Alex and Annie: The Real Women of Vacation Rentals

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 that experience pulled her deeper into vacation rental advocacy and showed her why operators need to get involved before policy decisions are finalized.
She explains how relationships with local officials, Realtors, tourism organizations, legislators, and fellow property managers can help shape clearer, more reasonable regulations. Tyann also shares how collaboration in Missouri has supported progress on state legislation and the development of a model short-term rental ordinance.
The conversation also covers Kansas City’s preparations for the 2026 FIFA World Cup, including how vacation rentals helped address the city’s lodging needs and the resources created to help new hosts operate responsibly.
We discuss:
03:31 - Why vacation rental operators need to pay attention to local policy
04:46 - How property tax changes affected Missouri vacation rentals
14:05 - Why relationships are essential to effective advocacy
20:28 - How operators can get involved in shaping local regulations
25:51 - What Kansas City’s World Cup preparations can teach other destinations
36:43 - How last-minute bookings are changing operational planning
 42:16 - Why human connection still plays an important role in vacation rental marketing 
If you want to better understand how local decisions are made and how operators can have a meaningful voice in the process, this episode is for you.
Connect with Tyann:
LinkedIn: https://www.linkedin.com/in/tyannmarcink/ 

✨ Exclusive Offer to Alex & Annie Listeners: 
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Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 

Thinking about the next chapter for your vacation rental business? 
Connect with Monarch Collective to explore what growth could look like with the right platform behind you.
👉 Learn more: https://gomonarch.com/partnerships/ 

#vacationrentals #shorttermrentals #regulations
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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 to become a consumer habit and what needs to change for travelers to find, trust, and use it more easily.
Eric shares how Savvy evolved from BNB Finder into a book-direct marketplace for professional property managers. The conversation gets into why lower fees alone are not enough to change booking behavior, how OTAs have shaped traveler expectations, and why direct booking needs a better discovery path if it is going to scale.
Episode Chapters:
06:21 - How professional property managers can build stronger guest relationships
06:53 - Why repeat business starts with owning guest data
07:56 - Why direct booking has struggled to reach the consumer
09:04 - How traveler behavior has been shaped by OTAs
18:16 - Why property managers still need OTAs while building a stronger direct strategy
20:55 - How destination content can support discovery and conversion
27:05 - Why property managers cannot rely on direct booking websites alone
33:28 - How trust, reviews, verification, and clear pricing influence conversion
34:18 - Why saving money is not always enough to win the booking
42:00 - What AI and structured data could mean for the future of travel search
If you are a vacation rental operator trying to reduce OTA dependency, build more repeat business, or understand how travelers are discovering and booking stays today, this episode is for you.
Connect with Eric
LinkedIn: https://www.linkedin.com/in/ericgoldreyer/ 
Connect with Savvy:
Website: https://www.savvy.com/
LinkedIn: https://www.linkedin.com/company/stay-savvy/
Instagram: https://www.instagram.com/savvy_stay
Facebook: https://www.facebook.com/savvystays 

✨ Exclusive Offer to Alex & Annie Listeners: 
Reach more direct-booking travelers with Savvy.
List your professionally managed properties for free.
👉 Get started here: https://savvy.com/list

Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 

Thinking about the next chapter for your vacation rental business? 
Connect with Monarch Collective to explore what growth could look like with the right platform behind you.
👉 Learn more: https://gomonarch.com/partnerships/ 

