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
A Thanksgiving Message for Women Building Something Meaningful
Some episodes are strategy-packed. This one is heart-packed.
If you’re listening while the turkey’s in the oven or you’ve escaped to the quiet of your car for a few minutes, this is your moment to breathe. Today I’m sharing what I’m deeply grateful for — the women who show up, the twists that shaped me, the friendships that became family, and the joy that comes from building meaningful work alongside meaningful people.
Inside this solo episode, I reflect on the courage it takes to build a business while living a full life… and why your spark, your presence, and your dreams matter more than you know.
Whether you’re craving momentum, clarity, or simply the reminder that you’re not doing this alone, I hope this message lands right where you need it.
In this episode, I share:
- The bravery required to be a woman entrepreneur today (especially for women 45+)
- Lessons learned from years in direct sales and coaching
- How friendships became the heart of my business journey
- The joy-fueled beginnings of Wine Camp and the Sipper Club
- Why Serving Superstars brings women back to life
- A Thanksgiving gratitude list just for you
Key Topics:
- Entrepreneurship with heart
- Gratitude and mindset
- Community and connection
- Seasons of reinvention
- Courage, clarity, and momentum
- Building a business that feels meaningful
If this episode stirred something in you and you’re ready for support, Serving Superstars is open. Women who join now get private coaching before the February cohort begins. Let’s build your momentum together. You can book a call with me here: https://www.pennyforyourshots.com/call
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/discovery-call
Wine Camp 2026: Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp
Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider
Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip
Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com
Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald
A Thanksgiving Message for Women Building Something Meaningful
[00:00:33] Penny Fitzgerald: [00:00:00] Hello, friends. Happy Thanksgiving. If you're listening today, maybe you're cooking, maybe you're driving, or maybe you're hiding from the chaos for a few minutes. And if that's the case, I'm glad you're here with me. I wanted to keep today simple. No long interviews, no deep dives into tools or strategy.
Just a moment of reflection and gratitude from one woman, building something meaningful to another. Being an entrepreneur, especially as a woman with a [00:01:00] full life, full responsibilities and a full heart is one of the bravest things we can do. It takes courage, right, to show up, to allow ourselves to be seen.
To step out of the busyness of life and make the effort to make an impact for the people we serve to try to create a better life for ourselves and for the people we love.
And today, I'm just really genuinely grateful for it. I'm grateful for the purpose, this podcast and you all give me.I'm grateful to give back, and I'm so, so grateful For the fun, it's truly rewarding to share the stories of so many brilliant women and seeing so many of you name and claim your own path.
I'm honored to support you in your journey. When I look back at how I got here, it's been a ride and a good one, but a twisty one. I spent years being in business for myself, but not by myself, building something inside someone else's company, and I didn't always get to control the direction of the ship.[00:02:00]
There were highs and there were some big lessons, but what I did get to control were the moments, the small, powerful moments with my team. And honestly, those were my favorite parts. Helping a woman map out a plan for a goal she wasn't sure she could reach. Seeing her show up, stretch herself, and go for it.
Watching a sprint together at the end of a month, refreshing numbers, cheering each other through text threads, celebrating it all, when it clicked, those memories, those live rent free in my heart. That's the stuff that taught me what I was meant to do. That's what made me fall in love with coaching.
Leading with helping women see what they're capable of. And honestly, the friendships, oh my goodness, the friendships. Some of the closest girlfriends I have today started as women in my business years ago. Now they're the ones I sip wine with. Vent to dream with, travel with. They're the ones who will say, girl, adjust [00:03:00] your crown when life gets rough, and they're the ones who will cry with me.
When someone is struggling, then help me get back up and keep going. If entrepreneurship had given me nothing else, the friendships alone would've been worth it. I'm also grateful that business has sometimes meant just following the fun. Wine camp started as, Hey, what if a moment like that between Robin and me, and today it's turned into this beautiful, joyful, full resort experience in the Finger Lakes with 18 of the 30 spots already filled, and I have zero doubt. We'll fill the rest in the next couple of months. Women need this community connection, little adventure and joy.
We all crave it and I'm grateful that something we created out of pure love is becoming a tradition. Women look forward to year after year. I am also grateful for the Sipper Club, which started as a fun cocktail night and has grown into this beautiful gathering of women who show up with their stories, [00:04:00] their creativity and their hearts.
We're expanding it now. More connection, more curated recipes, more experiences, more girlfriend energy. It just feels rightAnd it feels like something that will keep evolving as we do, and of course, serving superstars. This program has changed me as much as it's changed the women in it.
So many female entrepreneurs come to me after putting one foot in front of the other for so long, carrying families, jobs, caregiving responsibilities, aging parents, grand babies, all of it. And somewhere along the way they lose just a little bit of their spark. They get discouraged when something outside their control knocks them sideways.
They push their business to the back burner because life gets lifey and the confidence they used to feel so naturally just gets quieter. That's why I'm grateful for this program because it brings back joy, [00:05:00] it brings back momentum, it brings back confidence, and I'm especially grateful for the women who are joining now because I get to work with them privately
before the cohort begins in February, helping them build skills, clarity, and confidence right now instead of waiting until the new year to feel supported. I love watching women reignite the spark they thought they'd lost. So today, on this Thanksgiving morning, here's what's really on my heart.
I am grateful for the women who trust me to walk with them.I'm grateful for the twists that taught me resilience. I'm grateful for the friendships that changed the whole trajectory of my life. I'm grateful for the fun ideas that turned into traditions. I'm grateful for every woman who has texted me, DMd me, or joined one of my programs and said, I think I can do this, but I need a little help. I'm grateful for you, for your courage, your heart, your willingness to dream, even if those dreams [00:06:00] feel small right now.
Because when women step into who they really are, everybody wins. And when women collaborate and support each other, it creates magic. so wherever today finds you in a busy kitchen, on a quiet walk, in the car, on the way to somewhere warm and loud, I hope you take a moment to feel proud of yourself.
You're building something, you're showing up, you're making an impact, even on the days it doesn't feel like it. and if you're craving more joy, more clarity, more momentum, more you.
Serving superstars might be exactly what you need to start 2026, feeling alive again. The February cohort is open and the women who join now get private coaching with me before we kick off, so you're not waiting until the new year to build momentum. You're creating it now. But today, just soak in the gratitude, enjoy your people, and know that I'm cheering for you.
Always happy Thanksgiving my [00:07:00] friend. Cheers.