
Advertise on podcast: Leadership in Land
This podcast has
32 episodes
Language
EnglishPublisher
Dave DennistonExplicit
No
Date created
2026/04/01
Latest episode
2026/11/04
Average duration
42 min.
Release period
8 days
Description
Leadership in Land is a podcast for land investors who believe better decisions are made together. Hosted by Dave Denniston, this show focuses on the leadership side of land investing, how to think clearly, act responsibly, and grow with integrity in a business that is often misunderstood. Each episode draws from real-world experience, honest conversations, and the shared wisdom of investors who value collaboration over competition. As part of the REtipster Podcast Network, Leadership in Land is built for investors who care about long-term success, strong character, and learning from others who are walking the same path.
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Check latest episodes from Leadership in Land podcast
Why Most Land Investors Quit Too Soon | Chris Duff
2026/11/04
What separates land investors who survive and grow from the ones who disappear after a year?
Chris Duff of Sirius Land Capital shares what he’s learned about leadership, focus, hiring, and land deal funding from working with operators across the country. As both a land investor and funder, Chris has seen one trait separate the people who last from those who disappear: the willingness to stay committed long enough to solve the problems in front of them.
Chris and his partners nearly left the land business after a difficult 2022, but instead they narrowed their focus around what they did best---underwriting and capital structuring. That shift helped the business take off. We also talk about shiny object syndrome, hiring mistakes, managing virtual assistants, building accountability without micromanaging, and why great leaders serve their people first.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
Why Great Leaders Put Their People First | Drew Haney & Kelley Hinze
2026/10/28
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 he changed to eventually reach the top 25%. His realization was surprisingly simple: the best leaders weren't necessarily the smartest people in the room. They were better with people.
Drew also shares his three traits of a great leader: competence, dependability, and care.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
Why She’s Leaving a 35-Year Career for Land with Danielle Shaley
2026/10/21
“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 much of her own capital shook her confidence, and why she still believes land is the right long-term path.
We also discuss how she is restructuring her team, taking seller conversations back on herself, using incentives to motivate team members, documenting processes with Loom, mapping responsibilities with XMind, tracking KPIs and missed leads through OpenPhone, and using coaching to rebuild confidence and create a more focused land business.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
Ended 15 Years in Medical Sales and Led to Land with Larry Jarnigo
2026/10/14
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 yearWhy his first key hire became life-changingHow he compensates his assistant with 3% of net profitWhy he now treats new hires like a 45-day trialThe hiring mistake he let drag on too longHow specialists help keep his team leanWhy transaction coordination is still a major time drainHow he uses Airtable, Monday, Slack, and Google DriveWhy his assistant creates training videos for future hiresHow “Who Not How” shapes his approach to leadershipLarry also explains why he does not want a large W-2 team, how he plans to grow direct mail from roughly 2,500 to 3,000 pieces per week toward 5,000, and why strong leadership means showing your team that you are doing everything you can to grow the business.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
The Risk of Keeping Your Best Player Part-Time with Peter Nukasan
2026/10/07
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 teamsWhy he prefers keeping the business leanHow HireMyMom and Indeed have worked for hiringHow he generated 81 applicants in five daysWhy self-starters are so valuable on a small teamHow being overwhelmed actually made his team more independentHow he uses Trello to organize projects and responsibilitiesWhy he wants to start tracking simple weekly KPIsThe leadership books and systems that have influenced himPeter also shares how he thinks about investing in great people financially, emotionally, and personally. If you are building a land investing business and want a team that can solve problems without depending on you for every decision, this conversation offers plenty of practical ideas.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
Want to Lead a Team but Hate Managing? with JT Olmstead
2026/09/30
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 clearlyWhy he uses personality assessments and project-based testingHow weekly one-on-ones and KPI reviews keep the team alignedHow he approaches compensation and employee growthWhen he chooses domestic versus international hiresWhy company culture needs to be defined early
For land investors who want to lead a growing team without getting buried in management, JT’s experience offers a practical look at how better hiring, communication, and clear expectations can make leadership more manageable.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
The Land Deal That Cost Heber Perez $70K
2026/09/23
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 the partnership mistake that cost him roughly $60,000 to $70,000.
Heber also breaks down his blind offer strategy, why he focuses deeply on just a few markets, how he’s finding on-market land deals, and why bigger subdivision projects are the next step for his business.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
75 Deals Showed Him the Power of a Great Team ft. Clay Hepler
2026/09/16
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 discuss how he built a seven-person team, how he hires and tests candidates, and how he uses KPIs and the cash conversion cycle to track performance. Clay also shares why self-awareness, accountability, training, and culture are essential for becoming a stronger leader and building a business that can adapt and grow.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
What happened at the unconference experience in 2026
2026/09/09
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 investing businesses.
Sometimes the event you didn't plan turns out to be exactly the event you needed.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
How They Escaped the Corporate Grind with Steve and Tonsha Hokanson
2026/09/02
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, building a strong team culture, mindset, accountability systems, and how to scale a land business without sacrificing what matters most.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
Why Trusting Your Gut When Hiring Can Cost Your Business
2026/08/26
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 business.
We’ll talk about why a job description isn’t enough, why hiring out of desperation can backfire, how to structure interviews without turning them into an all-day ordeal, and why real-world assignments can tell you much more than a polished interview.
I’ll also explain where I think the book’s advice needs to be adapted for land investors. Most of us aren’t hiring Fortune 500 executives. We’re looking for acquisitions managers, transaction coordinators, pricing analysts, dispositions people, and virtual assistants, and the hiring process needs to make sense for those roles.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
How AI Changed His Land Investing Workflow ft. Steve Lynch
2026/08/19
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 Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
The Mailing Data Nobody Expected with Jessey Kwong
2026/08/12
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 real-world data and actionable insights.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
From CPA to Million-Dollar Land Deals with Austin Hendrickson
2026/08/05
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 Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
3 Land Investing Case Studies from Q2 2026
2026/07/29
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, land flipping, or building a real estate portfolio, I think you'll find these real-world examples helpful as you evaluate your own business and strategy.
🤝 Leadership in Land Skool Community (It's FREE!)
A private community for land investors who want to grow as leaders.
🏕️ Land UnConference
A live event where land investors share real deals and lessons learned.
🙋🏻♂️ Get the REtipster Newsletter (It's FREE)!
Stay updated with top real estate investing insights and strategies
⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)
Avoid the 21 most deadly land-buying blunders
🚀 Land Investor’s Action Plan (Free 5-Day Course!)
Solve the 5 mistakes that keep investors stuck
👉 LAND UNLOCKED! (Webinar)
Rethinking Real Estate Investing from the Ground Up
📊 Manage Land Deals Like a Pro with Stride CRM
Built for Land Investors! Organize leads, t...
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