Penny for your Shots

Hosted by Penny Fitzgerald

Business Entrepreneurship Arts Food

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Episodes

157

Latest episode

Oct 2026

Language

EN-US

About the show

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!

Listen to episodes

60 recent

October 15, 2026Episode 15849 min

Building a Business That Fits Your Life | Kym Brake

What does it take to build a business when your family’s needs have to come first? For Kymbirley “Kym” Brake , it began in a hospital room. While caring for her daughter, she started helping other parents with taxes and insurance paperwork. That work grew into a business that allowed her to support them both while remaining available for her daughter’s care. Kym joins me to talk about financial independence, finding confidence in your own abilities, and making business decisions that reflect the life you actually need. We also discuss taxes, asking for professional guidance, and the challenge of knowing when to keep going and when to change direction. In this episode: • How helping other families became the beginning of Kym’s business • A teacher who saw her gift for numbers • Building a career around caregiving • Asking better questions about your business and taxes • Perseverance, pivoting, and the pressure to keep your word • Choosing your clients and protecting your energy • Making room for travel, connection, and a little fun Connect with Kym: Website: https://www.octaxbrake.com/ Instagram: https://www.instagram.com/octaxbrake/ Visit her website to explore her services, courses, and membership. Know a woman who is building a business around a complicated life? Share this conversation with her. This conversation is for general information and is not individualized tax or legal advice. Consult a qualified professional about your circumstances before acting on any tax strategy discussed. 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

October 8, 2026Episode 15758 min

Build a Business That Fits Your Life | Lisa Somers

What happens when growth turns the business you wanted into a job you no longer recognize? Lisa Somers joins me for an honest conversation about building Marketplace Superheroes with her brother, navigating a million-dollar debt, and learning that there is almost always another solution, even when the numbers feel overwhelming. Lisa shares how she moved from psychology training into entrepreneurship, why she eventually chose a lean team over a large corporate-style structure, and what makes a family business work without damaging the family relationship. We also talk about therapy, confidence, the people you call when a problem feels enormous, and why human connection matters even more in an AI-heavy world. In this episode, you'll hear: ▪️ How Lisa found her way into entrepreneurship without a business degree ▪️ The hard lessons that came from bad business deals and major debt ▪️ Why agency and problem solving matter more than having every answer ▪️ How Lisa and her brother divide roles and protect their relationship ▪️ Why bigger is not always better when you are designing your business ▪️ What authentic connection looks like when so much content is automated Connect with Lisa: Marketplace Superheroes Instagram Free resources: Go Live Get Paid training Free companion guide 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

October 1, 2026Episode 15653 min

What Happens When Your Body Stops Responding the Way It Used To | Corry Matthews

What happens when you’ve spent decades understanding fitness and nutrition, and suddenly your own body stops responding the way it always has? Corry Matthews spent more than 25 years in fitness and nutrition, including competing as a professional bodybuilder. But in her 40s, the strategies she had always relied on stopped working the same way. We talk about perimenopause, hormones, food, strength training, HRT, changing bodies, and why the answer in midlife isn’t always to simply try harder. We also talk about learning to work with the body you have now and giving yourself some grace along the way. In this episode: • Why Corry’s 40s changed what she thought she knew about fitness • Perimenopause and hormone changes • Food, blood sugar, and learning your individual triggers • Resistance training and everyday movement • HRT and the evolving conversation around menopause • Confidence, aging, and giving yourself grace • A family trip to Italy involving gelato, limoncello, and some fabulous memories Connect with Corry: https://corrymatthews.com/ Corry also mentioned a symptom tracker during our conversation. Find it here: https://strengthandgracefitness.com/hormonequiz/ 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

September 24, 2026Episode 15555 min

Find Yourself First, Then Watch Who Shows Up | Rose Lambert

A lot of us have quietly expected one person to be everything: best friend, travel partner, confidant, our whole social life. It rarely works, and it's not really fair to ask it of anyone. Rose Lambert has been married twice, twenty-four years the first time, twelve the second. Today she's single, and she says she has more friends than she's ever had in her life. Rose is a professional matchmaker who works with some of the wealthiest clients in the country, and she came to the work sideways, after losing a close friend to suicide during what she calls the loneliness epidemic, and after a spiritual awakening that changed how she saw her own marriages. In this episode, you'll hear: Why Rose calls it "the loneliness epidemic," and what she watched it do to her own life Chosen family, and why some friendships outlast marriages Numerology and Vedic astrology as tools for understanding compatibility Where Rose and Penny disagree on marriage, divorce, and "fixing" a partner Why real richness can't be taken from you Guest: Rose Lambert, professional matchmaker Website: roselambertmatchmaker.com Facebook: facebook.com/roselambertmatchmaker Instagram: instagram.com/roselambertmatchmaker 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

September 17, 2026Episode 15457 min

The Conversation Most of Us Avoid (And Why It's an Act of Love) | Lynn Lambrecht

If something happened to you tomorrow, would the people who love you know where to start, or would they be left guessing? This week's guest is Lynn Lambrecht, a former aviation executive turned contingency planning advisor whose work started the day she volunteered on airplane crash sites in her 20s. She's since walked her own parents through illness and decline, written a book on getting prepared, and built a career on making a scary-sounding topic feel doable. In this episode, you'll hear: Why this is daily life, not a doomsday plan The one feature already on your phone that could help EMTs help you What ER doctors say is the hardest part of an emergency (and the fix) Why baby steps beat trying to do it all in a weekend Show notes and Lynn's links: thelivingplanner.com | linkedin.com/in/lynnlambrecht 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

