The story of your friendly time manager

Updated: Mar 10


How Tope Awotona managed to get an investment after 3 failed startups?


Calendly is a free SaaS built around simple functionality. It’s a platform which provides a quick way to manage open spaces in your calendar and helps others easily schedule meetings with you. It also connects with your other accounts like Google or Microsoft and includes features like business meetings, classes, etc. But how did the idea start? That’s the most interesting part of

Tope Awotona – CEO and founder of Calendly grew up in Nigeria and moved to the US when he was a teenager. He developed his career in sales, however, the eagerness of becoming an entrepreneur never left him. So, he started spending his weekends building his own business.


Of course, like every successful entrepreneur, Tope faced failures and not only once, but three times! Firstly, he decides to build a dating site, however, he realized that he didn’t have the resources or skills. He never ended up launching the app on the market due to various reasons .


His second and third startups were based on e-commerce, but they failed at the very early stages of development. Tope realized that he made a mistake when focusing on making money, not solving a problem.


It took another year before he found that problem. He'd spent a day wasting a lot of time going back and forth over email to schedule meetings. So he started searching for a scheduling tool.


All the products he found were slow and clunky, so after months of research, he decided to go all-in with this idea. He put every single dollar he had made into this new business, but surely, the business wasn’t going well.


Although Awotona's startup was based in Atlanta, the city with one of the largest tech talent pools in the USA, he decided to relocate the company to San-Francisco to try and gage more interest from the tech ecosystem in the Silicon Valley.


After years of little or no interest, Tope decided to continue building his business in Ukraine. This was in 2014, when Ukraine was in the middle of a civil conflict and was not a very safe place to be, however Tope kept taking the risk and flying in and out of a conflict zone to make sure that his product was being developed the best way possible. That was exactly what caught the eye of the startup ecosystem in the US and eventually the investor’s.

“It’s been the bane of my life,” he said in one of his interviews with TechCrunch.

After returning back, he got an investment from OpenView and Iconiq. Today, Tope's company does around $30 million in annual revenue.


This is the story that shows two crucial points:

  1. Never be afraid of failure. Spot your mistakes, fix them and try again.

  2. Perseverance and dedication pay off .

Hope you enjoy it, now let’s make your startup happen!