What does it take to run a successful vacation rental business? For Jeremy Gall, Founder and CEO of Breezeway, a big part of the answer is operations. Vacation rentals are operationally complex by nature. You are managing unique homes, different owner expectations, changing guest needs, and countless details that have…
Growth can look impressive on paper. More doors, more markets, bigger numbers. But the businesses that last tend to be built with a much longer view. In this clip from Expedia Group’s Powering Travel Podcast, Alex reflects on what legacy vacation rental companies can teach operators about sustainable growth. Many…
In this episode, Alex & Annie sit down with Jeremy Gall, Founder and CEO of Breezeway, to explore how the continued professionalization of vacation rentals is raising the bar for what strong operations look like. Jeremy shares what led him to tackle one of the industry's most complex challenges: coordinating…
In this episode, Alex & Annie sit down with Jeremy Gall, Founder and CEO of Breezeway, to explore how the continued professionalization of vacation rentals is raising the bar for operations. Jeremy shares what led him to tackle one of the industry's most complex challenges: coordinating the people, properties, and…
Vacation rental tech can get complicated quickly, especially when new tools are constantly promising more automation, more efficiency, and better results. In this clip from Expedia Group’s Powering Travel Podcast, Annie shares why operators need to look beyond what is new and ask whether a tool actually fits the way…
Owner questions feel very different when you have the receipts. If a homeowner asks how often their property was checked, who was there, or what was actually done, relying on memory can make an already uncomfortable conversation harder. In this clip from Pour Decisions: When Stays Go Sideways, Rachel Alday…
A vacation rental company can have plenty of inventory, but that alone does not make it a business worth building around. In this clip, Igor Simkin, CEO of Monarch Collective, shares what they pay attention to when entering a new market: an established brand, a strong team, long-tenured employees, and…
The moment a guest flags a potential safety issue, your response is critical. In this clip from Pour Decisions: When Stays Go Sideways, Amanda Martins of Safely explains the idea of being “on notice” and why even a seemingly small complaint deserves attention. Once your team knows about a potential…
The vacation rental industry has changed dramatically over the years. The technology is smarter, distribution is broader, competition is stronger, and AI is reshaping how operators work. But some of the most important parts of the business have not changed at all. In this special reshare, Alex & Annie step…
The vacation rental industry has changed dramatically over the years. The technology is smarter, distribution is broader, competition is stronger, and AI is reshaping how operators work. But some of the most important parts of the business have not changed at all. In this special reshare, Alex & Annie step…
SEO has been declared dead more than once. The reality is that search keeps changing, and the strategy has to change with it. In this clip, Vanessa Humes of ICND shares why vacation rental operators should be careful about handing everything over to the latest “all-in-one” solution or chasing whatever…
Vacation rental businesses often have plans for protecting properties when a storm, fire, flood, or other emergency hits. But true preparedness goes much further than securing the homes. In this YouTube-exclusive episode, Alex & Annie are joined by Rachele Hobbs, Sue Jones, and April Burns of Hospitality Heroes for a…
Vacation rental businesses often have plans for protecting properties when a storm, fire, flood, or other emergency hits. But true preparedness goes much further than securing the homes. In this YouTube-exclusive episode, Alex & Annie are joined by Rachele Hobbs, Sue Jones, and April Burns of Hospitality Heroes for a…
When an owner asks for more detail, questions why something was handled differently, or wonders why they were not told about an incident sooner, the question is usually about more than the immediate issue. They want to know their property is in good hands. In Episode 3 of Pour Decisions:…
Seeing organic traffic drop does not automatically mean your SEO is failing. Search behavior itself is changing. More travelers are getting answers directly from Google AI Overviews or doing part of their research in tools like ChatGPT, Gemini, and Claude before they ever reach a website. In this clip, Jill…
Growth in vacation rental management is often measured by one highly visible number: door count. 🚪 It is easy to track and impressive in a headline. But does it tell you whether those properties are profitable, whether owners are staying, or whether your team can support the growth? In the…
Vacation rental search is changing fast, and many operators are already seeing it in their website traffic. Google AI Overviews are answering more questions without a click, travelers are using tools like ChatGPT and Gemini to research their trips, and new terms like AEO and GEO are quickly becoming part…
Vacation rental search is changing fast. Organic traffic is declining, AI Overviews are taking up more space in Google, and travelers are increasingly using tools like ChatGPT, Gemini, and Claude to research where to stay. For property managers, that creates a new challenge: how do you stay visible when the…
There is a lot of value already built into a strong local vacation rental company. The brand has history, the team understands the market, homeowners know who they are working with, and that reputation has often been earned over years. In this clip, Igor Simkin, CEO of Monarch Collective, shares…
AI has been part of nearly every industry conversation this year, but one theme keeps coming with it: how do we use it without losing the human side of hospitality? In this clip from our mid-year recap episode, Jinnie reflects on the question many of our guests are navigating right…
For most guests, a vacation is a small window of time they have worked and planned for all year. That is what makes hospitality such a meaningful responsibility. In our August First of the Month Wrangle, presented by Lasoh, Orlie Benjamin shares why she believes vacations are deeply connected to…
Growth in vacation rental management is often measured by one highly visible number: door count. 🚪 It is easy to track and impressive in a headline. But does it tell you whether those properties are profitable, whether owners are staying, or whether your team can support the growth? In the…
What happens when a vacation rental company is sold? In this episode, we are joined by Igor Simkin, CEO of Monarch Collective, for a candid conversation about how buyers evaluate a business, what can raise concerns during the process, and what life after the sale can look like for founders,…
What makes a vacation rental business attractive to a buyer? Door count may get attention, but it does not tell the full story. Sustainable growth, clean financials, a trusted local brand, strong employees, and direct booking performance can all influence how a business is evaluated. In this episode, Alex &…