The Land Investing Business Secrets

Hosted by Jessey at Pebble

Business Marketing

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Episodes

165

Latest episode

Jun 2026

Language

EN-US

About the show

Learn how to fully utilize simple digital marketing strategies and tools for your vacant land investing business. Learn about tested methods and avoid some of the difficult lessons so that you can fast track your own investing with minimal risk. The Land Investing Business Secrets Podcast show by Pebble, hosted by Jessey Kwong, reveals the strategies to growing, scaling, and building your sustainable land investing business all behind your laptop and smartphone form anywhere around the world!

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60 recent

June 4, 2026Episode 16531 min

Behind the Scenes of a $3M Land Business (Podcast Ep#165)

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

May 21, 2026Episode 16445 min

Why Land Deals Die on the Phone (Podcast Ep#164)

Jessey sits down with Sumner Healey, land investor, founder of LIA and co-founder of Land Insights, for a candid conversation about what it actually takes to scale a land business in today's market. Sumner pulled back from his land business for two years, kept it on maintenance mode, and still did $500,000 in profit annually. Then in 2025 he went all in and everything exploded.In this episode Sumner breaks down the sales system behind 17 acquisitions in a single month, how he cut his days on market from 120 down to 21, and the one tactic that gave him a 50% lift in close rate that most land investors are completely skipping.If you have ever lost a deal after a good conversation with a seller, this episode will tell you exactly why and what to do about it.What you'll learn in this episode:- Why walking sellers through a contract live on the phone can lift your close rate by 50%- How to pre-qualify sellers using the Three Whys framework- Why objections are actually a good sign and vague ones are the real problem- The difference between cowboys and nerds in land and how to know which one you areConnect with Sumner Healey:LIA Community: https://www.skool.com/lia/aboutLand Insights: https://www.landinsights.coEmail: sumner@landinvestor.co30 day free trial to Land Insights Pro plus $200 in credits for podcast listeners

May 7, 2026Episode 16333 min

How To Follow The Market And Mail (Podcast Ep#163)

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

April 23, 2026Episode 16241 min

Why Your Mailer Needs to Be an Interrupter (Podcast Ep#162)

Jessey sits down with Rhea Campbell, a land investor, lender, and full time entrepreneur who has built a portfolio spanning land, hotels, RV parks, restaurants and a brand new golf course. But before any of that, she had to figure out how to get sellers to actually respond.In this episode Rhea breaks down why most land mailers are completely forgettable and what she does differently to make sellers stop, read and pick up the phone. She calls it the interrupter and once you hear it you will never look at your mailer the same way again.This one is part tactical, part inspirational and packed with real talk from someone who has done it at scale.What you'll learn in this episode:Why your mailer looks like every other land investor and how to fix itWhat an interrupter is and how to use it to get more callbacksHow to shift from a shotgun mailing approach to a sniper strategyWhy getting someone on the phone is where the real magic happensConnect with Rhea Campbell:Instagram: @rheacampbell_ORDFunding inquiries: reach out via Instagram

April 9, 2026Episode 16119 min

You’re Doing Due Diligence Wrong (Here’s Why) (Podcast Ep#161)

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

March 26, 2026Episode 16034 min

When You Know You Should Be Subdividing (Podcast Ep#160)

In this episode, Jessey talks with Casey Cavell about subdividing, bigger land deals, and how to think beyond just flipping one property at a time.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.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.What you’ll learn on this episode:Why Casey moved from real estate into land and started focusing on bigger dealsHow to think about subdividing and finding a property’s highest and best useWhy clear marketing and better messaging matter more than everHow to think long term about what kind of business and life you’re actually buildingShownotes:Casey@TheSubdivideGuys.comwww.TheSubdivideGuys.com

March 12, 2026Episode 15931 min

You're looking at doing land deals the wrong way. (Podcast Ep#159)

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

February 26, 2026Episode 15833 min

Buyer’s Market: How Deals Still Sell (Podcast Ep#158)

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

February 12, 2026Episode 15726 min

How I Consistently Close Land Deals (It’s Boring) (Podcast Ep#157)

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

February 5, 2026Episode 15635 min

Boring but it works! (Podcast Ep#156)

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