Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the 

opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

“What I have realized is people can take your paycheck, they can take your title, they can strip you of these different external things, but your personal brand can never be taken from you.”

In this episode of the Entreprenista Podcast, bestselling author, keynote speaker, and confidence expert Heather Monahan shares how losing her corporate executive role pushed her to reinvent herself from the ground up. She reveals the LinkedIn post that changed her life, how she turned a personal brand into a global speaking career, and why confidence is something you build—not something you're born with.

Heather also dives into the practical strategies behind growing a business through authenticity, landing paid speaking engagements, leveraging viral content, using AI to work smarter, and creating products your audience actually wants. Whether you're navigating a career transition, building your brand, or looking to scale your business, this conversation is packed with actionable advice and inspiring stories.

What We Talked About:

Reinventing After Rejection [7:36]

Monetizing Your Skills [21:21]

Leveraging LinkedIn for Speaking Engagements [27:30]

Building Your Signature Talk [33:32]

Utilizing AI for Business Growth [42:05]

Connect with Heather:

@Heathermonahan on Instagram 

Heather Monahan on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

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Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

Resources mentioned:

DealScore AI 

“I realized that everything I had built at task rabbit gave me the credibility, gave me the value ad to be a great investor and to be a great partner to other founders.”

In this episode of the Entreprenista Podcast, Stephanie sits down with Leah Solivan, founder of TaskRabbit and founder and general partner of Precedent VC, for an inspiring conversation about entrepreneurship, resilience, and what it really takes to build something that changes an industry.

Leah shares the story behind TaskRabbit, from getting the idea while living in Boston and running out of dog food, to quitting her secure job at IBM, cashing out $27,000 from her pension, and launching what would become one of the companies that helped pioneer the gig economy. She opens up about building the first version of the platform from her apartment, recruiting the first taskers, raising capital during the 2008 financial crisis, and eventually scaling TaskRabbit to 44 markets before selling the company to IKEA.

What We Talked About:

An Early Entrepreneurial Spark [1:43]

Launching TaskRabbit Locally [9:01]

Scaling TaskRabbit and Selling to IKEA [15:49]

What Investors Look for in Founder Pitches [23:17]

JOMO: The Joy of Missing Out [28:13]

Connect with Leah:

@leah_solivan on Instagram 

Leah Solivan on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

⁠⁠Apple Podcasts⁠⁠ | ⁠⁠TuneIn⁠⁠ | ⁠⁠Spotify⁠⁠ | ⁠⁠iHeart Radio⁠⁠

Be sure to share your favorite episodes across social media to help us reach more amazing female founders, like you.

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

“If you follow your own path and your own passion it will shine through and you will be successful.”

What does it really take to turn a personal brand into a thriving business? This week on The Entreprenista Podcast, Stephanie sits down with fitness entrepreneur Katie Austin to unpack the decade-long journey behind building the KA App—a bootstrapped digital fitness and nutrition platform with hundreds of workout classes, healthy recipes, habit tracking, and an engaged community.

Katie opens up about growing up with fitness icon Denise Austin, forging her own path in an industry where comparisons are inevitable, and why slow, steady growth has been one of her greatest competitive advantages. From balancing a career in sports broadcasting while building her business from scratch to leading a remote team, navigating social media as the face of her brand, and preparing for motherhood, Katie shares the honest realities of entrepreneurship behind the highlight reel.

What We Talked About:

How Her Background in Sports Influenced Her Business Path [2:30]

Managing Mental Health While Building a Personal Brand [8:12]

The Power of Snapchat for Niche Marketing [14:59]

Turning Social Media Followers into Customers [25:25]

Embracing Your Own Path as an Entrepreneur [33:02]

Connect with Katie:

@katieaustin on Instagram 

Katie Austin on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

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Resources mentioned:

Get Your FREE Copy of Allison Maslan's Wall Street Journal Bestselling Book, Scale or Fail, Here 

“Why this is so important is that most business owners have no idea where they are in the scaling process and that's why they get stuck”

In this episode of the Entreprenista Podcast, Stephanie and Courtney sit down with Allison Maslan—CEO of Pinnacle Global Network, Wall Street Journal bestselling author, and entrepreneur who has built and sold nine companies—to uncover the blueprint for creating a truly scalable business.

Allison shares the pivotal moments that shaped her entrepreneurial journey, from growing a successful advertising agency in her twenties to surviving a life-changing car accident that forced her to rethink what success really meant. She explains why so many founders become trapped inside the businesses they built and introduces her proven Five Phases of Scaling, revealing where entrepreneurs get stuck and how to move toward a founder-independent company.

