After a 3-time Failure

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

Tope Awotana is the CEO and founder of the $3 billion company, Calendly, a modern scheduling tool for high-performing teams and individuals that want to accelerate their business growth.

The scheduling platform, which was founded in 2013, has gained over 10 million users under Tope’s strategic management. The vision for Calendly began when Tope wasted the whole day going back and forth over email, trying to plan meetings.

This was the fuel for him to begin looking for a tool that makes scheduling easier and eliminates the need for back-andforth emails.

Most of the tools he discovered were slow and clumsy. He decided to go all-in with his idea after months of research, placing every penny he had earned into this new venture.

His wager paid off this time after three failed attempts. Tope’s company now generates about $30 million in annual revenue.

Early life and education

The 40-year-old founder is a born Nigerian, brought up in a middle-class family in Lagos. His mother worked at the Central Bank, while his father was a microbiologist and an entrepreneur. Awotona got a job as a sales rep at IBM. He worked in sales, for the following seven years, selling software for tech companies, including Perceptive Software, Dell Technologies and Vertafore, but he had always aspired to be a successful entrepreneur. Due to this budding entrepreneurial spirit, he spent his evenings and weekends trying to start a company.

Most of his idea for Calendly was sparked by his frustration as a salesman. It was difficult for him to set up meetings, it was a task that most times took dozens of emails and days to complete.

Lagos, which is Nigeria’s economic centre, is also riddled with violence. And Awotona came face-to-face with, when he witnessed his father being shot and killed in a carjacking at the age of twelve.

“There was a part of me, from a very early age, that wanted to redeem him,” he said.

In 1996, he migrated to the United States at the age of 15. And studied computer science at the University of Georgia, before switching to business and management information, and graduating with a degree.

“I loved coding, but it was too monotonous,” he says. “I’m probably too extroverted to be a coder.”

Tope’s first venture was to create a dating site after reading an article on PlentyofFish, he soon recognised, however, that he lacked the necessary finances and abilities, and hence the venture was aborted.

His second business venture was an e-commerce site that sold projectors. However, he didn’t sell many, and the profit margins were poor. In addition, he was uninterested in projectors.

His third venture was a grill-selling e-commerce site. However, he was confronted with the same issues. He also lacked enthusiasm for that line of work.

Tope soon realised that he was only thinking about strategies for businesses to make money. He told himself that unless he concentrated on a problem he was enthusiastic about fixing, he would fail.

He had to wait another year before he discovered the problem. He remembered in the past that he wasted a lot of time using email to plan meetings. This began his search for the right scheduling tool.

The beginning of Calendly

In 2013, Tope founded Calendly in Atlanta Tech Village, a coworking space for entrepreneurs. The company, however, no longer has any physical offices. Profile He dipped into his retirement savings and maxed out his credit cards to fund it.

Awotana hired the Ukrainian firm Railsware for programming assistance, and eight years ago, was in Kyiv as rioters fought government forces in the streets.

He had a marketable product by late 2013, but no funds. Then a half-milliondollar seed investment led by Cummings came to the rescue.

The platform raised $350 million in capital last year from OpenView Venture Partners and Iconiq Capital, valuing the company at $3 billion.

Awotona’s majority holding is worth at least $1.4 billion. Along with David Steward, the 70-year-old founder of Missouri-based IT company World Wide Technology. Awotona is one of just two Black IT billionaires in the United States.

Individual users can use Calendly for free, while businesses normally pay $25 per user every month.

In 2021, he won the Most Admired CEO Award from the Atlanta Business Chronicle, as well as the Comparably Best CEOs Award in 2019.

Tope Awotana prospects

Awotona is now expanding beyond meeting scheduling to include tools that assist recruiters, salesmen, and other whitecollar workers in managing meetings both before and after they take place.

This entails assigning meetings to the appropriate individual at a major corporation, including essential information, such as agendas and budgets, in the invitation itself to streamline the meeting.

It also enables tracking results via integration with productivity applications like Salesforce.

How Rediet Adebe is Using AI to Change the Narrative of Inequality and Social Justice

Recent documentaries have revealed how social media algorithms and other artificial intelligence (AI) technologies frequently discriminate against people from certain backgrounds. Phenomenal computer scientist Rediet Abebe wants to change that.

Abebe’s research focuses on developing mathematical and computational frameworks for investigating inequality and distributive justice issues.

