Startups in Stilettos

Startups in Stilettos

Have you recently started a business, or are you considering taking the leap to start? Do you find yourself alone or overwhelmed in the whirlwind of early challenges in your Entreprenista journey? Well, you’re in the right place - Startups in Stilettos is for you. Learn what it takes to grow your startup, from your peers in the startup world, and those who are in your shoes (or stilettos, if you will) We’re meeting you where you are to get you through your biggest challenges and toward your biggest goals. From the team behind the Entreprenista podcast, tune in to Startups in Stilettos as you take steps to build your startup from the ground up. So what can you expect from Startups in Stilettos? Each week, we’ll interview a startup founder in our community to uncover their early challenges, learn from the solutions they’ve found, make new connections, and strategize for the future growth of their business. You’ll walk away with practical tips and resources to help you along your journey and a new community member to connect with through the Entreprenista League!

Episodes

Courtney Boylan is Turning Postpartum Struggles Into Beautiful, Functional Solutions With Le Lolo

June 10, 2025 • 32 mins
“I had to do a lot of mindset work around starting to trust myself, building my confidence, telling myself that I could do this and there was nothing more empowering for me than actually launching and continuing to grow.” In this episode of Startups in Stilettos, Ingrid sits down with Courtney Boylan, founder of Le Lolo, a stylish postpartum essentials brand designed to remind new moms of their strength and beauty. After navigatin...
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Nomiki Petrolla’s Strategies for Scaling Startups and Empowering Women in Tech

June 3, 2025 • 28 mins
“Understand your mission. What are you trying to solve? That is the biggest thing. It's not about your idea, it's really about the problem.” Nomiki Petrolla is the founder of Theanna, a social network focused on action opportunity and collaboration for all women tech founders, from idea to scale. Tune in and hear what Nomiki has to say about having a high tolerance for risk, her six-step framework for clients, and maintaining wo...
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Shulamit Ber Levtov Shares Practical Tips to Protect Your Mental Health as a Founder

May 27, 2025 • 32 mins
“If you're having a hard time as a business owner, as an entrepreneur, I invite you to maybe, in this moment, placing a hand palm down over your heart space, and maybe the other hand on top of it, maybe you might like to take a breath, and you might like to say to yourself: ‘This is a natural part of running a business, and there's nothing wrong with me. There's nothing wrong with me.’ And that's where I start.” When Shulamit Be...
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Beth Nydick on Turning Media Appearances Into Impact and Profit

May 20, 2025 • 38 mins
"If you have something to say and something to sell, you're ready for media.” In this episode, we sit down with Entreprenista League member Beth Nydick, a media powerhouse with experience at NBC, MTV, and even creating a cocktail for Oprah Magazine. Beth is a sought-after speaker, author, and podcast monetization strategist who’s on a mission to help founders see their own boldness, step into visibility, and turn every mic momen...
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Kristen Chimack on the Power of Pivoting and Building a Life With Purpose

May 13, 2025 • 35 mins
“When you work for a large organization, everything is planned out, there's a million committees, a million meetings, things take years sometimes to happen. I knew one of the reasons that I really left was I felt like I had become who they wanted me to be and not who I truly am.” Welcome back to Startups in Stilettos! In this episode, we dive into the powerful story of Kristen Chimack, a business coach, Hotel Whisperer, and auth...
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Meet Your New Co-Host! Community Strategist and Entreprenista Ingrid Zapata Read

May 6, 2025 • 24 mins
“I feel so deeply connected to the Entreprenista League because I think having the right people around you makes a big difference.” In this very special Startups in Stilettos minisode, Carlyn Bushman introduces her new co-host, Ingrid Zapata Read! Ingrid shares her heartfelt journey from corporate to building thriving communities for moms and founders, highlighting how curiosity and genuine connections can lead to unexpected yet...
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Natalie Benamou’s Keys for Building Wealth and Impact as Woman Founder

April 29, 2025 • 32 mins
“We have an opportunity to really step into that power of the purse. In five years, [women] are going to own two thirds of the wealth in this country.” This week, Carlyn sits down with Natalie Benamou, founder of HerCsuite®, a platform dedicated to elevating leaders and advance women in the second half of their careers. Carlyn and Natalie talk about the need for women founders to connect and support one another, especially in...
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Liz Brunner Shares the Communication and Speaking Secrets Every Woman Needs

April 22, 2025 • 32 mins
“You have to have a brand today. It's more than just companies who are brands—people are brands today, too. That's the only way you're going to cut through the noise." Liz Brunner, founder of Brunner Communications, is sharing her best tips for making your voice heard and building a personal brand. After 28 years in TV news, Liz Brunner knew there was something else she was meant to do, but she could never pinpoint exactly what t...
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Melissa Armstrong Helps Founders Understand Their Finances to Make Better Business Decisions

April 15, 2025 • 29 mins
“I think that my favorite thing about numbers is that, to me, they are a language to decode, and the most beautiful language because it's the language of truth.” In today’s episode, Carlyn and Richelle speak with Melissa Armstrong, founder of SteadyHand Accounting and Advisory. Melissa has managed more than $500 million in corporate revenue over a 21 year career, and is passionate about helping women entrepreneurs decode their fin...
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Natalie Rosado on Balancing Passion and Purpose With Her Mental Health Expertise

