The New Reality of Land Investing w/ Dave Denniston

Dave Denniston is back to talk about his recent pivot into investing in curative stocks, why he stopped sending out 60,000 mailers a month, and what the land business really looks like from inside a $3 million-plus operation.

Dave is one of the most active investors I know, and in this conversation, he is surprisingly honest about what works and what doesn’t. He made over 800 cold calls just to close his first curative title deal. Along the way, he walked me through a $100,000 survey error in Maine, explained why his team pivoted from high-volume mailings to more efficient strategies, and shared why territory restrictions are killing deals that look good on paper.

We also delve into Land Unconference, which Dave founded and will be taking a break from in 2026 before bringing it back in 2027. He talks about why he started it as an introvert, what sets it apart from every other national event, and what exhausted him after running four or five of them in a single year. We also covered the problems he encountered with national title companies and his vision to grow from $3 million to $10 million in revenue.

Dave is also launching a new podcast on the REtipster network called Leadership in the countryfocused on the human 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 listening to.

Links and resources

Key takeaways

In this episode, you will be able to:

• Hear what it really takes to close your first curative title deal, including research, cold calling, and negotiations with heirs.
• Find out why Dave is moving away from large-scale mailings and what lower-overhead strategies he’s trying instead.
• Find out how Dave stress tests before making big moves so as not to overextend the business.
• Find out why the Land Unconference is on hiatus and what Dave has planned for 2027 and beyond.
• Get Dave’s honest look at the mistakes land investors are making right now and what due diligence really looks like in today’s market.

Transcript of the episode

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