The 29-year-old Ethiopian employs theoretical computer science techniques to assist in the development of algorithms and artificial intelligence systems that handle real-world challenges. She’s looked at how income shocks, such as losing a job or losing government benefits, might push people into poverty, and she’s interested in how to better allocate government financial aid.

She’s also collaborating with the Ethiopian government to improve the algorithm the country employs to link high school students with institutions in order to better account for the demands of a varied population.

Abebe is a co-founder of the organisation Black in AI - a community of Black AI researchers - and Mechanism Design for Social Good, which brings together researchers from other disciplines to address social issues. She is a Computer Science Assistant Professor at the University of California, Berkeley. She was previously a Junior Fellow at Harvard’s Society of Fellows.

Early life and education

Rediet Abebe was born and she grew up in Ethiopia’s capital, Addis Ababa. She attended Nazareth School, where she was taught the Ethiopian National Curriculum, before receiving a competitive meritbased scholarship to the International Community School of Addis Ababa for high school

She was a high-scoring student in Ethopia, and most students in this category were assigned to study medicine which made

Adebe panic because she wanted to study Maths.

“I was like 12 and super panicked that I might have to be a medical doctor instead of studying math, which is what I really wanted to do.” she said.

This brought about the idea for her to go abroad because she learned that

“In the US, you can get full financial aid if you do really well and get into the top schools.”

She got a Bachelor of Arts degree in mathematics and a Master of Science degree in applied mathematics from Harvard University. As an undergraduate, she co-authored research papers in mathematics, physics, and public health.

Throughout her time at Harvard she worked as a staff writer for The Harvard Crimson, focusing on the Cambridge public school system which was from 2009 to 2011.

Once she was done with college, she attended the University of Cambridge as a Governor William Shirley Scholar at Pembroke College.

Under the direction of Imre Leader, a Cambridge mathematics professor, she finished Part III of the Mathematics Tripos and earned a Master of Advanced Studies in pure mathematics.

American computer scientist, Jon Kleinberg assisted Abebe as she finished her doctoral degree in computer science at Cornell University.

Her dissertation received the 2020 Association for Computing Machinery Special Interest Group on Knowledge Discovery and Data Mining (ACM SIGKDD) Dissertation Award and an honourable mention for the Association for Computing Machinery Special Interest Group on Economics and Computation (ACM SIGecom) Dissertation Award for its contributions to numerous domains in computer science. She is the first Black woman in the history of the university to earn a Ph.D. in computer science.

The trigger for Adebe’s research

The trigger for the 29-year-old research started when she grew up in Ethiopia. Abede always tagged the country’s lack of enough resources for the residents as a community-level scarcity. But soon her argument was changed when she learnt about educational inequality in Cambridge’s public schools, which she noticed suffered in an environment of luxury.

Abebe began attending Cambridge school board meetings in order to learn more. She got increasingly motivated to assist as she learned more about the schools. However, she wasn’t sure how that desire fit in with her ambition to work as a research mathematician.

When Abebe was accepted into a doctoral program in mathematics, she decided to take a one-year intense math program at the University of Cambridge instead.

She changed her major to computer science while she was there, which allowed her to combine her talent for arithmetic with her strong desire to address social issues such as prejudice, unfairness, and lack of opportunity.

Adebe using AI

After garnering her skills in computer science, she has used her techniques to bridge the gap between who creates and deploys AI and those who use it. “Just as AI systems susceptible to bias are a problem, so too is inadequate focus on contributions that improve the lives of marginalised communities, such as Black and brown individuals, economically vulnerable populations and many other groups whose interests are underserved in society,” she wrote in an article.

“I see this gap in action every day. I was born and raised in Ethiopia…So I look out for AI research focused on helping the people of Ethiopia and the people of Africa more generally.”

Mechanism Design for Social Good

In 2016, Abebe and Kira Goldner cofounded the MD4SG research effort, a multi-disciplinary research collective that employs algorithms and mechanism design to combat inequality.

MD4SG hosts an annual workshop series to promote research and connect the community of researchers working to increase social wellbeing through algorithms.

She co-founded and served as the inaugural Program Co-Chair for the ACM Conference on Equity and Access in Algorithms, Mechanisms, and Optimization (EAAMO) in 2021.

Black in AI

In 2016, Abebe and Timnit Gebru cofounded Black in AI, a network of 1,500 AI researchers.

The group hosts annual workshops at the Conference on Neural Information Processing Systems (NeurIPS) and provides chances for networking and collaboration.

Abebe has led the Academic Program through Black in AI, for which she was named to the 2019 Bloomberg 50 list as a one to watch.