#vacationrentals #shorttermrentals #directbookings
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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 to an already busy season.
In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie are joined once again by Julie Brinkman, CEO of Beyond, for a practical conversation about what vacation rental operators should do when revenue plans do not go as expected.
Julie breaks down how property managers can respond to soft pacing, underperforming inventory, owner pressure, cancellation policy changes, paid placement opportunities, and shifting demand without jumping straight into reactive pricing decisions.
Julie also answers real revenue questions from operators in Nashville, Myrtle Beach, and Park City, covering what to do when a major event underperforms, how to handle inventory that is telling two different stories, and how to help owners understand the strategy when they want rates lowered too soon.
We discuss:
01:30 - Why revenue backup plans matter during a busy season
02:24 - Airbnb cancellation policy changes and what flexibility means for operators
05:38 - Direct bookings, OTA visibility, and finding the right channel mix
11:24 - VRBO paid placement and why marketing needs to align with revenue
16:39 - When a major event weekend does not pace as expected
23:46 - When part of the portfolio is falling behind
31:28 - Helping nervous owners understand the pricing strategy
37:51 -Stop, Start, and Scale: building more proactive revenue plans
Tune in for this episode of Revenue Reality Check, brought to you by Beyond, and learn how to build better revenue backup plans for the moments when the market does not go according to plan.
Connect with Julie:
LinkedIn: https://www.linkedin.com/in/jrbrinkman/ 
Connect with Beyond:
Website: https://beyondpricing.com/
LinkedIn: https://www.linkedin.com/company/beyond-pricing/ 
Instagram: https://www.instagram.com/beyondpricing/ 
Facebook: https://www.linkedin.com/company/beyond-pricing/ 
#vacationrentals #shorttermrentals #strindustry
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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 Destinations. His career has taken him from building a local vacation rental company in Colorado to helping lead large-scale portfolios across some of the most recognizable names in the industry.
Now, with First Chair Destinations, Bob is returning to a more focused, locally grounded model of vacation rental management.
Throughout the conversation, Bob shares what he has learned from building and scaling vacation rental companies, what the industry can take away from the Vacasa to Casago transition, and why the future of vacation rental management still depends on strong local teams, trusted owner relationships, and consistent guest hospitality.
He also discusses the role of technology, AI, distribution, OTAs, private equity, and consolidation in shaping what comes next for the industry.
Episode Chapters:
03:22 - Bob’s path through Steamboat, Wyndham, Vacasa, Casago, and First Chair

06:26 - What the Vacasa to Casago transition revealed about the industry

10:25 - How First Chair is approaching its next chapter

15:29 - What rapid growth has taught the vacation rental industry

16:18 - Why local teams still matter in a scaled industry

17:05 - How hospitality can get lost as companies grow

23:56 - What operators can learn from the Vacasa to Casago transition

27:51 - What consolidation could mean for the industry

30:06 - Where AI can support vacation rental operations

33:16 - Building a hospitality-first culture across local teams

40:47 - Why OTAs still play a major role in distribution

46:56 - How owner expectations around channel visibility are changing

49:34 - Why the future of vacation rentals is still local

51:57 - How guest expectations are changing

Connect with Bob:
LinkedIn: https://www.linkedin.com/in/robertemilne/ 
Website: https://www.firstchair.com/ 

✨ Exclusive Offers to Alex & Annie Listeners: 

Thinking about the next chapter for your vacation rental business? 
Connect with Monarch Collective to explore what growth could look like with the right platform behind you.
👉 Learn more: https://gomonarch.com/partnerships/ 

Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 

Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 

#vacationrentals #shorttermrentals #local
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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 The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in London, Richard and Mark continue the discussion around what AI could mean for vacation rental marketing, website strategy, and guest acquisition.
Richard argues that AI will reshape websites, search, and distribution in ways the industry has not fully prepared for yet. Mark makes the case that strong website infrastructure, brand strategy, PMS connectivity, and niche positioning still matter, especially for operators who want to grow direct bookings.
Together, they explore whether AI search will create new opportunities for independent vacation rental companies or make it even harder to compete with OTAs.
Episode Chapters:
05:29 - How AI is changing the future of vacation rental websites
07:10 - The debate between WordPress websites and AI-built websites
10:00 - Why website design alone is not enough to drive direct bookings
28:25 - How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior
36:29 - Why broad search terms are becoming harder for local operators to compete for
18:00 - How AI search could make niche positioning more important
21:53 - The growing role of TikTok, creators, and social media in travel discovery
46:03 - Why brand trust still matters in an AI-driven search environment
48:22 - How PMS data, integrations, and distribution may evolve
53:22 - What vacation rental operators should be thinking about now as search changes
As guest behavior shifts, vacation rental operators are being pushed to think more carefully about how people find them, what makes their brand memorable, and how they can stay visible beyond the major booking platforms. 
Connect with Richard:
LinkedIn: https://www.linkedin.com/in/richardvaughton/ 
Website: https://yes.consulting/ 
Connect with Mark:
LinkedIn: https://www.linkedin.com/in/mrmarksimpson/ 
Website: https://boostly.co.uk/ 

✨ Exclusive Offers to Alex & Annie Listeners: 

Thinking about the next chapter for your vacation rental business? 
Connect with Monarch Collective to explore what growth could look like with the right platform behind you.
👉 Learn more: https://gomonarch.com/partnerships/ 

Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 

Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 

#vacationrentals #shorttermrentals #ai
Send us a message!