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“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 author of "The Cost of Staying." Join us as she shares her journey of deliberate networking, discovering her unique skills, and of course, making the big leap.
Learn how she navigated the fears, built confidence through community, and created a new path filled with purpose. If you're contemplating a career pivot or struggling with the fear of change, this episode offers invaluable insights on listening to your intuition, planning your leap, and stepping into a life you truly love.
Kristen is also part of our Entreprenista Expert Council, where she offers expert advice to help women founders grow and scale their businesses. Kristen also shares how she helped Entreprenista secure the perfect location for Founders Weekend 2026!
What we talked about:
Her New Book, "The Cost of Staying" [3:00]
How Kristen Prepared to Leave Her Corporate Job [10:25]
Her Hotel Whisperer Expertise [20:25]
Advice for Planning an Event [25:00]
Closing Thoughts [32:00]
Connect with Kristen:
Members of our Entreprenista League get access to live Office Hours with top founders that have been on our show! Join the Entreprenista League today! We can’t wait to welcome you, support you, and be part of your business journey!
Get Featured on Startups in Stilettos
Want a chance to be featured on Startups in Stilettos? We’re currently accepting applications from our Entreprenista League members to be featured on the show! Think of the Entreprenista League as your team members in what can be a lonely startup founder’s journey. You’ll have access to a private community of like-minded female startup founders 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, social channels – and, of course, the Startups in Stilettos podcast – and so much MORE!
Grow Your Startup with Startups in Stilettos
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Guests
Kristen Chimack
Hosts
Carlyn Bushman
Carlyn Bushman is a seasoned business consultant, entrepreneur, and advocate for female founders. She founded POP Business Academy to empower women entrepreneurs with tools for building sustainable, profitable businesses. As CEO of Carlyn Bushman Consulting, she specializes in helping product- and service-based business owners navigate financials, marketing, and growth strategies. With extensive corporate experience, Carlyn, a mom in a blended family and lifelong learner, has been featured on Good Morning America and in Times Square. She's here to help you make money and stay in business.
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