From Three Failed Businesses to a $3 Billion Empire: The Tope Awotona Story

Some people see problems and complain. Others, like Tope Awotona, build solutions, and in doing so, they change the world.

Today, we are diving into the incredible journey of Tope Awotona, the visionary behind Calendly, who transformed dissatisfaction into a $3 billion empire.

He didn’t come from wealth, and he wasn’t handed opportunities on a silver platter. Instead, he was a Nigerian immigrant with a vision and an incredible determination to see that vision come to life.

So, what can you learn from his journey? Let’s break it down.

The Failures Before the Breakthrough

Tope Awotona’s journey began in Lagos, Nigeria, where he witnessed the entrepreneurial spirit firsthand through his father. His father’s tragic death in a carjacking left a mark on Tope, but it also fueled his determination to create a legacy of his own.

Moving to the U.S. as a teenager, Tope was driven by one goal: to build something impactful.

Before launching Calendly, Tope faced several business failures. The first was a projector-selling venture, followed by an attempt to sell garden tools, and then even an online dating site. These ventures didn’t fail because the ideas weren’t worth pursuing, but because Tope didn’t have the right timing, market fit, or perhaps the knowledge to navigate the business world at the time.

But rather than giving up, these setbacks taught him valuable lessons. In fact, his previous failures were the very foundation of his success. They forced him to refine his approach, develop a keen sense for what the market needed, and understand that building a business is as much about perseverance as it is about the idea itself.

Betting It All on Calendly

By 2013, after years of learning from his mistakes, Tope was ready to build something that would truly work. He had a vision: to make scheduling meetings seamless. He’d experienced firsthand the chaos of juggling time zones and constant back-and-forth emails while working at Dell EMC. The inefficiency was maddening. There had to be a better way.

With a bold belief in his idea, Tope risked everything. He emptied his savings account of $200,000 and maxed out his credit cards, putting his financial future on the line. The road was tough in the early years. Calendly didn’t have a flashy marketing campaign or a big launch. It grew purely by word of mouth, trusted by small teams and busy executives who realised the value of a tool that simplified scheduling. In those first few years, Tope worked tirelessly, often bootstrapping the operation and doing everything himself.

From Underdog to Industry Giant

After years of bootstrapping and building momentum, Calendly’s breakthrough moment came in 2021 when the company secured a $350 million investment, valuing it at $3 billion. But it wasn’t just the money that made this moment significant; it was the recognition that Tope’s vision had turned into something much bigger than he ever anticipated.

Calendly became the go-to tool for over 10 million users across the world, including teams at industry giants like Google, Zoom, and Lyft. It wasn’t just the tool's functionality that set it apart; it was the fact that it resonated with the way modern professionals worked and lived fast-paced, global, and in need of efficiency. What started as Tope’s personal frustration with scheduling had now evolved into an indispensable part of the daily workflow for millions.

Today, Tope still owns a substantial stake in Calendly, making him one of the wealthiest Black tech founders, with a net worth of $1.4 billion. His rise to the top has been a testament to the power of resilience, vision, and the ability to spot an opportunity where others might not see it.

Lessons from Tope Awotona’s Playbook

Your Struggles Hold the Seeds of Your Success
Tope’s early failures were learning opportunities that allowed him to fine-tune his skills, build a deeper understanding of the market, and eventually develop a solution that filled a critical gap in the business world. The key takeaway here is that struggle often precedes success. In fact, your greatest challenges might just be the first step to your breakthrough.

Resilience Separates the Quitters from the Builders
Tope didn’t stop after three failed businesses. He understood that success doesn’t come from avoiding failure but from learning how to bounce back and keep moving forward. His resilience allowed him to go from one failure to the next until he found the right formula. If you stay committed and continuously refine your approach, the setbacks will eventually lead to triumph.

Bet on Yourself, Even When No One Else Will
Tope’s decision to put everything on the line for Calendly was a risky move, especially after experiencing multiple failures. But it’s this very kind of self-belief that sets great entrepreneurs apart from the rest. If you don’t have faith in your idea and yourself, it’s nearly impossible to convince anyone else to do the same.

Tope Awotona’s Legacy

Tope Awotona’s journey highlights that with a relentless vision, a willingness to take risks, and the courage to learn from failures, you can build something that not only changes your life but the lives of millions.

Never give up; keep learning and building!

David.