Ep 194 | Carolyn Childers

How This Unlikely Entrepreneur Went From Corporate to Founding a Billion-Dollar Business

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Carolyn Childers is the CEO and co-founder of Chief, a revolutionary private membership network designed to uplift, empower and connect women executives. Chief has since achieved unicorn status, holding members in over 77% of Fortune 100 companies with a $1.1 billion valuation. 

Although Carolyn never originally set out to become an entrepreneur, her journey from investment banking to strategic and business development positions at companies like Victoria's Secret, Avon Products, and eventually her role as SVP of Operations at Handy led her to a problem she wanted to solve: supporting women executives. She teamed up with her co-founder Lindsay and together they were committed to building a private platform with community groups, member meetups, flagship clubhouse access, and most importantly, a powerful, vetted community. 

It’s said best by Carolyn herself, “It gets lonely at the top,” but for women, it gets lonely a lot earlier.” Today, Chief holds a wait list of tens of thousands of women and continues to empower women at all stages through its educational blog, podcast, and annual impact fund for female-focused causes. It’s clear investing in women pays off. 

In our episode, Carolyn shares her unique journey to entrepreneurship, how she evaluated the risks when leaving her stable job that she was doing well in, and the many myths we all have around entrepreneurship. She also shares how she built momentum early in the business, how she dealt with rejections from many investors, and the importance of having a laser focus on community and building the best experiences. Carolyn also provides her insights on finding co-founders and important aspects to consider, how she's tackled perfectionism, imposter syndrome, and so much more. 


Show Notes:

  • Myths about women in entrepreneurship. [03:26]

  • Journey from investment banking to entrepreneurship. [06:72]

  • Traits of a successful company. [14:35]

  • Running operations at Handy, and how the idea for Chief came about. [18:27]

  • Executing the concept of Chief. [21:14]

  • Carolyn's financial planning for startup risk. [25:03]

  • Carolyn's alignment with co-founder Lindsey. [28:00]

  • Building the early momentum and raising capital. [32:50]

  • Pushing Chief through word of mouth and organic channels. [36:30]

  • Prioritizing essentials and community engagement. [41:52]

  • Navigating entrepreneurship pressure. [41:52]

  • Chief's focus and beneficiaries. [55:15]

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Ep 193 | Dr. Jolene Brighten