September 10, 2026Episode 15358 min

What Can't Come With You? A Lesson in Letting Go to Level Up

Ever notice how "leveling up" always seems to mean doing more? More hours, more offers, more on your plate? This week, Andrea Engstrom joins me to make the case for the opposite. Andrea's built a business generating six figures a month while working three days a week, and she got there by figuring out exactly what needed to go, not what needed to be added. In this episode: - The hot air balloon analogy that reframes what growth actually requires - How mental load quietly limits what women build - The process Andrea used to shrink a four-day sales process into three - A simple journaling prompt for reconnecting with what you actually want - Why your circle either grows you or keeps you exactly where you are Learn more about Andrea and grab a spot for her free Nail Your Niche coaching call at andreaengstrom.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

September 3, 2026Episode 1521 hr 1 min

It's Not Bragging. It's Letting the Right People Find You. | Lynn Harris

Have you ever done something meaningful and kept it to yourself because talking about it felt like bragging? Lynn Harris is the founder of Gold Comedy , the online school and community helping women and non-binary creators build comedy careers, side hustles, and creative confidence — but this conversation goes way beyond comedy. Lynn and I talk about the real difference between bragging and simply letting people know what you do, and why staying quiet about your gifts isn't humility, it's a habit that keeps you small. In this episode: - Why staying quiet about what you do isn't humility, it's a habit - How two of Lynn's students changed their careers in midlife by no longer keeping quiet - The real difference between an anecdote and a story worth telling - Why being specific, not broad, is what actually makes people relate to you More from Lynn Harris & Gold Comedy: - Gold Comedy: https://www.goldcomedy.com/ - Explore classes & community: https://club.goldcomedy.com/ - Build and Pitch Any Idea with Ryan Cunningham (starts Sept 28): https://goldcomedy.com/ - Use code GOLD10PERCENTOFF for 10% off any Gold Comedy class or membership - Book a free comedy consult with Lynn: https://calendly.com/chat-with-lynn-harris/chat-about-your-comedy-goals-w-lynn-harris-gold-comedy Also mentioned in this episode - Dead Moms Club: It'll Be Funny, We Promise: https://youtu.be/vYwpnawcC1M 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

August 27, 2026Episode 15154 min

Build a Life You Control: What's the Worst That Could Happen? with Melissa Broughton

Ever caught yourself wondering if the "safe" job is actually the risky one? This week I'm sitting down with Melissa Broughton, owner of Busy Bee Advisors and creator of the One Hour Bookkeeper training system, to talk about what it really takes to leave corporate behind and build something that's actually yours. Ten years into her own business, Melissa's found a rhythm most corporate jobs could never offer — the freedom to fly out for her son's college football games every weekend, fire a client who isn't a fit, and build an income on her own terms. We talk about: - Why corporate "job security" isn't what it used to be - A simple exercise for facing the fear that keeps women stuck ("what's the worst that could happen?") - The real story behind a $90,000 fraud catch — and why the human touch still matters even with AI in the mix - What to actually plan for before you take the leap Melissa's sharing a free 3-step guide to work-life balance with our listeners: https://gift.1hourbookkeeper.com/penny 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

August 20, 2026Episode 15055 min

You Already Have the Skills, with Sarah Noked

Have you ever looked at your own past (a job, a business, twenty years of running a household) and quietly decided that none of it counts toward what you want to do next? This week I'm sitting down with Sarah Noked, a 20-year Online Business Manager (OBM) and the founder of OBM School, who admits she believed exactly that when she started her own business, even though she'd already run a landscaping company from the ground up. In this episode, you'll hear: What an OBM actually does, and why it's different from hiring a VA Why Sarah calls the idea of "having no transferable skills" a total farce How to know if your "why" is strong enough to carry you through the hard days Why documenting your systems (yes, even the ones in your head right now) might be the single biggest thing missing from your business What quality of life actually looks like on the other side of twenty years of building something real Sarah's free resources for our community: OBM Starter Kit: https://www.obmschool.com/penny-starter SOP Kit: https://www.obmschool.com/penny-sop-kit Find Sarah at https://www.sarahnoked.com/, on Instagram (https://www.instagram.com/sarahnoked/), LinkedIn (https://www.linkedin.com/in/sarahnoked/), and on YouTube at The OBM Show with Sarah Noked. Read the full blog post: https://www.pennyforyourshots.com/blog/you-already-have-the-skills 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

August 13, 2026Episode 14952 min

Your Story Doesn't Have to Be Polished to Matter | Elizabeth Brett

Have you been telling the same version of your story for so long it started to feel like a performance instead of the truth? This week I sit down with Elizabeth Brett, a former NBC reporter turned storytelling coach, to talk about what happens when we stop polishing our stories and start telling the true ones. Elizabeth spent almost a decade shaping thirty-minute interviews into ninety-second segments, covering everything from presidential campaigns to hurricanes, to the Olympics. Somewhere in the middle of that career, she left it all behind after a heartbreak that made her question everything, and built a new one helping women find their voice. We talk about: - The difference between your origin story and what Elizabeth calls your North Star story - Her sovereignty filter for knowing what's actually yours to share, and when - A near-death experience in the ocean with her daughter that reshaped how she shows up - Why your story was never really about you in the first place And yes, we also talk mocktails, because a girl's gotta relax at the end of the day too. Find Elizabeth at elizabethbrett.com or on Instagram @elizabethsbrett. 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