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Spotlight on Calendly's Founder: From 3 Failed Startups to Building a $70M SaaS platform

THC Spotlights is shining a light on creative technologists who are helping to solve problems in their community and doing it with maximum impact.

Tope Awotona founded Atlanta-based online scheduling startup Calendly in 2013 as a free and simple online meeting tool that takes the hassle out of setting up appointments. Today Calendly is used by over 10 million people, but while the tool has grown in popularity, the story of the company's founder is relatively unknown.

Growing up in Lagos, Nigeria, Awotona comes from a long line of entrepreneurs and credits his family as his inspiration. His maternal grandma built an import-export textile business without any formal degree or training, his mother co-owned a small pharmacy with his aunt, and his father, a microbiologist, left his job at Unilever to start multiple successful business ventures. The entrepreneurial influences were heavy and no doubt shaped the way the Awotona saw the world.

When Awotona was 12, he witnessed his father be fatally shot in a carjacking, a traumatizing event that both haunts him in adulthood and also inspired him to carry on his father's entrepreneurial spirit and journey. He traveled to America, and after graduating from the University of Georgia, he landed a job at IBM as a sales rep where he worked for 7 years while trying unsuccessfully to get a startup of his own off the ground.

Awotona attempted numerous startups, none of which were solving a problem he was passionate about. It wasn't until he decided to address his own frustrations at the lack of tools for scheduling meetings in an efficient way that he landed on an idea worth going all in on.

And going-all-in is exactly what the founder chose to do. To build Calendly, Awotona drained his 401K and bank account, and eventually had to seek investment funding. VC investing is unsurprisingly riddled with racism and bias, and Awotona faced great difficulty in acquiring funding for his business idea. But we've never met a Nigerian that didn't get what they wanted! He used the challenges to fuel his efforts and resiliently continued to push for funding. In January 2021, the company raised $350 million in a Series B funding round led by OpenView and is now valued at over $3 billion. Calendly has crossed $70 million in subscriptions sales and is projected to break the $1 billion mark in the near future.



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