Show Notes: https://retipster.com/281 What actually works in land investing when the market slows down? 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. 0:00 - The future of the land market 0:42 - Introducing Drew Haney and Mike Baucom 1:07 - A chaotic trip through severe weather 5:29 - What changed at Rooster Capital 7:15 - How Rooster Capital funds land deals 8:16 - When the land market slowed down 9:14 - Lessons from analyzing 850 deals 10:41 - Are value-add strategies necessary? 13:08 - The power of a boring business machine 15:22 - When marketing campaigns fail 17:10 - Will the COVID land market return? 18:13 - Could another real estate crash happen? 20:12 - Why transaction volume matters most 22:34 - Why land investors are leaving 24:52 - Staying motivated through rejection 26:32 - Expectations and entrepreneur mindset 28:55 - How I stayed consistent with REtipster 31:43 - When land investors should diversify 33:18 - Diversification vs. shiny objects 35:42 - Becoming emotionally bulletproof 37:30 - Transferable entrepreneurial skills 40:22 - The loneliness of entrepreneurship 42:14 - Learning from entrepreneurs outside land 45:17 - Most problems are dumpster fires 48:02 - Why business struggles are normal 49:08 - Social media creates false expectations 50:24 - Is AI making people more isolated? 52:07 - When AI replaces human connection 53:20 - Human connection as a business moat 56:21 - Would you rather struggle or feel bored? 58:42 - Why success can feel empty 1:00:44 - Your next goal does not need money 1:03:07 - Appreciating time, health, and freedom 1:05:49 - Rooster Capital funding criteria 1:06:24 - Stride CRM tools for land investors 1:09:42 - AI automation inside Stride CRM 1:11:22 - Upcoming land investing events 1:12:51 - Final thoughts #landinvesting #landinvestor #landflipping #realestateinvesting #realestatestrategy #landbuyingtips #landfunding #entrepreneurship #realestateportfolio #landdevelopment #businessmindset #realestatecrash #directmailmarketing #artificialintelligence #retipster *📊 Manage Land Deals Like a Pro with Stride CRM* https://go.retipster.com/stride/yt-BvtA30bc8lA *Land Portal: The Data Edge Every Land Investor Needs* https://go.retipster.com/landportal/yt-BvtA30bc8lA (REtipster Affiliate Link) *🏡 Invest in New-Construction Rental Properties 🏡* https://go.retipster.com/sdira/yt-BvtA30bc8lA (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=BvtA30bc8lA *🚀 Land Investor’s Action Plan (Free 5-Day Course!)* https://tools.retipster.com/land-investing-action-plan/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=BvtA30bc8lA *⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)* https://tools.retipster.com/survival-guide/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=BvtA30bc8lA *👉 10X Your Income from Land Investing* https://welcome.retipster.com/webinar-invite/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=BvtA30bc8lA *😀 Join the REtipster Forum!* https://forum.retipster.com/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=BvtA30bc8lA *🛠️ All My Favorite Tools and Resources 🛠️* https://retipster.com/resources/?utm_source=youtube&utm_medium=social&utm_campaign=podcast&utm_content=BvtA30bc8lA