The Land Investing Business Secrets

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/]

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

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 switched from mass cold calling to hyper-targeted lists• How he uses handwritten mail to get 6–7% response rates• Why local relationships still matter• The three exit strategies he's using now• Tips for staying efficient, scaling lean, and managing your time• How regulations in South Carolina are reshaping his approach

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

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 he’s doubled down on what works instead of chasing trends, and how his approach to land has evolved in today’s shifting economy.What you’ll learn:Why the “spray and pray” approach is no longer workingHow to vet builders before locking up a dealWhat tighter inventory and rising rates mean for exit plansTips for pulling cleaner, more targeted land listsHow to keep direct mail simple and effectiveWays to hedge risk by working backward from your buyerHow to avoid retrades and protect seller relationshipsWhat’s inside Action Land Academy and who it’s forWhere to reach Scott / Learn more about Action Land Academy:🌐 https://actionlandacademy.com📸 Instagram: @scottmorongell

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, and cold calling, and why the real key to growth is focusing on your unique ability.What you’ll learn:- Why most land investors try to scale too early and end up burned out- How to hire based on calendar and constraints, not emotions- What it means to reach escape velocity in your land business- Clay’s honest take on the state of the land industry right now- How to identify your “4 percent” and focus only on what moves the needle- The truth about gross profit vs net profit and what you should be chasing- Common marketing channel returns and what numbers to aim for

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 the two up) How Josh uses story-based direct mail that gets real responsesThe Traction system that helped him build better processesHow to test your copy, budget smarter, and still stay genuineTurning 2 acres into a solid subdivide deal (and what he’d do differently)Why slowing down and focusing on people beats chasing every dealHow Josh’s Air Force training shaped how he runs his business Where to reach Josh: https://bluebird.group/

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 is a safer play than spec building- The step-by-step approval path from concept plan to grading permit- How per-pad pricing drives smarter deal analysis- The biggest mistakes new developers make with cities and engineersWhere to find Brandon Cobb:• Investor resources and ebook: https://hbgcap.net• Free course and community: https://learnlanddevelopment.comIn this episode, we cover:0:00 Introduction to Brandon and land development1:54 Transitioning from flips to development3:04 Losing a dream job and finding real estate7:10 Horizontal development explained9:58 Pre-selling lots and builder deposits11:12 How the entitlement process really works13:51 The role of the preliminary plat and city feedback15:16 Civil drawings and multi-department approvals16:28 SWPPP and grading permits16:58 Typical timelines for approvals17:44 Finding land deals and outreach strategies20:15 Building relationships with national builders21:48 Price discovery and negotiation tactics22:58 The hard parts: cities, delays, and red tape25:17 Developer vs. investor roles and cash flow realities27:58 Targeting markets by following builder activity29:17 74-lot case study with numbers and margins31:03 When a local builder clouded title and how it played out33:16 Who Brandon serves and how to connect35:20 Closing thoughtsShownotes:[https://www.linkedin.com/in/hbgcapital/](https://www.google.com/url?q=https://www.linkedin.com/in/hbgcapital/&sa=D&source=calendar&ust=1755437108684007&usg=AOvVaw1QCch1ov1G40DroLB4BBiC)

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 on market, why 60 cents on the dollar is his current offer anchor, and the simple pre-development moves that make land fly off the market.In this episode:- Zoning and residential density as the real profit drivers- A simple county test using DOM and price bands- Subdivide or develop, how Rick decides deal by deal- Mobile home packages for affordable demand

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 multiple business cycles, why he doubled down on land, and the creative strategies that keep him winning no matter where the market moves.In this episode:From hockey injuries to building wealth through real estateWhy land deals can outperform houses in profit and simplicityThe marketing channel Scott trusts most in today’s marketHow to pivot, cut losses fast, and stay creative in business

Alex Toma didn’t just shift from commercial real estate to land investing. He transformed overlooked dirt into high-value deals using solar partnerships, zoning plays, and smart automation. In this episode, Jessey sits down with Alex to break down the systems, strategies, and mindset behind his rapid success.You’ll hear how Alex filters and evaluates land for solar, uses AI to streamline due diligence, and pulls off commercial plays that boost property value before resale.In this episode:- How Alex wholesales land to solar companies without buying it- Commercial zoning strategies that 10x property value- AI tools that help analyze deals and generate property visuals- The daily 50-text method that fuels high-quality leads

