The REtipster Podcast | Land Investing & Real Estate Strategies

289: What if real estate booms and crashes aren't random?

(Show Notes: REtipster.com/289)

In this episode, I sit down with Philip J. Anderson, author of The Secret Life of Real Estate and Banking, to unpack his research on a recurring real estate cycle that he says has played out for generations.

Philip's thesis centers on an approximately 18.6-year land cycle (roughly 14 years of rising real estate prices followed by a period of decline and recovery). His research led him to anticipate the 2008 downturn years in advance, and his book pointed to...

288: In this episode, I sit down with Joe McCall to talk about why some of the simplest real estate strategies are still the hardest to execute consistently.

(Show Notes: REtipster.com/288)

Joe has been investing in real estate, teaching, coaching, and marketing for years. We cover his experience with internet critics, the good and bad sides of the “guru” business, and an expensive coaching program that taught him an unexpected lesson about taking responsibility and doing the work.

Then we dig into land investing. Joe explains why he prefers neutral direct mail...

287: In this episode, I sit down with Keith Crystal, founder of StoreMyTruck.com, to explore a real estate strategy most investors have probably driven past without noticing: secure semi-truck parking.

(Show Notes: REtipster.com/287)

Keith got started almost by accident when an unused piece of land began generating far more calls for tractor-trailer parking than RV and boat storage. That experiment eventually grew into a truck parking operation that has included roughly 100 locations.

We dig into what makes a truck parking property work, why some locations fail, how Keith evaluates vacant...

286: Most real estate investors know how to chase deals. But what happens when you don't want to do that forever?

(Show Notes: REtipster.com/286)

In this episode, I talk with Matt Love from SDIRA Wealth, a builder and developer that constructs brand new single-family homes designed from the ground up to be rental properties. Matt explains how his team picks markets (right now, four of them across Texas), why they build with rental-friendly materials like brick exteriors and luxury vinyl plank flooring, and how buyers get direct deeded ownership instead of...

285: In this episode, I sit down with Jeremiah Boucher, founder and CEO of Patriot Holdings, to unpack how he went from losing everything in the 2008 real estate crash to building a commercial real estate portfolio of roughly 100 properties.

(Show Notes: REtipster.com/285)

Jeremiah has spent more than two decades investing in alternative real estate assets, with a major focus on self-storage, manufactured housing communities, and small bay industrial properties.

What I found especially interesting is how his strategy has evolved.

He started in single-family real estate, got wiped out...

263 (Encore): AI isn't just answering questions anymore. It's getting legitimate work done in our businesses.

(Show Notes: REtipster.com/263)

In this conversation with Callan Faulkner, we dig into what that means for land investors, real estate entrepreneurs, and business owners who are tired of being the bottleneck in their own companies.

Since we originally recorded this episode, I've implemented several of these ideas in my own business. One AI system can take a state, county, and parcel number and hand me back a due diligence report with a satellite map—something th...

In this episode, I’m digging into one of the biggest economic questions of our lifetime: what happens when intelligence becomes cheap?

(Show Notes)

AI can already write, code, research, analyze documents, answer customers, create images, automate workflows, and help one person accomplish work that once required an entire team. But what does that mean for employees, entrepreneurs, investors, parents, and the future of real estate?

The evidence so far is complicated. AI isn’t causing mass unemployment across the economy, but there are early warning signs, especially for youn...

In this 2026 Q3 market update, I’m sitting down with Neil Clements to look at what’s actually happening with buyers, sellers, home prices, migration, interest rates, land investing, and the broader real estate cycle.

(Show Notes)

One of the biggest changes is the growing imbalance between buyers and sellers. According to the data Neil discusses, many of the markets that boomed during COVID, including parts of Texas, Florida, Tennessee, Arizona, and other Sunbelt markets, have shifted dramatically toward buyers.

We also talk about why new construction is creating problems for exis...

284: In this episode of the REtipster Podcast, I'm sitting down with Logan Fullmer for our third deep dive into curative title investing, a real estate strategy built around properties most investors won't touch.

(Show Notes: REtipster.com/284)

Logan buys ownership interests in properties with broken chains of title, unresolved estates, multiple owners, liens, judgments, delinquent taxes, and other problems that can make conventional buyers walk away.

But this conversation goes well beyond explaining what curative title is.

We talk about how Logan has shortened his cash conversion...

283: Most land developers sell lots. TJ Visiodei is trying to build something much bigger.

(Show Notes: REtipster.com/283)

In this episode, I sit down with the founder and CEO of ACTS Decentralized Real Estate to understand how he acquires massive ranches, divides them into 5- to 15-acre parcels, and builds communities around land ownership, food production, off-grid utilities, family, faith, and long-term resilience.

