook you can use in any market. You’ll hear how he vets counties by days...

What happens when a pro hockey player walks away from the rink and reinvents himself in real estate? In this episode, Jessey talks with Scott Morongell, who went from chasing pucks to chasing deals. After concussions cut his hockey career short, Scott dove headfirst into sales, multifamily syndications, and eventually found his stride in land investing. You’ll hear how Scott pivoted through multip...