The Hideaways Show

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 lear...

In this episode of The Hideaways Show, Mike and Jordan unpack what’s shaping the short-term rental world heading into 2025 — and it’s clear the game is evolving fast. They dive deep into the newest data, predictions, and trends defining where the industry is headed, especially when it comes to building unique, experiential properties that truly stand out. Pulling insights from a recent AirDNA arti...

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 anecdot...

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, an...

In this engaging episode of The Hideaways Show: Behind the Curtain, hosts Jordan Holmes and Mike Sebastian delve into a critical topic for real estate investors—how to make your property stand out in the short-term rental (STR) market. They discuss the common misconception that buying and minimally upgrading a property is enough for it to be an investment, emphasizing the need for bold, unique fea...

In this episode of The Hideaways Show: Behind the Curtain, hosts Mike and Jordan delve into the intricacies of short-term rental profitability, emphasizing the importance of understanding net income over gross revenue. They discuss the excitement of flurries of reservations and launch new silo cabins. The conversation shifts to critical financial insights, highlighting how gross revenue can be dec...

In this episode of The Hideaways Show: Behind the Curtain, Jordan and Mike explore the top five factors to consider when selecting a market for unique short-term rentals (STRs). They discuss navigating regulations and restrictions, assessing tourist demand and infrastructure, evaluating land acquisition costs, understanding competition, and examining marketability. The episode also features their...

In this engaging episode of The Hideaways Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian, delve into the remarkable transformation of their 420-square-foot cabins. They share how strategic investments turned ordinary cabins, originally earning around $3,100 per month, into high-revenue assets, achieving a staggering 115% increase in monthly revenue and peaking at $11,000 in July....

In this episode of The Hideaways Show, Jordan and Mike dive into the transformative power of storytelling and social media marketing for short-term rentals (STRs). The hosts discuss how brands have successfully leveraged platforms to document their journeys, attract massive followings, and secure pre-bookings worth millions. They highlight examples like Bolt Farm Treehouse, Pacific Bin, and unique...

In this engaging episode of The Hideaway Show, hosts Jordan Holmes and Mike Sebastian explore the future of short-term rentals, emphasizing the shift from traditional 'location, location, location' mindsets to creating unique, experiential stays. Set in July 2025, they discuss the potential of acquiring large parcels of land at minimal costs, overcoming building challenges, and crafting un...

In this exciting episode of The Hideaway Show, hosts Jordan Holmes and Mike Sebastian dive deep into the allure of unique short-term rentals. They discuss the significance of direct bookings as a buffer against platform changes and argue the advantages of focusing on high-quality, 'polished gem' properties over mere door counts. Their conversation covers a variety of fascinating topics, in...

In this edition of the Hideaway Show behind the Curtain edition, hosts Jordan Holmes and Mike Sebastian, also known as Mr. Red River Gorge, delve into the intricacies of building bespoke short-term rentals. They discuss the initial excitement of breaking ground, the logistical challenges encountered as projects near completion, and the unique joys and frustrations of customizing properties. Mike s...

In this episode of The Hideaways Show: Behind the Curtain, hosts Jordan Holmes and Mike Sebastian dive into the pitfalls of investor complacency and the unexpected costs associated with older rental properties. They discuss the importance of using data to paint a comprehensive picture for property performance comparisons and the challenges of maintaining top rankings on multiple booking platforms....

In this episode of The Hideaway Show 'Behind the Curtain' edition, Jordan Holmes and Mike Sebastian dive into the significance of property reviews, the perks of unique amenities, and the psychology behind choosing one accommodation over another. They list their top five dream features for Short Term Rentals (STRs) if budget were no issue, including unique water features, container pools, g...

In this episode of The Hideaways Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian explore their adventures in the short-term rental market, focusing on how unique amenities can dramatically transform guest experiences and boost revenue. They discuss the impact of installing a hot tub at their properties, leading to eye-popping increases in direct bookings and revenue, largely driven...

In this lively episode of The Hideaway Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian catch up after a break, diving into the importance of creating engaging content for short-term rentals (STR).  The conversation transitions into their biggest STR investment mistakes, revealing the pitfalls and lessons learned from financing through a primary residence HELOC and the complications...

In this edition of The Hideaway Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian discuss Airbnb's major summer release and its potential impact on the short-term rental market. They dive into the details of new services offered by Airbnb, such as chef and massage services, and relaunching experiences, portraying Airbnb's vision to be a one-stop platform for all things travel. The ho...

In this episode of The Hideaway Show: Behind the Curtain, hosts Jordan Holmes and Mike Sebastian discuss the challenges and strategies in owning short-term rentals, emphasizing the need for unique properties and business diversification. They address recent policy changes by Airbnb aimed at preventing hosts from taking guests off-platform, highlighting the importance of not relying solely on any o...

In this edition of the Hideaway Show - Behind the Curtain, hosts Jordan Holmes and Mike Sebastian discuss the exciting developments in their cabin building endeavors. They emphasize the importance of not needing to be perfect from the start and learning from experience. The main highlight is their daring project of placing a hot tub on top of a boulder at their Rock Haven Hideouts Trio of cabins....

In this episode of the Hideaway Show, Jordan Holmes interviews Wendy Doris, owner of Mostess Property Management. Wendy shares her journey from flipping houses to managing short-term rentals in Phoenix. Highlighting the importance of design and branding, Wendy reveals that Mostess' properties, including unique themed homes like 'Swifty' houses dedicated to Taylor Swift fans, prioritize providing u...

In this engaging episode of The Hideaway Show, host Jordan sits down with Jandy Salguero, the innovative owner behind Out of Bounds Retreats, which features unique properties in Banner Elk, North Carolina, and Holden Beach. They delve into Jandy's journey from long-term rentals to short-term beach and mountain retreats, highlighting the pivotal moments, challenges, and triumphs along the way....

In this episode of The Hideaway Show, hosts Mike and Jordan share insights and takeaways from the 'Level Up Your Listing' Summit in Phoenix. They discuss the confidence needed to improve in the short-term rental industry and highlight the enhanced experience of doing something multiple times. The episode reveals their experience with thunderstorm surprises in Phoenix, meeting industry lead...

In this episode of The Hideaway Show, hosts Jordan Holmes and Mike Sebastian delve into the importance of diversifying one’s short-term rental business beyond platforms like Airbnb. They discuss potential implications if a co-founder, Joe Gebbia, causes disruptions leading to an Airbnb downfall. Mike emphasizes the critical need for establishing direct booking systems, collecting email lists, and...

In this episode of 'The Hideaway Show: Behind the Curtain,' hosts Jordan Holmes and Mike Sebastian return to discuss their journey in 2024 and their ambitious plans for 2025. They dive into their experiences and the lessons they learned last year, focusing on the importance of social media for bookings and the value of on-site management. The hosts are excited about their upcoming unique projects,...

In this episode of The Hideaway Show, host Jordan Holmes speaks with Dustin Baker, the owner and founder of Hidden Gem Media. They discuss the importance of branding and marketing for vacation rental businesses, emphasizing the need to differentiate and build trust to achieve premium pricing and higher occupancy rates. Dustin shares his journey in the marketing industry and how it led him to focus...