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

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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Lauren Bercuson Helps Founders Lock in Their Legacies

January 21, 2025 • 34 mins
“In the beginning, if you don't have a team or a system or community around you, it's very easy to feel lost. There are these amazing communities out there for amazing female founders that will really help guide and support you. So, the greatest lesson I learned pretty quickly was that you're never alone. Or, if you feel alone, there are ways to get out of that.” When trademark attorney Lauren Bercuson began the process of foundi...
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Metrics Matter: Growing Your Business With Data

January 14, 2025 • 16 mins
“This is the month to revisit your benchmarks. Measure where you are and plan where you need to go." In this episode, Carlyn Bushman shares actionable strategies to help entrepreneurs set meaningful benchmarks and track their progress effectively. From building dashboards to leveraging AI tools like ChatGPT for growth, Carlyn breaks down how to measure success and prepare for the year ahead. Whether it's growing your email list or...
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Sharing The Secrets of Our Business Journeys

January 7, 2025 • 14 mins
“Just getting started, just stepping into it is so critical. And don't worry about what everybody else thinks all the time. That is the one thing I wish I would have really thought about when I started my business is, don't worry. Comparison is the thief of joy. So just get out there and just do it." Today’s Startups in Stilettos is a minisode all about US! Tune in to hear Carlyn Bushman and Richelle Pena formally introduce oursel...
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6 Biggest Steps to Growing Your Business

December 31, 2024 • 15 mins
“We can all get URLs, we can get tax IDs set up, we can open up a business bank account—those things we can do. We can create a website. We can all put our footprint out there. But entrepreneurship is no joke. It's a journey.” Entrepreneurship can feel overwhelming—but it doesn't need to be! Today’s Startups in Stilettos is a minisode all about the first steps you need to take when building your business. Carlyn and Richelle share...
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Finding Financial Freedom With Alejandra Rojas

December 24, 2024 • 32 mins
“We didn't learn anything that has to do with the emotional and mindset side of money. You might know the instruments, you may know the old literacy that you want. But if you're lacking this other part, it's never going to work.” Alejandra Rojas is an Entreprenista League member and a finance professional who specialized in financial trauma. Alejandra’s interest in finance started at a young age when she would help her parents, wh...
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Our Biggest Tips for Prioritizing Your Mental Health

December 17, 2024 • 17 mins
“Surround yourself with things that are going to uplift you to help you get through those difficult times. And don't be afraid to ask for help." Today’s Startups in Stilettos is a minisode all about mental health and the importance of taking time to pause and prioritize. Tune in to hear Carlyn Bushman and Richelle Pena talk all about the growing pains that come with entrepreneurship, the importance of building a support network, a...
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