Building Confidence, Building a Brand: Inside Gabby Goodwin’s Entrepreneurial Journey

Image courtesy of Gabby Goodwin

“A lot of trial and error. A lot of learning along the way. And having the courage to take one step at a time.”

What started as a solution to a frustrating everyday problem has grown into a company reaching young girls across the world. Recently celebrating its 12th anniversary, GaBBY Bows is the product of a journey shaped by determination, confidence, and community. Its CEO and Co-Founder, Gabrielle “Gabby” Goodwin, is an Ingram Scholar in her first year at Vanderbilt University originally from Columbia, South Carolina, majoring in mathematics and economics and minoring in business and data science.

To better understand what it means to be a youth entrepreneur, I knocked on the dorm room across the hall from mine to find out.

What inspired the company?

“The main problem was that I wanted to stop losing my barrettes,” Gabby explained. “My mom would spend 15-20 minutes doing my hair in the morning. She would drop me off at school looking very nice, and then she would pick me up to find out my hair was a complete mess, and she would have to replace those barrettes I had lost.”

“I noticed that a lot of other girls who looked like me had the same issue. I’ve always known that I wanted to inspire people, so my motivation was not only to stop getting in trouble with my mom, but also to encourage young girls like me in whatever way I could” Gabby shared.

At the time, entrepreneurship wasn’t part of the plan: “I was five years old when I started thinking about this. I didn’t know about entrepreneurship. I didn’t even know where to start. I just pushed my mom to at least create a bow, but that turned into a business two years later.”

That’s how her company Confidence by GaBBY Goodwin got its start.

Learning as they went

Neither Goodwin nor her family entered the entrepreneurial process with traditional business experience: “We’re first and second-generation entrepreneurs,” she said. “So we didn’t really know what to do. We just kind of learned as we went.”

Building the brand, she explained, relied heavily on outside guidance and continued support.

“It was a lot of mentoring and continues to be a lot of mentoring. We have great coaches and great communities that we lean on to ask questions, especially during the beginning. And now that we’re 12 years in, we’re able to also be those people for others who are starting, which is great.”

What has been your biggest setback?

For Gabby, one of the biggest challenges was internal rather than operational: “My biggest setback was my confidence,” she said. “I was a really shy kid. I didn’t want to talk to people I didn’t know, which is not really apparent now. That’s really because entrepreneurship pushed me in a way to be more confident in myself and to have more courage to speak up.”

“Along with being shy, I was also not confident in the way that I looked and who I was as an individual. That could be because of representation reasons, or not really seeing people who looked like me doing other things that I was interested in.”

“When starting a business, the main thing you have to do is talk to people: advertise yourself, advertise your business. And that was really hard for me at first because I didn’t want to use my voice.”

But what helped her the most was finding comfort in the uncomfortable: “That was the biggest setback, especially when it came to speaking to different groups and organizations. It took me a minute to really grow into that, and I’m glad that I have.”

Gabby also pointed to challenges that came with expanding beyond the product itself. For a couple years, the company operated a salon out of its headquarters, an effort tailored to address a clear need within the community: “I know this personally: it’s really hard to find hairstylists who love doing girls’ hair. It’s very tedious. You have to deal with anxiety, tender-headedness, the ability to move around all the time, so it’s a very demanding job.”

“We saw that there were people who wanted the services, needed the services,” she explained. “So when we purchased our headquarters [Columbia, SC], there was salon space in our building. We wanted to use it to provide that space for hairstylists to come in, work with us, and create the entire experience.”

The salon was meant to immerse customers in the brand itself: “They’re not only getting their hair done,” she said. “They might meet me, they’re going to see behind the scenes of the business, see the inventory that we have, it becomes an experience.”

Despite the promise of the idea, managing a service-based operation introduced unexpected complications: “Even though the concept sounds great, it was tough,” she said. “Hiring certain stylists, them not showing up when they need to, not doing their job, having to chase people down to get access to the building… it’s a whole bunch of things you don’t think about when it comes to owning a service-based entity.”

Ultimately, the demands of running the salon diverted attention away from the company’s core priorities. The location still functions as the company’s headquarters, and the salon space is rented out to different stylists.

