After learning how fear kept him out of his basketball dreams, Don Charlton went on to develop a $180 million HR tool

BY Preta Peace Namasaba March 19, 2024 8:28 AM EDT
Don Charlton. Photo credit: Rochester Institute of Technology

Leaving his small town with two suitcases, Don Charlton was excited for the promises college held. He had planned on trying out for the basketball team but withdrew halfway through because he was afraid of being cut. A few months later, he realized that he was better than many of the players who made the team. Charlton learned to embrace the possibility of failure and to remain strong in the face of challenges. He carried these lessons into entrepreneurship, building an HR platform that he ultimately sold for $180 million.

“Four months after [backing out of the decision to play basketball], I was playing with the guys on the team and I was actually better than a lot of them. If I had stuck it out and worked past that fear, I probably would have found success. It’s a lesson I carried with me into entrepreneurialism,” Charlton said about how he leaned to navigate fear.

Growing up, Charlton depended on government assistance to get by. His mother was mentally ill and accessing basic needs such as proper meals, clothes, and shelter proved to be a challenge. Charlton loved drawing and was always the best in arts and crafts. However, he couldn’t afford paper and resorted to using cereal boxes to draw. Hunger, poverty and a longing for a dignified livelihood inspired him to take control of his destiny.

But a world where he went to college and became an entrepreneur was difficult to conceive. Charlton wanted to have food every single day and he knew that required hard work. His worldview was eternally altered when his guidance and counselling teacher showed him a proper career path. Charlton was introduced to graphic design and its bigger financial benefits compared to normal drawing. He moved to New York where he started working at McDonald’s to support his struggling family. In 1999, he enrolled at the Rochester Institute of Technology for a bachelor’s in Graphic Design.

“Growing up… I had never thought about being an entrepreneur. I didn’t think about going to college either. I just thought about wanting to have food every single day. I wanted to be able to eat and I knew that required hard work,” Charlton told Forbes of his impoverished upbringing.

After college, Charlton worked for a multinational design firm as a web designer. He began thinking of starting his venture during his time with the firm. His confidence in presenting to the company’s senior personnel motivated and boosted his morale as a good businessman. With ten years of experience, Charlton started a content management company. His first attempt at business was unsuccessful but he never gave up. The desire to own a company pushed him to give entrepreneurship another shot.

In 2009, Charlton founded Resumator (later renamed JazzHR), a company that provides recruiting software for small businesses. He took lessons from his failed first venture and was prepared to avoid the same mistakes. The idea behind JazzHR was inspired by his hectic experience hiring web designers. Charlton had thought immensely about how his platform would revolutionize the hiring process and had done all the necessary research. But that was the easy part.

“I think during the early days at my first company there was a fear of the unknown – I didn’t have much experience selling software online, so I kept creeping back to my comfort zone in product. I think you actually made me aware of that. But once I started to focus on sales, I realized I had a natural knack for it, and my love of the product rubbed off on customers,” Charlton said about how letting go of fear helped him succeed.

Charlton’s ultimate test came during a critical point in the company’s growth. JazzHR had grown to almost 200 employees but had limited cash to continue operations. Charlton had approached 30 investors who were all non-responsive. He wanted to quit and give everyone three months of severance but was embarrassed to deliver such news. He remembered to embrace the possibility of failure, persevered and was willing to risk the worst possible scenario. JazzHR ended up raising $15 million.

JazzHR became the first widely adopted start-up recruiting solution in Silicon Valley. It raised $24.5 million in venture capital over six rounds. The company offers small to medium-sized business customers a custom recruiting and applicant tracking solution that has been used by over 15,000 companies, which have processed more than 15 million resumes and filled over 200,000 jobs. JazzHR served many big-brand companies at the early launch stage, including Instagram, Dropbox, Uber, and Barack Obama for America, among others.

In 2021, Charlton sold JazzHR in 2021 for $180 million.