TJ explains why his buyers are not primarily motivated by saving money. They want independence, control over essential resources, and neighbors they can count on when life gets...

282: In this episode, I sit down with Joe and Jenn DelleFave to break down one of the most powerful real estate acquisition strategies available today: seller financing.

(Show Notes: REtipster.com/282)

Most investors understand the mechanics of owner financing, but very few know how to have the conversations that actually get sellers to say "Yes."

Joe and Jenn share the exact framework they use to find motivated sellers, structure creative finance deals, negotiate terms, and acquire properties without relying on traditional bank loans.

We discuss how they...

281: What actually works in land investing when the market slows down?

(Show Notes: REtipster.com/281)

In this episode, I sit down with two of my good friends: Drew Haney of Rooster Capital and Mike Baucom, my business partner at Stride CRM. We had no formal agenda, but the conversation quickly turned into a candid look at the current land market, the strategies that still work, and what separates the land investors who survive from those who quit.

Drew shares insights from analyzing approximately 850 funded land deals. One of the biggest conclusions...

280: In this episode, I sit down with Neil Clements and Dave Dennison to discuss the evolution of the REtipster Podcast Network, how the land investing market has changed, and what strategies are still producing results today.

(Show Notes: REtipster.com/280)

We talk about on-market subdivides, seller financing, specialization, AI tools, lead generation, money velocity, and the biggest mistakes land investors are making in today's market.

If you're a land investor trying to adapt to changing conditions, this conversation offers an honest look at what's working, what's not, and where opportunities still...

279: A lot has changed since Seth Drehle-Ewan first appeared on the REtipster Podcast.

(Show Notes: REtipster.com/279)

Back then, he was a young land investor building a business with his brother, Bryce. Today, they're running a very different operation, focused on larger land deals, minor subdivisions, and a more targeted real estate strategy.

But this conversation goes far beyond land investing.

About a year ago, Seth experienced a severe case of Ramsay-Hunt syndrome that completely changed his life. We talk about what happened, how recovery has impacted his identity...

278: In this episode, I sit down with Rick Sheldon to discuss how he built a highly intentional Google Ads strategy for finding off-market land deals.

(Show Notes: REtipster.com/278)

Rick shares how he transitioned from residential wholesaling into land investing, why his first acquisition model failed, and how a simple PPC funnel transformed his business. We also break down lead qualification, conversion tracking, negative keywords, AI tools, land subdivisions, seller funnels, and scaling a land investing business through partnerships.

One of the most interesting parts of this conversation is how Rick...

277: Most land investors think success comes from pricing, data, and marketing

(Show Notes: REtipster.com/277)

But after talking with Katie Desmarais, it’s clear that sales conversations, leadership, and team development are what separate struggling operators from scalable land investing businesses.

In this episode, Katie breaks down how she transitioned out of the day-to-day grind, trained her team to operate independently, and improved land deal conversions through better communication and sales systems.

We also talk about:

277: Most land investors think success comes from pricing, data, and marketing

(Show Notes: REtipster.com/277)

But after talking with Katie Desmarais, it’s clear that sales conversations, leadership, and team development are what separate struggling operators from scalable land investing businesses.

In this episode, Katie breaks down how she transitioned out of the day-to-day grind, trained her team to operate independently, and improved land deal conversions through better communication and sales systems.

We also talk about:

276: In this episode, I sit down with Luke Harris to talk about how the land business has changed over the past decade and why some investors are still thriving while others have disappeared.

(Show Notes: REtipster.com/276)

Luke shares how he evolved from the old desert square model into larger land deals with multiple exit strategies, including timber harvesting, listings, and creative acquisitions. We also get deep into the realities of timber deals, how to evaluate wooded land, what most investors miss, and why becoming a licensed real estate agent opened up new...

276: In this episode, I sit down with Luke Harris to talk about how the land business has changed over the past decade and why some investors are still thriving while others have disappeared.

(Show Notes: REtipster.com/276)

Luke shares how he evolved from the old desert square model into larger land deals with multiple exit strategies, including timber harvesting, listings, and creative acquisitions. We also get deep into the realities of timber deals, how to evaluate wooded land, what most investors miss, and why becoming a licensed real estate agent opened up new opportunities in...

275: Most real estate investors think lead generation is the hard part. But in reality, the biggest problem is usually lead conversion.

(Show Notes: REtipster.com/275)

In this episode of the REtipster Podcast, I sit down with Nicholas Nick from Lead Mining Pros to talk about what actually happens after the leads come in. We cover cold calling, seller psychology, follow-up systems, emotional intelligence, and why so many investors accidentally kill deals before they ever have a chance to close.

