Leadership in Land

Episode 11: Ryan Love talk about his journey from studying mechanical engineering at Cal Poly to building a growing land investing business with a full team. Ryan shares how he got started in land flipping, the tough early months of building momentum, and the leadership lessons he’s learned while scaling his company. We also dive into hiring virtual assistants, building accountability, implementin...

Episode 10: Let's talk about skip tracing, DNC compliance, and the real cost of outreach in land investing. I tests Direct Skip vs Skip Matrix head to head, reviews DNC scrubbing tools like TCPA Litigator List and DNC Project, and compares cold calling, ringless voicemail, and mailing from both a compliance and cost perspective. If you are building your 2026 land marketing strategy and want t...

Episode 9: I sit down with Josiah Ronco to talk about leadership, systems, and what it really takes to grow a successful land investing business. Josiah shares how he went from working as a guitar tech to building a streamlined land business with clear KPIs, forecasting systems, and a focused team structure. We also talk about business coaching, quarterly planning, and the tools helping his compan...

Episode 8: After using DataTree for 4 to 5 years, we tested whether better data sources exist for medium-sized land flips. We mailed counties nationwide and compared record counts, filtering accuracy, APN consistency, and access scrubbing. The results were surprising. Record counts varied widely, mislabeling created inefficiencies, and alternate APNs caused tracking issues. Land Portal’s AI found...

Episode 7: We dig into the increasing regulatory hurdles around texting, ringless voicemail, cold calling, direct mail, assignments, and double closings. While land investing has never been “easy,” it’s definitely more complex than it used to be. We unpack what scaling really looks like in a land business. The idea that you can “just add a zero” to your marketing budget and multiply your results i...

Episode 6:  In this episode, I break down exactly where my land sales came from and what the data shows is working right now. After analyzing 283 land deals across multiple price ranges, I share how LandWatch, Land and Farm, Lands.com, LandSearch, Facebook, realtors, and my buyers list actually performed. The real insight is how results shifted by price point. If you are deciding where to focus yo...

Episode 5: with Ciaran Sheil, a land investor based in Ireland who runs a fully virtual land investing business in the United States. At just 24 years old, Ciaran has built a 4-person remote team, sends 16,000 mailers and 50,000 text messages every month, and consistently closes land deals from overseas. We dig into how he got started with Land Academy, what it takes to manage acquisitions virtual...

Bonus episode: I sit down with Cameron from our team at Generation Family Properties to pull back the curtain on the land investing mistakes we’ve made recently and the lessons we’re taking from them. We talk through a 6-figure land mistake in Maine, painful easement and legal access issues in South Carolina and Arizona, and why national title companies didn’t work out the way we hoped.  If you’re...

Episode 4: I sit down with Mike Balcom to talk about building and leading a high-performing land investing team. Mike has scaled to 8 core team members and 25–30 data scrubbers across multiple countries. We talk about hiring overseas virtual assistants, building leaders inside your business, and creating systems that allow you to step back. One of the most interesting parts of this conversation is...

Bonus episode: I break down what really happened in our land investing business during Q1. We brought in about $700K in revenue, but the cash flow tells a different story. Between buying land, paying off hard money loans, and deals taking longer to sell, this quarter showed how easy it is for profits to shrink. I also walk through our numbers, strategy, and what we are changing going into Q2. From...

Episode 3: Kendall LeJeune talk about his shift from house wholesaling to land investing. He shares why he moved away from high volume deals and chose fewer, larger land deals instead, including subdivides and rural recreational property. We also cover leadership, building a small remote team, and creating ownership through clear systems. Kendall explains why defining success for yourself matters...

Bonus episode:  I’m breaking down four real land investing deals we’ve completed across different markets and sharing exactly what happened, both good and bad. I walk through the numbers on each deal, including purchase price, resale value, holding costs, and final profit. Some deals performed as expected, others didn’t, but all of them offer valuable lessons for land investors trying to adapt to...

Episode 2: With my partner Eric Wong, we share the story behind Generation Family Properties and why leadership, not just making deals, is the key to building a lasting land business. We talk about how we got started in real estate, our early days flipping small desert parcels, and our decision to merge our companies to pursue larger opportunities. We also share the real challenges of scaling, fro...

Bonus episode: I’m pulling back the curtain on something most land investors never show you: the real numbers. Not the highlight reel. Not just revenue screenshots. I’m sharing what actually mattered this year, including what the business paid me, where cash flow fell short, why only one quarter hit my goal, and how debt, seasonality, terms deals, and expenses changed everything. If you’ve ever wo...

Episode 1: This episode pulls back the curtain on running a land business when margins tighten and easy wins disappear. Buying and selling get harder, inventory builds, and even good deals force uncomfortable decisions. I share what’s really happening behind the scenes, from misaligned seller expectations and price cuts to note issues, slower cash cycles, and our first real losses. More importantl...