Mar 26 2025 66 mins
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, Newman-Dailey Resort Properties), Valerie Hawkins (Co-Owner & CEO, Perdido Key Realty), and Audrey Miller (Co-Founder & CFO, Cottage Connection of Maine) - each with a story full of grit, heart, and game-changing innovation.
From starting with whiteboards and spiral notebooks to pioneering tech adoption and leading through legislative battles, these trailblazers reveal how they built thriving companies in a male-dominated industry - before vacation rentals were even “a thing.”
Key Topics Discussed:
1️⃣ Jeanne Dailey’s Story
2️⃣ Valerie Hawkins’ Story
3️⃣ Audrey Miller’s Story
4️⃣ The Early Days of Vacation Rentals
5️⃣ First Software, Systems & Tech Innovation
6️⃣ Being Women in a Male-Dominated Industry
7️⃣ Finding Community in the Industry
8️⃣ Early Networking, Software Choices, and Mentors
9️⃣ The First Leap into Property Management Software
🔟 Working with Family & Building a Legacy
Connect with Jeanne:
LinkedIn: https://www.linkedin.com/in/jeannedailey/
Connect with Valerie:
LinkedIn: https://www.linkedin.com/in/valerie-hawkins-04aa0a43/
Connect with Audrey:
LinkedIn: https://www.linkedin.com/in/audrey-leeds-miller-23748b4/
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