All Episodes

March 26, 2025 66 mins

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, 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/

Ready to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.

Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie

#VacationRentals #WomenInLeadership #ShortTermRentals

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.