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