The Land Investing Business Secrets

Casey Cavell, land developer and principal of The Subdivide Guys who turns subdividing profits into cash-flow investments. He discusses when to pursue subdivision, finding a property’s highest and best use, and building a focused niche and marketing that actually gets responses. Short, practical conversations about scaling beyond single flips and planning the business you want long term.

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 is finding bigger deals, why direct mail is still a huge part of his business, and why he thinks a lot of investors are approaching land deals the wrong way.Mason also shares some hard lessons from buying a 17-lot portfolio, why owner financing has become such an important strategy, and what it actually takes to treat land investing like a real business.If you're sending mail, doing land deals, or trying to scale your land business, there’s a lot in this one.What you'll learn:• Why Mason says many investors are approaching land deals the wrong way• How becoming a broker opened up new deal opportunities• Why direct mail still works (when the messaging is right)• The strategy Mason uses to find large acreage deals• Why owner financing brings more buyers to the table• Lessons from buying a 17-lot portfolio• How Mason balances his own business with a larger acquisitions role• Why land investing needs to be treated like a real business

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 is up.They also dive into creative deal structuring, navigating difficult acquisitions, and why focusing on one business can be more powerful than chasing multiple opportunities.If you’re investing in land or real estate in today’s market, this episode offers practical insight on how to adapt, stay profitable, and play the long game.✅ What You’ll Learn:• Why fewer small deals are working in today’s market• How Serious Land Capital evaluates higher-value properties• What “elbow grease” really looks like in tough deals• Why cash flow and discipline matter more than ever• How to think long-term in a buyer’s market• Lessons from running and scaling multiple businesses• Market outlook for land investing in 2026Shownotes:🔗 Learn more about Chris and Serious Land Capital:https://seriousland.capital

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 business to run on 20 hours a week or less.What You’ll Learn:• Why most deals come from long-term follow-up• How Andrew runs profitable mail campaigns every month• The real ROI of postcards vs letters• How many mailers it takes to close a deal today• How to tighten your lists and target better properties• Why tracking KPIs matters more than chasing new tools• How to stay consistent in slow markets• How Andrew runs a lean team and protects his time• How to manage emotions when deals fall through• Why simple systems outperform “shiny” strategiesShownotes:Andrew's Deal funding/JV Form: https://docs.google.com/forms/d/1uDTg...Contact: andrew@vacantlandsolutions.comJoin us this coming Feb 17, 2026 at 11am PST/2pm EST for Winning Postcard Framework Webinar:www.pebblerei.com/winningpostcards

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 transaction volume looks like post-COVID• Trends that distract vs strategies that compound• Marketing channels his top operators are using• What a good operator looks like in today’s market• How masterminds can create decade-long partnerships• The “hot seat” secret of making hard decisions faster• Drew’s bullish take on off-grid tech and rural land demand🔗 Resources & Links www.drewhaney.com Bali Land Mastermind - https://balilandmastermind.lovable.app Contact Drew drew@drew-haney.com

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’ll learn:- Why Dan stopped flipping infill lots in Florida- What kind of rural land deals are working right now- Lessons from a 640-acre subdivide with seller financing- How he used a process server to unlock a 93-acre deal- What still works in cold calling and direct mail- How Dan is building long-term income with seller-financed deals- Why rental property quality matters more than projections- What personalization looks like in Dan’s direct mail strategyLearn more about the More, Better, New framework:• Blog explaining the idea of doing more, better, and then new for customer acquisition: https://creatorscience.com/more-better-new/Shownotes:[https://danhaberkost.com/] [https://www.instagram.com/danhaberkost/]

In this lively discussion, Scott Morongell, an experienced land investor, delves into the challenges of infill lots and how rising rates are affecting builders. Kay Walker shares insights on her successful in-house direct mail tactics and creative financing strategies, while Josiah Ronco discusses the complexities of rural Florida deals and the importance of project management. The panel offers a candid look at what worked in 2025, shifting buyer profiles, and predictions for 2026.

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 A2P, USPS changes, the psychology of print, and the role of branding even in off-market marketing.Whether you’re mailing for land, houses, or local services, this one cuts through the fluff with real insights from both sides of the table.What you’ll learn:- Why consistency still beats creativity in direct mail- What a good response rate actually looks like in 2026- The biggest mistake investors make when mailing lists- How USPS changes and A2P are affecting deliverability- Why your postcard design probably isn’t the problem- How branded mail works better than generic offers- What’s changed in consumer behavior since 2020

Kay Walker, a savvy vacant land investor, shares her unconventional strategy of mailing through the holidays. This bold move yielded nine signed purchase agreements in January! She discusses the importance of consistency over volume, how to filter emotional decisions, and the advantages of in-house mailing for quick A/B testing. Kay also emphasizes personalizing marketing to stand out and explains her lean operation model that amassed over $500k in net revenue, all while encouraging others to experiment and learn fast.

Hunter and Kevin share their insights on why laziness among land investors can be a competitive advantage. They discuss effective marketing strategies, highlighting the resurgence of custom mailers and the importance of follow-up. The duo delves into using VAs for tasks like market selection and building strong relationships with realtors. They also reveal metrics on mail ROI and provide a sneak peek into their community-focused course aimed at scaling land businesses smartly.