Penny for your Shots

By Penny Fitzgerald

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 e

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FAQs about Penny for your Shots:

How many episodes does Penny for your Shots have?

The podcast currently has 152 episodes available.

Penny for your Shots episodes:

June 25, 2026 How to Stay Open and Connected in a Guarded World with Tracey Elam
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/
Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
39min
June 18, 2026 How Women Build Confidence Through Connection with Jillian Johnson
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
Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
1h 1min
June 11, 2026 Follow the Nudge: What's Ahead on Penny for Your Shots
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/call
Wine Camp 2027 - 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
...more
14min
June 04, 2026 Trust Your Gut: Danielle Frank on Reinvention & Joy
What if the thing you're supposed to do next doesn't make sense to anyone but you?
Danielle Frank has built a fascinating career that took her from Hollywood publicity to the luxury wine and spirits industry, where she's spent more than two decades representing some of the world's most iconic brands. Along the way, she's made some bold decisions, including ending relationships that no longer fit, walking away from toxic work environments, and finally publishing a book she wrote 14 years earlier.
In this conversation, Danielle shares why trusting your gut is often the first step toward finding the life you're actually meant to live.
You'll hear:
• How Danielle went from Hollywood to the world of champagne
• Why she quit a toxic job without having a backup plan
• The difference between intuition and impulsiveness
• How confidence is built through action, not certainty
• The story behind A Wine Lover's Guide to Parenting
• Why it's never too late to pursue a dream you've put on hold
• The importance of becoming your own hype woman
This episode is for any woman standing at a crossroads and wondering whether she should take the leap.
Connect with Danielle:
Website: www.daniellefrankauthor.com
Instagram: @createagreatstory
LinkedIn: Danielle Frank
Email: [email protected]
Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
53min
May 28, 2026 How Caring for Her Mom Inspired Vicky McGrath’s Business
What do you do when a deeply personal heartbreak opens the door to your life’s next purpose?
After watching her mother decline from Alzheimer’s and seeing her father struggle as the primary caregiver, Vicky McGrath realized how many families were navigating aging and dementia completely overwhelmed and unsupported. Instead of saying “someone should help,” she became the person who did.
In this episode, Vicky shares how she started a senior home care business in her 40s with zero healthcare experience and built a company that now supports hundreds of seniors and families across Ontario.
This conversation is honest, emotional, practical, and deeply relevant for anyone caring for aging parents or wondering if it’s too late to start over.
In this episode:
• The early signs of dementia families often miss
• Why caregiving can feel so isolating
• The importance of having a care plan before a crisis
• What families need to know about aging at home
• Starting a meaningful business later in life
• Why your hardest experiences can become your purpose
Connect with Vicky: https://seniorcarebusinesscampus.com/
Learn more about Ladies' Executive Golf Society (LEGS): https://ladiesexecutivegolfsociety.com/
Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
53min
May 21, 2026Feeling Stuck? Small Shifts to Help You Feel Better Again
Feeling stuck lately? You’re not alone.
In this follow-up to last week’s vulnerable conversation about overwhelm, Penny shares gentle, practical ways to begin moving forward again when life feels heavy, messy, or emotionally off.
This isn’t about hustling harder or pretending everything’s fine. It’s about small shifts that help you reconnect with yourself, your joy, and the people you serve.
Through stories, mindfulness practices, sensory grounding, and reflections on community, connection, and Wine Camp memories, Penny offers encouragement for anyone navigating overwhelm, burnout, or uncertainty right now.
In this episode:
Why asking a better question changes everything
The difference between hustle culture and feminine momentum
Simple grounding practices that help you feel better fast
How mindfulness helps move you from overwhelm into action
Why joy and connection matter more than perfection
The role community plays in healing and growth
If you’ve been waiting to “get it together” before showing up again, this episode is your reminder that you don’t have to do this alone.
✨ Book a complimentary Connection Call:
Penny for Your Shots Coaching Call
🥰 Get 30 days of Calm:
https://www.calm.com/gp/766EHFRXKF376Y46FJ
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
13min
May 14, 2026 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 pre-recorded guest episodes and realizing: “Oh… this week it’s just me.”
