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 & Annie sit down with Igor Simkin, CEO of Monarch Collective, for a candid look at what owners should understand before exploring a sale. Igor shares what Monarch looks for in a company, where sellers are often unprepared, and why the conversation should begin long before an owner is ready to step away.

They also explore what happens after the transaction, from protecting the local brand and retaining employees to helping founders choose the role they want in the company’s next chapter.

Episode Chapters:

05:22 - Why Monarch Collective was created and the opportunity it saw in the market
08:07 - Preserving local brands, teams, and community relationships
11:12 - Anchor acquisitions versus tuck-in acquisitions
11:51 - The qualities Monarch looks for in an established business
13:57 - When owners should begin preparing for a potential sale
16:14 - Creating a transition plan around the founder’s goals
22:16 - The performance indicators buyers consider
25:03 - Financial readiness, valuation, and common seller blind spots
28:04 - Building a shared data layer across different technology platforms
33:43 - How Monarch is approaching AI across operations and marketing
38:13 - What an acquisition can mean for employees and local leadership
46:48 - How owners can get feedback before they are ready to sell

Connect with Igor:

Email: isimkin@gomonarch.com

LinkedIn: https://www.linkedin.com/in/igor-simkin-4902993/

Connect with Monarch Collective:

Website: https://gomonarch.com/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what your options could look like and how to prepare before the time comes.

👉 Learn more: https://gomonarch.com/partnerships/

✨ 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

#vacationrentals #shorttermrentals #propertymanagement #businessvaluation #mergersandacquisitions

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In this third episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Patti Ziegler, Orlie’s longtime mentor and former leader at Scotts Miracle-Gro.

Before building Lasoh, Orlie worked with Patti across direct-to-consumer marketing, brand building, innovation, and partnerships. That experience shaped how she thinks about customer relationships, distribution, and the value of knowing the people behind each purchase.

That same thinking applies in vacation rentals. OTAs may help bring guests in, but operators still need a way to understand who those guests are, stay connected, and create reasons for them to book again.

Orlie and Patti also share the mentorship behind that journey, including what it means to take a chance on someone, recognize when a role is no longer the right fit, and support a person as they move toward something bigger.

We discuss:

00:51 - Meet Patti Ziegler and learn how she worked with Orlie

02:04 - Building a direct-to-consumer brand from zero to one

03:19 - How established brands create new pathways to the customer

08:39 - What retail distribution can teach operators about OTAs and direct bookings

11:50 - How direct-to-consumer thinking shaped Lasoh

13:36 - The mentorship behind Orlie’s move into entrepreneurship

21:46 - How a career pivot brought Orlie closer to her purpose

28:33 - What vacation rental operators can learn from full-funnel marketing

30:46 - Why awareness, conversion, and guest loyalty all need attention

36:23 - Building a business in a way that still supports people

40:22 - Why the guest experience is central to Orlie’s work in vacation rentals

Learn more about Lasoh:

Website: https://tinyurl.com/52nvyw8t
LinkedIn: https://www.linkedin.com/company/lasoh/
Facebook: https://www.facebook.com/people/Lasohio/61575721958679/
Instagram: https://www.instagram.com/lasoh.io

Connect with Orlie:

LinkedIn: https://www.linkedin.com/in/orliebenjamin/
Facebook: https://www.facebook.com/profile.php?id=61585160391720
Instagram: https://www.instagram.com/orlie.benjamin/

Connect with Patti:

LinkedIn: https://www.linkedin.com/in/patti-ziegler-4649173/

✨ Exclusive Offer to Alex & Annie Listeners:

Turn every guest interaction into more revenue with Lasoh.

Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through September 30, 2026.

👉 Learn more: https://explore.lasoh.io/alex-annie

#vacationrentals #vacationrentalmarketing #directbookings

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Nearly 300 episodes in, the Alex & Annie Podcast is entering one of its most exciting chapters yet.

In this special mid-year episode, Alex & Annie are joined by Jinnie Randolph, who has been working behind the scenes to help shape the show’s content, partnerships, strategy, and future growth.

