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I just brought together four active land investors for a candid roundtable conversation about what's really happening in the land business right now. If you've been struggling to get deals or feeling like the market has gotten harder, this episode is for you.

Katie Desmarais, JT Olmstead, Shelby Wengreen, and Arturo Paturzo are all running real land operations and using Stride CRM to manage their businesses. They're actively in the trenches, testing new strategies, and adjusting on the fly. The goal here isn't to create a highlight reel; it's to have an honest conversation about what's working, what's not, and what it takes to stay competitive.

We talk about the massive shift from “spray and pray” marketing to intentional, targeted strategies. You'll hear how these investors handle lead management and follow-up, why automation and AI are now table stakes, and what deal types are actually making money right now. We also dig into team structure, sales skills vs. data, and the uncomfortable truth about the cost of entry into this business in 2026.

If you're serious about building a land investing business or scaling the one you have, the insights in this conversation will save you months of trial and error. You'll learn what to focus on, what to ignore, and how to make decisions based on facts instead of feelings.

Links and Resources

Key Takeaways

In this episode, you will:

  • Hear why strategies that were working two years ago are producing very different results today
  • Discover how active investors are structuring their teams and deal types to stay competitive in a tighter market
  • Learn how to identify when something in your business has actually broken and how to avoid changing too many variables at once
  • Find out what each investor considers their unfair advantage and how they're using it to stay ahead
  • Understand what realistic expectations look like for anyone entering or scaling in the land space right now

Episode Transcript

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