Laura Wayland on being an Entrepreneur, Asking for help, and Believing in Yourself

Laura Wayland's episode was the first interview I recorded for my podcast. I knew right away that I wanted to interview her. When I first started my wine business with Traveling Vineyard, Laura was one of the people I tried to emulate. She was savvy, enthusiastic, and fun! I wanted what she had, and asked her for help and insight as I built my team. 

Back in 2010, when Traveling Vineyard reorganized, Laura took the opportunity to buy a wine shop and has since built that one business into many stores and tasting rooms, including wine, beer, cigars, olive oil, and coffee! Her story is fascinating, filled with grit, determination, and inspiration. A resounding theme is to ask for advice and then TAKE IT. 

We've stayed friends through the years and we now travel together at least every-other year if not more frequently. I'm grateful to share these experiences with her and my other wine friends and hope you enjoy the Lessons from Laura.

Laura Wayland is the owner and operator of a retail group of coffee shops and gourmet experience stores throughout the Outer Banks of North Carolina. She developed her business skills while building a direct sales team through an in home wine tasting company as a stay at home mom. She took the knowledge she gained through her experience and purchased a wine and beer store, subsequently developing unique olive oil wine shops and owning three coffee shops in a highly competitive tourist beach market. With 20 years in the wine industry and 13 years as a retail store owner, Laura has achieved success through pursuing her passions while always betting on herself. Getting a bank loan, during the Great Recession with no collateral in a repressed economy taught her to be resourceful and strategic. She is a master at creating retail experiences and memorable moments for her customers. Her background in a direct sales business shaped her knowledge in dealing with customers, managing and motivating a team of employees, and working effectively when every dollar counts. Her focus now is on expanding the footprint of her coffee shops through franchising. https://franchise.frontporc

FREE 3-day workshop—Stop Selling, Start Serving—where I’ll show you how to swap sleazy scripts for service, crush limiting beliefs, and finally have fun showing up for your business.

📅 September 16–18, 2025
 👉 Grab your free spot here: https://pennyforyourshots.com/workshop

This workshop is designed for female entrepreneurs who want more impact without feeling salesy. Let’s get you unstuck!

Join my Insiders crew for weekly updates, tips, inspiration, and fun: https://www.pennyforyourshots.com/insider

Register for my FREE Workshop: Stop Selling, Start Serving
https://www.pennyforyourshots.com/workshop

Looking for my courses or options to work together? https://www.pennyforyourshots.com/about

Wanna sip with us? Join my Sipper Club here: https://pennyforyourshots.com/sip

Learn More, get on the list, or Register for Wine Camp 2026:
https://www.pennyforyourshots.com/winecamp

To connect with Penny, get notified, or learn more, check out www.pennyforyourshots.com

- Follow Penny on Instagram: @penny4yourshots
- Or Facebook: Penny (Kuhlers) Fitzgerald