What We Talked About:

Growing Up in an Entrepreneurial Family [1:47]

The Car Accident That Changed Everything [5:44]

The Five Phases of Business Scaling [11:29]

Designing a More Scalable Business Model [20:27]

Becoming a Bestselling Author [27:26]

Allison’s Morning Vision-Crafting Ritual [34:01]

Connect with Allison:

@allisonmaslan on Instagram 

Allison Maslan on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

⁠⁠Apple Podcasts⁠⁠ | ⁠⁠TuneIn⁠⁠ | ⁠⁠Spotify⁠⁠ | ⁠⁠iHeart Radio⁠⁠

Be sure to share your favorite episodes across social media to help us reach more amazing female founders, like you.
Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

“I just really think that the team at possible really puts together conversations that are future facing. Everything that I have seen happen here as stoked a little fire in my brain of how can build towards this.”

In this episode of the Entreprenista Podcast, Courtney sits down with Nikki Scott, Head of Partnerships at TikTok, angel investor, and creator economy expert. Nikki shares how she helped build TikTok's brand partnerships organization from the ground up, why saying "yes" before you're ready can transform your career, and the mindset shifts that separate successful founders from everyone else.

From growing global teams and identifying standout talent to investing in early-stage startups, Nikki offers an inside look at what she's learned working at the intersection of technology, creators, and entrepreneurship. She also reveals how small business owners can leverage TikTok authentically, why storytelling is one of the most valuable business skills you can develop, and the simple confidence-building habit that has changed the way she approaches opportunities.

What We Talked About:

Nikki's Career Journey and Early Experiences [3:10]

The Importance of People and Community [8:54]

Mindset Shifts for Small Business Owners [14:51]

Hiring for Grit and Etiquette [21:02]

Advice for Building a Career [27:04]

Tools and Secrets for Business Success [33:08]

Connect with Nikki:

@nikkibogoscott on Instagram 

Nikki Scott on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

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“I want people to have the financial freedom and independence and really steer the boat when it comes to their businesses, by understanding how to market themselves properly and share their stories.”

In this episode of The Entreprenista Podcast, Courtney sits down with creator, entrepreneur, and CEO Valeria Lipovetsky to discuss how she transformed a passion for storytelling into Valeria Inc., a media company generating more than $25 million in annual revenue.

Valeria shares the pivotal moment she decided to bet on herself, how her husband and co-founder Gary helped recognize the massive opportunity in creator-led media, and why protecting her creativity became the key to scaling her business. From hiring a CEO early to building long-term partnerships with brands like Dior and Paige Denim, she offers an inside look at the systems, mindset, and leadership required to grow beyond being "just an influencer."

‍

What We Talked About:

Scaling and Structuring a Creative Business [5:55]

Navigating Challenges in Entrepreneurship [11:21]

Creating Value and Long-Term Partnerships [17:19]

The Dynamics of Co-Founding with a Partner [23:23]

Future Aspirations and Investments 29:26]

‍

Connect with Valeria:
@valerialipovetsky on Instagram 

​​Valeria Lipovetsky on LinkedIn

‍

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

⁠⁠Apple Podcasts⁠⁠ | ⁠⁠TuneIn⁠⁠ | ⁠⁠Spotify⁠⁠ | ⁠⁠iHeart Radio⁠⁠

Be sure to share your favorite episodes across social media to help us reach more amazing female founders, like you.

‍

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

“I want people to have the financial freedom and independence and really steer the boat when it comes to their businesses, by understanding how to market themselves properly and share their stories.”

In this episode of The Entreprenista Podcast, Courtney sits down with creator, entrepreneur, and CEO Valeria Lipovetsky to discuss how she transformed a passion for storytelling into Valeria Inc., a media company generating more than $25 million in annual revenue.

Valeria shares the pivotal moment she decided to bet on herself, how her husband and co-founder Gary helped recognize the massive opportunity in creator-led media, and why protecting her creativity became the key to scaling her business. From hiring a CEO early to building long-term partnerships with brands like Dior and Paige Denim, she offers an inside look at the systems, mindset, and leadership required to grow beyond being "just an influencer."

What We Talked About:

Scaling and Structuring a Creative Business [5:55]

Navigating Challenges in Entrepreneurship [11:21]

Creating Value and Long-Term Partnerships [17:19]

The Dynamics of Co-Founding with a Partner [23:23]

Future Aspirations and Investments 29:26]

Connect with Valeria:on Instagram 

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

⁠⁠Apple Podcasts⁠⁠ | ⁠⁠TuneIn⁠⁠ | ⁠⁠Spotify⁠⁠ | ⁠⁠iHeart Radio⁠⁠

Be sure to share your favorite episodes across social media to help us reach more amazing female founders, like you.

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

Resources mentioned:

Entreprenista listeners can receive 30% off your The Breadwinners annual subscription here.  

