The Old Way of Land Investing Doesn't Work Anymore
Dave Denniston discusses how the land investing business has fundamentally changed since 2021-2022, requiring investors to shift from volume-based marketing to specialized, high-quality deal sourcing. He shares his journey from sending 50-60k mailers monthly with declining returns to focusing on subdivides and messy title deals in select markets, emphasizing the importance of continuous learning, team development, and adapting to market conditions.
Summary
Dave Denniston, a multi-stream entrepreneur with experience in financial planning, hard money lending, and land investing, joins Ron to discuss the dramatic evolution of the land investment industry. Denniston started in land in 2017-2018 using cheap desert property strategies in Arizona and similar markets, buying 5-acre parcels for $800-900 and selling them through direct mail at 0.2 response rates. This strategy worked exceptionally well through 2021-2022 when any land product sold easily, often above asking price due to post-COVID demand and low interest rates. However, by 2023-2024, Denniston discovered that his previously successful playbook had become ineffective. Despite sending approximately 50-60,000 mailers per month over eight months in 2024, his cost per acquisition rose to $6,000 (approximately 10,000 mailers), while selling prices collapsed from expected $80,000 to $50-70,000 for properties purchased at $40,000, dramatically reducing margins. This forced him to cut marketing entirely in October 2024 and fundamentally restructure his business. Denniston attributes the market shift to multiple macroeconomic factors: rising interest rates cooling home construction demand, reduced government stimulus, increased inflation tightening consumer budgets, and the maturation of popular markets like Texas and Florida. He successfully pivoted to focusing on two primary deal types: minor subdivides and messy title properties. His current strategy involves dramatically reduced marketing spend (2,500-3,000 mailers monthly instead of 50-60k), specializing in five states instead of thirty, and building deeper relationships with county officials, surveyors, and realtors. By focusing on higher-value properties ($250,000+) with better margins through careful product selection, he aims to achieve $6-20 million in revenue while maintaining healthy net profits. Denniston emphasizes the importance of learning through action rather than endless education without execution, and stresses that team building requires hands-on oversight, clear systems via SOPs, and regular feedback mechanisms. He discusses using AI tools to automate administrative tasks and develop business systems, investing in specialized coaching (currently for messy title deals), and creating career paths for team members to enable eventual business independence. Denniston notes that product selection is now critical—properties with mobile home restrictions, HOA limitations, or covenants perform poorly, while mobile-friendly land with fewer restrictions moves faster. He advises new investors to pick one channel and one market, commit to meaningful volume (20-30,000 mailers minimum, not 2,000), and analyze their own business data rather than relying solely on tools like Land Portal. Finally, he predicts that relationship-building and geographic specialization will increasingly define success, with investors developing deep expertise in 2-3 counties through years of networking and deal experience.
About this episode
<p><strong>Want to quit your job and build a real land investing business?</strong></p><p><strong>👉</strong><a href="https://landportal.com/subscriptions?a_aid=LandInvestingOnline&a_bid=9e9b000b"><strong>Land Portal</strong></a> gives you access to the fastest-growing land software <em>plus</em> <a href="https://landportal.com/subscriptions?a_aid=LandInvestingOnline&a_bid=9e9b000b"><strong>Land Portal University</strong></a>, where we walk you step-by-step through getting your first land deal.</p><p>🎯 Looking for <strong>1-on-1 Land Flipping or Subdividing coaching</strong>? Schedule a <a href="https://landinvestingonline.com/pages/consultation"><strong>FREE strategy call</strong></a> here.</p><p>================================</p><p>In this episode, Ron sits down with Dave Denniston to break down how he’s scaling his land investing business in 2026. They discuss shifting from high-volume marketing to specialized deals, the power of focusing on the right markets, using tools to grow your business, and knowing when it’s time to pivot. </p><p><br /></p><p>If you’re looking to build a more focused, efficient, and profitable land investing business, this episode is packed with practical strategies you can put into action.