Nicholas shares his exact process for handling seller objections, building trust, grading...

275: Most real estate investors think lead generation is the hard part. But in reality, the biggest problem is usually lead conversion.

(Show Notes: REtipster.com/275)

In this episode of the REtipster Podcast, I sit down with Nicholas Nick from Lead Mining Pros to discuss what actually happens after leads come in. We cover cold calling, seller psychology, follow-up systems, emotional intelligence, and why so many investors accidentally kill deals before they ever have a chance to close.

Nicholas shares his exact process for handling seller objections, building trust, grading leads, and staying persistent...

274: What happens when your side hustle becomes your only income?

(Show Notes: REtipster.com/274)

In this episode, I talk with Ann Danielson about leaving behind a decades-long teaching career overseas to go all in on land investing. Ann shares the reality of walking away from stability, navigating uncertainty, and building a land business centered on freedom rather than constant hustle.

We talk about subdivides, why straight land flips stopped working for them, how they find off-market deals without direct mail or cold calling, and what it feels like when the stakes...

The land investing market has changed dramatically over the past few years, and in this episode, Neil Clements joins me to break down what's really happening behind the scenes.

(Show Notes)

We discuss why the market has become increasingly buyer-friendly, how interest rates continue to shape land values, why margins are shrinking, and what successful investors are doing to adapt. We also dive into competition, cash flow strategies, AI tools, land pricing trends, and the habits that separate investors who survive tough markets from those who struggle.

If you're a land...

The future of land investing isn't coming; it's already here, and it's creating a bigger gap between investors every day.

(Show Notes)

The land investors pulling ahead today aren't necessarily smarter or working harder. They're using automation, AI agents, CRM workflows, and property data tools to eliminate busywork, respond faster, and make better decisions.

I'll walk through the specific capabilities your CRM and operating system should have, including AI call handling, automated follow-up systems, call summaries, direct mail tracking, e-signatures, API integrations, and agentic AI tools like Claude that can actually...

273: In this episode, I talk with Robert Howell, a mobile home investor and land developer who’s built an incredible business around affordable housing.

(Show Notes: REtipster.com/273)

Robert owns 28 mobile home parks and focuses heavily on land-home packages: buying raw land, placing manufactured homes on it, and selling them to first-time homebuyers. It’s a powerful real estate strategy that combines land investing, development, and retail sales into one scalable model.

We break down how he finds land, funds deals, avoids costly mistakes, and consistently sells finished homes in just a fe...

272: In this episode, I sat down with Ari Page, CEO of Fund & Grow, to break down how investors can access 0% business credit and use it like a line of credit to fund real estate deals.

(Show Notes: REtipster.com/272)

We talked about how this strategy actually works, how much funding you can realistically expect, and where it makes sense (and where it absolutely doesn’t). If you’re a land investor or real estate investor trying to scale without relying on traditional lenders, this is a powerful tool—but it comes with r...

271: In this episode, I sat down with Jason Brown to unpack how stock trading (especially options) can actually mirror real estate investing more than you might think.

(Show Notes: REtipster.com/271)

We talked about how he lost six figures early on, rebuilt from scratch, and eventually made a $400K trade by spotting trends before they played out. What stood out to me is how similar his approach is to land investing: finding undervalued opportunities, understanding market behavior, and acting with calculated risk.

If you’ve ever wondered how active stock trading wo...

270: In this episode, I sat down with John Bernard from Southview Timber to break down how timberland investing actually works, and why it’s one of the most overlooked real estate strategies out there.

(Show Notes: REtipster.com/270)

We talk about how timberland produces income, how deals are structured, and why this asset class has quietly created long-term wealth outside of traditional real estate and stocks. John also explains how they find deals without marketing, how timber is valued, and the multiple ways you can monetize rural land.

If you’ve ever...

269: In this episode, I sat down with Ajay Sharma about why deals feel harder to find, what’s changed since the “easy deal” days, and the one skill that can completely transform your results: sales.

(Show Notes: REtipster.com/269)

Ajay also shares how he’s pivoted into curative title work, how he’s still doing high-margin deals, and why most investors are leaving serious money on the table.

If you’ve been wondering whether land investing still works in 2026, this conversation will give you a clear answer and a path forward...

266: In this episode, I sit down with Travis King to break down what’s really going on in today’s land investing market.

(Show Notes: REtipster.com/266)

A lot of investors are doing the work, sending mail, generating leads, and talking to sellers, but they still aren't seeing results. So what’s actually broken? Is it the market, the marketing, or something deeper?

We dig into the biggest challenges land investors are facing right now, including market selection, lead quality, deal structure, and why dispositions have become the hardest part of the bu...

