THE PODCAST

After 17 and a half incredible years, Traveling Vineyard has officially closed its doors. For many, including myself, it was more than a job—it was a journey filled with connection, personal growth, a...

Laura Wayland's entrepreneurial story began with a bold decision during a challenging economic time. Starting with a single wine shop in 2010, she navigated risks, setbacks, and opportunities to build...

In this episode of Penny for Your Shots, I had the privilege of speaking with Susan Angermann—a woman whose life journey spans ballet, costume design, entrepreneurship, and consulting. Her story is a ...

In this inspiring episode of Penny for Your Shots, I sat down with Isabelle Stephenson, a life coach with a heart for helping women in midlife rediscover themselves, find joy, and navigate life's tran...

In this special solo episode of Penny for Your Shots, I took a moment to reflect from one of my happiest places—Siesta Key Beach. The calm waters, warm sand, and joyful sounds of beachgoers reminded m...

In this episode of Penny for Your Shots, I had the joy of sitting down with my niece, Kalli Fitzgerald—a passionate educator, instructional coach, and all-around amazing human. Kalli’s story is one of...

In this episode of Penny for Your Shots, I sat down with the inspiring Laura Fogarty—a safety educator, advocate, and champion for women’s empowerment. Laura’s journey is rooted in a lifetime of servi...

From Dance Floors to Cheer Gyms: Meet Jill Craven
In this inspiring episode of Penny for Your Shots, I sat down with Jill Craven, an entrepreneur, coach, and mom of four who has turned her passion...

Taking the Leap and Letting Go of Fear
What makes Robin’s story so inspiring is her just go for it mindset. Whether starting a new business, driving a school bus as a high school prank (yes, you read...

Helloooo, Friends!
Pour yourself a glass because it’s time to celebrate a little joy, a little wisdom, and a whole lot of connection. I’m Penny Fitzgerald—entrepreneur, friend, wife, bonus mom, and p...

Today I’m sharing my own story—how wine, connection, and a little leap of faith brought me to where I am today. If you’ve ever wondered how I got started with wine tastings or what sparked this podcas...