Show Notes: https://retipster.com/264-roundtable/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c I just brought together several 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. 0:00 - Episode intro: A special roundtable on what's working in land investing 1:10 - Guest introductions: Katie, JT, Shelby, and Arturo 1:29 - Katie's business: Team of 10, flips and subdivisions 4:06 - How these businesses have changed in the past year 6:00 - JT's massive business shift: Rebuilding every 60 days 12:00 - What marketing channels are actually working right now 19:00 - What's stopped working: The end of easy deals and blind offers 30:00 - Sales skills vs. data: Which matters more? 39:00 - Owner financing as a game-changer strategy 45:00 - Team structure and where to invest first 56:00 - Advice for investors struggling in 2026 1:06:00 - Unfair advantages in the competitive land space 1:10:00 - Final thoughts and wrap-up #LandInvesting #RealEstateBusiness #LandFlipping #StrideCRM #BusinessStrategy #RealEstateMarketing #LeadGeneration #Entrepreneurship #LandBusiness #InvestingAdvice #BusinessAutomation #SalesStrategy #AIAutomation #RealEstateInvesting #podcastepisode #retipsterpodcast *📊 Manage Land Deals Like a Pro with Stride CRM* https://go.retipster.com/stride/yt-4oUTJee2g-c *Land Portal: The Data Edge Every Land Investor Needs* https://go.retipster.com/landportal/yt-4oUTJee2g-c (REtipster Affiliate Link) *🙋🏻‍♂️ Get the REtipster Newsletter (It's FREE)!* https://welcome.retipster.com/newsletter/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c *🚀 Land Investor’s Action Plan (Free 5-Day Course!)* https://welcome.retipster.com/5-day-email-course/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c *⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)* https://welcome.retipster.com/survival-guide/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c *👉 10X Your Income from Land Investing* https://welcome.retipster.com/webinar-invite/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c *😀 Join the REtipster Forum!* https://forum.retipster.com/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c *🛠️ All My Favorite Tools and Resources 🛠️* https://retipster.com/resources/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=4oUTJee2g-c