The Land Investing Business Secrets

Jessey at Pebble
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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!

  1. 1d ago

    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

    29 min

  2. 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

    32 min

  3. 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

    46 min

  4. May 7

    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

    33 min

  5. Apr 23

    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 happens Connect with Rhea Campbell:Instagram: @rheacampbell_ORDFunding inquiries: reach out via Instagram

    42 min

  6. Apr 9

    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

    20 min

  7. Mar 26

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

    In this episode, Jessey talks with Casey Cavell about subdividin​g, 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 H​ow to think long term about what kind of business and life you’re actually building Shownotes: Casey@TheSubdivideGuys.com www.TheSubdivideGuys.com

    34 min

  8. Mar 12

    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

    32 min
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About

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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