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- đź“… Would you risk it all on a scheduling tool? He did.
đź“… Would you risk it all on a scheduling tool? He did.
The risky decision that made Calendly unstoppable
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Investors dismissed it, Google and Microsoft could kill it at any moment, and Tope Awotona risked his life savings anyway. The question wasn’t if Calendly could succeed—it was if it could survive.
"I raided my bank account and 401(k) to launch Calendly in 2013."
Here’s what’s scheduled for today’s issue:
The bold $200,000 gamble that nearly wiped out Tope Awotona’s savings before Calendly took off
Why early investors laughed off the idea of a billion-dollar scheduling tool—and how Tope proved them wrong
How integrating with competitors instead of fighting them turned Calendly into an unstoppable force
The secret to Calendly’s explosive growth without a single dollar in venture capital
The risky decision that could have killed the company overnight—but instead made it worth $3 billion
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A Scheduling Problem, Solved
In 2013, Tope Awotona had one goal: make scheduling meetings less painful. Like many professionals, he was tired of the endless back-and-forth emails to find a mutually convenient time.
The solution seemed obvious—build a better scheduling tool. But Tope knew the challenge wasn’t just about creating something new; it was about solving a universal problem in a way that people would actually use.
The market wasn’t exactly empty. There were tools like Doodle that were already trying to simplify scheduling, but they still required extensive steps to mark availability and create calendar events. Building something better was no small task.
Tope poured his entire savings into Calendly—over $200k—bootstrapping the company from day one. Investors were skeptical, but he was determined to prove them wrong. The idea? Create a tool that was simple, intuitive, and solved a real pain point.
But Tope had one more decision to make—a decision that would shape Calendly’s future.
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The Big Bet: Build Bridges, Not Walls
Instead of creating a standalone calendar app, Tope did something unexpected: he designed Calendly to integrate seamlessly with existing platforms like Google Calendar and Outlook.
This decision wasn’t popular. Investors questioned the wisdom of building a product entirely dependent on other tech giants’ systems. What if Google or Microsoft changed their APIs? What if they created a competing feature?
But Tope saw things differently. By complementing existing tools rather than competing with them, Calendly removed friction for users. It didn’t ask them to switch calendars or change how they worked—it simply made scheduling easier.
The strategy was deceptively simple:
Seamless Integrations: Calendly worked across platforms, allowing users to schedule meetings effortlessly, even if both parties used different calendar systems.
Focus on Simplicity: The tool was intuitive and required no learning curve, making it easy for people to adopt.
The result? Calendly quickly became the tool professionals didn’t know they needed. Instead of fighting the giants, Tope built bridges between them, and that made all the difference.
Winning the Scheduling Game
The skeptics were wrong. By focusing on integrations, Calendly carved out a space where it didn’t have to compete directly with the big players. Instead, it became indispensable to their users.
This approach paid off massively. Without spending a dollar on venture capital, Calendly grew to generate $70 million in annual revenue by 2020. Today, it’s valued at over $3 billion, used by millions of people worldwide.
Calendly’s story is a masterclass in strategic thinking. It’s a reminder that sometimes the best way to succeed isn’t to reinvent the wheel—it’s to make the wheel spin smoother. Could your next big idea do the same?
🍫 Snackable Stats
$352 million – Total funding raised by Calendly over six rounds from eight investors.
15 minutes – The length of demo meetings that are often booked more frequently than 30-minute sessions, suggesting a preference for shorter engagement
20 million – Total active users on Calendly
100+ – The number of partner integrations Calendly as of now
8 – Calendly is available in these eight languages (English, French, Spanish, German, Dutch, Italian, Ukrainian, Brazilian Portuguese)
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