
Leadership in Land
by Dave Denniston
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On the show
Recent episodes
How They Escaped the Corporate Grind with Steve and Tonsha Hokanson
Sep 2, 2026
42m 35s
Why Trusting Your Gut When Hiring Can Cost Your Business
Aug 26, 2026
21m 24s
How AI Changed His Land Investing Workflow ft. Steve Lynch
Aug 19, 2026
49m 36s
The Mailing Data Nobody Expected with Jessey Kwong
Aug 12, 2026
42m 24s
From CPA to Million-Dollar Land Deals with Austin Hendrickson
Aug 5, 2026
39m 55s
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 9/2/26 | How They Escaped the Corporate Grind with Steve and Tonsha Hokanson | Episode 19: I sit down with Steve and Tonsha Hokanson to talk about leadership, land investing, team building, and creating a lifestyle business that aligns with family and freedom. Steve shares his transition from a 25-year corporate career into full-time land investing and bookkeeping for land investors, while Tonsha explains how her background in health, fitness, and entrepreneurship prepared her for business ownership. We also dive into leadership lessons, managing virtual assistants, b... | 42m 35s | ||||||
| 8/26/26 | Why Trusting Your Gut When Hiring Can Cost Your Business | One of the biggest lessons I’ve learned in land investing is that the problems holding your business back aren’t always “what” problems. Eventually, they become “who” problems. My friend Brian McCarthy recommended the book Who by Geoff Smart and Randy Street. After reading it, I wish I had picked it up sooner. In this episode, I’m breaking down the book’s A Method for Hiring: Scorecard, Source, Select, and Sell, and looking at how these ideas actually apply to a small land investing busines... | 21m 24s | ||||||
| 8/19/26 | How AI Changed His Land Investing Workflow ft. Steve Lynch | Epsisode 17: Steve Lynch talk about how his decades in software leadership shaped the way he runs his land investing business today. Steve shares how he balances a full-time tech career while building a scalable land business using systems, automation, AI tools like ChatGPT, and Agile-inspired leadership principles. We also discuss team building, delegation, collaboration, and how creating the right culture can completely change the trajectory of your business. 🤝 Leadership in Land Skool C... | 49m 36s | ||||||
| 8/12/26 | The Mailing Data Nobody Expected with Jessey Kwong | Episode 16: Jessey Kwong from Pebble joins me to discuss what millions of land investing mailers reveal about today’s market. We talk about direct mail response rates, postcards versus letters, remarketing strategies, rising mailing costs, hyper-personalization, AI, and what separates successful land investors from those who quit too early. If you're a land investor looking to improve your marketing, generate more leads, and increase your return on ad spend, this conversation is packed with... | 42m 24s | ||||||
| 8/5/26 | From CPA to Million-Dollar Land Deals with Austin Hendrickson | Episode 15: Austin Hendrickson talk about his journey from CPA and oil field worker to pursuing million-dollar land deals and commercial real estate projects. Austin shares how he transitioned from smaller land flips into larger development opportunities, why he keeps a lean team, and the systems he uses to stay organized while managing long deal cycles. We also discuss leadership, delegation, cash flow, and the mindset shifts required to scale a land investing business. 🤝 Leadership in La... | 39m 55s | ||||||
| 7/29/26 | 3 Land Investing Case Studies from Q2 2026 | Episode 14: This quarter, I wanted to show you exactly what's happening inside our land investing business. I'll walk through our current inventory, explain why we're shifting away from smaller land deals, and share three real case studies that highlight what's working and what isn't. We cover deals that took nearly a year to sell, unexpected buildability issues, pricing mistakes, and the lessons we're using to improve future acquisitions. If you're involved in land investing, lan... | 26m 54s | ||||||
| 7/22/26 | Inside Our Q2 2026 Cash Flow Report | Episode 13: I'm pulling back the curtain on our Q2 2026 financials and showing exactly what happened inside our land investing business. Instead of focusing only on revenue or profit, I explain why cash flow is the metric I care about most, how we account for owner-financed land deals, why our best month ever wasn't as simple as it looked, and what these numbers actually mean for running a real business. 🤝 Leadership in Land Skool Community (It's FREE!) A private community for land inv... | 17m 40s | ||||||
| 7/15/26 | The Hiring Mistake Most Land Investors Make with Reggie Wright | Episode 12: I sit down with Reggie Wright from Generation Family Properties to talk about his journey from teaching history to becoming a leader in the land investing business. We discuss company culture, hiring the right people, leadership lessons, team accountability, KPIs, employee motivation, and a unique competition we used to boost performance inside our land investing company. If you're building managing a remote team, or looking for better real estate strategies, this conversation o... | 43m 51s | ||||||
| 7/8/26 | Why He Quit Engineering for Land Investing with Ryan Love | 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, implementing EOS, and creating systems that help a land business grow sustainably. 🤝 Leadership in Land S... | 52m 11s | ||||||
| 7/1/26 | My Experiment in Skip Tracing | 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 to balance cost, compliance, and efficiency, this episode will help you make smarter decisions. 🤝 Lea... | 26m 50s | ||||||
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| 6/24/26 | The KPI That Changed His Land Business with Josiah Ronco | 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 company stay organized and profitable. If you’re a land investor looking to improve your leadership sk... | 1h 03m 35s | ||||||
| 6/17/26 | Datatree vs Landportal vs Lightbox | 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 11% more records than manual VA scrubbing while lowering costs. If you’re building land lists in... | 20m 06s | ||||||
| 6/10/26 | The Regulatory Squeeze on Land Investors with Seth Williams | 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 isn’t reality. Scaling requires better leadership, stronger systems, and often a solid team. 🤝 ... | 47m 31s | ||||||
| 6/3/26 | Where Our Land Sales Really Came From | 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 your land investing marketing in 2026, this will help you prioritize the channels that drive t... | 10m 46s | ||||||
| 5/27/26 | How Ciaran Runs a US Land Business from Ireland | 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 virtually, how he structures his team, and the leadership lessons he’s learned including the hard real... | 53m 42s | ||||||
| 5/20/26 | Our 100k Mistake | 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 a land investor, land flipper, or trying to build a smarter real estate strategy, this epi... | 1h 08m 52s | ||||||
| 5/13/26 | How Mike Balcom Built a 30-Person Land Team | 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 how Mike uses AI in his land business. He built a custom GPT that grades sales calls, gives fe... | 1h 04m 06s | ||||||
| 4/30/26 | Our Q1 2026 Cash Flow Report (Real Numbers) | 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 subdividing land to choosing between debt and equity, I share what is working and what is not. ... | 20m 08s | ||||||
| 4/29/26 | Scaling Down to Scale Up with Kendall LeJeune | 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 and how personal branding can create new opportunities. 🤝 Leadership in Land Skool Commu... | 1h 02m 17s | ||||||
| 4/22/26 | 4 Case Studies in Q1 2026 | 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 today’s market. If you’re involved in land investing, land flipping, or building a real esta... | 16m 11s | ||||||
| 4/15/26 | Our Journey, Vision, and Leadership in the Land Business | 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, from building a remote team to improving systems, and how we are structuring the company for long t... | 55m 01s | ||||||
| 4/8/26 | My 2025 Cash Flow Report (Real Numbers from a $3.3M Land Business) | 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 wondered what a multi-million-dollar land business really looks like behind the scenes, this is the... | 28m 21s | ||||||
| 4/1/26 | Lessons from 2025 and Thoughts on 2026 | 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 importantly, this conversation shows how those experiences are shaping our direction. The focus is now on d... | 20m 33s | ||||||
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