Leadership in Land

Dave Denniston
  • 5.0 (2)
  • Investing

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.

  1. 1d ago

    The Risk of Keeping Your Best Player Part-Time with Peter Nukasan

    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. 📊 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 ...

  2. Sep 30

    Want to Lead a Team but Hate Managing? with JT Olmstead

    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. 📊 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 ...

  3. Sep 23

    The Land Deal That Cost Heber Perez $70K

    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. 📊 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 ...

  4. Sep 16

    75 Deals Showed Him the Power of a Great Team ft. Clay Hepler

    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. 📊 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 ...

  5. Sep 9

    What happened at the unconference experience in 2026

    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. 📊 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 ...

  6. Sep 2

    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, 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. 📊 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 ...

  7. Aug 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 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. 📊 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 ...

  8. Aug 19

    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 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. 📊 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 ...

See All (28)

Ratings & Reviews

5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Dave Denniston
  • Years Active
    2026
  • Episodes
    28
  • Rating
    Clean
  • Copyright
    © 2026 REtipster Publishing LLC
  • Show Website
    Leadership in Land

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