Penny for your Shots

Hosted by Penny Fitzgerald

Business Entrepreneurship Arts Food

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Episodes

160

Latest episode

Oct 2026

Language

EN-US

About the show

Welcome to Penny for your Shots. I’m Penny Fitzgerald, and each week I sit down with a brilliant woman for the kind of honest, interesting conversation you might have with a good friend over a glass of wine or your favorite cocktail. Some of my guests are building businesses. Others are finding their voice, changing direction, or figuring out what they want in this next chapter. We talk about the good parts, the hard parts, and what they’ve learned along the way. You might come away with a new idea, a little encouragement, or the thought, “Maybe I could do that, too.” So pour yourself something you love and join me every Thirsty Thursday. There’s always a good conversation, and sometimes a girlfriend story that deserves a toast. Cheers!

Listen to episodes

60 recent

November 5, 2026Episode 16144 min

Why Selling Feels Icky (Even When You Love What You Do) | Karina Klaus

You can love your work, care deeply about your clients, and still put off telling anyone about your offer. Karina Klaus , a sales confidence coach living in Portugal, joins me to talk about why selling can feel so uncomfortable and the beliefs we bring into those conversations. We talk about the corporate habits that follow us into our own businesses, why a full calendar doesn’t necessarily mean freedom, and making changes without putting every other part of your life on the line. Karina also explains the subconscious-work approach she uses with clients, while we both come back to the importance of connection, service, and actually taking action. In this episode: Why “I don’t want to be pushy” can keep you from sharing useful work Recognizing the associations you’ve built around selling Giving yourself room to build a business alongside other responsibilities Bringing the same enthusiasm to your offer that you bring to a favorite restaurant Combining inner work with action so people can find you Karina’s move to Portugal and the chocolate mousse worth returning for Connect with Karina: Free on-demand Sales Blocks Masterclass Website Instagram LinkedIn Become a Penny for your Shots Insider for weekly conversations and updates. 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 29, 2026Episode 16045 min

You Did Everything Right. Why Do You Feel Stuck? | Lori Montry

What happens when you’ve done everything you thought you were supposed to do, and still don’t feel at home in your own life? Lori Montry knows that feeling. A Harvard Law graduate, former attorney, and now a somatic practitioner and author, she shares how a life built around achievement and other people’s expectations led her to ask what she actually wanted. We talk about those familiar “good girl” patterns, trying to prove we’re enough, and learning to notice our own needs. Lori shares her perspective on the coping patterns we carry forward and demonstrates two exercises. I try them with her and describe the change I feel in my shoulders. And, of course, there’s wine! Lori’s memory of sharing a meal with her daughter and choosing a favorite Barolo brings this conversation about self-worth into a wonderfully everyday moment. In this episode: - Questioning a life built around everyone else’s expectations - Recognizing people-pleasing and the pressure to achieve - Exploring Lori’s approach to old coping patterns - Trying the “voo” and “creating space” exercises - Asking for support and allowing change to take time - Choosing something you love without talking yourself out of it Connect with Lori: - Website - Free guide: Your Nervous System Is Talking: Learning to Listen - Book: You’re Not the Problem - Instagram - YouTube - Facebook community Find more conversations and ways to connect at Penny for your Shots , or explore Wine Camp . Follow the show for a new conversation every Thirsty Thursday, and share this one with a girlfriend who might recognize herself in it. Content note: This conversation includes discussion of childhood sexual abuse and emotional eating. Lori shares her personal experience and approach. This conversation is for education and reflection, not medical or mental health advice. If you choose to try the exercises, do so somewhere safe, not while driving, and stop if you feel uncomfortable. 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 22, 2026Episode 15942 min

After Taking Care of Everyone Else, What About You? | Jen Mentesana

After years of taking care of everyone else, what do you want for yourself? Jen Mentesana knows how easily that question can get buried beneath family responsibilities, work, and being the person who keeps everything going. Her path took her from corporate America to coaching, then into the restaurant business with her husband. Eventually, she realized she had lost touch with the work and interests that made her feel like herself. Jen joins me for a conversation about finding your way back, making room for joy, and choosing where your time and energy go. In this episode: The moment Jen realized she needed to change direction How women’s roles and responsibilities can crowd out their own interests Remembering how to play and have fun Making space for quiet, reflection, and intuition Practical language for saying no Recognizing the cost of always saying yes Honoring your own version of a fulfilling life We also talk French rosé, vodka sodas with lemon, and the girlfriends who’ve known us through all our different chapters. Connect with Jen: Website: https://jenmentesana.com/ Instagram: https://www.instagram.com/jen_mentesana/ Podcast: Where Passion Meets Purpose, available through her website Follow Penny for your Shots: Conversations (and Cocktails) with Brilliant Women and join me every Thirsty Thursday. 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 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