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We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing.

Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relationships with every guest.

Together, they explore what it really takes to build stronger guest relationships, improve direct booking performance, and think more strategically about marketing in vacation rentals.

In this first episode, Orlie shares the thinking behind Lasoh and the problem she believes the industry still has not solved. While many of the core systems in vacation rentals are designed to manage properties, pricing, and distribution, far fewer are built to help operators understand guests, strengthen relationships, and market in a way that creates long-term value.

The conversation looks at what happens when hospitality gets overshadowed by operations, why guest data matters far beyond the initial booking, and why marketing deserves a bigger role in growth strategy.

Episode Chapters:

01:56 - Why Orlie Benjamin built Lasoh for vacation rental marketing

04:19 - What’s missing from most vacation rental PMS platforms

07:58 - Vacation rental tech vs. hotel tech: where the gaps still exist

09:47 - Asset management vs. guest experience in hospitality

11:01 - Why hospitality gets harder to scale in vacation rentals

13:42 - Why revenue management and marketing should work together

16:33 - The real levers of growth: customers, spend, and repeat stays

21:03 - How Lasoh helps operators capture guest data and personalize marketing

25:46 - Guest-first marketing vs. inventory-first marketing

This episode sets the tone for the series ahead and offers a valuable perspective for anyone looking to build a more thoughtful, guest-centered marketing strategy.

✨ Exclusive offer for Alex & Annie listeners ✨

Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie.

Access the offer here: https://explore.lasoh.io/alex-annie

Valid through May 31, 2026.

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/lasoh.io/

#vacationrentals #vacationrentalmarketing #directbookings