How to Run Smarter STR Operations with Breezeway

Host Planet: Expert Insights for Short-Term Rentals

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3M ago 30:48

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In this episode of the Host Planet Podcast, powered by Hostfully, we sit down with Jeremy Gall, the Founder and CEO of Breezeway, to explore what it really takes to run smart operations in the short-term rental (STR) world. From his early days building FlipKey to his current mission with Breezeway, Jeremy brings a wealth of experience and insight into the operational challenges hosts and property managers face today – and how technology can help them overcome these hurdles.

Jeremy dives into the balance between automation and human touch, how to build better systems for proactive guest communication, and the most common mistakes STR operators make. Whether you're managing five listings or 50, this episode is packed with strategies to help you streamline operations, scale effectively, and create better guest experiences.

Key takeaways:

1. Operations make or break the guest experience. Clear processes, task automation, and a proactive approach to communication are essential. Operational gaps can lead to missed cleanings, poor guest reviews, and unnecessary stress.

2. Proactive messaging builds trust. Jeremy outlines the ideal guest communication schedule – from pre-arrival to post-checkout – and explains how Breezeway helps hosts deliver timely, informative messages that solve issues before they arise.

3. Tech can’t replace human connection – but it can enhance it. The future of STR operations isn’t just AI and automation. It’s about finding the right tools to support human decisions and deliver service at scale – without losing the personal touch.

0:00 Episode starts

1:05 How STR hosts can improve operations

3:54 Common mistakes

7:25 How to get your operations running smoothly

8:59 Getting the balance right between automation and the human touch

11:25 The importance of proactive guest communication (and how Breezeway can support)

15:22 The optimum proactive messaging schedule

18:20 Solving issues quickly with guest comms

20:03 How Breezeway helps hosts

21:53 From FlipKey to Breezeway

24:05 Exciting tech trends in short-term rentals

25:15 The impact of AI on STR operations

26:45 Favourite brand: Casago

27:32 Individual shout-out: Tim Cafferty from Outer Banks Blue in North Carolina

28:24 What Jeremy would change about the STR industry

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Email Frank: [email protected]

Host Planet: https://www.hostplanet.club/

James Varley: https://www.linkedin.com/in/jdsvarley/

Jeremy Gall: https://www.linkedin.com/in/jeremiahgall/

Breezeway: https://www.breezeway.io/vacation-rental?utm_campaign=11079539-Host%20Planet&utm_source=Host%20Planet

Episode to check next: Is Your Direct Booking Website Useless? https://www.youtube.com/watch?v=sGewt3ZV6UA&t=8s

The Host Planet Podcast is presented by James Varley, a holiday let investor and property manager who is also the Founder of Host Planet. Before founding Host Planet, James spent 20 years in the media, including a decade leading corporate communications for the FIFA World Cup Qatar 2022.

Contact the show: [email protected]

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