The REtipster Podcast | Land Investing & Real Estate Strategies

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 call...

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 mar...

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...

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, acq...

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 ...

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,...

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 million...

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'...

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 shoul...

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 mai...

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...

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 ...

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...

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...

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 directl...

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...

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 Grou...

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 actuall...

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 o...