Calculate Revenue
Research Markets
Find For Sale Properties
Compare My Listing
Airbnb Revenue Calculator
Custom Comp Sets
Submarket Insights
Custom Search Filters
Rate Recommendations
Performance Benchmarking
Competitor Comparison
Property-level performance data
Tourism Insights
Real Estate Investment Analytics
Individual Plans
Business PlansBuilding a Design-Driven STR Portfolio with Red Cottage CEO Matthew Orley
In this episode of STR Data Lab, Jamie sits down with Matthew Orley, CEO of Red Cottage, to explore the company’s unique approach to short-term rentals. Matthew shares the story behind Red Cottage, which he acquired two years ago, and explains its focus on design-centric homes in the Catskills and Hudson Valley regions. Red Cottage primarily caters to weekend travelers from New York City, Boston, and Philadelphia, with an emphasis on aesthetically appealing properties across various price points.
Matthew highlights how Red Cottage provides unique value to homeowners by attracting a distinct clientele and curating listings that stand out in the competitive short-term rental market. He also touches on their impressive direct booking rate and the recent launch of a membership program offering exclusive perks like discounted rates, waived fees, concierge services, and early access to new properties.
He explains how the steady demand for weekend getaways in their market helps them manage lower seasonality compared to other vacation destinations. Matthew also reflects on the impact of COVID-19, noting the initial surge in demand followed by market normalization. To stay competitive, he emphasizes the importance of adopting new software, leveraging technology, and building strong partnerships.
Matthew also dives into the operational challenges of property management, stressing the need for scalable systems and efficient information management. He wraps up by discussing the future of the property management industry, predicting continued consolidation and professionalization as a response to rising operational costs and the increasing need for advanced tech solutions.
You don’t want to miss this episode!
~~~~
https://www.linkedin.com/in/mattheworley
~~~~
Signup for AirDNA for FREE👇
~~~~
Connect with Jamie on LinkedIn and Twitter:
LinkedIn: https://www.linkedin.com/in/jamiehlane/
Twitter: https://twitter.com/Jamie_Lane
~~~~
Connect with Scott on LinkedIn:
LinkedIn: https://www.linkedin.com/in/sagescott
~~~~
Connect with AirDNA on LinkedIn, Twitter, TikTok, and Instagram:
LinkedIn: https://www.linkedin.com/company/airdna/
Twitter: https://twitter.com/airdna
TikTok: https://www.tiktok.com/@airdna.co
Instagram: https://instagram.com/airdna.co
~~~~
Find AirDNA at these upcoming events!
Up Next:
Celebrating 100 Episodes of STR Data Lab: A Look Back at AirDNA’s Journey with Co-Founders Scott Shatford and Tom Caton
As we hit this 100th episode milestone, we want to take a moment to thank all of our listeners for your support. Whether you’ve been with us from the beginning or joined us along the way, we appreciate you being part of this journey!
In this 100th episode of the STR Data Lab, Jamie celebrates the milestone by sitting down with AirDNA co-founders Scott Shatford and Tom Caton to reflect on the company’s journey and what lies ahead. They recount the early days, starting with Scott’s 2014 project—a book and website analyzing short-term rentals in Santa Monica. Despite regulatory hurdles, this effort quickly evolved into a key resource for understanding Airbnb listings, laying the groundwork for AirDNA.
Tom joined Scott in 2015, forming a business partnership during a sailing trip. From there, they pushed forward to build AirDNA into a powerful data platform, with the development of MarketMinder being a critical turning point. They also discuss the transition from delivering insights via simple PDF reports to creating a comprehensive SaaS platform that continues to shape the short-term rental industry. Throughout the episode, they highlight their decision to bootstrap the company, staying independent of external funding.
The episode explores the technical and business challenges they faced, including the complexities of data scraping, adapting to changes in Airbnb’s algorithm, and the massive impact of the COVID-19 pandemic. Beyond the business, Scott and Tom share how they managed stress, balanced luck with hard work, and navigated key decisions that led to AirDNA’s success and eventual sale.
Post-sale, Tom has turned his attention to new projects, including developing a murder mystery board game and investigating business fraud. Scott, meanwhile, enjoys traveling and personal hobbies like golf and ping pong, though both hint at possible new ventures in the future.
This episode offers a detailed look at how AirDNA grew from a niche idea into an industry-leading platform. You don’t want to miss it!
~~~~
Signup for AirDNA for FREE👇
~~~~
Connect with Jamie on LinkedIn and Twitter:
LinkedIn: https://www.linkedin.com/in/jamiehlane/
Twitter: https://twitter.com/Jamie_Lane
~~~~
Connect with Scott on LinkedIn:
LinkedIn: https://www.linkedin.com/in/sagescott
~~~~
Connect with AirDNA on LinkedIn, Twitter, TikTok, and Instagram:
LinkedIn: https://www.linkedin.com/company/airdna/
Twitter: https://twitter.com/airdna
TikTok: https://www.tiktok.com/@airdna.co
Instagram: https://instagram.com/airdna.co
~~~~
Find AirDNA at these upcoming events!