He Made Every Land Mistake So You Don't Have To (Podcast Ep#166)
Joshua Kagan, author of 'The Smart Land Investor,' discusses his two-year journey in land investing, including market shifts, competition increases, and costly mistakes he made along the way. He shares his methodology for evaluating markets using three key metrics and describes a recent successful subdivision deal in Northern Arizona. The episode also touches on macroeconomic concerns affecting the land market in mid-2026.
Summary
Joshua Kagan, a real estate veteran with 15 years of experience in commercial and residential real estate, shares his land investing journey that began just two years ago after reading 'Dirt Rich' while vacationing in Europe. He started with the desert squares model and delinquent tax lists before evolving toward larger deals and simple subdivisions. Despite his relatively short tenure in land, he has published a book titled 'The Smart Land Investor: Build Wealth with the Most Overlooked Asset in Real Estate,' which reached #1 in new releases on Amazon's real estate category.
Joshua discusses notable market shifts he has observed, including increased competition in previously hot markets, with some sellers reporting receiving four or more mailers per month. He describes a growing 'bake-off' phenomenon where sellers solicit best-price offers from multiple investors simultaneously. He also notes slower sales in previously strong markets, which he tentatively attributes to broader macroeconomic concerns including a global oil shock occurring at the time of recording in mid-April 2026.
His market evaluation methodology centers on three metrics: parcel count sales within a specific acreage band over the last 6-12 months, sell-through rate (a supply-vs-demand ratio), and days on market. He emphasizes the importance of examining six-month windows rather than just annual data to account for recent trends, while remaining mindful of seasonal patterns in certain markets.
On marketing, Joshua is an active A/B tester, experimenting with price points, envelope color, envelope transparency, handwriting styles, and messaging such as being a family-owned business. One surprising finding was that color versus black-and-white envelopes made no measurable difference. He also highlights the importance of remarketing — resending mailers to the same areas every two to three months — and notes that while there are diminishing returns, deals continue to emerge from repeated mailings.
Joshua describes three primary buyer archetypes he encounters: first-generation Latino buyers motivated by the American dream of land ownership, multigenerational families wanting to create a family compound, and individuals concerned about societal instability who want tangible, government-proof assets.
He walks through a recent deal involving a 40-acre parcel in Northern Arizona, sourced through a referral from a seller of a different property. The land was inherited with no emotional connection, and rather than listing with an agent, the sellers preferred the simplicity of a direct sale. The parcel was subdivided into two 20-acre lots due to road layout constraints, and both were purchased by a returning military servicemember financing half over 10 years. The deal closed cleanly within approximately two months.
The book itself is described as highly technical, covering chain of title, zoning, physical access, market analysis, selling strategies, and ongoing ownership responsibilities. Joshua donates 100% of the book's profits to a conservation fund, explicitly rejecting any upsell or coaching program. He encourages readers who disagree with his content to contact him directly at [email protected].
About this episode
<p>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: [email protected]: The Smart Land Investor on Amazon (Kindle and paperback) https://a.co/d/0hrIKpVjWebsite: smartlandinvestors.com</p>
Key Insights
- Joshua argues that the land market has become noticeably more competitive, with sellers increasingly receiving multiple mailers per month and running 'bake-off' auctions among investors, commodifying the acquisition process in ways that weren't common when he started two years ago.
- Joshua claims that examining sell-through rate — the ratio of recent sales to active listings — is one of the most important demand indicators, and that looking at six-month windows rather than full-year data is critical because it reveals whether a market is accelerating or cooling.
- Joshua found through A/B testing that color versus black-and-white envelopes made no measurable difference in response rates, contradicting his hypothesis that color would increase visibility, and he argues that message quality matters more than visual presentation tactics.
- Joshua asserts that the most common and costly mistake new land investors make is neglecting chain of title, particularly when buying outside of a title company — he personally bought a property where title was not properly transferred and nearly purchased one that was effectively landlocked despite an assumed easement.
- Joshua describes a residential real estate recession occurring at the time of recording, characterized by the lowest home sales since 2006, caused by a lock-in effect where homeowners who borrowed at 2.5–3% cannot afford to sell into a 6%+ interest rate environment, and he argues land operates as its own distinct asset class somewhat insulated from these dynamics.
Topics
Transcript
Hey, how's it going? It's Jesse here from the Land Investing Business Secrets Podcast. I've got an awesome guest here. His name is Joshua Kagan, and Joshua has been involved in land for the last few years, but he's put together a really special book that he's going to talk a little bit about as well when it comes to land. We're going to talk about some of the realities that he's seen with land, but he's not stopping and he's finding it an awesome asset to be involved with when it comes to real estate investing. He's going to talk a little bit about his marketing, some of the things he's seeing, as well as some of the bigger…
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