Leadership Shows

June 1, 2025

Rewriting the Rules: Orlie Benjamin on Building Lasoh for a Better Gu…

Send us a message! In our first-of-the-month bonus episode, we are joined by Orlie Benjamin, founder and CEO of Lasoh, a marketing technology platform designed to help vacation rental operators own their guest relationships a...

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May 21, 2025

DesignedVR & Casiola Announce a Game-Changing Partnership in STR

Send us a message! In this episode, we sit down with two industry powerhouses: Dennis Goedheid , CEO of Casiola, and Shahar Goldboim , CEO of Boom and founder of DesignedVR, to unpack the story behind their groundbreaking new...

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May 7, 2025

Rebel in a Gown: Breaking the Rules We Never Agreed To - with Shelley…

Send us a message! In this empowering episode of Alex & Annie: The Real Women of Vacation Rentals, Shelley Brown joins us to talk about how breaking outdated expectations and embracing your weird can lead to more authentic le...

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April 30, 2025

Inside Booking.com’s Strategy to Become the Best Partner for Property…

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we’re joined by Ian Ackland, Managing Director of the Americas at Booking.com, for a candid look at how one of the world's largest travel...

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April 23, 2025

Here Goes Nothin’ – Matt Landau on Leading with Connection

Send us a message! In this week’s episode, Matt Landau returns to the show to share one of the most personal and transformational shifts of his career — a journey from building systems and scaling success to rediscovering the...

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April 16, 2025

Behind the PMS: Meet TravelNet Solutions New CEO Boogie Wittenburg

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Boogie Wittenburg, the new CEO of TravelNet Solutions, makers of Track PMS. With a background in mission-critical techno...

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April 9, 2025

How Beyond is Redefining Revenue Management for Property Managers — w…

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Julie Brinkman, CEO of Beyond, to explore how the company is transforming the way property managers approach pricing and...

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April 2, 2025

Saying No to Say Yes: Brittany Blackman’s Path from Burnout to Self-D…

Send us a message! In this soul-stirring episode of Alex & Annie: The Real Women of Vacation Rentals , we sit down with Brittany Blackman, former vacation rental business owner turned leadership coach and founder of Discover ...

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March 26, 2025

The OG Women of Vacation Rentals: Honoring the Trailblazers that Shap…

Send us a message! In this special episode, Alex & Annie sit down with the original queens of vacation rentals: three powerhouse women who helped shape the industry from the ground up. Meet Jeanne Dailey (Founder & CEO, Newma...

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March 5, 2025

One Industry, One Mission: The Power of Partnership Between VRMA & VR…

Send us a message! In this episode, we are joined by some of the most influential leaders in the vacation rental industry. From VRMA (Vacation Rental Management Association), we welcome Executive Director Anne Gardner and Cha...

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Feb. 26, 2025

VRBO’s Strategy for 2025 & Beyond: Exclusive Interview with Tim Rosol…

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Expedia Group, to discuss VRBO’s vision for 2025 and beyo...

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Feb. 19, 2025

Building a Podcast Empire: How Wil Slickers Scaled Hospitality.FM int…

In this episode, we sit down with Wil Slickers - an industry legend who transformed a single podcast into Hospitality.FM, a full-fledged media company. Wil shares how he scaled his brand from a passion project into a thriving...

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Jan. 29, 2025

Breaking the Mold: How Fred Boothby’s Bold Business Model is Shaking …

In this week’s episode, Alex & Annie sit down with Fred Boothby, CEO of Enjoy Unique Stays, to explore how he’s breaking the mold in the vacation rental industry. What started as a small side business has grown into a thrivi...

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Dec. 18, 2024

For the Love of Gatlinburg: How Tom Goodwin Uses Storytelling to Pres…

In this week’s episode, we’re thrilled to welcome back Tom Goodwin, CEO of Mountain Laurel Chalets and host of " For the Love of Gatlinburg" Podcast. Tom shares insights into his family-run vacation rental business in Gatlinb...

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Dec. 11, 2024

From the Vault: Get Out of Your Own Way and Step into Your Power, wit…

In this special throwback episode, we revisit a powerful conversation with Amber Hurdle, CEO and founder of Employer Brand Central. Originally aired around this time last year, this episode marks a pivotal moment for Alex & A...

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Nov. 27, 2024

From 2 to 70: Declan McGonigal’s Blueprint for Vacation Rental Success

In this week’s episode, we sit down with Declan McGonigal, the dynamic owner-operator of My Beach Vacation Rentals, based in North Myrtle Beach. Declan’s story is one of grit, growth, and ingenuity, as he shares how he went f...

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Nov. 13, 2024

Building a Boutique Brand: How Steve Turk Brings Hotel Standards to V…

In this episode, we sit down with Steve Turk, founder of Tangy Management, a vacation rental management company known for its unique hotel-inspired approach to hospitality. With over 24 years of experience in luxury hotels, S...

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Oct. 30, 2024

Throwback to Our Fan-Favorite Episode with The OG’s of the Panhandle:…

In this special re-air of one of our most popular episodes, Alex & Annie brings together a powerhouse panel of industry experts, known as the OGs of the Panhandle. Our guests— James Olin, Steve Caron, Lino Maldonado, and Paul...

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Oct. 16, 2024

Building a Global Vacation Rental Brand Through Franchising with Casi…

In this week’s episode, we welcome back Dennis Goedheid, founder and CEO of Casiola Vacation Homes. Dennis returns to share exciting updates on his company's growth, including the launch of a new franchise model. Since its in...

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Oct. 9, 2024

Insights from Ian Carter, former CEO of Hilton International: How to …

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Ian Carter, the former CEO of Hilton International and current Chair of the Board for Watches of Switzerland, Eataly, The Boston University...

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Oct. 1, 2024

1st of the Month Bonus News Announcement: Extenteam Announces New Sta…

Exclusive offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & A...

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Sept. 11, 2024

Boom Launches the World’s 1st AiPMS, with CEO Shahar Goldboim

In this week’s episode, we sit down with Shahar Goldboim, CEO of Boom, to discuss the world’s first AI-driven Property Management System (AiPMS). Shahar shares the story behind Boom’s inception and how his passion for innovat...

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Sept. 4, 2024

Heather Bayer’s Trust-Based Blueprint for Vacation Rental Success

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex and Annie sit down with Heather Bayer, a ...

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Aug. 28, 2024

High-Altitude Culture: Nurturing Teams in Luxury Vacation Rentals wit…

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode of Alex & Annie: The Real Women of Vacation Ren...

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