A Night With San Diego’s Top Two Female CEOs

April Rieger
  • By: April Rieger
  • In: Entrepreneurship, Events, Fireside Chat, Networking
  • Posted: November 12, 2018

Chelsea-Kaufman-and-Flossie-HallOn Thursday, November 8th, Girls in Tech San Diego held the first entrepreneurship roundtable in their Speaker Series. Members of the community from all different backgrounds and stages of professional growth gathered at PetDesk in downtown San Diego to drink in the wisdom of two prominent and brilliant local entrepreneurs: Flossie Hall, founder of Healthy Mama, and Chelsea Kaufman, founder of LEARN Academy. After light bites and introductions, Girls in Tech San Diego’s Program Director Rajni Roshan moderated the discussion about the startup journey in which Flossie and Chelsea spoke candidly on the rocky, the rewarding, and everything in between.

Misconceptions Destroyed

One misconception that was destroyed early on in the evening is that you need to have a business background to start a successful company. If you’ve had an idea for a business but you’ve been afraid that you missed the boat just because you haven’t been channeling all your energy into entrepreneurship since that first childhood lemonade stand, it’s time for you to breathe a sigh of relief. Flossie started out in the medical field and Chelsea’s background is in theater. Although their businesses and stories are very different, there is one thing they share: both women identified a need in their community, rose up to meet it, and refused to give up when the going got tough.

Flossie Hall, CEO & Founder of Healthy Momma

Flossie noticed that doctors would tell patients to eat right and exercise, but would never give them the tools to carry out those orders. She also noticed that the existing meal prep delivery businesses were expensive and lacked child-friendly options. In 2016 she founded Healthy Mama, providing families in her community with affordable and healthy meal options. Looking back, her lack of business acumen turned out to be an asset: she wasn’t afraid to try because she didn’t realize how hard it would be. “I failed all over the place,” she admitted, “but I just kept doing it every day.” That same grit and determination led her to teach herself everything she could about business by researching online and reaching out to people in her circle with knowledge in different areas, and meanwhile, Healthy Mama continued to grow and thrive.

Chelsea Kaufman, CEO & Co-Founder of LEARN Academy

Chelsea Kaufman was always a theater kid, and her original plan was to run her own theater company. She was building educational programs for nonprofits when she found herself feeling frustrated with the people in charge and knowing there had to be a better, more effective way of running things. She earned her master’s degree and was managing a theater company when she met her husband. “I think we began making a business plan for some kind of business on our first date,” she recalled. They saw people and companies leaving San Diego because the tech talent they needed wasn’t there, and so Chelsea and her husband decided to start a coding bootcamp. They didn’t just build a business, though – they built a family. Their family continues to grow with new classes and community partners.

It hasn’t always been smooth sailing

Both Flossie and Chelsea experienced setbacks, and they were kind enough to share the lessons they learned. When Flossie entrusted the website for her e-commerce business to a company who claimed to be experts, she ended up losing millions of dollars in revenue and having to reduce her staff; it took four months for her business to recover. She encouraged the audience to trust their instincts and be prepared – and legally protected – for a professional parting of ways. Chelsea also struggled with staffing and the consequences of trusting the wrong people with certain roles. She learned how to hire good people, do damage control, and move forward. Flossie of Healthy Mama and Chelsea of LEARN Academy faced adversity head on and came out the other side stronger than ever more than once, proving that the most important thing an entrepreneur can do is keep on keeping on.

Our San Diego Community

Girls in Tech San Diego CommunityOver the course of the night, one theme emerged above the rest: it takes a village. Whether you’re starting a business, growing a business, changing careers, or figuring out your path, the importance of community cannot be overstated. Find your posse, your tribe, your team – surround yourself with people who build you up. Fostering a supportive community is just one of the ways that Girls in Tech San Diego is empowering women and contributing to their success. If you’d like to stay connected with the Girls in Tech San Diego community, sign up for our newsletter and follow us on social media for news, resources, and event announcements.

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