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Unveiling the Hidden Trailblazer: Tope Awotona’s Journey to a $3 Billion Startup – Calendly

In the vast landscape of modern entrepreneurship, where success stories often take center stage, some narratives remain obscured, waiting to be uncovered. The meteoric rise of Calendly, now a formidable $3 billion startup, is undoubtedly impressive.

Yet, amidst the acclaim and admiration it has garnered, a crucial chapter has been overlooked – the story of its visionary Nigerian founder, Tope Awotona. His journey from humble beginnings to the helm of a billion-dollar company is a tale of determination, innovation, and resilience.

As we delve into the six short clips that illuminate his path, we’ll witness the transformative moments that shaped Calendly’s trajectory and the indomitable spirit that propelled Tope Awotona to his remarkable achievement.

1. Concepts for Innovation

Tope was a sales agent in a small business. He used to book a lot of meetings with clients, but the back and forth of 5 to 6 emails was painful.

So he searched for software to solve it but didn’t find good ones. Eventually, he built his own software.

2. Embracing Failure

Tope built many failed businesses before Calendly. Like Dating websites, projectors and Saas.

He said, “ instrumental in his learning and success.” Tope learned the importance of what not to do. It developed his guts and sharpened his instincts.

3. Mastering Versatility

Like most great founders, Tope was curious. After working on many small startups as a salesman, he became a good generalist. Curiosity led him to learn multiple business skills every day, and it paid off. He learned to build a business from point zero.

4. Deceptive Fervor

Passion can’t be faked for too long. Tope believes that founders who are in the business to make money don’t last. Someone who cares for their customers will always leave them behind. Best startups serve their customer devotedly.

5. The Pillars of Excellence

Great founders focus on talent recruitment. Tope believes that elite teams run great startups. Exceptional talent makes progress inevitable. You just need to create an environment where they thrive. Recruit and let them do their job.

6. Fostering Creativity

Tope finds inspiration in everyday life. If a product creates a good experience, then how can he replicate it? , if bad, find out whether your product makes the same mistakes. He creates eternal feedback to improve constantly.

7. Navigating Capital

Tope bootstrapped Calendly. He literally burned his savings not to lose ownership. And he even advises young entrepreneurs not to fundraise early. They should focus on developing products instead of looking for a big exit.


Tope Awotona’s narrative is more than just a story of entrepreneurial triumph; it’s a testament to the potential that lies within individuals who dare to dream and relentlessly pursue their aspirations.

His journey, chronicled through these six illuminating clips, reminds us that innovation knows no geographical boundaries, and the seeds of transformative ideas can sprout in unexpected places. As Calendly continues to flourish and leave an indelible mark on the business landscape, let us not forget the unassuming genius behind its inception.

Tope Awotona’s journey from anonymity to the forefront of the tech world serves as an inspiration to aspiring entrepreneurs and a reminder that every breakthrough is grounded in a unique and often untold story.

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About me

Inaam is Serialpreneur, a Digital Marketer by passion and renowned SEO specialist having 15+ Years of Experience. He has offered his services to Top business brands across the globe. He has a wealth of knowledge in a multitude of domains.

He is wearing multiple hats some of which include, Chairman TechMentions, Co-Founder EPTeck, Master Trainer at NFTP, PITB, CEO and Founder EpicWoo, and many more.

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