The REtipster Podcast | Land Investing & Real Estate Strategies

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...

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 realiti...

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 accidental...

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 fli...

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, A...

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 sh...

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, dev...

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 inves...

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 undervalu...

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 explai...

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’v...

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...

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 creat...

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...

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 market shifts...

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 massiv...

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 ...

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, ...