The REtipster Podcast | Land Investing & Real Estate Strategies

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...

258: In this episode, I'm talking with Don Healy, the creator of the Site Facts Report, a tool I used myself, and was shocked at what it uncovered.

(Show Notes: REtipster.com/258)

If you're investing in land or planning to build, you should understand what this report is and what it can reveal. For $500, it can save you tens of thousands, and even help you avoid some deals you'd otherwise regret.

We break down who should use this report, when to order it, and how it fits into your land-buying strategy. Whether...

257: In this episode, I’m joined by Kay Walker, a former short-term rental powerhouse who built a portfolio of 100+ Airbnb units before pivoting into land investing.

(Show Notes: REtipster.com/257)

We talk about her first accidental land deal, how she made more money with fewer headaches, and why she intentionally keeps her business small. Kay reveals how her STR experience shaped her land approach, how she transformed her direct mail strategy, and why control and creativity give her the edge.

We also dig into her standout marketing tactics, why she mails ev...

256: In this episode, I sit down with Jon Jasniak. Jon built a $13M+ land empire by specializing in large-scale land deals, subdividing properties, and selling with seller financing. He even bought an entire town in West Texas (yes, really).

(Show Notes: REtipster.com/256)

We talk about how he got started, why he left a $200K engineering job, the power of Facebook ads, big wins and costly mistakes in subdivisions, and how he plans to scale to $100M. If you’re into land flipping, seller financing, or developing property at scale. This is a mu...

255: In this episode, I talk with Jeremy Brown, a land investor with a fascinating backstory. Before land, Jeremy spent 17 years in publishing, helping authors write and market books in a way that built authority and launched businesses.

(Show Notes: REtipster.com/255)

But when his son was born with severe bilateral clubfoot, everything changed. His family hit the road in a sprinter van, traveling the country for treatment, and land investing became the only thing that could keep them financially afloat while working 10–15 hours a week.

We cover Jeremy’s pivot from publ...

254: In this episode, I’m talking with Claude Diamond, a legendary sales coach, real estate investor, former attorney, and the creator of the G.U.T.S. Sales Method. In this conversation, we dive deep into how real persuasion works in real estate and why most land investors get it completely wrong.

(Show Notes: REtipster.com/254)

We covered the real psychology of sales: why most training misses the mark, how to turn prospects into the salesperson, the power of silence, emotional decision-making, qualifying fast with a 3-minute timer, and why enthusiasm + value beats ev...

253: I sat down with Drew Haney, founder of Rooster Capital, to get an inside look at what it’s really like to be a land funder. Drew has funded over 700 land deals, and in this episode, he shares his entire process, from vetting operators, managing money partners, structuring JV agreements, to protecting against losses.

(Show Notes: REtipster.com/253)

Drew also opens up about the emotional toll this business can take, why he chooses people over profits, and how he balances relationships on both sides of the deal.

Whether you're a land fl...

252: In this episode, I sat down with Brandon Parker, founder of Land AI, to talk about how AI is revolutionizing the land investing world.

(Show Notes: REtipster.com/252)

Brandon’s company has made over 10 million cold calls and helped clients close more than $20 million in land acquisitions this year alone. His AI voice assistant (Maya) can now handle full seller conversations, qualify leads, and send high-quality prospects directly into your CRM.

We dig into how this technology works, the compliance rules around AI, the tech stack powering it, and ho...

251: In this episode, I talk with Rod Khleif, an immigrant-turned-multifamily mogul who built a $50M net worth, lost it all, and came back stronger. We dive into the mindset behind success, the pitfalls of fast growth, the current real estate market, senior housing, and much more.

(Show Notes: REtipster.com/251)

Rod’s story is filled with raw honesty, powerful life lessons, and specific advice on how to thrive in real estate (even if you’re starting from zero).

📌 Want to hear what a $50M loss sounds like? You’re about to find out...

250: For the 250th episode of the REtipster Podcast, I invited five top land investors back to the show for a roundtable discussion on where the land market is right now.

(Show Notes: REtipster.com/250)

We talked about what's working, what's not, how the game has changed, and what they're doing differently to stay profitable in 2025.

You’ll hear from:
- Dave Denniston (Land UnConference)
- Justin Piche (The Ground Game Podcast)
- Mike Balcom (Stride CRM)
- Neil Clements (The Real Deal w/ Neil Clements Podcast)
...

249: In this episode, I’m talking with intuitive money coach Danielle McKinley about money stories, contentment, and the infinite banking concept (IBC), a strategy I’ve personally used for the past five years.

(Show Notes: REtipster.com/249)

We dig into why her nine-figure software exit felt strangely empty, how childhood money trauma shaped her drive for safety, and how she created a “contentment filter” to build wealth that actually supports the life you want… instead of chasing numbers that don’t make you any happier.

Then we take an honest, non-pitch look at infi...

248: In this episode, I’m talking again with civil engineer and land investor Mitch Klein about a major issue land investors often overlook: water access.

(Show Notes: REtipster.com/248)

We cover everything from private wells, rural water districts, and municipal systems to the shocking realities of contamination, costs, and whether your property can even get drinking water.

Whether you're subdividing a large parcel or building on a small rural lot, this critical info is an episode you don't want to miss.

📊 Manage Land Deals Like a Pro with Strid...