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
105 episodes
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—...
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Episode 105
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49:53
Breaking Period Taboos: Arielle Loupos on Flower Girl’s Mission
Most of us grew up whispering about periods—and using products that were far from ideal. Pads, tampons, discomfort, and silence were just part of the deal.But what if there’s a better way?In this week’s episode, I’m talking with <...
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Episode 104
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49:23
Women, Wealth & Worth: Nancy Griffin on Owning Your Power
What if your health, your wealth, and your self-worth were all part of the same story?This week, I’m joined by Nancy Griffin, founder of Women Worth and Wellness. Nancy believes women are their own greatest asset—and that...
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Episode 103
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48:12
Presence Over Hustle: Kristi Chaves on Aligned Business
What if your business didn’t run on hustle—but on presence?This week, I sat down with Kristi Chaves, a business coach who helps women build successful businesses rooted in alignment and authenticity. Raised in a family of coaches,...
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Episode 102
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39:29
Why Hustle Culture Fails Women—and What to Build Instead
Hustle harder. Push through. Work until you make it.Sound familiar? For so many women, hustle culture has become a badge of honor—but behind the scenes, it’s leaving us burned out, resentful, and completely disconnected from the work we’...
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Episode 101
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56:02
Cheers to 100 Episodes: Stories, Lessons, & Momentum for Women
One hundred episodes. One hundred conversations. Countless lessons, laughs, and reminders that women are powerful beyond measure.In this milestone episode, I look back on the stories that have shaped Penny for Your Shots—from Ka...
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Episode 100
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10:33
Reinvention, Confidence, & the Messy Middle with Angel Wilborn
Reinvention isn’t just about starting fresh—it’s about showing up, even when life feels messy.This week, I’m joined by Angel Wilborn, the vibrant host of the GLOE podcast (God, Life, Organization, & Entrepreneurship). Angel ...
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Episode 99
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58:43
How Sara Vezensek Went from Yacht Chef to a Life of Freedom
From yacht kitchens to coaching women around the world, Sara Vezensek has never played by the rules—and in this episode, she shares how courage (not confidence) shaped her journey.Sara’s story takes us from waitressing in Slovenia to ris...
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Episode 98
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1:00:51
Chicago Boudoir with Liz Hansen: Safe, Empowering, Unapologetically You
Chicago boudoir photography meets radical self-confidence in this conversation with photographer Liz Hansen. If you’ve ever wondered what actually happens during a boudoir session—and why so many women call it life-changing—this episode is your...
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Episode 97
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45:00
What Really Happens at Wine Camp...
What do you get when you mix sunshine, sisterhood, a few bottles of rosé, and a whole lot of heart? Wine Camp 2025—and it was pure magic.This solo episode is part recap, part invitation, and 100% a celebration of what happens when women ...
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Episode 96
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10:04
From Bartender to Brand Builder: April Wachtel’s Cheeky Pivot
What happens when a cocktail educator, brand strategist, and former Bacardi ambassador decides to launch her own product line—in the middle of a global crisis? You get Cheeky Cocktails…and one seriously inspiring journey.April Wachtel di...
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Episode 95
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59:30
From CEO to Coach: Terri Levine’s Joy-First Business Shift
Dr. Terri Levine spent years climbing the corporate ladder, eventually becoming CEO of a national healthcare company with nearly 3,000 employees. But behind the title, she felt exhausted, disconnected, and deeply out of alignment. So she walked...
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Episode 94
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54:36
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PR with Heart: How to Be Visible and in Integrity
What if being more visible didn’t mean being more “salesy”?Rachel Van Dolsen built a thriving PR agency in her twenties, but it wasn’t until she became a mom that she fully stepped into the kind of work that lights her up. Now a s...
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Episode 93
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54:38
From Burnout to World Champion: Aoife Roche on Identity, Grit, and Growth
What happens when you climb the ladder of success—only to realize it’s leaning against the wrong wall?This week, I’m talking with Aoife Roche, a fiercely honest, wildly inspiring entrepreneur who walked away from a high-powered co...
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Episode 92
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1:04:44
Better Hair, Less Plastic: Why Dip is Changing the Shampoo Game
Sustainable haircare that actually works? Yes, please.In this week’s episode, I’m chatting with Kate Assaraf, founder of Dip—the bar shampoo and conditioner brand that’s winning over luxury lovers and plastic-free ...
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Episode 91
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53:44
Grit, Grapes, & 25 Vintages: Emily Hodson on Making Great Wine
If you’ve ever wondered what really goes into making a world-class bottle of wine—or even imagined sipping wine in Virginia with the woman who made it—this episode is for you.Emily Hodson is the powerhouse winemaker behind Veritas,...
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Episode 90
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59:53
Elizabeth Pelly on Merrie Mill & Virginia Wine Country
What happens when an art-loving couple trades London for Virginia Wine Country with a baby in tow and a wild idea to start a vineyard? You get Merrie Mill Farm & Vineyard—one of the most visually stunning, community-focused, and creative wi...
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Episode 89
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46:24
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Reclaim Your Creative Power with Pia Mailhot-Leichter
What if creativity isn’t just about what you make—but how you move through life?In this soulful and energizing conversation, Pia Mailhot-Leichter shares her journey from agency creative director to purpose-driven coach ...
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Episode 88
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1:00:54
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Rebuilding Worth: Kacey Voelker on Sobriety, Confidence & Purpose
What does it take to rewrite your story—on your own terms?In this heartfelt episode, I catch up with Kacey Voelker, a former wine guide I hadn’t seen in years. And wow... what a journey she’s been on. Kacey opens up about her decision to...
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Episode 87
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1:02:13
Pivot, Pitch, Repeat: Larissa Banting’s Reinvention Story
What do you do when your business takes a hit—then another, and another?Larissa Banting built a seven-figure destination wedding company in Costa Rica, only to be hit with economic downturns, internal theft, and a pandemic shutdow...
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Episode 86
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58:46
Spring Clean Your Life: Let Go, Reset, and Refocus for the Rest of 2025
Is it time for a mid-year reset?In this solo episode, I'm sharing what I’ve been up to lately—including some deep spring cleaning that’s gone way beyond closets and cabinets. From dusty old Wine Spectator magazines to a pink Goo...
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Episode 85
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6:53
From Cancer to Calling: Erica Carrico’s Million-Dollar Pivot
When Erica Carrico was diagnosed with cancer in her 30s, she found herself rocking her baby and questioning everything. What followed was a promise to stop living for everyone else—and to start showing up for the purpose she was meant to fulfil...
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Episode 84
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50:34
Joy as Your Soundtrack: Stories, Healing & French Rosé
What if the stories you tell yourself are the very things keeping you stuck?In this episode, I chat with Carrie Rowan—author, musician, speaker, coach, and joy-bringer—about the power of rewriting your inner narrative. From person...
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Episode 83
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41:48
Big Boobs, Bigger Dreams: How Wrax Is Changing the Game
What happens when your sports bra is the thing holding you back?This week, Penny interviews Frankie Elder-Reedy, athlete, entrepreneur, and the creator of Wrax—a revolutionary boob-harnessing bra system that’s empowering women to move wi...
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Episode 82
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1:13:24
Follow the Fun: Rediscovering Joy to Find What’s Next
What if the key to your next chapter isn’t buried in a business plan… but in a playlist, a memory, or a moment of laughter?In this solo episode, Penny explores the idea that joy isn’t a luxury—it’s a clue. Through stories of missed highw...
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Episode 81
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11:53