281: What actually works in land investing when the market slows down?

(Show Notes: REtipster.com/281)

In this episode, I sit down with two of my good friends: Drew Haney of Rooster Capital and Mike Baucom, my business partner at Stride CRM. We had no formal agenda, but the conversation quickly turned into a candid look at the current land market, the strategies that still work, and what separates the land investors who survive from those who quit.

Drew shares insights from analyzing approximately 850 funded land deals. One of the biggest conclusions was surprisingly simple: boring, smaller land flips often produce the strongest returns. While the industry constantly promotes new real estate strategies—subdivides, entitlements, distressed property, and other value-add plays—some of the most successful land investors continue using the same basic systems they have refined for years

We also discuss why the land market no longer feels like the COVID-era boom, whether another real estate crash could be coming, and why transaction volume may matter more than rising land prices.

Mike, Drew, and I also get honest about entrepreneur mindset, inconsistent cash flow, failed marketing campaigns, diversification, shiny object syndrome, loneliness, AI, and the importance of building real relationships with other business owners.

This conversation is about more than land flipping. It is about staying in the game, improving your systems, and learning to appreciate the difficult seasons of entrepreneurship.

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The Business Model That Survives Every Recession w/ Drew Haney and Mike Balcom

The REtipster Podcast | Land Investing & Real Estate Strategies

The Business Model That Survives Every Recession w/ Drew Haney and Mike Balcom