</p><p><br /></p><p>🌐Connect with Dave Denniston: </p><ul><li><p><a href="https://www.skool.com/leadershipinland"><u>Leadership in Land</u></a></p></li><li><p><a href="https://www.landunconference.com/august2027"><u>Land Unconference Website</u></a></p></li><li><p><a href="https://www.facebook.com/people/Dave-Denniston/pfbid02KBi9V2wbb6Yt6g8xS2VT9UrfW3wicF7dR3TBKN2NR9hJhEksvQE2Y3sHmxDSV3Eml/"><u>Dave’s Facebook</u></a></p><p><br /></p></li></ul><p>================================</p><p>SOCIAL</p><p><strong>Ron's Instagram </strong>📸:<a href="https://www.instagram.com/ronapke/"><u> </u><strong>https://www.instagram.com/ronapke/</strong><u></u></a></p><p><strong>Dan's Instagram </strong>📸:<a href="https://www.instagram.com/danielapke/?hl=en"><u> </u><strong>https://www.instagram.com/danielapke/</strong><u></u></a></p><p><a href="https://www.instagram.com/danielapke/?hl=en"><u></u></a></p><p>================================</p><p><strong>TIMESTAMPS:</strong></p><p><strong>00:00</strong> – Intro</p><p><strong>00:38</strong> – Land journey & learning</p><p><strong>06:10</strong> – Providing value</p><p><strong>09:49</strong> – Specialized focus in land</p><p><strong>15:38</strong> – Scaling marketing</p><p><strong>25:18</strong> – Pick a niche & pivot</p><p><strong>30:45</strong> – Dave's 2026 strategy</p><p><strong>33:27</strong> – Building & leading a land team</p><p><strong>42:31</strong> – The future of land investing</p><p><strong>45:12</strong> – AI & demand</p><p><strong>51:09</strong> – Outro</p>
Key Insights
- Denniston argues that the dramatic market shift between 2021-2022 and 2023-2024 was caused by interconnected factors: rising interest rates reduced home construction demand, government stimulus ended, inflation tightened consumer spending, and lumber prices fell due to reduced building activity.
- Despite sending 50-60,000 mailers monthly in 2024 with 0.5-0.6% response rates, Denniston's cost per acquisition reached $6,000, which consumed most profit margins when properties sold at $50-70,000 instead of anticipated $80,000, demonstrating that volume alone no longer compensates for market conditions.
- Denniston claims that the old strategy of sending cheap mailers to desert properties nationwide no longer works because the market conditions that enabled easy sales (low interest rates, government stimulus, migration trends) have fundamentally reversed.
- Denniston observed that properties with restrictions—HOA requirements, mobile home prohibitions, or covenants—now move slowly and struggle to sell, while mobile-friendly land with fewer restrictions sells relatively quickly, indicating buyers have become more selective.
- Denniston argues that learning without action is ineffective; he emphasizes 'learning with action' meaning investors should test marketing channels with meaningful volume (20-30,000 mailers minimum) and adjust based on real data rather than waiting for perfect conditions.
- Denniston states that team building requires hands-on quality control and cannot be rushed; leaders must review work, catch mistakes, and gradually build trust before truly delegating, which is a 'messy process' that demands constant attention.
- Denniston asserts that geographic specialization and deep relationships are becoming the primary competitive advantage, with successful investors developing expertise in 2-3 counties through years of networking with county officials, surveyors, and realtors.
- Denniston claims that the proliferation of marketing channels (mail, texting, PPC, cold calling, TikTok) simultaneously creates both opportunity and confusion, requiring investors to pick one channel initially and avoid analysis paralysis from too many options.
Topics
Transcript
All right, everybody, welcome back to the Real Estate Investing Podcast. Super excited to have Dave Denniston with me today. Dave, welcome to the show. Ron, glad to be here, man. Thanks so much for having me. I was looking at our guests previously. I'm like, there's no way we haven't had Dave on. I know Daniel's had meetings with Dave. I've talked to Dave before. Dave's a big name in the industry. It's crazy we haven't had you on the podcast yet, but super excited for this conversation today. Well, I appreciate the compliments. I always feel like I'm just kind of getting started. So I guess always learning and relearning, as I'm sure we're going to be talking…
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