In this episode of The Hideaways Show: Behind the Curtain, Mike is finally back after what felt like a 12-day grind in the Gorge — we’re talking 16-hour days, nonstop tasks, and the kind of behind-the-scenes chaos most people never see when building out short-term rentals. He sits down with Jordan to unpack everything he just went through and to reflect on the real, unfiltered lessons they’ve learned while bringing these unique stays to life.

Together, they walk through the top five lessons every STR investor should know — the hard-earned kind that only come from experience. They hit on why you should never assume anything, the power of getting second opinions, and why documenting every single detail can save you thousands down the road. They dive into the importance of multiple inspections (because one is never enough) and highlight the crucial role a structural engineer plays in protecting your investment, your timeline, and your sanity. It’s real, raw, and packed with wisdom for anyone thinking about building or renovating a short-term rental.

After the deep-dive, Mike and Jordan switch gears and head into their fan-favorite segment: “Would You Book It?” This week, they break down two incredibly unique stays — an unreal skyscraper treehouse in North Carolina and a rugged, scenic hut in New Zealand that looks straight out of a travel documentary. They go back and forth on what makes these properties magical from a guest’s perspective, and what challenges (and opportunities) they present from a host’s point of view.

The result is a fun, thoughtful conversation about the charm, effort, risk, and massive reward of creating truly experiential properties. If you’re obsessed with unique stays, curious about the behind-the-scenes grind, or actively building your own STR, this episode delivers insights you won’t want to miss.

The Hideaways Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/discoverthehideaways/⁠⁠⁠⁠⁠⁠⁠

The Hideaways TikTok:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠https://tiktok.com/@discoverthehideaways⁠⁠⁠⁠⁠⁠⁠

Check out the properties we talk all about at The Hideaways: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://thehideaways.co⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

About the show:

Join us every week for The Hideaways Show! We're the team behind The Hideaways, a collection of unique vacation rentals across the U.S. Our goal is to share our journey with you, from the challenges we've overcome to the lessons we've learned. Tune in to learn and grow with us!

More ways to connect with Mike Sebastian:

• Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://instagram.com/matmiike⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• LinkedIn:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://linkedin.com/in/matmiike/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• X:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://x.com/matmiike⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

More ways to connect with Jordan Holmes:

• Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://instagram.com/jkholmes_rei⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• LinkedIn:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://linkedin.com/in/jkholmes-rei/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• X:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://x.com/jkholmes_rei

In this episode of The Hideaways Show, hosts Jordan Holmes and Mike Sebastian dive into the critical discussion of 'concept versus execution' in the world of hospitality and short-term rentals.

They explore the common pitfall where great ideas often stagnate due to the daunting realities of time, cost, and resources, coining the term 'Conceptual Seduction.'

Through personal anecdotes and expert advice, they emphasize the importance of thorough planning, robust operations, and effective marketing to transform a unique idea into a successful venture.

The hosts compare two similar properties with drastically different outcomes, illustrating the significance of exceptional execution in achieving high occupancy rates and guest satisfaction.

Key takeaways include validating your concept, meticulous planning, solid operations, strategic marketing, and continuous adaptation based on feedback.

This engaging discussion aims to inspire and guide investors to bring their unique hospitality projects to life with confidence and precision.

The Hideaways Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠https://www.instagram.com/discoverthehideaways/⁠⁠⁠⁠

The Hideaways TikTok:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠https://tiktok.com/@discoverthehideaways⁠⁠⁠⁠

Check out the properties we talk all about at The Hideaways: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://thehideaways.co⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

About the show:

Join us every week for The Hideaways Show! We're the team behind The Hideaways, a collection of unique vacation rentals across the U.S. Our goal is to share our journey with you, from the challenges we've overcome to the lessons we've learned. Tune in to learn and grow with us!

More ways to connect with Mike Sebastian:

• Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://instagram.com/matmiike⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• LinkedIn:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://linkedin.com/in/matmiike/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• X:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://x.com/matmiike⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

More ways to connect with Jordan Holmes:

• Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://instagram.com/jkholmes_rei⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• LinkedIn:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://linkedin.com/in/jkholmes-rei/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• X:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://x.com/jkholmes_rei

In this episode of The Hideaways Show, hosts Jordan Holmes and Mike Sebastian dive deep into the art of raising capital in the STR and real estate investment space.

They discuss the critical role of passion and genuine conversations in securing investments, sharing fascinating personal anecdotes about their experiences. The duo emphasizes the importance of accurate numbers, a strong reputation, and a robust network, while debunking the myth of a rigid 26-step process.

Shifting gears, they then analyze two unique property listings—a star-gazing dome cabin in Arkansas and an earth-sheltered home in New Mexico—debating their appeal and investment potential.

With a blend of practical advice and entertaining stories, this episode is a treasure trove for aspiring investors and hosts alike.

The Hideaways Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠https://www.instagram.com/discoverthehideaways/⁠⁠⁠

The Hideaways TikTok:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠https://tiktok.com/@discoverthehideaways⁠⁠⁠

Check out the properties we talk all about at The Hideaways: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://thehideaways.co⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

About the show:

Join us every week for The Hideaways Show! We're the team behind The Hideaways, a collection of unique vacation rentals across the U.S. Our goal is to share our journey with you, from the challenges we've overcome to the lessons we've learned. Tune in to learn and grow with us!

More ways to connect with Mike Sebastian:

• Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://instagram.com/matmiike⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• LinkedIn:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://linkedin.com/in/matmiike/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• X:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://x.com/matmiike⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

More ways to connect with Jordan Holmes:

• Instagram:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://instagram.com/jkholmes_rei⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• LinkedIn:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://linkedin.com/in/jkholmes-rei/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• X:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://x.com/jkholmes_rei