Tope Awotona was raised, alongside his three siblings, by parents who were medical personnel, in Lagos.
As a parental team they continually reminded the young Awotona brothers to be forever grateful for what they had.
One day, when Tope was 12 years old, he witnessed his father being shot dead by armed robbers who came to steal his car. That scene left him traumatised for six months, unable to muster even an appetite.
A few years prior to his father’s death, Tope’s Dad had quit his job at Unilever to build his own company. Young Tope decided that he would continue building that legacy, to honour his late father.
A witty child, Tope bagged a University scholarship offer to study in the United States, at age 15. His mother stopped him, because she felt he was too young. However, she moved the entire family to America so they could all complete high school and gain university admissions there.
Fast-forward to graduating from university, Tope explored a few jobs, shortly after, before settling in at Perceptive Software, a growing startup in Kansas City, as a salesperson.
With grit and perseverance, he climbed the sales leaderboards, excelling at the job. However, he was intent on starting his own company when the time was right.
‘The Meeting that Changed His Life’
One afternoon, Tope attended a staff meeting where Perceptive’s founder, Scott Coons, led the discussion.
Rather than discussing revenue growth, staffing plans, or quarterly roadmaps, Scott did something different. He used the meeting to tell the story of Perceptive.
Scott dove into the details of how he came up with the idea for the company.
He even elaborated on the many twists and turns that the company went through, and mistakes he’d made.
Most importantly, Scott emphasized the team’s persistence.
They had fought through the slumps, learned from their mistakes, and eventually things turned around.
This was the first time Tope realized that companies did not always have a straight path to success.
“It made entrepreneurship all of a sudden more attainable. I knew if they could do it, I could too.”
Tope left that meeting thoroughly inspired.
He didn’t need to wait for the perfect time to start a company. His moment was now.
However, when the future seemed as bright as day, life seemed to have had other plans. Tope’s mother had been diagnosed with cancer, and he moved back to Atlanta to be there for her.
Tope reflected back on the staff meeting with Scott. And in that moment, amidst all the personal hardship on the horizon, he chose to persist. He quit his sales job and started to build.
His first three startup ideas failed.
A dating website that never launched. A projector company that had lackluster sales. An outdoor grill brand that he didn’t have a passion for.
Yet, he persisted.
Tope eventually stumbled upon an idea to get rid of the back and forth emails when scheduling a meeting. And then and there, Calendly was born.
“I went for broke and put every single dollar I had ever made into it, I literally put everything on the line”
The same year Tope founded Calendly, his mother passed away.
He never told his mother what he had been working on, as she was very risk-averse; he feared it would have worried her too much.
Despite his grieving, Tope again chose to push forward, and over the next seven years he built Calendly into an industry leader, with over 20M customers and revenues of $60M+.
Tope persisted through personal and professional hardship.
After losing the two most important people in his life, he built something that would have made them both beam with pride.
He achieved his Dream.
“I wish they could see what Calendly is now.”