Jinnie shares her journey through vacation rental marketing, technology, and operations, along with the full-circle story of how she went from longtime listener and sponsor partner to becoming an important part of the Alex & Annie team.

Together, Alex, Annie, and Jinnie reflect on the conversations and industry themes that have defined 2026 so far. They discuss the rapid evolution of AI, the continued importance of human connection, and why intentional growth, consistency, and education have become increasingly important across the vacation rental industry.

They also take listeners behind the scenes of the show’s evolution into Aha Moments Media. Alex & Annie share how the Growth Blueprint has shaped this year’s content and how new recurring series, roundtables, on-site interviews, private podcasts, and thought leadership opportunities are helping the platform grow beyond its original format.

Episode Chapters:

04:19 – How Jinnie became part of the Alex & Annie Podcast team

11:24 – The industry themes shaping the first seven months of 2026

16:14 – How AI and human connection are evolving together

22:25 – Why smaller operators need better access to credible education

15:56 – The Growth Blueprint behind this year’s podcast content

13:11 – How the show is expanding into Aha Moments Media

27:30 – New series, roundtables, partnerships, and storytelling formats

31:31 – What nearly 300 episodes have taught Alex and Annie about consistency

36:46 – Alex’s decision to dedicate more time to the podcast

38:49 – Annie’s work with Booking.com and smaller vacation rental operators

49:00 – What the team is building for the rest of 2026 and beyond

Tune in for a candid look at where the show has been, what is changing, and why the second half of 2026 could be its most exciting yet.

Enjoying the Alex & Annie Podcast?

Leave a rating to help more vacation rental professionals discover the show:

https://alexandanniepodcast.com/review

✨ 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 #hospitality

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What does it take to build a vacation rental company that can grow, evolve, and remain successful for nearly seven decades?

In this episode, Alex & Annie sit down with Rick Elliott and Brandon Cox of Elliott Realty to explore the people, systems, leadership decisions, and business fundamentals behind the company’s longevity.

Elliott Realty has been part of the Myrtle Beach vacation rental industry since 1959. Over those 67 years, the company has navigated new technology, changing traveler behavior, higher homeowner expectations, and an increasingly complex distribution landscape.

Rick and Brandon share why long-term success requires a willingness to evolve, strong systems, careful attention to detail, and people who can grow with the organization. They also discuss Elliott Realty’s approach to homeowner relationships, property standards, direct bookings, OTA distribution, brand development, and local tourism advocacy.

Episode Chapters:

06:42 - How Elliott Realty Has Evolved Since 1959

07:15 - Why Strong People and Systems Matter More Than Technology Alone

12:20 - Hiring Intentionally and Promoting Future Leaders From Within

15:59 - Understanding Individual Homeowner Goals and Expectations

19:05 - Maintaining Property Quality Across a Large Portfolio

27:52 - Balancing Direct Bookings With OTA Distribution

35:56 - The Importance of Local Advocacy and Community Involvement

48:00 - Why Investing in Your Brand Creates Long-Term Value

48:47 - How Founders Can Step Back and Empower Their Leadership Team

For vacation rental leaders thinking about the future of their business, this episode offers practical lessons on building a company that can adapt, develop new leaders, and remain strong for generations.

Connect with Rick:

LinkedIn: https://www.linkedin.com/in/rick-elliott-192aba11/

Connect with Brandon:

LinkedIn: https://www.linkedin.com/in/brandon-cox-87930a56/

Connect with Elliott Realty:

Website: https://www.elliottbeachrentals.com/

Facebook: https://www.facebook.com/elliottrealty

Instagram: https://www.instagram.com/elliottbeachrentals?igshid=YmMyMTA2M2Y%3D

LinkedIn: https://www.linkedin.com/company/elliott-beach-rentals/about/

✨ Exclusive Offer to Alex & Annie Listeners:

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

Join through the link below for a chance at featured launch placement and a $250 Amazon Gift Card. Drawing August 15, 2026.

👉 Get started: https://partners.vacationfinder.com/alexandannie

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

Send us a message!

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:

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 #regulations

Send us a message!

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

Send us a message!

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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