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 through a $100,000 survey mistake in Maine, explained why his team moved away from high-volume mailers toward leaner strategies, and shared why land restrictions are killing deals that look good on paper.

We also dig into the Land Unconference, which Dave founded and is taking a break from in 2026 before bringing it back in 2027. He talks about why he started it as an introvert, what makes it unlike any other land event, and what burned him out after running four or five of them in a single year. We also cover the problems he ran into with national title companies and his vision for growing revenue from $3M to $ 10M.

Dave is also launching a new podcast under the REtipster network called Leadership in Land, focused on the people side of the business. If you want to know what it really takes to build and sustain something in land investing right now, this is an episode worth hearing.

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...

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 completely broken. But new opportunities are emerging for investors willing to adapt.

Katie runs a structured operation with a team of 10, focusing on flips and subdivisions. JT has been in the game for years and just rebuilt his business midyear after realizing his old playbook wasn't working anymore. Shelby moved from casting a wide net to targeting deals with $20K+ profit margins. And Arturo is running a multi-strategy business while serving as an active-duty Navy officer in Italy. Together, they share what's actually working: hyper-intentional lead management, strategic follow-up cadences powered by automation and AI, owner financing as a new leverage point, and a ruthless focus on sales skills.

You'll also hear what's broken. Blind offers, spray-and-pray marketing, and the days of easy one-touch closes are gone. We dig into team structure, KPIs, the role of data vs. human connection, and the uncomfortable reality of competing against smarter operators. If you're struggling to get deals in 2026 or just looking to stay ahead of the curve, this conversation will give you the clarity and direction you need.

If you're serious about scaling your land investing business, this conversation is packed with honest, practical insights from people doing it right now!

📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster

🔎 Land Portal: The Data Edge Every Land Investor Needs
Get the Data You Need to Find Deals & Make Smarter Land Buys

🙋🏻‍♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies

🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck

⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders

👉 10X Your Income from Land Investing
Learn how to start and supercharge your land investing business

...

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 (especially land investors) can start using AI to gain a serious edge.

If you’re trying to scale your business, free up time, or just understand where things are going, this is a conversation you don’t want to miss.

📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster

🔎 Land Portal: The Data Edge Every Land Investor Needs
Get the Data You Need to Find Deals & Make Smarter Land Buys

🙋🏻‍♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies

🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck

⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders

👉 10X Your Income from Land Investing
Learn how to start and supercharge your land investing business

...