Penny for your Shots
Welcome to Penny for your Shots, the podcast that uncorks the stories and insights of exceptional female entrepreneurs and leaders. Hosted by Penny Fitzgerald, this show is your front-row seat to engaging and inspiring discussions served over a glass of your favorite libation.
Each episode, brilliant women from diverse fields and backgrounds will share their journeys, challenges, and experiences with stories that empower, educate, and entertain. And, we'll include memories shared with friends over a glass of wine or favorite cocktail!
Subscribe now, grab your favorite beverage and join us every Thirsty Thursday for your weekly dose of inspiration, as we toast to the incredible women who are leading the way, one conversation (and cocktail) at a time. Cheers!
Penny for your Shots
From Caregiver to CEO: How Systems Saved Carrie’s Sanity
What if the skills you’ve used to care for your family could become the foundation of a business that cares for you?
This week’s guest, Carrie McWherter, is a virtual assistant who turned her natural gift for organization—and a season of caregiving—into a thriving business that helps entrepreneurs reclaim their time (and their sanity).
In our conversation, Carrie shares how she went from caring for her mother-in-law to running a successful VA business that keeps her clients organized, supported, and growing. We dive into the systems that make life and business easier—and the mindset shifts that make it all possible.
Here’s what we talk about:
- How caregiving inspired Carrie’s business journey
- Why strong systems create calm, not chaos
- Simple ways to automate tasks and free up energy
- The confidence that comes from clarity and organization
- How to use your real-life skills to serve others and build income
💡 If every month feels like recreating the wheel, it might be time to create simple SOPs—repeatable checklists that save time, reduce stress, and make delegation easy.
If you’ve been craving a little more breathing room, sometimes it just takes a nudge, a fresh set of eyes, or a new way of looking at what’s already working.
Curious where to begin? You can reach out to me here to explore what might bring more ease and flow into your days: 👉 pennyforyourshots.com/chat
To learn more about Carrie's business: https://www.allinorderwithcarrie.com/
When’s the last time you did something just for YOU? 🍷✨
Wine Camp 2026 is your chance to escape, sip fabulous local Rieslings, cruise at sunset, laugh around the fire pit, and soak up the magic of New York’s Finger Lakes.
📍 Dates: July 31–August 2, 2026
🏡 Spots are limited, so grab yours now: https://www.pennyforyourshots.com/winecamp
Wine Camp 2026 is calling. Are you in?
Join my Insiders crew for weekly updates, tips, inspiration, and fun: https://www.pennyforyourshots.com/insider
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