The Boostly Podcast: "I Tried THIS PMS for 3 Years... Here’s What Happened!"

Host: Mark Simpson
Guest: Toby Dior (Cajun Stays)
Release Date: March 31, 2025

Introduction

In this episode of The Boostly Podcast, host Mark Simpson delves deep into the practical experiences of a seasoned Airbnb host with property management systems (PMS). Joining him is Toby Dior from Cajun Stays, who shares his three-year journey with the PMS platform Uplisting. This discussion aims to provide hosts with invaluable insights into selecting and utilizing a PMS that caters to diverse hospitality needs.

Guest Introduction: Toby Dior

[01:19] Toby Dior:
Toby introduces himself as an Airbnb host based in Lafayette, Louisiana, a hub of Cajun culture and a major tourist destination. With 13 years of experience in short-term rentals, Toby has evolved from managing individual properties to running a property management company. Additionally, he is a travel blogger known as the Cajun Traveler and serves as a full-time Sports Psychology professor at the University of Louisiana.

Choosing Uplisting: Factors and Decision-Making

Mark Simpson:
Mark sets the stage by highlighting the importance of selecting the right PMS and introduces Toby’s experience with Uplisting.

[03:02] Toby Dior:
Toby recounts his initial engagement with various PMS options while managing Cajun Stays, originally known as Cajun Hostel. After facing glitches and subpar customer service from a previously used PMS—post its acquisition by a larger company—he sought alternatives. At a VRMA conference, Toby met John Ann from Techtape, who guided him toward Uplisting. The decision was further influenced by Uplisting’s compatibility with his existing tools like Boostly and Price Labs, as well as the inclusion of Turno (formerly Turnover), a housekeeping software offered for free with Uplisting membership.

Key Quote:
"Uplisting was a done deal. And so we never look back after that." — Toby Dior [06:36]

Key Features of Uplisting that Benefited Toby

1. Calendar Management

[07:42] Toby Dior:
Toby discusses the initial learning curve with Uplisting’s calendar system. Despite being accustomed to a different PMS layout, the calendar features eventually became intuitive, enhancing his virtual assistants' efficiency in managing bookings.

Quote:
"I was like, I don't know if I'm gonna get used to it and then it grew on me and then now I can't imagine I do demos every now and then because I'm just kind of, kind of a techno." — Toby Dior [07:42]

2. Lock Integration and Automation

[07:42] Toby Dior:
A standout feature for Toby is Uplisting’s seamless integration with Schlage smart locks. This integration automates code changes upon guest check-out, enhancing security and saving time. Uplisting distinguishes between smart and traditional locks, managing their codes appropriately without manual intervention.

Quote:
"If you have Schlage encode app locks... then you don't have to worry about anything. It automatically changes the code." — Toby Dior [09:30]

3. Versatility in Property Management

[12:42] Toby Dior:
Toby emphasizes Uplisting’s adaptability to various property types, from bunk bed hostels to multi-bedroom houses with amenities like pools. This versatility was crucial for Cajun Stays, which manages a wide range of accommodations catering to different guest preferences.

Quote:
"Uplisting does have that feature to provide you with owner statements." — Toby Dior [20:42]

4. Pricing Flexibility

[15:45] Toby Dior:
Uplisting’s pricing model, which scales based on the number of properties, proved economical for Toby, especially as his operations downsized post-COVID. This contrasts with other PMS platforms that often impose higher costs regardless of the number of units managed.

Quote:
"Uplisting was able to be versatile enough and we never thought about changing because, you know, their pricing is based off of individual properties." — Toby Dior [16:01]

5. Financial Analytics and Owner Statements

[17:13] Toby Dior:
Though initially unaware, Toby discovered Uplisting’s financial analytics and owner statement features, which have streamlined his financial management processes. This integration allows for comprehensive financial oversight without relying on external tools.

Quote:
"There's a financial analytics feature and the reason we don't use it is because it wasn't there... but now it's fixed." — Toby Dior [17:13]

6. Turno Integration for Housekeeping

[20:42] Toby Dior:
Turno’s integration with Uplisting has been a game-changer for managing housekeeping tasks. The free access to Turno allows housekeepers to clock in and out seamlessly, facilitating efficient payroll management without additional software costs.

Quote:
"Turno is free and... allows you to clock in and clock out, and then it pays them 10 days later with a credit card." — Toby Dior [20:42]

Areas for Improvement and Future Features

[17:13] Toby Dior:
While Toby is largely satisfied with Uplisting, he identifies areas for enhancement, such as deeper utilization of existing features like financial analytics and owner statements. He suggests that better onboarding and feature discovery could help users maximize the platform’s potential.

Quote:
"We have the option of allowing your owner to see their information only instead of logging in. And there's a small monthly fee for that." — Toby Dior [20:40]

Benefits of a Reliable PMS: Enhanced Efficiency and Growth

[22:07] Toby Dior:
Toby reflects on how a robust PMS like Uplisting has empowered him to manage multiple roles efficiently. The combination of reliable software and virtual assistants has streamlined operations, allowing him to focus on expanding his travel blog and maintaining a high standard of guest service.

Quote:
"Having a PMS that is easy to use and that they don't have to keep coming back to me and asking me questions." — Toby Dior [22:07]

Conclusion and Takeaways

Mark summarizes the key points discussed, highlighting Uplisting’s adaptability, pricing flexibility, and feature-rich platform as major advantages for hosts of varying scales. He underscores the importance of selecting a PMS that aligns with individual business needs and encourages hosts to leverage community insights, such as those shared by Toby, to make informed decisions.

Final Quote:
"That's the cool thing about doing this kind of podcast because you've got first hand experience... Uplisting is such a win." — Mark Simpson [26:12]

Connecting with Toby Dior

For listeners interested in learning more or connecting with Toby Dior, he can be reached through his travel blog, The Cajun Traveler, available at cajuntraveler.net. Additionally, Toby is accessible via various social media platforms, including Facebook, Instagram, and LinkedIn. His direct email is email@tobyjantraveler.net.

Final Thoughts

This episode provides a comprehensive look into the practical benefits and considerations of using a PMS like Uplisting through Toby Dior’s extensive experience. Hosts contemplating a switch or upgrade in their property management systems will find Toby’s insights particularly valuable in navigating the complexities of the hospitality industry.

Stay Connected:
For more episodes and insights, visit the Boostly YouTube channel at boostly.co.uk/youtube.