Caroline took a leap from a career in investment banking to one launching a high-end luxury retail line that sold in more than 400 stores worldwide from Neiman Marcus to Bloomingdales. But that was only the first chapter in this now-established entrepreneur’s startup career.

When this first company failed two years later, Carolyn wasn’t deterred. Instead, she launched a multi-million dollar interactive marketing agency, Cake Communications. And, she also used the failure as an opportunity to give a very real and very vulnerable TEDx talk.

Today Carolyn is running global women’s collaborative accelerator, Circular Board, a virtual, 12-week program. “[As] an entrepreneur myself, I’ve helped raise billions of dollars in capital through my work as an investment banker for JPMorgan and as founder of Cake Communications,” she says. In her role, Carolyn teaches others how to do the same, and she serves as an advocate for women in business, connecting female entrepreneurs to the capital, resources, mentors and partners to fuel their growth.

Additionally, Carolyn serves on the board of the Texas A&M Mays College of Business, as a member of the Dell Women’s Entrepreneur Network and as a United Nations Global Accelerator delegate. She is the recipient of the American Express Micro to Millions Award, a Sam Walton Emerging Entrepreneur and an Entrepreneur magazine 2016 “Woman to Watch.” She’s also been featured in The Huffington PostFortuneTime and on MSNBC, among others.

In episode 14 of I Want Her Job: The Podcast, Editor Polina Selyutin speaks with Carolyn about the lessons learned from launching two businesses; her goals for growing Circular Board; and the vital importance of connection, collaboration and curiosity.


  • Who Run The World? Girls!: “All of us reap the rewards when women succeed. It’s job creation. It’s economic growth. It’s social impact. There are so many different benefits that we achieve when women succeed. It isn’t just about gender equality, but about quality of life for each and every person.”
  • Breaking Barriers: Carolyn discusses the difficulty many female entrepreneurs face when they look to relocate for an accelerator program, and shares how Circular Board is the ultimate answer to that conundrum.
  • Get There Quicker: For entrepreneurs, Carolyn advises not to compromise on the big vision and to seek funding earlier to achieve that vision. “What happens is [women] compromise that vision because they don’t have the resources on hand today, and they start to bootstrap in a way that changes that path.”
  • Ladies Leading: “Women are incredible leaders. We are really empathetic. We understand our customers in a real unique way, which I think is a huge advantage,” Carolyn says.
  • Give And Get: During Carolyn’s business experience, she noticed women didn’t ask for enough help often enough. She addresses that at Circular Board via a “Give and Get” exercise that encourages women to practice asking for help.
  • On Diversity: “When you bring that to the table it creates this infusion of energy, and people start bouncing ideas off one another and bring a different lens to a problem,” Carolyn says.
  • The Hardest Part Of Starting A Business: Carolyn believes the middle stage is the hardest part – when your company is growing and one needs the capital to hire, but doesn’t have the funds yet to do so.
  • Let It Go: How transparency, honesty and letting go of fear can liberate an entrepreneur to grow even faster.
  • Word Of Mouth Cultivation: Carolyn shares how she used referrals to grow her businesses and reduce marketing costs.
  • That X Factor: “Ask others what you’re good at,” Carolyn says. Hearing what others list as your strengths is a great way to find out what you might be taking for granted that actually can help set you – and your business – apart.
  • Favorite Resource: Harvard Business Review
  • Learn More: Connect with Carolyn on TwitterInstagram and the Circular Board website