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How Tope Awotona Fought Through Life’s Challenges to Build a $60m Startup in The US

Babatope Awotona is the founder and CEO of Calendly- a simple and beautiful scheduling tool that helps you schedule meetings without all the back and forth emails. 

Calendly in less than 7 years has served close to 30 million people worldwide and is currently growing 100% yearly and has also risen to become an industry leader.


Tope Awotona was born and practically lived most of his childhood years in Lagos, Nigeria. He was the third of four children (all boys), and the Awotona’s big family meant their house was always filled with people and laughter.

“I got into just the right amount of trouble growing up…to where I had a lot of fun, but no one ever called my parents. I knew exactly what I could get away with and toed that line.” 

His Mom was the Chief Pharmacist for the Central Bank of Nigeria. His Dad was a microbiologist and worked for the Nigerian division of Unilever, but he was an entrepreneur at heart. 

His Mom grew up in a wealthy family but his Dad came from a very poor and broken home. Tope’s father picked himself up and through a lot of hard work and a bit of luck – he was able to escape that cycle

These two parental perspectives gave Tope a lot of insight into what he wanted for his life

In Tope’s words, he was “lucky to have two of the coolest parents in the world.” His Dad was the more lenient and easy going one, a beloved father with a big heart. His Mom was quite conservative- a tough woman who was ambitious, driven, and strict. She was always asking “What is your plan looking like in the next 10 years?”

Losing his Father at 12

Tope was just 12 when he saw his father come home being followed by a group of men, the men demanded the keys to the car. As his father threw them the keys, they shot and killed him.

His world was shattered. Tope went through the trauma for 6months, he couldn’t eat or sleep, his mentor and father has been taken away.

A few years before this, his father had quit his job at Unilever to build his own company. Tope decided he would now take up the torch.

This solidified Tope’s desire to fulfill his Dad’s dreams of being a successful entrepreneur. 

For the time being, he focused his attention back to where he excelled – school.

Coming to America

Tope’s mom packed the whole family from Lagos to Marietta, GA, joining other Awotona family members, so he could attend Wheeler High School. In his words, “It was super frustrating. I felt like I was wasting time because I had my plan in place.” But, he admits it worked out well. “My mom was wise. Those two years helped me assimilate well to the US and gave me time to learn the culture here.” Tope graduated high school and attended the University of Georgia where he studied Management Information Systems

His STARTUP Failed 3 times

First, Tope decided to build a dating site after reading a New York Times article about He read about the founder who was making $10M/year working 10 hours a week.

Tope was inspired. He looked up their website, knowing he could build something better. He created STT Media which stood for “Single To Taken.” But…was never launched, he realized he didn’t quite have the means or skills to do it as well as he wanted.

His second startup was an e-commerce site selling projectors.

A business broker had convinced Tope to build a website around selling projectors. ( According to Tope, he didn’t sell many and the margins were terrible. “I didn’t know anything about projectors! And honestly? I didn’t want to know about them.

His third startup was another e-commerce site selling grills.

Moving forward from projectors to grills and started ( He had a bit more success selling knock-off Big Green Eggs, but quickly realized he had the exact same problem. He was pulling more profits, but he still wasn’t passionate or knowledgeable about what he was selling. In Tope’s words, “Once again, I didn’t know anything about grills and I didn’t want to! I lived in an apartment, and never even grilled.”

The meeting that shift his thinking 

Tope had been working on few paid jobs right from his high school days, after graduating from college settled in at Perceptive Software, a growing startup in Kansas City, as a salesperson.

He spent the next seven years working in sales job, but deep down he always wanted to become a successful entrepreneur. So he spent his evenings and weekends trying to build a business.

Tope climbed the sales leaderboards, but was still keen on starting his own company, but didn’t have the gut to Until one day, when Perceptive had a staff meeting where their Founder, Scott Coons, told the story of how the company went from idea to fruition.

For the first time, Tope realized that successful companies do not always take a straight path forward. The Perceptive startup story had many twists and turns, but they learned from their mistakes, kept persisting, and it still led to great success.

He learned first hand that people who start great companies are smart but, more importantly, they take action when they see opportunity and stick with it to make it work.

Tope was inspired “It made entrepreneurship all of a sudden more attainable. I knew if they could do it, I could too.”

Loss of his mom

It was around this time that Tope received the sad news that his mom was diagnosed with cancer. So he quickly packed up and moved back to Atlanta to be with her.

During this times, Tope reflected back on the staff meeting with Scott. And in that moment, amidst all the personal challenges, he chose to persist.

He quit his sales job and started to work on his idea fully.

Tope’s Mom passed away the same year he started Calendly. His loving, protective mother would have been so scared of the risk, Tope knew she wouldn’t have been able to be supportive. So he never told her what he was doing.

In Tope’s words, “I wish my mom could see what Calendly is now. Parents do so much and sacrifice so much for their kids that I believe it’s the ultimate accomplishment for a parent to see their child be successful. I would give anything for my mom to see what she has done”

Birthing Calendly

Through his grieving, Tope again chose to push forward. Looked at his previous mistakes and realized that he had been more focused on making money. He told himself that he wasn’t going to succeed unless he focused on a problem that he was passionate about solving.

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. But all the products he found were slow and pretty clunky. 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.

Calendly officially launched in September of 2013, and came to Atlanta Tech Village two months later. In Tope’s words, “I fell in love with the atmosphere, everything the building stood for, and just the excitement and the passion of the people there. Everyone was building something, and I knew instantly that I wanted to be there.”

Villagers quickly began using Calendly (and tweeting about it) which caught David Cummings’ attention. This ultimately led to Tope’s first investment with Atlanta Ventures which helped catapult Calendly into their next growth phase.

Through the difficult experience, He achieve his dream in honour of his parent.

Tope’s advice to young entrepreneurs

If you look at the time I spent working on Calendly, it took seven years for the rest of the world to learn about Calendly and then before I ever got the opportunity to work on Calendly, first, I had to fail three different times. Before I got the opportunity to fund Calendly, I had to do the corporate jobs that I had before really well.

“If you want to be an entrepreneur, become really good at something. Make sure you fully understand the problem, and be well informed enough to have strong opinions about the solution. Only then are you ready to start a company. I learned that the hard way. 

“Your background is what you make of it. It can be an asset or an excuse. I have never accepted lowered standards.  

I have learned that growing up black in America is very different

“Whenever I felt like I wasn’t in a place (in a role) where I couldn’t learn more, I always sought out new opportunities”

“Don’t try to solve a problem you don’t understand and be honest with yourself about what you are really good at.”

“There has to be much more that drives you than just money”

“Everything I did along the way helped me get here. No part could be omitted and have me still end up where I am today.”  

The future for Calendly

Tope’s company was created through his grits and resilience to build on his Father’s legacy. Like most entrepreneurs, it hasn’t been a straight path to success. But Tope is the kind of person who values the journey – “

“The path forward certainly seems straight. Over the next three years, We plans for Calendly to literally serve hundreds of millions of people worldwide”.

Source: Techibytes

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