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.
​They also break down marketing and messaging, what’s actually getting responses right now, and why most people are doing it wrong.
And they get into the bigger picture too, not just chasing deals, but what you’re actually trying to build long term.
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If you’re looking to get into subdividing or just want to level up how you think about your land business, this one’s worth a listen.
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What you’ll learn on this episode:

• Why Casey moved from real estate into land and started focusing on bigger deals

• How to think about subdividing and finding a property’s highest and best use

• Why clear marketing and better messaging matter more than ever

• H​ow to think long term about what kind of business and life you’re actually building

Shownotes:

• [email protected]

• www.TheSubdivideGuys.com

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: [email protected] 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 [email protected]

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 strategy
Learn 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/]

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 are shifting their approach and planning for what’s next.What you’ll learn:- What worked in 2025 and what did not- How infill lot demand is changing- Why creative financing is becoming essential- Direct mail strategies that are still working- Why some investors are mailing while others have stopped- What to expect from tighter markets and shifting buyer profiles

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

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 Kay mailed during the holidays and got real results

• Her exact volume and cost breakdown for mail

• How she filters emotional decisions from her business

• Why follow-up and consistency matter more than volume

• What to track to find your own success pattern

• Kay’s experiments with envelope design and creative messaging

• How she thinks about hiring and staying lean

• What it takes to stand out when everyone’s copying templates

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 land business in 2025.What you’ll learn:• Why mailing is back and still performing• The ROI of custom mailers vs bulk volume• Cold calling and texting tips from a house-flipping background• Why most land investors don’t follow up (and how to win by doing it)• How to train VAs for market selection, data scrubbing, and pricing• Building a lean team with clear roles (Hunter’s setup)• How to find good realtors and build long-term relationships• The one thing they’d do differently if starting over today• A behind-the-scenes look at their Plot Profit Academy course