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We chat with Casey Halloran, CEO of Costa Rican Vacations and the Namu Travel Group, to get his take on the current state of Costa Rica’s tourism and real estate markets. They discuss how global economic uncertainty is affecting demand, where Costa Rica’s strongest tourism markets are coming from, whether the country is becoming too expensive, what makes a hotel or vacation rental commercially successful, and the mistakes developers consistently make. Casey also shares where he sees the biggest untapped opportunities over the next decade, what he believes people understood about Costa Rica 20 years ago that newcomers often miss, and where he would invest $500,000 in Costa Rica today.

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

Casey Halloran: https://www.linkedin.com/in/caseyjhalloran/

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Today, we’re joined by Daveed Hollander, President and Master Franchisor of Coldwell Banker Costa Rica. Daveed has been in Costa Rica real estate for more than two decades and knows the market from both the business side and from living in the Southern Pacific around Dominical and Uvita. Today, we’re going to get his take on what’s really happening in Costa Rica real estate in 2026—from how global uncertainty is affecting buyers and sellers, to whether the right properties are still commanding a premium. We’ll also dive into the growing world of wellness real estate: is it a genuine shift in what people want, or just another clever marketing buzzword?

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

Arenal Ridge:  https://www.arenalridge.com/

Daveed Hollander: [email protected]

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Richard Bexon, Developer of Arenal Ridge and Managing Director of Belong Costa Rica, sits down with Jake Alexander to talk about how the vision for Arenal Ridge came to life, what the project is all about, what makes it unique, and why he believes La Fortuna is the right place for such a significant investment. They also discuss the lessons learned from developing the Manuel Antonio Tree House Villas, how those experiences have shaped the Arenal Ridge masterplan, and what’s next for this ambitious project.

Arenal Ridge: www.arenalridge.com

Contact us: [email protected]

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We sit down with Daniel Gehring, owner of El Remanso Lodge in Costa Rica’s remote and spectacular Osa Peninsula.  We discuss what’s really happening in Costa Rica’s tourism market in 2026, how global economic uncertainty is affecting visitors, and the unique opportunities and challenges of operating a high-end hospitality business in one of the country’s most remote destinations. Daniel shares the realities behind running an eco-lodge, from staffing and logistics to the hidden costs guests never see, as well as what investors often get wrong when looking at Costa Rican tourism projects. They also explore whether the Osa represents one of Costa Rica’s biggest untapped tourism opportunities, where Daniel would invest his own money today, and what he would do if he inherited $500,000 to invest in Costa Rica.

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

El Remanso Lodge: https://elremanso.com/

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Richard Bexon, Managing Director and Head Developer of Belong Costa Rica, joins Jake Alexander to talk through the final stretch of developing the Manuel Antonio Tree House Villas — the triumphs, the setbacks, and the lessons learned along the way. They dig into what made these villas different, how the team cut development time by 25%, and what's next as Belong moves into its newest project in Arenal.

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Arenal Project:  https://www.arenalridge.com/

Contact us: [email protected]

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We sit down with relocation, investment and real estate specialist Pilar Vargas to explore why Costa Rica's Central Valley is becoming one of the country's most attractive regions for investors, retirees and those seeking a better quality of life. Pilar shares her insights on how global economic uncertainty has influenced buyer demand, why areas such as Grecia, San Ramón and Atenas continue to grow in popularity, and how these markets compare to Costa Rica's beach destinations. We also discuss rental opportunities, expected investment returns, emerging neighborhoods, long-term market trends and where Pilar would invest $500,000 today.

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

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We chat with Shelby Dobreff of Coldwell Banker Jacó to take a deep dive into one of Costa Rica's most talked-about real estate markets. We discuss how global economic uncertainty is influencing buyer behavior, whether Jacó is currently a buyer's or seller's market, who's investing in the area, and which property types are generating the strongest demand. Shelby also shares his thoughts on luxury real estate, the best opportunities for cash-flow investors, common mistakes buyers make, and which neighboring areas could become the next investment hotspots. 

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

Shelby Dobreff: [email protected]

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Today I'm joined by Scott Cutter, founder of 2 Costa Rica Real Estate and one of the country's most experienced brokers. Scott has watched Costa Rica evolve over the past few decades from a relatively undiscovered destination into one of the world's hottest markets for investors, retirees, families, and lifestyle buyers. We'll dive into how global uncertainty is impacting real estate, where the biggest opportunities exist today, which markets are heating up, and what buyers should be paying attention to before making an investment. As always, expect plenty of practical insights, honest opinions, and the kind of information you won't find with a quick Google search. 

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

Scott Cutter: mailto:[email protected]

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Today, we're joined by someone who has spent decades turning ambitious ideas into reality in Costa Rica—Neal Herman. From helping shape Las Catalinas into one of the country's most recognized master-planned communities to leading Punta Cacique, home to the highly anticipated Waldorf Astoria Costa Rica, Neal has had a front-row seat to some of the biggest successes, toughest challenges, and most interesting lessons in Costa Rican development. In this episode, we'll go beyond the glossy marketing brochures and LinkedIn headlines to discuss what it really takes to develop, operate, and invest in large-scale projects here. We'll cover everything from the current state of the market and what foreign investors often get wrong, to creating places people actually want to live in, not just visit for a week. And, of course, we'll finish by asking Neal the question everyone loves to answer when it's hypothetical: if he inherited $500,000 tomorrow, where would he put it in Costa Rica?

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

Neal Herman: https://www.linkedin.com/in/morrisonherman/

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We chat with Alex Stripe, owner and chief inspector of Stripe Signature Inspections, to discuss what every buyer should know before purchasing property in Costa Rica. Drawing on years of experience inspecting homes across the country, Alex shares what he's seeing on the ground in 2026, why not all home inspectors are created equal, and how buyers can find the right professional to protect their investment. The conversation dives into the unique challenges of owning property in a tropical climate, common construction defects, septic and water system concerns, and the red flags that should make buyers think twice. Alex also explains why even brand-new homes need inspections and reveals what he would personally invest in if handed $500,000 today.

Free 15 min consultation:  https://meetings.hubspot.com/jake806/crconsult

Contact us: [email protected]

Alex Stripe: [email protected]