Calendly Owner Failed at Entrepreneurship Before Becoming Billionaire

Nigeria-born Tope Awotona took a risk when he put his entire life savings into starting Calendly, and almost ten years later, it's now worth more than $3 billion.

Since 2016, the firm has been turning a profit by signing on corporate clients like Lyft,, and La-Z-Boy. In 2021, its revenue was more than $100 million, and it raised $350 million in funding from private equity firms OpenView Venture Partners and Iconiq Capital. The firm’s current valuation is over $3 billion, with Awotona's majority stake worth an estimated $1.4 billion.

Become a Subscriber

Please purchase a subscription to continue reading this article.

Subscribe Now

However, this was not Awotona's first attempt at a start-up. Previously, he had tried to start a dating app, a video projector vendor, and a company that sold gardening tools. But each of these attempts failed. With Calendly, Awotona saw a new opportunity. He was passionate about the mission of the company. He found the challenges of organizing his own schedule to be overwhelming sometimes, and he sought to help others with this issue as well. But rather than follow the same failed business models he had tried before, this time he went all in – and he didn't give himself a safety net.

"With my previous businesses, I hedged my bets a little bit and gave myself a way out," he told "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."

While working for the software company EMC, he maxed out credit cards and invested his life savings of $200,000 into Calendly. He also withdrew from his 401(k). After draining his resources and developing a product, he acquired seed investors, led by David Cummings, Founder of Atlanta Ventures. That $550,000 seed investment seven years ago led to Calendly's continued success to this day.