The Land Investing Business Secrets

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:landunconference.comcameron@genfamland.com

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 right zip codes, and sending simple ugly postcards that get sellers calling. No fancy systems, no secret lists. Just brilliant basics done consistently.If you have been on the fence about direct mail or second guessing your market, this episode will set you straight.What you'll learn: - How to use Landwatch, Redfin and ChatGPT to find the most active markets right now- Why ugly plain text postcards outperform glossy mailers every single time- How Joe averages $750 to $1,000 in marketing cost per deal using direct mail- Why 75% of deals come from follow up and how to build a system around it0:00 Introduction1:11 Why Joe thinks the doom and gloom narrative is wrong2:55 13% response rate on postcards and what that means4:49 How to follow the money using Landwatch and Redfin6:01 Drilling down from state to county to zip code8:38 How to use ChatGPT to analyze sold data fast9:01 Building your list and filtering for motivated sellers10:17 The third notice postcard and how Joe softened it11:06 The ninja trick: answer the phone live when they call12:46 Why 75% of deals come from follow up15:49 Why uglier postcards get more calls18:05 Direct mail response rates are actually rising right now19:03 How many postcards Joe sends per week and per zip code23:49 Why postcards outperform letters every time28:02 Stop reinventing the wheel, go where the money is going32:38 Sell people what they want, not what you haveConnect with Joe McCall:YouTube: https://www.youtube.com/@Joe-McCallPodcast: search Joe McCall on any podcast platformBook: FlipDirtBook.comShownotes:Winning Postcards Framework Webinar / May 12 at 11am PST/2pm ESTSave your spot: www.pebblerei.com/winningpostcards

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: andrew@vacantlandsolutions.comJoin 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

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

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 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

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