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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The New Reality of Land Investing w/ Dave Denniston

The REtipster Podcast | Land Investing & Real Estate Strategies

The New Reality of Land Investing w/ Dave Denniston