10 Things You Didn’t Know about Tope Awotona

Tope Awotona

Tope Awotona is the founding CEO of Calendly, a company that specializes in scheduling software that aims to simplify the process of scheduling meetings and appointments. Since its inception in 2013, the start-up has enjoyed exponential growth. In its most recent funding round, it closed an investment of $350 million from OpenView Venture Partners and Iconiq. The funding round values the start-up at just over $3 billion. To find out more about the man behind Calendly’s success, read on for ten things you didn’t know about Tope Awotona.

1. He grew up in Nigeria

Awotona was born in Lagos, Nigeria. His maternal grandmother was the founder of a successful import-export textile business. Its success allowed her to send all of her children to university, a rare accomplishment at the time. His mother held down two jobs, the first as co-owner of a small pharmacy and the second as a manager at the Nigerian Central Bank. His father started out as a microbiologist for Unilever but later left the company to become a serial entrepreneur. Of the many businesses he founded, his greatest success was as a distributor of industrial chemicals. Awotona has since credited his parents as his greatest role models.

2. He witnessed his father’s murder

When Awotona was 12 years old, his father was murdered in a carjacking. He’s since recalled how a group of men followed his father home and demanded the keys to his car. After he threw the keys at them, they shot him at point-blank range. Awotona witnessed the entire thing. The tragedy left him with post-traumatic stress disorder. For six months, he couldn’t eat or sleep. Even now, he still suffers from insomnia, something he attributes directly to the experience.

3. He graduated two years early

Shortly after the death of his father, Awotona and his family moved to the US, where they settled in Atlanta. A gifted student, Awotona graduated high school at just 15 years old. He was subsequently offered admission to a university. Although he was happy enough to go, his mother was concerned about his ability to adjust to college life at such a young age. After she stepped in, it was decided Awotona would finish his Junior and Senior years first. After finally leaving school, he studied management information systems at the University of Georgia.

4. He ventured into business at 18

As MSN writes, Awotona’s first foray into business came at the tender age of 18. After noticing how the cash register he used at his part-time job in a pharmacy didn’t add up properly, he devised a feature for registers that allowed them to use optical character recognition to determine which bills were being used and dispensed. After patenting his idea, he reached out to NCR, the leading cash registry company at the time, to pitch his idea. They were impressed. But at that point, Awotona froze. Thrown by how quickly things were moving, he ultimately turned down NCR’s offer to buy his patent and abandoned taking his plans any further.

5. He cut his teeth at IBM

As Fortune notes, like many founders, Awotona’s first career steps were taking in tech companies. After graduating from the University of Georgia, he cut his teeth at IBM. From there, he took on various sales roles at Perceptive Software, Vertafore, and Dell EMC.

6. His first startup was a dating website

Calendly might be the startup that’s made Awotona’s name, but it’s by no means his first. His first foray into the sector came with a dating website. As Atlanta Tech Village explains, he got the idea after reading a New York Times piece about how the founder of Plenty of Fish made $10 million a year working 10 hours a week. After checking out the Plenty of Fish website, he decided he could create something much better. Whether he could, we’ll never know – the result, “Single To Taken,” died a quiet death long before launch. After Single to Taken, Awotona founded a company called ProjectorSpot that sold projectors, followed by YardSteals, a platform for home and yard equipment. Neither one proved a success.

7. Personal need drove him to start Calendly

After several years of floating various start-up ideas, Awotona hit gold in 2013 when he came up with the idea of Calendly. During an interview with MSN, Awotona explained how the idea was inspired by personal need. “What led me to create a scheduling product,” he explained, “was my personal need. I just trying to schedule a meeting, but it took way too many emails to get it done, and I became frustrated.” After searching the market for scheduling products, Awotona hit on a problem. None of them allowed multiple users to share availability. Spotting a gap in the market, he decided the time was ripe to fill it.

8. He self-funded Calendly

After deciding his idea for a scheduling product had potential, Awotona founded Calendly entirely with his own money. Eventually, his personal finances reached a breaking point. With no further savings to bankroll the company, Awotona began seeking VC funding. But there was a problem: no one wanted to invest. Rather than give up, Awotona persevered. He focused all his efforts on developing Calendly and learned to stretch each and every dollar to its limit. His efforts paid off. Within three years of launch, Calendly was in profit. He’s since credited the lack of early cash with much of Calendly’s success, saying it forced him to “double down.”

9. He’s turned Calendly into a $3 billion success story

Calendly may have struggled to attract investors in 2013, but those days are well behind it. This January, Awotona announced he’d closed an investment of $350 million from OpenView Venture Partners and Iconiq. The funding round values the start-up at just over $3 billion.

10. He wants to start giving back

Having turned Calendly into one of the success stories of the decade, Awotona is now looking to inspire more young people to follow in his lead. As he explained to Tech Crunch, pandemic restrictions permitting, he hopes to be able to visit Nigeria later this year to become more involved in the ecosystem of his birth country. “I know the country that produced me,” he explained. “There are a million Topes in Nigeria. The difference for me was my parents. I want to get involved in some way to help with that full potential.”


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