Podcast: Tope Awotona, CEO at Calendly on ‘Simplify Meeting Scheduling’

Podcast: Tope Awotona, CEO at Calendly on 'Simplify Meeting Scheduling'

Tope Awotona grew up in a community where everyone knew each other. Tope and his parents had an unspoken expectation of him being able to succeed. He recounts his traumatic experience of losing his father and how it changed the environment, both internal and external, which affected his life later on. 

He also shares his first-time experience living in the US and his first job as a salesman. We gain insights into his work ethic and his beginnings as an entrepreneur. He tells us how he handled rejection and how he changed his methods to better relate to his customers that enabled him to get his commissions.

He explains how he deviated from his parent’s expectations on practices concerning business or employment. Tope shares why he chose the fast track in business, working with smaller companies. This is where Tope had a perspective of how entrepreneurship works. He then set out to become one, specializing in tech.

Tope tells us how he learned the fastest method to set up a successful e-commerce business. The secret was on keywords, and that he should be aiming for products that people are actively searching for. The margins 

After the business launched, he realized that he wasn’t really interested in the products and he had to be passionate about the products he’s putting out in the market. He wasn’t regretful of the investment but he tells us this was a turning point for him to set up his own.

The returns were better than his first e-commerce business and he tells us how he saw a pattern of a problem that persisted until the second one. Both businesses weren’t addressing a problem or a need and this is where he conceptualized Calendly.

He describes how his idea of a solution to a problem was merely in bits and pieces in a simple online search but none really addressed the problem. It took him six months to do the research and preparation for outlining the necessary steps he will be taking to implement the product. Find out more on what happened to Calendly and why Tope Awotona eventually had to give it away…for free.


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