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Penny for your Shots

Penny for your Shots

By: Penny Fitzgerald
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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!

© 2026 Penny for your Shots
Art Career Success Cooking Economics Food & Wine Leadership Management & Leadership
Episodes
  • How to Stay Open and Connected in a Guarded World with Tracey Elam
    Jun 25 2026

    How do you stay open to people while still trusting your instincts?

    In this week's conversation, Tracey Elam and I explore one of the biggest challenges many of us face: balancing discernment with connection.

    We talk about the conditioning that shapes our beliefs, the ways fear can quietly influence our decisions, and why staying curious may be one of the most powerful tools we have for creating meaningful relationships.

    While we don't see every topic exactly the same way, that's part of what makes this conversation so valuable. It's a reminder that we can stay open, ask questions, and learn from one another without abandoning our own inner knowing.

    In This Episode:

    • The difference between instinct and fear
    • How conditioning influences the way we see the world
    • Why assumptions often block genuine connection
    • The importance of curiosity in relationships
    • What it means to be fully present with another person
    • Being prepared versus living in fear
    • Learning to trust yourself without shutting others out

    Key Topics

    • Self-trust
    • Personal growth
    • Midlife mindset shifts
    • Connection and relationships
    • Curiosity and discernment
    • Fear versus intuition
    • Women rediscovering themselves

    Connect with Tracey: https://www.instagram.com/iamtraceyelam/

    When’s the last time you did something just for YOU? 🍷✨
    Wine Camp 2026 is your chance to escape, sip fabulous local wines, cruise at sunset, laugh around the fire pit, and soak up the magic of New York’s Finger Lakes.

    📍 Dates: July 30–August 2, 2026
    🏡 Spots are limited, so grab yours now: https://www.pennyforyourshots.com/winecamp

    Bring your besties or come solo—you’ll leave with new favorites either way. Wine Camp 2026 is calling. Are you in?

    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

    Show More Show Less
    38 mins
  • How Women Build Confidence Through Connection with Jillian Johnson
    Jun 18 2026

    What if confidence isn't something you find... but something you build?

    In this week's conversation, Penny sits down with Jillian Johnson, founder of LEGS (Ladies Executive Golf Society), to explore how connection, community, and a little bit of courage can transform the way women show up in their lives and businesses.

    While golf may have brought these women together, this conversation is really about something much bigger: creating opportunities, embracing joy, and stepping into spaces where we may not have always felt invited.

    Jillian shares how she went from corporate employee benefits consulting to building a national organization designed to help women feel confident, connected, and empowered through golf.

    They also explore why play matters, how community supports our mental health, and why women deserve spaces that encourage collaboration over competition.

    Please note: This episode includes discussion of trauma and attempted assault. Listener discretion is advised.

    In this episode:

    • How Jillian turned an idea into a national community for women
    • Why confidence is built through connection and experience
    • The networking opportunities many women miss and how to change that
    • Why fun and play are essential, not optional
    • The role community plays in women's well-being
    • How to stop worrying about what others think and start showing up authentically

    If you've been craving more confidence, meaningful friendships, or permission to try something new, this conversation is for you.

    Connect with Jillian:
    Website: legs.golf
    LinkedIn: Jillian Johnson, founder of #LEGS

    When’s the last time you did something just for YOU? 🍷✨
    Wine Camp 2026 is your chance to escape, sip fabulous local wines, cruise at sunset, laugh around the fire pit, and soak up the magic of New York’s Finger Lakes.

    📍 Dates: July 30–August 2, 2026
    🏡 Spots are limited, so grab yours now: https://www.pennyforyourshots.com/winecamp

    Bring your besties or come solo—you’ll leave with new favorites either way. Wine Camp 2026 is calling. Are you in?

    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

    Show More Show Less
    1 hr
  • Follow the Nudge: What's Ahead on Penny for Your Shots
    Jun 11 2026

    What if the ideas that keep nudging you aren't random at all?

    In this special solo episode, Penny shares an exciting preview of what's ahead on Penny for Your Shots and the experiences she's creating for women who are ready for more connection, confidence, courage, and joy.

    From upcoming conversations about building confidence through golf and advocating for women's health, to Wine Camp, Sipper Club, and launching Pour Decisions with Penny and Jeff, this episode is a reminder that you don't have to wait until everything is perfect to begin.

    Sometimes the bravest thing we can do is simply follow the nudge.

    In This Episode:

    • Upcoming conversations about confidence, connection, and women's health
    • Why women need more spaces to show up exactly as they are
    • What Wine Camp is really all about
    • How Sipper Club creates community one cocktail at a time
    • The six-year journey behind launching Pour Decisions with Penny and Jeff
    • Why joy deserves a place on your priority list
    • The permission slip to stop waiting and try something new

    Whether you're considering your next chapter, craving deeper connection, or simply need a reminder that it's never too late to follow what lights you up, this episode is for you.

    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

    Show More Show Less
    14 mins
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