The REtipster Podcast | Land Investing & Real Estate Strategies

288: In this episode, I sit down with Joe McCall to talk about why some of the simplest real estate strategies are still the hardest to execute consistently.
(Show Notes: REtipster.com/288)
Joe has been investing in real estate, teaching, coaching, and marketing for years. We cover his experience with internet critics, the good and bad sides of the “guru” business, and an expensive coaching program that taught him an unexpected lesson about taking responsibility and doing the work.
Then we dig into land investing. Joe explains why he prefers neutral direct mail over blind offers, why he wants as many seller conversations as possible, and why he believes almost every motivated seller should receive a written offer.
One of the biggest numbers from this conversation: Joe and his business partner reviewed 58 deals from a 12-month period. Only four came from the initial seller conversation. The other 54 came from follow-up.
We also talk about how the land business has changed since 2019, why blind offers can require substantially more marketing spend, why competition may actually be easing in some markets, and how simple fundamentals like talking to sellers, making offers, and following up can still create an edge.
If you're a land investor trying to figure out which real estate strategies are still working, and which parts of the old playbook need to change.
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster
🔎 Land Portal: The Data Edge Every Land Investor Needs
Get 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
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
...

287: In this episode, I sit down with Keith Crystal, founder of StoreMyTruck.com, to explore a real estate strategy most investors have probably driven past without noticing: secure semi-truck parking.
(Show Notes: REtipster.com/287)
Keith got started almost by accident when an unused piece of land began generating far more calls for tractor-trailer parking than RV and boat storage. That experiment eventually grew into a truck parking operation that has included roughly 100 locations.
We dig into what makes a truck parking property work, why some locations fail, how Keith evaluates vacant land, and why proximity to a highway isn't always as important as you might think.
Keith also explains the numbers behind truck parking capacity, including his rule of thumb of roughly 24 tractor-trailers per acre and why property shape can have a huge impact on usable space.
We also get into one of the biggest hurdles in this real estate strategy: zoning. Keith explains why municipalities have become increasingly resistant to truck parking, what investors need to investigate before buying land, and why assuming you can simply rezone a property can be an expensive mistake.
Security is another major theme. Keith walks me through his high-security Atlanta facilities, where truckers can get live check-in, trailer locks, security personnel, cameras, and even robot dogs patrolling the property.
If you're interested in land investing, industrial outdoor storage, cash flow from land, or unconventional real estate strategies, this conversation offers a fascinating look at a niche with real demand, and plenty of operational complexity.
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster
🔎 Land Portal: The Data Edge Every Land Investor Needs
Get 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
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
...

286: Most real estate investors know how to chase deals. But what happens when you don't want to do that forever?
(Show Notes: REtipster.com/286)
In this episode, I talk with Matt Love from SDIRA Wealth, a builder and developer that constructs brand new single-family homes designed from the ground up to be rental properties. Matt explains how his team picks markets (right now, four of them across Texas), why they build with rental-friendly materials like brick exteriors and luxury vinyl plank flooring, and how buyers get direct deeded ownership instead of a share in someone else's syndication.
We also talk through the numbers: the 6 to 9 percent cap rates his team targets, what kind of cash flow a $250,000 new build actually produces, and how cash flow, principal paydown, depreciation, and appreciation stack together into a return you won't see by looking at your bank account alone.
Matt also breaks down cost segregation, 1031 exchanges, financing options from DSCR to non-recourse loans, and the Freedom Five formula, the idea that five well-chosen rentals can replace about $100,000 a year in passive income. We also spend some time on who this model is NOT for, because it definitely isn't for everyone.
If you've ever wondered how you'll eventually step back from active deals, this conversation will give you a real framework to think about!
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster
🔎 Land Portal: The Data Edge Every Land Investor Needs
Get 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
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
...

285: In this episode, I sit down with Jeremiah Boucher, founder and CEO of Patriot Holdings, to unpack how he went from losing everything in the 2008 real estate crash to building a commercial real estate portfolio of roughly 100 properties.
(Show Notes: REtipster.com/285)
Jeremiah has spent more than two decades investing in alternative real estate assets, with a major focus on self-storage, manufactured housing communities, and small bay industrial properties.
What I found especially interesting is how his strategy has evolved.
He started in single-family real estate, got wiped out in 2008, rebuilt through mobile home park investing, expanded into self-storage, and eventually found another opportunity hiding in plain sight: small bay industrial or flex industrial space.
We talk about why these seemingly different asset classes have more in common than you might think, why diversified streams of tenant income matter, and why “boring” real estate can sometimes provide a much stronger competitive edge.
Jeremiah also explains how greed and FOMO influenced his decisions before 2008, and what he looks at differently today when deciding whether an opportunity is actually worth pursuing.
We also cover owner financing, raising private capital, real estate funds, value-add investing, property management, manufactured housing development, and the challenges of scaling a real estate portfolio across multiple markets.
If you're interested in self-storage investing, mobile home parks, small-bay industrial, commercial real estate, land development, or finding a real estate strategy with sustainable cash flow, there’s a lot to unpack here.
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster
🔎 Land Portal: The Data Edge Every Land Investor Needs
Get 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
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
...

263 (Encore): AI isn't just answering questions anymore. It's getting legitimate work done in our businesses.
(Show Notes: REtipster.com/263)
In this conversation with Callan Faulkner, we dig into what that means for land investors, real estate entrepreneurs, and business owners who are tired of being the bottleneck in their own companies.
Since we originally recorded this episode, I've implemented several of these ideas in my own business. One AI system can take a state, county, and parcel number and hand me back a due diligence report with a satellite map—something that used to take me the better part of an hour to assemble manually.
Callan explains how she's using Claude, Claude Cowork, AI skills, scheduled tasks, and more than 50 AI employees inside her business. We also talk about building an AI knowledge base for complicated real estate deals, training AI on your own land investing expertise, helping VAs make better decisions, and capturing the valuable intellectual property that's already sitting inside your head.
But this isn't a conversation about handing every decision over to AI.
We also get into where humans still matter most, why critical thinking may become more valuable as AI improves, the risks of giving AI access to sensitive information, and how to decide which automations and software projects are actually worth building.
If you're a land investor wondering how AI fits into your real estate strategy, this conversation should give you a lot of practical ideas.
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, track deals, and close faster
🔎 Land Portal: The Data Edge Every Land Investor Needs
Get 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
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
...