Alex and Annie: The Real Women of Vacation Rentals

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
Send us a message!

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
Send us a message!

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!