Tope Awotona, the founder of scheduling app Calendly, is one of the most successful African-American entrepreneurs. Though Calendly competes with Square, Doodle, and Microsoft in the scheduling software market, it can to stand out due to its simple interface and freemium business model.
The average office worker spends hours in meeting every week. Calendly makes scheduling meetings efficient – especially with people outside the company.
1. He was born in Lagos, Nigeria. His family moved to Atlanta in 1996
Awotona grew up Lagos, Nigeria. His family moved to Atlanta in 1996 after his father’s death. While Atlanta was similar to Lagos in some ways – a big city with traffic- it was also different in many ways. Moving to the US and going to college in the US played a key role in his success.
2. His father died when Awotona was 12 in a carjacking
Awotona’s father died in a carjacking incident in Lagos when Awotona was 12. A group of guys followed his dad, demanded keys to his car, and after getting the keys, shot him. That incident left an indelible mark on Awotona but also made him resilient.
3. His family ran many businesses
Awotona’s maternal grandmother ran an import-export textile business. His mom owned a pharmacy and his dad was a distributor of chemicals. So Awotona was able to learn to run a business from his family. His dad was a microbiologist and his mom worked at the Central Bank of Nigeria. His parents were his role models.
4. Awotona was a gifted student
Awotona attended the University of Georgia and received a degree in management information systems. He was a gifted student – he graduated high school two years early. But his mom felt that he wasn’t ready for college. So finished his junior and senior years in high school.
5. First first few startups failed
Calendly was not his first entrepreneurial venture. He founded a dating company, Single To Taken, which died quickly. He founded two other companies – ProjectorSpot, which sold projectors, and YardSteals, a platform for selling home and yard equipment. Those two companies also failed early.
6. How he came up with the idea for Calendly
Awotona accidentally stumbled on the idea for Calendly. When scheduling personal meetings, he realized that there was no way for users to share their availability. Scheduling a meeting typically meant writing multiple emails. He could not find a product on the market that solved his scheduling needs. Thus came the idea for Calendly.
7. Awotona was not a software engineer. But he held multiple sales roles in software companies
Awotona is not a software engineer. He loved writing code in college but he felt that it was boring. He held sales roles at IBM, Perceptive Software, Vertafore, and Dell EMC. Though he didn’t write software, he was close enough to software development to understand its power to transform a business.
8. He flew to Ukraine while the country was in chaos to meet with software developers
Calendly partnered with a Ukrainian company Railsware to build its software. In 2014, when Ukraine was dealing with protests against the government, Awotona took a huge personal risk by flying Ukraine’s capital Kiev to continue developing Calendly.
9. He didn’t raise money from VC funds for many years
Calendly was founded in 2013. Awotona built the company by maxing out his credit cards, emptying his bank accounts and 401(k)s, and getting small business loans. By 2020, the company had just raised just $550,000 in venture capital funding since its founding. In 2020, the company generated $70 million in annual recurring revenue.
Awotona, like many black founders, struggled to raise money from VC funds. While other founders with poor business ideas were raising money easily, he couldn’t. This forced Awotona to be prudent and focused with his spending at Calendly.
