Penny for your Shots

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

October 9, 2025 49 mins

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 succ...

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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 Arielle Loupos, founder of Flower Girl, a period underwear brand designed to be safe, sustainable, and actually cute. Arielle shares her journey from e-commerce consultant to mission-driven entrepreneur, an...

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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 taking care of yourself is the first step to building wealth, giving generously, and leading boldly.

In this conversation, we dive into:

  • Why women should never apologize for building wealth
  • How giving back can ac...
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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, Kristi brings a unique perspective on leadership, embodiment, and growth.

We covered so much good ground, including:

  • The surprising benefits of growing up in a coaching household
  • How somatic practices ca...
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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’re meant to do.

This week’s conversation is all about breaking free from hustle and building something better. You’ll hear the story of a woman who walked away from abuse, built and scaled multiple b...

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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 Kami Guildner’s wisdom on raising our voices, to Larissa Banting’s reinvention story, to Frankie Elder Reedy’s fire for justice, to Shirah Benarde’s scrunchie-turned-nightcap invention that’s keeping women saf...

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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 recently rebranded her show and stepped into a new chapter with boldness and faith—and she’s here to share what that process really looked like.

Inside this conversation, we cover:

  • The courage (and clarity...
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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 risking it all on a yacht job she technically wasn’t “qualified” for, to building a business that helps women claim true freedom: time, money, and location.

In our conversation, we cover:

  • Why chasing...
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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 backstage pass. “Sexy is a vibe, not a size” sets the tone for a body-positive, age-inclusive approach to portraits that feel like you.

About Liz:
Liz Hansen is the owner and photographe...

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August 7, 2025 10 mins

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 gather with intention. Whether you were there in Virginia or watching from afar, this peek behind the curtain will give you all the feels—and a little FOMO (don’t worry, 2026 is calling).

Inside this...

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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 didn’t just stumble into entrepreneurship. She tested, pivoted, and reimagined her way into it—learning from failure, navigating trolls, and bottling mixers by hand to meet demand. In this candid conv...

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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 away—without a backup plan—and said yes to coaching, authenticity, and a business built around service.

In this episode, Terri shares how she:

  • Went from speech pathologist to multi-million...
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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 sought-after media strategist and soulful storyteller, Rachel helps female founders pitch themselves in a way that’s rooted in purpose—not pressure.

In this episode, we dive into:

  • How to pitch yourself wi...
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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 corporate role to become a world champion fitness model and launch a purpose-driven marketing agency. Her story is full of bold pivots, mindset gold, and more than a few truth bombs.

Inside this episode, Aoif...

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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 skeptics alike. Kate’s not just a beauty founder. She’s a truth-teller, label-reader, and lifelong hair nerd on a mission to make sustainability approachable, affordable, and actually enjoyable.

We talk about:

  • Why most ...
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 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, Merrie Mill, and Flying Fox Vineyards. But before she was blending Bordeaux-style reds, she was studying infectious diseases. (Yep. You read that right.)

In this conversation, Emily shares:

  • Her unexpe...
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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 wine experiences in the region.

In this episode, I’m joined by Elizabeth Pelly, co-owner of Merrie Mill and one of the women I’m most excited for our Wine Camp crew to meet this summer. She shar...

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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 and author. We talk about how to trust yourself in uncertain seasons, why your past experiences are never wasted, and how embracing creativity as a way of being can lead to more joy, courage, and freedom.

Whether you&...

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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 get sober nearly three years ago, the healing work she’s done since, and how she’s now using her experience to coach other women who feel stuck, unworthy, or like they’ve lost their spark.

We talk a...

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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 shutdown. But instead of giving up, she pivoted—again and again—and found her next calling in public relations.

In this episode, Larissa shares:

  • How she went from publicist to wedding planner (and back again)
  • Wh...
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