But what unfolds is a powerful reminder that overwhelm does not mean you’re failing. It often means you’ve been carrying too much for too long.
This conversation is for the women who are:
• Holding everything together
• Building businesses while supporting everyone else
• Feeling stuck between excitement and exhaustion
• Wondering if they’re the only ones struggling with visibility, confidence, or momentum
Penny shares honest reflections on midlife reinvention, imperfect action, asking for support, and why women were never meant to quietly shrink themselves with age.
Key Takeaways:
• Why “foggy brain” seasons don’t mean you’re off track
• The mindset shift that helps overwhelmed women move forward
• How small actions build confidence and clarity
• Why visibility can feel vulnerable for women entrepreneurs
• The importance of community, connection, and letting yourself be supported
Key Topics:
• Midlife reinvention
• Women entrepreneurs and overwhelm
• Visibility and confidence
• Rediscovering yourself after 40
• Taking imperfect action
• Community and support for women
• Building a meaningful life and business
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
13min
May 07, 2026Women, 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 most meaningful parts of my work. Yes, there’s incredible wine. Yes, there’s beautiful scenery. But what happens at Wine Camp goes far beyond tastings and vineyard tours.
It’s about connection.
It’s about friendship.
It’s about women giving themselves permission to slow down, laugh, reconnect, and remember who they are outside of their daily responsibilities.
I’m also sharing:
How Wine Camp first began
Why these friendships form so quickly
What makes the Finger Lakes wine region so special
The wines I’m most excited to share this year
What women really leave with after the experience ends
Whether you’re already joining us, Wine Camp curious, or simply craving more joy and connection in your life, this episode will give you a feel for what Wine Camp is truly about.
Wine Camp 2026:
📍 Finger Lakes, New York
📅 July 30 – August 2, 2026
Learn more: pennyforyourshots.com/winecamp
Key Topics:
Women reconnecting with themselves in midlife
Why friendship matters more than we realize
The power of shared experiences for women
Finger Lakes wine country and Riesling wines
Saying yes to yourself again
Creating meaningful connection through travel and community
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
15min
April 30, 2026Why 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 visibility.
Shauna shares her journey from corporate consulting to helping entrepreneurs publish books; and how her own fear of being seen showed up at the exact moment she was stepping into something bigger.
This conversation is about more than books. It’s about becoming the woman who’s willing to be seen.
In This Episode, You’ll Hear:
Why visibility feels so uncomfortable (and what to do about it)
How writing a book can elevate your authority and impact
The surprising ways fear can show up in your life and body
Why your business growth is directly tied to your personal growth
How to move through the blocks that are keeping you stuck
Key Topics:
Visibility and mindset for women entrepreneurs
Writing and publishing a business book
Overcoming fear of judgment
Personal growth and business success
Building authority as a female entrepreneur
Connect with Shauna:
Website: askshauna.com
LinkedIn: Shauna VanderHoek
Excerpt from The Book You’re Meant to Finish: A Reflective Journal for Nonfiction Writers to Overcome Blocks, Gain Clarity, and Get Unstuck: http://askShauna.com/gift
Free summit for business owners and message-driven writers: https://yourbookyourmessage.com/
Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
39min
April 23, 2026Reinventing 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 shares her journey from social worker to financial advisor, building a career from scratch in her 40s, and then starting over again in a brand new community in her 80s. Her story is layered with courage, curiosity, and the kind of wisdom that only comes from doing the thing, even when it’s uncomfortable.
This conversation is also a gentle (and sometimes not-so-gentle) nudge for women to take ownership of their financial future. Because being “taken care of” isn’t the same as being informed.
In this episode:
What it really takes to reinvent yourself at any stage of life
The courage behind changing careers later in life
Why fear doesn’t mean stop; it means GO
The importance of financial literacy for women
What happens when you don’t understand your money
How to stay curious, connected, and engaged as you age
If you’ve been waiting for the “right time” to make a change… this might be it.
Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call
Wine Camp 2027 - 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
...more
1h 17min

FAQs about Penny for your Shots:

How many episodes does Penny for your Shots have?

The podcast currently has 152 episodes available.