How Calendly Got 10 Million Users

From risking it all to being valued at $3 billion

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How Calendly mastered the Calendar 

This week we spotlight Calendly, a scheduling startup that has changed how people manage their time. Founded in 2013 by Tope Awotona, Calendly is now valued at $3 billion and has become a go-to tool for over 10 million users.

Startup Story of Calendly

The Founder Creating Connections

With overflowing inboxes, double-booked diaries, forgotten dinners with friends, and that ever-elusive PT session you’ve been trying to squeeze in for months, it's hardly surprising that many of us long for a way to escape the sometimes-messy schedule to keep track of our meetings.

“I saw how broken scheduling was and realized nobody was thinking creatively enough to find a solution, so I gave it a shot.”

CEO & Founder Tope Awotona

The Growth Story

Calendly’s success story is built on solving a common problem: scheduling. When Tope Awotona launched Calendly, he invested all his savings to get it off the ground. After six months of research, the product launched and grew organically through word-of-mouth and a product-led growth model.

“I put every single dollar I had ever made into the start of Calendly. I didn’t quantify how big it could be, but I knew it was a big problem to solve, so I put everything on the line”

The viral nature of Calendly's growth—70% of new users came through meeting invites—allowed it to scale without heavy reliance on traditional marketing​. With a product first focus, Tope decided to offer Calendly for free up until a year after launch. By bootstrapping the initial development Calendly quickly found product market fit and was able to generate over $110 million in revenue last year - paying off in the long-run.

“I wanted people to love the product. Keeping it free allowed me to grow aggressively when it launched while building new features.”

The 3 Billion Dollar Meeting

Calendly’s razor-sharp focus on understanding user needs and leveraging product-led growth catapulted it to the top of the scheduling game. While its mantra might have been “quality over quantity”, there was certainly no shortage of the latter.

In 2021, the startup raised a $350 million in series B round, bringing its valuation to $3 billion. A year later, Calendly boasted an impressive 53% share of the U.S scheduling market and 21% globally, becoming the scheduling tool of choice for over 10 million users.

“I’m not just building a business; I’m solving a real problem that people face daily.”

Today, Calendly stands as a leading software startup. With sights set on an ambitious $1 billion in annual recurring revenue, its next chapter involves a move to B2B (business-business) marketing. 

Tope Awotona’s journey from betting it all to a $3 billion dollar startup is not an uncommon story of founders taking immense risk. By eschewing traditional marketing in favor of creating a seamless, user-driven product, he has charted a growth story that highlights the priority of product over marketing.

Startup News This Week 📰

Greece plans to offer golden visas to startup investors.
Through new changes, internationals will be eligible to obtain a five-year residence permit through a €250,000 investment in Greek startups.

WeWork founder’s crypto startup refunds investors
Flowcarbon, a startup co-founded by Adam Neumann, is reportedly refunding investors after its “Goddess Nature Token” failed to launch.

OpenAI is reportedly in discussion to raise $6.5 billion.
OpenAI's new valuation could skyrocket to $150 billion in new fundraising, positioning it among the world's most valuable startups.

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See you next week,
Odin & Hari

How Calendy mastered the Calendar