The Land Investing Business Secrets

Jessey at Pebble
  • 4.8 (43)
  • Marketing
  • Updated Monthly

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!

  1. 5d ago

    Boring Land Deals Are Winning (Podcast Ep#171)

    After being involved in nearly 1,000 land deals, Drew Haney has enough data to start seeing some pretty clear patterns.In this episode, Jessey and Kevin sit down with Drew to talk through what the numbers are actually showing inside Rooster Capital, including which deals have produced the strongest returns, which ones tend to sit the longest, and why chasing bigger spreads is not always the better move.Drew shares why the sweet spot in their data has been smaller rural and recreational properties, why six-figure infill lots have been much harder to move, and how hold time can matter just as much as the profit on paper.They also get into seasonality, why August and September have historically been tougher months to buy, the danger of drawing conclusions from tiny marketing samples, and why operators should think beyond spreadsheets when evaluating risk, capital, and opportunity.What you’ll learn on this episode: • What nearly 1,000 land deals reveal about the best-performing buy box• Why bigger deals can create more risk, longer hold times, and more mental overhead• What Drew’s data shows about seasonality and when deals tend to perform best• Why small sample sizes can lead investors to make the wrong marketing decisions Chapters00:00 Intro02:59 Drew’s path from land flipping to Rooster Capital05:17 What the data actually says after nearly 1,000 deals07:23 Why six-figure infill lots have struggled08:04 The buy box producing the best returns13:10 Why bigger deals are not always better19:14 Risk, hold time, and mental bandwidth22:49 What the data says about seasonality25:16 Why small marketing samples can mislead you28:38 What Drew looks for in funding partners30:02 Looking beyond the spreadsheet31:48 The reality of losses across nearly 1,000 dealsConnect with Drew Haney:Rooster Capital: https://roostercapital.landEmail: drew@roostercapital.landWant to learn more about Pebble and what we’re seeing across land investor direct mail? Hop on a call with us at www.pebblerei.com/demo

  2. Aug 27

    How I Handle Messy Property Titles (Podcast Ep#170)

    Jessey catches up with Karl James, a familiar face on this show and someone who was there for a lot of his early days in land. Karl retired from a decades long career a few years back and now treats land as a hobby he takes seriously, focusing on properties with messy titles, heirship issues, and delinquent taxes. In this episode, Karl walks through how he pulls leads straight from tax court filings, why he only works a handful of counties in Texas, and how he decides between self-closing a deal or going through a full title process. He also shares a real case study where he turned $5,000 into $25,000 profit in about three months, and talks candidly about the ethics of buying distressed land at a discount. Karl also opens up about bringing his son and daughter into the business, what worked, what didn't, and what he'd tell anyone thinking about mixing family and land deals. What You'll Learn: How Karl finds messy title and tax delinquent leads directly from court records Why he sometimes self-closes deals and pays back taxes only at the time of sale How he thinks through the ethics of buying distressed land for cents on the dollar Lessons learned bringing his son and daughter into the family land business

  3. Aug 6

    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 listConnect with Dave Denniston:🌐 landunconference.com🌐 leadershipinland.com📧 dave@genfamland.com

  4. Jul 16

    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:

  5. Jul 2

    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 youHow to compare data platforms and know which one actually fits your investing goalsHow to segment a market by acreage, ownership type, and land use instead of mailing blindWhy following up with warm leads outperforms chasing new ones, and how to build that into your process

  6. Jun 18

    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

  7. Jun 4

    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 operations Shownotes: landunconference.comcameron@genfamland.com

  8. May 21

    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

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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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