Running a land business from halfway across the world might sound impossible, but Efrat proves it’s not.In this episode, Jessey sits down with Efrat, an Israeli land investor and former architect who’s flipping land in the U.S. without ever setting foot there. From navigating a completely different bureaucracy to building a supportive land investing community in Israel, Efrat shares how she turned every obstacle into an advantage.You’ll hear how she launched her business with zero experience in U.S. real estate, what finally pushed her to hire a VA, and the unique ways she tailors her ads by truly understanding her buyers — all while juggling time zones and cultural gaps.In this episode:- How Efrat built a thriving U.S. land business from Israel- Why cultural awareness makes her a better marketer- What finally convinced her to hire help (and how it changed her business)- The power of learning by doing and mentoring others along the way

What if the best sales training didn’t come from a textbook — but from a Miami bar?In this episode, Jessey chats with Jen Way, a real estate investor turned sales coach, who’s helped countless land investors close more deals by simply learning how to talk again. From her days behind the bar to flipping houses and buying land, Jen shares how conversation — not persuasion — is the foundation of great sales.You’ll hear Jen’s journey from marine science grad to multi-faceted investor, and why she believes anyone can become good at sales with the right mindset and structure. No gimmicks. No pressure tactics. Just real rapport, real listening, and a whole lot of curiosity.In this episode:How Jen went from wholesaling houses to coaching investors on salesWhy “likability” isn’t about personality — and what to lean on insteadJen’s repeat-relate-resume method to unlock better conversationsHow to front-load objections before they kill your deal

Some investors go big to win big — but Hunter built a thriving land business by doing the opposite.In this episode, Jessey sits down with Hunter to break down how he flips smaller, rural parcels at scale for outsized returns. You’ll hear how a college side hustle turned into a full-time business, why he avoids blind offers, and how he’s built passive income by offering seller financing to buyers who weren’t even looking.With just two VAs and a tight system, Hunter is moving 100+ deals a year — using creative direct mail, a smooth checkout experience, and 27 marketing channels to keep his pipeline full.In this episode:How flipping low-cost rural parcels led to 100+ deals a yearCreative seller financing that converts casual browsers into buyersDirect mail strategies that stand out — without using blind offers

What if the land you buy could pay you monthly without flipping it, developing it, or lifting a finger?In this episode, Matt Sands breaks down the world of mineral rights, a whole side of land investing most people overlook. With over 26 years in oil and gas and now hosting The Mineral Rights Podcast, Matt shares how land investors can unlock passive income from what’s under the ground.We’re talking royalties, pooling, deal structures, and how to find areas where mineral rights actually cash flow.In this episode:What mineral rights are and how they really workHow royalties are calculated and what those checks can look likeWhere the best states are for mineral investingWhat to watch out for before making your first mineral play

What if your land offers weren’t just educated guesses—but backed by data, strategy, and AI?In this episode, Chris and Aaron share the pricing method behind their $500K+ land business. From using county-assessed values to anchor offers, to building consistency through neutral letter campaigns, their approach blends personal touch with data-driven systems.They also reveal how they use AI-powered tools to compare comps, assess markets, and avoid the spray-and-pray mailing method—resulting in smarter offers and higher ROI.In this episode:- Combine AI with comps for better offer accuracy- Target the right markets without guessing- Structure mail and follow-up for consistent deals- Build a lean land business without cold callingShownotes:[www.ailanddealz.com](https://www.google.com/url?q=http://www.ailanddealz.com&sa=D&source=calendar&ust=1745090899026499&usg=AOvVaw1KWDrpy-g-KQeCkjllPOFN)[info@ailanddealz.com](mailto:info@ailanddealz.com)

Kay Walker didn’t scale with a massive team or high-volume cold calling. Instead, she built a lean, local operation that closes high-value land deals using direct mail, in-house systems, and trusted people she already knows.In this episode, Kay shares how she keeps her operations tight but effective, relying on local relationships across NC, SC, and GA, and a close-knit team that understands her process.From managing mail campaigns in-house to coordinating with realtors, soil testers, and contractors she’s worked with for years, Kay shows that smaller teams can move fast, stay personal, and win big.IN THIS EPISODE:Why local relationships make the differenceHow a smaller team keeps things efficient and profitableRunning direct mail campaigns in-houseLessons from scaling a busy short-term rental businessWhat developers really want when buying landHow to build a high-trust, low-chaos team