🗓 Calendly

How Calendly got their first 1000 customers?

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Today we dive deep into Calendly


The basics:

Elevator Pitch

Calendly is a scheduling platform that makes it really easy to schedule meetings

In the 36 case studies we did so far, I think Calendly would win the prize for defying VC advice...and I couldn't be more excited to write this issue.

Here is a summary of everything Calendly’s founder Tope did that would go against the advice you typically hear from YC, Andreessen, Benchmark..etc

  1. Based out of Atlanta

  2. Build a profitable business from the get-go! Only raised $550k for the first 9 years of the company

  3. Outsourced the initial product to Ukraine. Tope, Calendly's founder, put in over $50k for a dev shop to create the MVP. He didn't write a single line of code.

  4. Spent the first six months doing market research, not building the product

  5. Did not interview a single customer before starting or launching the product

  6. Was obsessed about his competitors products, in fact he spent 3-4 months trying out every single scheduling app that existed

  7. Started by a single non-technical black immigrant founder


Who started Calendly?

Calendly was founded by Tope Awotona, who graduated school at just 15 and went on to join the University of Georgia.

Tope spent his 7 year working stint in sales. On the side he started 3 failed businesses: a dating company that never launched, an ecommerce website selling projectors and an ecommerce website selling grills. 

Tope as many of us, wanted to make money and it took him 3 runs to figure out that unless you care really deeply about the problem you are trying to solve...it just won't work.

"To scale a business and be successful, I couldn't just be mercenary. I truly needed to care about the problem and be motivated to solve it."


How Calendly got started?

Calendly founding story starts with Tope's previous failed attempts at starting a business, Tope decided to take a sabbatical from side-hustles and would only go for another run if

  1. He is not starting a business for the sake of starting a business.

  2. He could see himself quitting his daily sales job to pursue that project full-time.

A year into his sabbatical, he was organizing a large meeting across 3 different companies and 10 people and the process of finding a time everyone agreed on was brutal. He took an afternoon to evaluate a few scheduling tools to see which one he can expense the company to make his life aa little bit easier. The more he looked, the more he realized how ample an opportunity was for modern scheduling software that was easy for the recipient to use.


Reasons not to start Calendly:

After being burned by his previous side hustles, Tope spent the next few months trying to invalidate why he shouldn't build another scheduling tool. But the more time he spent playing around with his potential competitors, the more conviction he gained. When it was finally time to pull the trigger, he went all in! All in as used every single last dollar to his name to pay a dev shop in Ukraine to develop V1 of the app. 


Validating the idea:

  • Did not talk to customers! Tope spent his last 7 years selling enterprise software. So he liked to think he knew a thing or two about the pains of scheduling meetings...To his credit, he did!

  • He spent his time learning what people loved about the 30 competitors on the market. Tope respected his competition and was humble enough to try to learn from their wins, and maybe he Zucked a feature or two along the way.

  • His market validation was seeing many decent businesses built in the space that had horrible products. Fragmented market, with low NPS and many profitable SMBs.... isn't this the perfect startup recipe?


First 10-> 1000->10,000 users

The viral loop:

The growth strategy for a product like Calendly screams product virality. The nature of sending out invites means that you share them every time you are using the product. But as is the case with any product lead growth, the product needs to be pretty differentiated for it to catch on. Calendly's product innovation came in 4 different flavors:

  1. The product experience was optimized for the recipient, not the sender! All previous scheduling software was optimized for their actual customers, the people who pay the bills! Calendly focused ruthlessly on the recipient, minimizing steps taken to schedule a meeting as much as possible.

  2. Consumer vs. Enterprise: that meant shaving off any feature people didn't love in the existing software, and just doubling down on features people loved in other software...and making it better.

  3. Integrations Integrations Integrations

Flywheel in effect

So a funny story here, Calendly grew like 🔥 in the early days because it was free. This was not a conscious decision made by Tope. What happened was he ran out of money and couldn't pay his dev shop to build a billing software...so he had to launch for free for the first year before raising those $550k that would last him almost a decade

First 10 customers:

His first 10 users were customer success agents at Bright Bytes. Bright Bytes is a data and analytics company in the education space that contracted the same dev shop as Calendly to develop a software product. Calendly came up in random check up a meeting between the dev shop and Bright Bytes exec team, and they do so happen to have the same problem Calendly was trying solving. So the dev shop agreed to give them early access (with Tope's consent) to test out the product and provide feedback

First 1000 customers:

Bright Bytes customer success used Calendly to schedule calls with parents in K through 12. A few Parents (who were clients of Bright Bytes) then started to sign up to Calendly and use it for parent-teacher conferences. Schools started to take notice of Calendly and started to officially run all their parent-teacher conferences on Calendly. Other schools then started getting some real FOMO and signed up to see what all this hype was about. Within less than a year, tens of schools and thousands of schools in the Atlanta area ran all their external meetings on Calendly.

From 1000 => 10,000 users

It started with teacher-conferences and then product grew organically from there to a few thousand people. But Tope with his sales acumen, needed to know where to put fuel on the fire. So what happened next was pretty genius (and simple actually). 

He went after feature requests. By that I mean, every time someone asked for a feature, he would try to get on a call with the customer and understand how they use the product. People who request features from a company usually tend to be super users of the product. So Tope leveraged that fact to identify exactly who to go after, who were the people getting the most value out of his product and hit that domain with some old fashioned sales. After all thats what he did for a living for the previous decade or so!


That's it for today, folks..but before your go you should know my friend Jawad Shriem just started a pretty 🔥 podcast called Thinking Backwards

Thinking Backwards features actionable convos w/ super creators who will show you how to start and get things done! 

I listened to the episode with Wes Kao cofounder of AltMBA two times already!

See you next week 😉,