The REtipster Podcast | Land Investing & Real Estate Strategies

Keith Cristal, entrepreneur and founder of StoreMyTruck.com, reveals the overlooked business of secure semi-truck parking. He shares how an accidental opportunity grew into a national operation, what makes land profitable or problematic, and why zoning can make or break a deal. Explore site selection, pricing, partnerships, facility design, customer acquisition, and high-tech security featuring cameras, guards, and robot dogs.

Matt Love is a real estate builder and developer specializing in investor-focused rentals and self-directed retirement accounts. He discusses designing durable build-to-rent homes, Texas market selection, financing from DSCR to non-recourse loans, cost segregation, 1031 exchanges, and the four-part wealth-building mix of cash flow, paydown, depreciation, and appreciation. He also introduces the “Freedom Five” portfolio concept and explains who turnkey investing may not suit.

Jeremiah Boucher, founder of Patriot Holdings, rebuilt after losing everything in 2008 and now controls roughly 100 commercial properties. He discusses self-storage, manufactured housing, small-bay industrial, and the resilience of diversified tenant income. They explore owner financing, private capital, scaling property management, development hurdles, FOMO, and why timing, debt, and fundamentals can matter as much as location.

Callan Faulkner, an automation specialist and founder of The Uncommon Business, explores AI’s leap from answering questions to completing real business workflows. They discuss AI employees, scheduled SEO systems, land-investing research and due diligence, knowledge bases for complex deals, data security, and turning expertise into reusable AI skills. The conversation also examines human judgment, critical thinking, and choosing worthwhile AI projects.

What happens when intelligence becomes cheap? This discussion explores AI’s uneven impact on jobs, the risks facing younger workers, and the rise of one-person companies. It also examines why trades, ownership, land, energy, infrastructure, and data centers could become more valuable, how housing markets may shift, and which human qualities could matter most in an AI-shaped future.

Neil Clements, a real estate investor, broker, developer, and entrepreneur, joins the conversation for a 2026 Q3 market update. They examine buyer-seller imbalances, Sunbelt oversupply, mortgage lock-in, fading exurban migration, rising rates, and the potential end of the 18-year cycle. They also explore tighter underwriting, stale inventory, land risk, and why manufactured homes may offer relative strength.

Logan Fullmer, a real estate investor specializing in curative title investing, reveals how he acquires properties tangled in liens, probate issues, fractured ownership, and delinquent taxes. They explore finding overlooked opportunities, shortening deal timelines, managing risk with a margin of safety, navigating family conflicts and ethics, building a disciplined team, and avoiding costly AI overengineering.

TJ Visiodei, founder of ACTS Decentralized Real Estate, develops values-based rural communities for families seeking independence, food production, and off-grid living. He discusses paying full asking price while negotiating better terms, financing multimillion-dollar ranches, selecting properties with his “Tinder rule,” and using pre-reservations instead of absorption rates. He also explores faith, resilience, governance, and what true community looks like in a crisis.

Jenn DelleFave, a creative-finance operator who sources and structures deals. Joe DelleFave, a seller-finance specialist with a multimillion-dollar portfolio. They walk through seller conversations, lead generation on Facebook, screening scripts, the four pillars of creative finance, and practical steps for wraps, subject-to deals, and follow-up systems.

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 yearsWe 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. 📊 Manage Land Deals Like a Pro with Stride CRMBuilt for Land Investors! Organize leads, track deals, and close faster🔎 Land Portal: The Data Edge Every Land Investor NeedsGet the Data You Need to Find Deals & Make Smarter Land Buys🙋🏻‍♂️ Get the REtipster Newsletter (It's FREE)!Stay updated with top real estate investing insights and strategies🚀 Land Investor’s Action Plan (Free 5-Day Course!)Solve the 5 mistakes that keep investors stuck⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)Avoid the 21 most deadly land-buying blunders👉 10X Your Income from Land InvestingLearn how to start and supercharge your land investing business...