“The end goal and the mission for why we exist is to create a safe space where the community replaces guilt with a sense of agency and confidence.”

In this episode of The Entreprenista Podcast, Alexis shares her journey from corporate executive to founder, the unexpected lessons she learned after stepping away from a career she spent decades building, and how a single dinner sparked a movement. She opens up about the realities of building a business while raising three young children, navigating the emotional highs and lows of entrepreneurship, and why she's committed to creating intimate, intentional spaces where women can connect authentically.

Alexis and Stephanie also discuss the evolving definition of ambition, the power of community-first business building, leveraging AI tools like Claude to launch and grow a company, the future of education in an AI-driven world, and why meaningful in-person connections matter more than ever.

What We Talked About:

Creating a Safe Space for Women [2:11]

The Birth of The Breadwinners [10:35]

Building a Community from Scratch [23:15]

Leveraging AI Tools for Business Efficiency [30:48]

The Importance of Giving in Community [39:14]

Exploring Substack as a Creative Outlet [43:29]

Connect with Alexis:
 @wearethebreadwinners on Instagram

Alexis Contos on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

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“I became really enamored not necessarily with the technology but with the people hosting the events and bringing people together. That was just the root of our mission.”

In this episode of The Entreprenista Podcast, Stephanie and Courtney sit down with Julia Hartz, co-founder and former CEO of Eventbrite, to unpack her extraordinary 20-year journey from aspiring ballerina to one of the few women to found and take a company public as CEO. Julia shares how a chance meeting with her future husband and co-founder led to the creation of Eventbrite, the lessons learned from 27 consecutive investor rejections, and how relentless curiosity, resilience, and customer obsession fueled the company's growth. 

Julia opens up about navigating some of the toughest moments in entrepreneurship—including leading Eventbrite through the COVID-19 pandemic when the company's revenue effectively disappeared overnight. She discusses the mindset shifts that helped her grow as a leader, the realities of raising capital, taking a company public, and the emotional process of stepping away following Eventbrite's acquisition. 

‍

What We Talked About:
The Journey of Julia Hartz [2:17]
Building Eventbrite: Idea to Execution [15:31]
Navigating Challenges During Covid [22:08]
Leadership During Crisis [29:27]
Taking Eventbrite Public [37:45]
Life After the Sale [45:52]

‍

Connect with Julia:
@juliahartz on Instagram

Julia Hartz on LinkedIn

‍

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

⁠⁠Apple Podcasts⁠⁠ | ⁠⁠TuneIn⁠⁠ | ⁠⁠Spotify⁠⁠ | ⁠⁠iHeart Radio⁠⁠

Be sure to share your favorite episodes across social media to help us reach more amazing female founders, like you.

‍

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

Join our ⁠Entreprenista League⁠ community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our ⁠website⁠ and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!

Curious about joining the Entreprenista League? ⁠Sign up ⁠here⁠⁠ for a free info session.

Resources mentioned:

Entreprenistas get 35% off Dubsado with code ENTREPRENISTA35 at dubsado.com/entreprenista.

“But at the end of the day we want to show who we really are as a company and we have a lot of fun as a company. So the strategy in our marketing is to just show up as who we are.”

In this episode of The Entreprenista Podcast, Stephanie sits down with Becca Berg, co-founder and CEO of Dubsado, the all-in-one business management platform beloved by creative entrepreneurs. Becca shares how a childhood love of entrepreneurship, a successful photography business, and a personal need for better systems inspired her and her husband to create Dubsado from their kitchen table. 

From bootstrapping a SaaS company to serving more than 30,000 customers, Becca opens up about the realities of building a business alongside her spouse, navigating major business challenges, scaling a lean team, and maintaining profitability for over a decade without venture capital. She also reveals how Dubsado is leveraging AI to streamline operations, why customer trust is the foundation of every business decision, and the lessons she's learned about leadership, resilience, and taking time away from the business to avoid burnout. 

What We Talked About:

Building Dubsado [7:11]

Navigating Business with Family Dynamics [12:38]

Self-Funding: The Path Less Traveled [18:34]

Leveraging AI for Team Efficiency [25:41]

Challenges in Subscription Businesses [36:17]

The Importance of Self-Care for Founders [41:24]

Connect with Becca:

@beccaliz_ on Instagram 

Becca Berg on LinkedIn

Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.

⁠⁠Apple Podcasts⁠⁠ | ⁠⁠TuneIn⁠⁠ | ⁠⁠Spotify⁠⁠ | ⁠⁠iHeart Radio⁠⁠

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Disclosure: This episode is sponsored by Dubsado. We only partner with brands we believe in and think our community will love. As always, all opinions are our own.