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!
Episodes
136 episodes
You Don’t Have to Carry It All Alone | Solo Episode
What happens when the woman who’s always encouraging everyone else suddenly feels overwhelmed herself?In this vulnerable solo episode, Penny opens up about feeling foggy, stretched thin, and unexpectedly emotional after running out of pr...
Women, Wine, & Connection: What Makes Wine Camp Special
What if the thing you really needed wasn’t another productivity hack… but a few days away with women who simply get you?In this solo episode, I’m sharing the story behind Wine Camp and why this experience has become one of the m...
Why Women Hide Their Brilliance (and How to Be Seen) with Shauna VanderHoek
Why do we hold ourselves back from being seen? Especially when we know we’re meant for more..?In this episode, Penny sits down with author and book mentor Shauna VanderHoek to talk about the real reason so many women stay stuck: fear of ...
Reinventing Your Life and Money Mindset with Diane Farber
What if the life you’re living right now… isn’t the final version?In this episode, Penny sits down with Diane Farber — her neighbor, friend, and a woman who proves that reinvention doesn’t have an expiration date.Diane shar...
Your Hormones Aren’t the Problem, They’re Your Power | Dr. Aumatma Simmons
What if your hormones weren’t the problem, but instead were the key to everything?In this episode, I sit down with Dr. Aumatma Simmons, a naturopathic doctor who’s spent nearly 20 years studying hormones, fertility, and the deeper...
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Bougie on a Budget: Spend Without the Stress | Budget Besties
If the word “budget” makes you want to pour a glass of wine at 9am… stay with me.This conversation with the Budget Besties is not about restriction. It’s about freedom.Shana and Vanessa are on a mission to take the shame out of mo...
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Starting Over at 50: Building Freedom with Belinda Sandor
Starting over at 50 can feel overwhelming. Or, it can become the beginning of something extraordinary.In this episode, Belinda Sandor shares how she rebuilt her life during a major transition: divorce, financial stress, and becoming a si...
It’s Your Turn: Reinventing Life After 50 with Karen Ansen
What if the moment you’ve been waiting for… is right now?Karen Ansen joins me for a conversation that will feel very familiar if you’ve ever looked around your life and thought, “Okay… what’s next for me?”After years of bui...
Why the Finger Lakes Is the Next Must-Visit Wine Region with Caley McKnight
If the Finger Lakes isn’t on your travel list yet… it might be after this conversation.In this episode, I’m joined by Caley McKnight, an enology student at Cornell University who’s immersed in one of the most exciting (and underra...
Grow Your Business by Growing You: Breaking Free from Hidden Patterns with Dr. Shannon South
Sometimes the thing holding your business back isn’t strategy, marketing, or systems.Sometimes it’s the patterns you didn’t even know were there.In this episode of Penny for Your Shots: Conversations & Cocktails with Brill...
Control-Alt-Delete Self-Doubt: A Real Confidence Reset
What if the voice telling you to play small… isn’t telling the truth?In this episode, Penny sits down with keynote speaker, author, and confidence coach Simone Knego to talk about the stories women tell themselves—and how those st...
From Small-Town Bar to Children’s Author at 65
What if the dream you’ve been carrying for decades is still waiting for you?Susan Lienau is 65 years young. She’s spent over 40 years running a small-town bar in northeast Iowa. She’s helped launch a community museum, serves on the city ...
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Time Poverty Is Real: Stop Hiding in Busy
Busy doesn’t mean productive. And exhausted doesn’t mean successful.In this episode, Peggy Sullivan — former corporate executive turned researcher and speaker — shares what 12 years of data revealed about time poverty, burnout, an...
Busy, Capable, and Still Stuck? Let’s Talk Confidence
You can be busy, capable, and doing all the “right” things—and still feel stuck.If you’ve ever wondered why your results don’t match your potential, this episode is for you.In this conversation, Penny sits down with Nada Lena N...
You’re Not Starting Over—You’re Building on Everything
If you’re in a season of transition and quietly wondering, “Did I miss my window?”—this episode is for you.Penny is joined by Julie DeLucca-Collins, confidence coach, author, and fellow podcaster, for an honest conversati...
When Your BS Meter Gets Better With Age
There’s a moment many women reach—usually after a few decades of living—when things get clearer. The stories don’t quite add up anymore. The excuses land flat. And that inner voice gets a whole lot louder.In this episode of Penny for...
Self-Worth, Power, & Using Your Voice with Intention
If you’ve ever questioned your value, your voice, or whether you’re really using your seat at the table the way you’re meant to—this episode is for you.I’m joined by Sarah Barnes-Humphrey, a longtime logistics leader, pod...
You Don’t Need Consensus to Lead—You Need Clarity
If you’ve ever felt like you know what good leadership looks like—but still catch yourself waiting for agreement, approval, or buy-in—this episode will feel like permission you didn’t know you needed.I’m joined by Tami Reiss<...
From Overwhelmed to Organized: Systems That Give You Your Life Back
Have you ever hired help—only to feel more overwhelmed than before? More questions. More messages. More mental clutter than ever?In this episode of Penny for Your Shots, I’m joined by Melissa Morris, founder of A...
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Stop Treating Joy Like a Luxury: A New Year Reset
What if the most powerful New Year reset isn’t about doing more—but about finally letting yourself matter again?In this short solo episode, Penny shares a surprising insight from a recent workshop that revealed just how many women are qu...
When Entrepreneurship Is Hard—and You Keep Going Anyway
Entrepreneurship can be meaningful, joyful, and deeply fulfilling—and it can also be really hard.In this solo episode, Penny shares a candid look back at 2025 and the behind-the-scenes realities of building a purpose-driven business. Thi...
From Small Town Roots to Big Careers—and Finding Your Way Home
Some conversations feel like a catch-up over wine—and then turn into something deeper. This episode is one of those.I’m joined by Aimee Goeman, someone I knew of growing up in small-town Iowa but didn’t truly know until now. Our...
From Crisis to Clarity: Melissa Hampton on What Matters Most
What happens when life brings everything to a full, heartbreaking stop?This week, I’m joined by Melissa Hampton, a financial planner, entrepreneur, and mom whose world changed overnight when her seven-year-old son faced a life-thr...
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Take the Trip: Travel Coach Laura Rahn on Designing Memorable Travel
If you’ve been waiting for a sign to finally take the trip, this episode is it.Travel Coach Laura Rahn spent 33 years in education before following a lifelong pull toward adventure. Raised as a military kid who moved cons...
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 deepl...