Advocacy can be easy to push aside when the day-to-day work of running a vacation rental business already demands so much attention. That changed for Tyann Marcink Hammond when one of her properties was reclassified from residential to commercial, increasing the tax bill from $4,000 to $10,000. In our latest…
Advocacy often stays on the back burner until a regulation directly threatens the business. For Tyann Marcink Hammond, that moment came when vacation rentals in parts of Missouri were reclassified from residential to commercial properties, causing some tax bills to rise dramatically. In this episode, Tyann returns to share how…
A strong website can help convert guests who already know your brand. The harder part is getting them there in the first place. In this clip, Eric Goldreyer, CEO and founder of Savvy, explains why great photos, a smooth booking engine, and a polished website are only part of a…
Direct booking is often only treated like a marketing problem. But another big challenge is discovery. Travelers do not want to search through countless websites to see what is available in a destination or even know which sites to search. They want enough inventory to compare, a booking experience they…
Owner conversations are strongest when they are backed by both data and a clear story. Because when an owner asks why a date is still open, why bookings are pacing slower, or why rates have not been changed yet, they usually need more than a report. They need context. The…
Direct booking has been part of the vacation rental conversation for years, but one challenge remains hard to solve. Travelers are not always searching that way. In this episode, we welcome back Eric Goldreyer, CEO and founder of Savvy, to talk about why the direct booking movement has a discovery…
Direct booking has been part of the vacation rental conversation for years, but one challenge remains hard to solve. Travelers are not always searching that way. In this episode, Alex & Annie sit down with Eric Goldreyer, CEO and founder of Savvy, to talk about why direct booking has struggled…
Getting more direct bookings is not always about getting more people to your website. Sometimes, the bigger opportunity is improving what happens once they arrive. In this clip, Chris Walker shares how Direct Booking Tools helped one of their clients increase website conversion by 500%. He explains why conversion matters…
Luxury may help a property stand out online. But once the guest arrives, the review is often earned through the basics. In the first edition of the Alex & Annie Real Talk Roundtable, Alex & Annie sat down with Koryn Okey of Breezeway, Miles Hobson of Hospitable, and Miller Hawkins…
Revenue strategy always starts with a plan, but the market does not always follow it. A major event may not pace the way it did last year, certain property types may start falling behind, owners may get nervous about open dates, and new channel updates can quickly add more complexity…
Revenue strategy always starts with a plan, but the market does not always follow it. A major event may not pace the way it did last year, certain property types may start falling behind, owners may get nervous about open dates, and new channel updates can quickly add more complexity…
Scaling a vacation rental company can create a lot of opportunity. But one of the hardest parts of growth is making sure hospitality does not get watered down along the way. When a company is small, the owner relationships feel personal. The guest experience is easier to protect because the…
Guest-related damage is never the call anyone wants to make. But the way that call is handled can shape how much confidence an owner has in the business. If the response is scattered, the owner feels the risk. But when the operator has a clear process, communicates quickly, and knows…
Every vacation rental operator wants 5-star reviews. But the path to earning them is not always about the flashiest amenity, the most premium design, or the property that looks best online. In the first edition of the Alex & Annie Real Talk Roundtable, Alex and Annie are joined by Koryn…
Welcome to the first edition of the Alex & Annie Real Talk Roundtable. Every operator wants 5-star reviews, but the path to earning them is not always about the flashiest parts of the stay. In this conversation, Alex & Annie are joined by Koryn Okey of Breezeway, Miles Hobson of…
AI can make it feel like everyone else is moving faster. Every day, there’s a new tool, a new workflow, a new opinion, and another conversation that makes it seem like you should already have a complete AI strategy in place. But the reality is that many vacation rental operators…
The vacation rental industry has been through a lot of growth, change, and recalibration over the last few years. Companies have scaled quickly, larger players consolidated, AI entered the scene, distribution became more complex, and for many operators, the business itself became harder to navigate. But for Bob Milne, President…
In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations. Bob has spent decades in the vacation rental industry, with leadership experience across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair…
In this episode, Richard Vaughton shares his perspective on what it really takes for vacation rental operators to build long-term value. His view is that the operators who are willing to invest more intentionally in their business may be better positioned as the industry continues to change. That includes areas…
AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building? In this episode, Alex and Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for…
AI is changing the way vacation rental operators work. And for companies willing to approach it thoughtfully, that shift can create more space for what hospitality has always been about. In this episode, we discuss how vacation rental companies can use AI to take the energy they have spent managing…
Welcome to the second episode of Pour Decisions: When Stays Go Sideways, presented by Safely. In this episode, Alex and Annie are joined again by Amanda Martins, VP of Business Development at Safely, for another round of real guest stories, summer stay surprises, and practical takeaways for short-term rental operators.…
Welcome to the second episode of Pour Decisions: When Stays Go Sideways, presented by Safely. In this episode, Alex and Annie are joined again by Amanda Martins, VP of Business Development at Safely, for another round of real guest stories, summer stay surprises, and practical takeaways for short-term rental operators.…
AI conversations in vacation rentals can get big very quickly. In this clip, Ed Ulmer of Barefoot talks about something much more practical. How can AI help a team understand what needs their attention today? For property managers, that is where the opportunity gets interesting. The daily work is full…