Leadership in Land

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 realities of firing a team member.

🤝 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

...

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 episode is packed with practical due diligence lessons.

🤝 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

...

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 feedback to acquisitions reps, and helps streamline operations. We also discuss leadership highs and lows, including letting go of a loyal early team member and how to handle tough conversations with empathy.

If you're building a land investing business and want to scale with systems, leadership, and AI, this episode is packed with practical 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.

📊 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

...

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. If you are a land investor or thinking about getting started, this is a real look at what it takes to build a profitable 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

...

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 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

...

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 estate portfolio, this is a realistic look at what deals actually look like right now.

🤝 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

...

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 term growth.

🤝 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

...

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 honest breakdown most people avoid.

🤝 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

...

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 discipline and capital control, fewer acquisitions, tighter standards, and sharper execution. If the market feels tougher and old strategies feel less reliable, this conversation will feel very real.

🤝 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

...