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Home Business Profiles 5 Business Lessons from Silent African Billionaire, Tope Awotona
Profiles - June 25, 2022

5 Business Lessons from Silent African Billionaire, Tope Awotona

Tope Awotona is the founder and CEO of Calendly, a scheduling tool currently valued at $3 billion.

Awotona is one of the newly honoured Nigerians in the world. His platform, Calendly, is highly rated for its seamlessness and how it eliminates the need for endless email exchanges.

Calendly was founded in 2013 and has since served close to 30 million people worldwide. It is currently growing 100% year over year. 

His success has exceeded most entrepreneurs’ dreams, and it all started in one of the world’s fastest-growing cities.

Here are 5 business lessons from silent African billionaire Tope Awotona.


How Tope Awotona Built a $3 Billion Company After a 3-time Failure

1. Preserving through trial and error

Tope Awotona sold home alarm systems door-to-door as a student at the University of Georgia. He made only $500 on his first day of work by selling three systems. 

Despite his quick start, the remainder of the week passed without him making another sale. Although he experienced more rejection on the job, Awotona learned valuable lessons about tenacity and from mistakes.

“I learned a lot from selling alarm systems. I learned a lot about rejection because there is no more humbling job than knocking on people’s doors and having them tell you no,” he said.

Awotona’s decision to start Calendly was influenced by all his experiences, including door-to-door cold calling, assisting startup companies with market software, and founding three unsuccessful businesses. 

Calendly uses contacts’ calendar information to determine meeting times that work for all participants. It was created to address the founder’s personal pain points while scheduling meetings and demonstrations with clients.

2. If you want it, do everything to get it 

For Tope Awotona, starting a business wasn’t cheap. He maxed out his credit cards and drained his 401,000 account to construct the program. While he acknowledged this was a risk, he insisted it was deliberate and educated.

Awotona advised people getting into tech or wanting to start a business to “know what you’re getting yourself into, so you can mitigate your risk and avoid unnecessary pitfalls.”

3. Solve a problem you are passionate about 

After three failed ventures, Tope Awotona saw what was wrong with his past business approaches. He became aware that all of his thoughts were focused on profit-making strategies. 

He told himself that if he didn’t focus on a problem he was passionate about solving, he would fail.

Before he identified a new problem, he had to wait another year. He recalled how he had previously wasted a lot of time scheduling meetings via email. He then started looking for the best scheduling application.

4. Don’t be scared to test ideas

After reading an article on ‘PlentyofFish,’ a dating website, Tope also decided to launch a dating website. He quickly realised, however, that he lacked the required resources and skills, and the endeavour was abandoned.

His second business endeavour was an online store where he offered projectors for sale. He didn’t sell many, though, and the profit margins were slim. He also had no interest in projectors.

His third business endeavour was an online store that sold grills. However, he ran into the same problems. He was likewise uninterested in that field of work.

5. Take a risk

For programming support, he recruited the Ukrainian company Railsware. Awotona was in Kyiv a few years ago as protesters clashed with police on the streets.

In the middle of the chaos, Calendly helped its ten contract developers in Ukraine to migrate to Railsware and provided financial support to them and their families.

“It could’ve gone horribly wrong,” he said. “I hedged my bets with my past firms and gave myself a way out. I flew into a battle zone with Calendly and threw everything I had into it. You have to go all-in if you’re going to do something.”


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