What is a piece of advice you have been given and what advice do you give others?

“I was about nine years old, I think,” Gabby said. “We were part of a pitch competition for The Washington Post. But I couldn’t even compete because it was 18 and over, so my mom competed for us. I was there though.”

“She pitches, it goes well, people figure out who I am, and I get called out on stage,” she recalled. “It was a very nice, energetic moment.”

But the awards ceremony didn’t end the way she expected: “We got fourth place, while third, second, and first place got prize money. We didn’t win at all,” she said. “I was like, ‘Oh, this was terrible.’ I ended up crying in the green room.”

It was there that she received advice that stayed with her: “My mom called my dad so that he could calm me down,” she said. “The main thing he told me was, ‘Tears are the nutrients of dreams, like sunlight is to plants.’ That taught me not to be afraid to show emotion and not to be afraid to cry. But also that these setbacks, these opportunities, and these lessons are really the fuel to push you toward your dreams and goals that you have. So in your next pitch competition, you know what it feels like to lose, and you prepare as much as you can to win.”

When asked what advice she would offer to young girls interested in business or entrepreneurship, Gabby emphasized confidence first and foremost.

“I would say first to believe in yourself,” she said. “I usually say, if you don’t believe in yourself, nobody else will. Not necessarily saying you won’t have your parents, your grandparents, your village, your guardians there, hopefully they are there to support you, but especially as a young entrepreneur, people aren’t always taking you seriously.”

She explained that young people with ambitious ideas often face skepticism simply because of their age: “Kids come up with ideas all the time. They want to do big, audacious things. But they’re not seen as focused or serious. So it’s very important to believe in yourself, believe in the idea you have, the business you want to have, and be passionate about it.”

“The last thing that I would say is a quote that I came up with: ‘NO is just an abbreviation for Next Opportunity®.’ After one NO, two NOs, a hundred NOs, however many you hear, because you will hear rejection, you can’t be afraid of that. Learn to be resilient. Learn to be fueled by rejection, because if you keep going, you never know how close you are to that dream that you’ve always had.”

What’s something people misunderstand about being a CEO?

When discussing misconceptions about leadership, Gabby emphasized the expectations often placed on CEOs: “The responsibilities are something people misunderstand,” she said. “People typically believe that CEOs know everything about their company…which they should mainly know their business, but they’re not the sole purpose of why the business is together.”

She emphasized that a company’s success is based on a collective effort rather than individual authority: “There are people working behind the scenes. There are team members. There are customers who advocate for you and talk about your brand,” she said. “So as much as you’re a CEO, and as big as your responsibilities are, you also have the control to either maximize or minimize that. You’re not doing everything.”

Part of the misunderstanding, she explained, stems from narrow expectations about leadership roles: “People have a specific image of what a CEO should look like and what a CEO should do,” she said. “But there is such a variety. Yes, I’m the CEO, but I can’t be in meetings every day because I have class. I can’t do everything.”

“Transitioning to college was definitely an adjustment because I’m not there to fill orders or write notes,” she said. “Last semester I wasn’t as involved in the business because I’m trying to be a college student and learn how to be successful here. And that’s something people misunderstand; CEOs aren’t doing every single thing. There are so many people behind the scenes continuing to push the business forward.”

Reflecting on the past and looking towards the future

Today, GaBBY Bows have been ordered in all 50 states, across 16 countries, and are carried in more than 600 Claire’s retail stores. Alongside expanding the company, Gabby has also authored the children’s book Naturally Me at the Confidence Salon (published by HarperCollins), expanding the brand’s mission of empowerment beyond a retail product.

“The message of the book is really all that I’ve continued to talk about in these past 12 years. I knew that if I wrote a book, the first thing I wanted to write about was confidence, authenticity, and just truly being yourself.”

As youth entrepreneurship becomes more established, she believes the path forward may look different for the next generation. Reflecting on her own experience navigating skepticism and age-related barriers, she expressed optimism about what lies ahead. With more young founders gaining recognition and access to platforms to share their ideas, Gabby shares her excitement for the future. She hopes that age will no longer be perceived as a barrier, allowing young entrepreneurs to focus on building their ideas rather than proving their competency.

By Madison Newman

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