The Land Investing Business Secrets

Hosted by Jessey at Pebble

Business Marketing

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Episodes

169

Latest episode

Aug 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

August 6, 2026Episode 16932 min

Why We're Falling Back On Mailing for Land (Podcast Ep#169)

essey catches up with Dave Denniston, a returning guest last on the show back at episode 96, two years and a lot of changes ago. Dave has shifted his business toward subdivides and messy title deals, but along the way his inventory ballooned to over 160 properties and he had to shut off all marketing just to sell through it.In this episode, Dave breaks down what happened, why he's pulling back to a smaller, more focused footprint, and what he learned testing PPC through an agency for a year. He also shares why, after exploring on market subdivides and cold calling, he's returning to mail with a smaller, more targeted list and a willingness to spend more per piece to get a response.If you've ever wondered whether PPC is worth it, or why mail keeps pulling investors back no matter how many new channels show up, this conversation lays out the real tradeoffs.What You'll Learn:- Why Dave shut off all marketing after his inventory grew past 160 properties- What PPC costs and what it's actually good and bad for in land investing- Why staying geographically and product focused is changing how Dave operates- Why Dave is going back to mail with a smaller, more targeted list Connect with Dave Denniston:🌐 landunconference.com🌐 leadershipinland.com📧 dave@genfamland.com

July 16, 2026Episode 16838 min

Winning Strategy to LandLocked Properties (Podcast Ep#168)

Jessey sits down with Travis King, a familiar face on this show and the host of The King Show, to talk about a strategy most land investors skip entirely: landlocked properties. While everyone else scrubs these parcels out of their lists, Travis has built a whole playbook around targeting them, and the discounts sellers are willing to give can be massive.Travis breaks down what actually makes a property landlocked, why it scares off traditional buyers, and how that fear creates opportunity for investors willing to do the work. He walks through his exact process for negotiating easement access with neighbors, structuring low offers sellers already expect, and even stacking in a subdivide to multiply returns.If you've ever passed on a deal because it lacked road access, this episode might change your mind. Travis shares real numbers from his own deals, including one property he picked up for around 5,000 dollars and resold for 50,000.What You'll Learn:- What actually makes a property landlocked and why title companies won't insure it- How to negotiate easement access with neighbors, including what to offer and what to say- Where to find landlocked properties and how to build a targeted list- How to price and structure discounted offers without scaring sellers off Connect with Travis King:📖 Free Book: travisking.com 📚 Landlocked Masterclass: thelandinvestorsplaybook.com 🔗 mylandportal.com 🎧 Book also available on Amazon, Audible, and Spotify:

July 2, 2026Episode 16630 min

The Data Mistakes Costing You Land Deals (Podcast Ep#167)

Jessey sits down with Courtney and Skyler, the team behind Terra Data Consulting, to break down what most land investors get wrong when it comes to their data. Courtney's background in data science led her into land investing years ago, and now she and Skyler help other investors clean up their lists, choose smarter markets, and stop wasting money on properties that were never going to work. They dig into the platforms investors rely on, why AI generated data still has gaps, and why trusting a list without double checking it can quietly kill your margins. The conversation also covers how to segment a market instead of mailing blind, and why the real money is often in following up with leads you already have rather than chasing new ones. If you have ever wondered whether your data provider is actually giving you accurate information, or you are unsure how to narrow down a market before you spend on mail, this episode lays out a clear way to think about it. What you'll learn on this episode: Why trusting your data 100% can lead to costly mistakes, and how to catch errors before they cost you How to compare data platforms and know which one actually fits your investing goals How to segment a market by acreage, ownership type, and land use instead of mailing blind Why following up with warm leads outperforms chasing new ones, and how to build that into your process

June 18, 2026Episode 16628 min

He Made Every Land Mistake So You Don't Have To (Podcast Ep#166)

Jessey sits down with Joshua Kagan, a real estate veteran with 15 years of experience across fix and flips, commercial real estate and single family rentals who discovered land investing just two years ago and has not looked back since. Joshua recently published The Smart Land Investor, an Amazon number one new release in real estate, and every lesson in it came from a mistake he made himself.In this episode Joshua gets candid about what is actually changing in land right now, from increased competition and seller bake-offs to markets that were hot a year ago and are now cooling down. He also walks through how he picks markets, how he A-B tests his mailers and a recent Arizona subdivision deal that came together cleanly from start to finish.If you are newer to land or just want to tighten up your due diligence, this episode is a practical and honest look at what it takes to do this right.What you'll learn in this episode:- The three metrics Joshua uses to find active markets: parcel count, sell through rate and days on market- Why title, zoning and access are the most common and costly mistakes new land investors make- How to A-B test your mailers without muddying your data- Why Joshua gives 100% of his book profits to a conservation fund and what drove that decisionTimestamps:0:00 Introduction0:57 Joshua's background and how he discovered land investing2:01 What has changed in land over the last two years3:40 How he adjusts when competition increases in a market5:09 Remarketing and mailing the same areas every two to three months9:12 The three metrics he looks at before entering any market11:15 What Joshua A-B tests in his mailers and what surprised him13:11 What rising interest rates mean for land investors right now15:20 His three buyer archetypes and what drives them to buy17:20 What a smart land investor actually looks like19:42 The biggest mistakes new land investors make on title and zoning22:48 The Arizona 40 acre subdivision deal breakdown25:53 The Smart Land Investor book and what is inside it27:19 How to connect with Joshua and where to find the bookConnect with Joshua Kagan:Email: joshua@smartlandinvestors.comBook: The Smart Land Investor on Amazon (Kindle and paperback) https://a.co/d/0hrIKpVjWebsite: smartlandinvestors.com

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 business How GFP keeps core values alive across a fully remote international team Why culture and the right people matter more than processes alone What to look for when hiring someone to run your operations Shownotes: landunconference.com cameron@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 are Connect with Sumner Healey: LIA Community: https://www.skool.com/lia/about Land Insights: https://www.landinsights.co Email: sumner@landinvestor.co 30 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 it 0:00 Introduction 1:11 Why Joe thinks the doom and gloom narrative is wrong 2:55 13% response rate on postcards and what that means 4:49 How to follow the money using Landwatch and Redfin 6:01 Drilling down from state to county to zip code 8:38 How to use ChatGPT to analyze sold data fast 9:01 Building your list and filtering for motivated sellers 10:17 The third notice postcard and how Joe softened it 11:06 The ninja trick: answer the phone live when they call 12:46 Why 75% of deals come from follow up 15:49 Why uglier postcards get more calls 18:05 Direct mail response rates are actually rising right now 19:03 How many postcards Joe sends per week and per zip code 23:49 Why postcards outperform letters every time 28:02 Stop reinventing the wheel, go where the money is going 32:38 Sell people what they want, not what you have Connect with Joe McCall: YouTube: https://www.youtube.com/@Joe-McCall Podcast: search Joe McCall on any podcast platform Book: FlipDirtBook.com Shownotes: Winning Postcards Framework Webinar / May 12 at 11am PST/2pm EST Save 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 it What an interrupter is and how to use it to get more callbacks How to shift from a shotgun mailing approach to a sniper strategy Why getting someone on the phone is where the real magic happens Connect 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 sellers Why doing due diligence on the seller (not just the property) changes your margins How to structure multiple offers so sellers negotiate against themselves Where Michael is actually finding deals and buyers right now 📱 Connect with Michael Robertson TikTok: Flip4RealPros Facebook Group: Flipping for Real Estate Professionals Phone: 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 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 How to think long term about what kind of business and life you’re actually building Shownotes: Casey@TheSubdivideGuys.com www.TheSubdivideGuys.com