The Land Investing Business Secrets

Drew Haney is back on the show, and this time Jessey and Drew dig into a question every land operator faces: where should the money for your deals come from? Drew went from flipping around 300 deals himself to funding over a thousand, so he has seen what works (and what keeps people up at night) from both sides of the table.They walk through the four main options: friends and family, bank loans, hard money, and JV funding. Drew shares why the lowest rate on paper often comes with hidden costs like stress, lost time, and risk to your relationships. He also explains why boring five-figure flips are the sweet spot, how a real profit split looks on recent deals, and why he calls the funder’s cut a “labor play” instead of an expense.Along the way, Drew shares his go-to lunch hack, a surprising stat about how financial stress affects your thinking, and a story about a former Amazon employee who earned $900 an hour on a single deal.What You’ll Learn:- The four ways operators can fund land deals and the real trade-offs of each- Why the cheapest money on paper can end up costing you the most- How JV funding works and what profit splits look like on real deals- How to vet capital partners and choose the right funding for where you are in your businessConnect with Drew Haney:🌐 drewhaney.com🌐 roostercapital.land📧 [email protected]

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 scaled land business from someone who is not the founder. Cameron talks about managing closings, putting out fires, building culture across a global remote team and what it actually takes to keep a business moving forward when you are not the one writing the checks.If you are building a team or thinking about your next hire this one is worth your full attention.What you'll learn in this episode:What an operations manager actually does inside a scaled land businessHow GFP keeps core values alive across a fully remote international teamWhy culture and the right people matter more than processes aloneWhat to look for when hiring someone to run your operationsShownotes:[email protected]

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 structures multiple offers so sellers end up choosing the deal that works best for him.This is one of those episodes where you’ll want to take notes.What you’ll learn on this episode:How to build a more targeted list by focusing on motivated sellersWhy doing due diligence on the seller (not just the property) changes your marginsHow to structure multiple offers so sellers negotiate against themselvesWhere Michael is actually finding deals and buyers right now📱 Connect with Michael RobertsonTikTok: Flip4RealProsFacebook Group: Flipping for Real Estate ProfessionalsPhone: 850-377-2203

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

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

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/]

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

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

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)• Lessons from launching 8+ businesses before land• Smarter strategies with SmarterContact vs LaunchControl• Why direct mail still pulls his highest-quality leads• The exact SOPs he gives his team• Mistakes with pricing and targeting (and how he fixed them)• His next marketing experiment