April 8, 2025 • 34 mins
“How can I meet the needs of my therapists, my staff, my clients, my prospective clients, and then the community at large? When you look at it through the lens of social psychology, the focus is on relationships.” In this insightful conversation, hosts Carlyn Bushman and Richelle Pena sit down with Natalie Rosado, a therapist, speaker, and founder of Tampa Counseling Place. Natalie blends her expertise in mental health with her pa...
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Bobbie Carlton's Top Tips for Overcoming Nerves and Mastering Public Speaking

April 1, 2025 • 31 mins
"Every time we get on stage, we have the opportunity to tell our story and to really be seen for what we're doing and what we know." This episode is packed with invaluable advice on the art of public speaking. As PR director for several enterprise software companies, part of Bobbie Carlton’s job is getting executives on stage at conferences and events. But after 20 years in the business, she was tired of supporting solely male exe...
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Ari Krzyzek Turns Founder’s Dreams Into Realities With Her Digital Brand Consultancy

March 25, 2025 • 24 mins
“We had to go back and figure it out because we did not start the business with proper strategy, let me tell you. We also did not have the right funds to start the business, we just were like okay, let's start it.” This week, Richelle Pena talks with Ari Krzyzek, co-founder and CCO of the Chicago-based digital brand consultancy, Chykalophia. With a background in design, strategy, and tech, Ari has cultivated a unique approach to h...
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Sharing our Biggest Podcasting and Public Speaking Secrets

March 18, 2025 • 13 mins
“A great podcast is when you can listen to something, you chuckle and you can say 'wow, that's happened to me,' and that's where you get people's attention.” In this highly requested minisode, hosts Carlyn Bushman and Richelle Pena dive deep into the art of being a captivating podcast guest and sharing your unique story as a founder. Carlyn and Richelle reflect on their own podcasting journeys, dishing out secrets they've learned...
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Samantha Gold’s Journey to Launching an Elevated, Sustainable Children’s Pajama Brand

March 11, 2025 • 32 mins
“I would say first and foremost, lean into that fear of the unknown...you are so much more capable than you think you are.” In this episode of Startups and Stilettos, we sit down with Samantha Gold, the innovative founder of Motette—an elevated children’s pajama brand that seamlessly blends comfort, style, and a sprinkle of magic. Join hosts Carlyn Bushman and Richelle Pena as they dive into Samantha's inspiring journey as a Mamap...
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Emily Esposito Helps People Learn to Dance With Comfort and Confidence

March 4, 2025 • 26 mins
“You know what? I am really good at this and I think if I put my whole heart into it, I can make this something.” In this episode of Startups and Stilettos, we celebrate the transformative power of dance with Emily Esposito, founder of Anyone Can Dance, a New York City-based dance studio. After 20 years of teaching children and performing in theater, Emily pivoted in 2020, discovering her passion for helping adult beginners learn ...
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How Winning Awards Elevates Your Business and Brand

February 25, 2025 • 11 mins
“[Applying for an award] caused me to pause in my business and reflect on the wonderful things that I’ve been able to accomplish.” Welcome back to Startups and Stilettos! In this minisode where your hosts Carlyn Bushman and Richelle Pena dive into tips and tricks for applying to this year’s Entreprenista 100 Awards. Having been both a judge and an applicant, Carlyn brings a unique perspective and tons of insider insights while Ric...
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Lindsey Breitwieser's Biggest Marketing Strategies to Boost Revenue

February 18, 2025 • 32 mins
“We don't have to do a million things, we just have to do the right things. We often feel like ‘I don't have a big budget to spend on ads and that's why I'm not successful.’ We're chasing all of these different marketing tactics… In truth, we don't actually need to be doing that much.” Lindsey Breitwieser spent nearly a decade of her career in marketing working in-house for international agencies, but after starting a family, she ...
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Secrets to Mastering Public Speaking

February 11, 2025 • 13 mins
“Every single successful speaker you admire started with their first speech.” In this empowering episode of Startups and Stilettos, host Richelle Pena tackles one of the most common fears among entrepreneurs: public speaking and media appearances. From shaking during her first TV interview to confidently hosting speaking events and podcasts, Richelle shares her journey and actionable tips to help you overcome your fears. Learn how...
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Richelle Pena Shares Her Biggest Keys to Business Success

February 4, 2025 • 15 mins
"Every obstacle becomes an opportunity. Every mistake becomes a lesson. And this mindset shift didn't just help our business, it transformed our marriage as well." In this special minisode, host Richelle Pena kicks off 2025 with a revealing discussion on balancing marriage and business alongside her husband, sharing insights from their newly released book, The Power Couple. Tune in as Richelle reflects on their transformative jour...
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Balancing Business With Parenthood

January 28, 2025 • 14 mins
"Community is everything, especially when you're balancing life as a single mom and an entrepreneur." In this heartfelt minisode, Carlyn Bushman reflects on the life lessons her children have taught her throughout the years and how those lessons have shaped her entrepreneurial journey. Carlyn also shares about the importance of building and leaning into a supportive community, sharing how her own experiences as a single mom in cor...
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