At the age of 12, Tope Awotona witnessed his father get shot and killed in a carjacking. He was parking his car in front of the family house in Lagos, Nigeria when the unfortunate event happened. The tragedy scarred Awotona and left him with post-traumatic stress disorder and insomnia that he still lives with. It also ignited a fire within him to carry on his father’s legacy, who had been a successful serial entrepreneur and microbiologist with Unilever. He decided to follow in his father’s footsteps and decided to become an entrepreneur – not in Nigeria but in the US.
“If that had happened in the United States, I would have gone through a lot of therapy. In Nigeria, it happened on Friday and I went to school on Monday. For six months, I couldn’t eat. I couldn’t sleep. That insomnia has carried on to my adult life. I’ll probably have it forever,” Awotona revealed about his trauma.
Today, Awotona is one of a rarity – Black tech billionaires in the United States. He is the founder and CEO of Calendly, a business communication platform developer valued at $3 billion.
Three years after the tragic incident, the family moved to Atlanta. Awotona was a brilliant student who graduated high school two years early and earned admission to a U.S. university by age 15. However, his mother would not have him go as she worried about his ability to adjust to a new environment in such a short time. Awotona consequently continued his high school education for two more years. He attended the University of Georgia where he initially studied computer science and later switched to business and management information.
After graduation, Awotona worked as a software sales representative at IBM. He worked in a similar role at tech companies such as Perceptive Software, Vertafore, and EMC. He dreamed of becoming an entrepreneur and founded businesses in his spare time. Awotona founded a dating site but had neither the resources nor the skills so the business was never launched. He also started an e-commerce site selling projectors and other selling grills but he wasn’t passionate about the business and they ended up failing.
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Awotona discovered a problem he was passionate about solving after wasting a lot of time scheduling meetings via email. He looked for a scheduling tool but the ones he found were slow and inept. He left his job selling software for EMC and set out to fix the broken scheduling system. He used all of his $200,000 life savings and reached his credit card limit.
“The obvious idea to me was that scheduling is broken. It could’ve gone really badly. With my previous businesses, I hedged my bets a little bit and gave myself a way out. With Calendly I flew into a war zone and put in every cent I had. If you’re going to do something, you have to go all in,” Awotona described the steps he took to build Calendly.
Since he wasn’t a software engineer, Awotona contracted with Railsware, a Ukrainian programming firm. He had a meeting with his technology developers amidst the 2014 Ukraine war. He had taken costly business loans and invested everything into a startup that was yet to generate any revenue. Awotona defied numerous warnings from friends and family, took the risk, and flew to Kyiv in a war zone. He had to make sure that the company building Calendly was in the country and stable enough for an enduring partnership.
The fact that Calendly is inspired by Awotona’s challenges with other scheduling platforms sets it apart. It has a consumer-friendly design and free model that gives it an edge over competitors. Calendly’s basic tier is free for individual users with consumers having to share their Calendly-branded schedule with friends to use it. Such user referrals have been vital in bringing in new customers and keeping marketing costs down.
On the other hand, corporations are typically charged $25 per user per month and can set up customized landing pages. Calendly also enables them to route meetings to specific groups of people and connect to other platforms such as Salesforce and Zoom. It is also available in multiple languages. The company has over 10 million users with prominent customers such as Lyft, Ancestry.com, and Indiana University.
Calendly is now scaling beyond scheduling meetings. The company is building tools to help recruiters and salespeople manage all aspects of meeting arrangements. Features that enable adding relevant documents like resumes, agendas, and budgets are in the pipeline. Awotona wants to make scheduling meetings and all related activities as effective as they can be. Awotona has created a $3 billion unicorn that generates more than $150 million in annual revenue.
“Initially it was for financial reasons—I literally needed to pay my bills. But the motivations have shifted over time. As Calendly has grown, I just get a lot of people who don’t fit the mold who reach out to me, who are women, men, people of color—that have been so inspired by the story— that keeps me going through the tough days,” Awotona explained.