268: In this episode, I sit down with Courtney Fricke to talk about a side of real estate investing that most people avoid.

(Show Notes: REtipster.com/268)

We’re talking about title problems, probate issues, stacked liens, and all the complicated situations that scare investors away… and how those problems can actually create some of the best opportunities.

Courtney explains how she’s built her business around creative finance, curative title work, and deal structuring, and why she’d rather create deals than just find them.

We also get into how she...

267: In this episode, I sit down with Chris Rood to break down how he went from running quick lube shops to building a massive real estate portfolio with mobile home parks, land home packages, and smart investing strategies.

(Show Notes: REtipster.com/267)

We talk about the concept of fast, medium, and slow money, how to pivot when markets shift, and why affordable housing (especially mobile homes) is one of the biggest opportunities right now.

Chris also shares the mistakes he made, how wholesaling saved his business, and the real roadmap to...

265: Dave Denniston is back on the REtipster Podcast to talk about his pivot into curative title investing, why he stopped sending 60,000 mailers a month, and what the land business really looks like from the inside of a $3M+ operation.

(Show Notes: REtipster.com/265)

Dave is one of the most active investors I know, and in this conversation, he gets refreshingly honest about what is working and what is not. He made over 800 cold calls just to close his very first curative title deal. Along the way, he walked me...

264: A special roundtable episode where four active land investors (Katie Desmarais, JT Olmstead, Shelby Wengreen, and Arturo Paturzo) come together to talk about what's really working in the land business right now, and what's not.

(Show Notes: REtipster.com/264)

One year after launching Stride CRM, I wanted to bring together a group of investors who are actively in the trenches to have an honest conversation about the market shifts we're seeing. The truth is, the land business has changed. Some strategies that worked just a year or two ago are now...

263: I sat down with Callan Faulkner to talk about what’s actually working with AI right now and how it’s changing the way we build and run businesses.

(Show Notes: REtipster.com/263)

A year ago, AI felt like a cool tool. Today, it’s becoming the operating system behind everything. In this conversation, we break down how AI agents, automation, and custom-trained systems are replacing manual work and unlocking massive leverage.

We also talk about what’s overhyped, what still requires human judgment, and how real estate investors (especial...

262: In this episode of the REtipster Podcast, I talk with Cody Cuvillier, a land investor who built a full-time land investing business while serving as an Army officer and Apache helicopter pilot.

(Show Notes: REtipster.com/262)

Cody shares how he went from treating land investing as a side hustle to building a structured, KPI-driven company with a team that handles cold calling, texting, acquisitions, and follow-up. We talk about the moment in early 2025 when he almost quit, why his business stalled, and the realization that changed everything: he simply wasn’t generating enough le...

261: Most people think their retirement accounts can only invest in stocks, mutual funds, and index funds. But that’s not actually true.

(Show Notes: REtipster.com/261)

In this episode, I talk with Henry Yoshida, CEO of RocketDollar, about how investors can use self-directed retirement accounts to invest in alternative assets like real estate, land deals, startups, and private investments.

Henry spent a decade at Merrill Lynch, built a robo-advisor acquired by Goldman Sachs, and now helps investors unlock retirement money for deals most people assume they can’t access.

260: A few years ago, JB was running a 7-figure land investing business built almost entirely on direct mail and blind offers.

Now? Things have changed.

(Show Notes: REtipster.com/260)

In this episode, we talk honestly about what’s not working in land investing anymore, why “send more mail” isn’t the answer, and how JB pivoted from small land flips to large subdivide deals and million-dollar acquisitions.

We talk about tighter margins, rising competition, double-closes, ROAS collapse, and the uncomfortable questions most land investors are asking privately but not publicly...

259: For years, Mike Ferreira was one of the heavy hitters in the land investing space. He built a highly automated land flipping business, selling owner-financed properties with huge margins and predictable cash flow.

Until it stopped working.

(Show Notes: REtipster.com/259)

In this episode, Mike shares how market shifts, junk land, seller financing risk, and ego led to the collapse of his real estate strategy—taking him from millionaire status to deep debt.

This isn’t a highlight reel. It’s an honest conversation about what happens when s...

In this quarterly market update, Seth Williams and Neil Clements unpack what’s happening in the land investing world right now. They discuss why some land deals are booming while others are bleeding money, how market demand has shifted since 2023, and what strategies are helping investors survive and thrive in 2026.

(Show Notes: REtipster.com/Feb2026)

Neil shares real-world case studies, lessons learned the hard way, and why he's all-in on manufactured homes as the next big opportunity. If you’re struggling with deal flow, funding, or figuring out where to invest, you’ll get a...