Leadership in Land

Leadership can make or break a land investing business and sometimes the best lessons come from getting it wrong first. In this episode with land investor and former Army officer Drew Haney, along with his executive assistant, Kelley Hinze, to unpack what great leadership actually looks like. Drew shares how peer evaluations in the Army consistently put him in the bottom 25% of his class and what...

“Here I am letting go of something very recession-proof for something with a much bigger question mark.” - Danielle Danielle Shaley is leaving a 35-year career as a hair colorist to go all in on the land investing business she has spent four years building. She shares why managing two careers became unsustainable, how a difficult year, changing market conditions, failed assignments, and using too...

In this episode of Leadership in Land, I sit down with Larry Jarnigo to talk about his transition from 15 years in medical device sales to building a land investing business that gave him more control over his time and eventually replaced his income in his first year. We get into: How Larry replaced his income in his first year Why his first key hire became life-changing How he compensates his ass...

Peter shares why one of his biggest leadership lessons has been to double down on your MVP, or most valuable player. He explains how making his top team member full-time changed the business, why he regularly talks with employees about their personal goals, and how those conversations help create stronger alignment and trust. We also get into: How Peter structures his retail and wholesale teams Wh...

In this episode, JT is open about the fact that managing people has never been his favorite part of business, so he has focused on building a team and systems that play to his strengths. We get into: How JT hires self-starters and defines roles clearly Why he uses personality assessments and project-based testing How weekly one-on-ones and KPI reviews keep the team aligned How he approaches compen...

Heber Perez built a successful land investing business without a traditional team, and he’s done it by staying remarkably focused. In this episode, Heber shares how he went from earning about $40,000 a year at UPS to making roughly $36,000 on his first successful land deal. We also get into why he quit his job during his worst year in land investing, how he built a network of trusted realtors, and...

In this episode of Leadership in Land, I sit down with Clay Hepler to talk about the shift from doing everything yourself to building a team that can grow with the business. After completing 75 wholesale deals in his first year, Clay brought those leadership lessons into land investing and learned to stop asking, “How am I going to do this?” and start asking, “Who is going to help me do this?” We...

I'll take you behind the scenes of what happened, why the smaller Land Unconference format worked surprisingly well, and what attendees thought about the experience. You'll also hear directly from land investors about the value of roundtable conversations, networking, AI discussions, acquisition strategies, land notes, subdividing, and openly sharing what's working in their land inv...

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 h...

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, S...

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 rig...

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 ma...

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, cas...

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, pricin...

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 runnin...

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'r...

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...