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

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

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

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

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

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

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

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