How Tope Awotona, a Nigerian Immigrant bootstrapped a software biz from 0 to $3 BILLION?

Lessons Learned from Calendly’s Founding 1) Solve a problem you have 2) Passion and grit WIN 🚀🥊 3) Ease of Use + Great Experience = organic growth In 2020, Calendly grew by 75%. The app’s description and value prop is the same as it was in the original 2014 seed announcement

Jesse Pujji
In less than 6 years, this Nigerian Immigrant bootstrapped a software biz from 0 to $3 BILLION The crazy part? He has no idea how to code. He was a sales guy. Time for another Bootstrapped Giant 🧵🧵 This one is a gem 👇🏽👇🏽👇🏽
@topeawotona was born in lagos to a biz family His grandma built a very successful textile import/export business His mom co-owned a pharmacy with his Aunt His dad was a microbiologist turned chemical distributor Their life was good, then tragedy struck…
At the age of 12, Tope was relaxing in his house when he saw his dad pull onto the driveway. Out of nowhere, several men rushed the car, forced him out and despite no resistance, they murdered him. Tope watched the whole thing and still has insomnia to this day bc of it.
That incident left a deep imprint on Tope. And he resolved to build a dream success for himself and his father Shortly after the tragedy, his mom moved the family to Georgia. The moved in with relatives and set off to realize the American Dream…
At 15, even though Tope graduated high school, his mom kept him enrolled to more deeply assimilate into american culture. From there, he went on to @universityofga at 17 and shortly after had his first biz idea…
Part time, He was working in a pharmacy, and it took too long to count all the 💰 after close… so He invented a device using optical character recognition to 👀 and count 💵 After patenting it, he cold called National Register.. they offered to fly him out but he froze up…
This experience motivated him to learn sales. After UGA, he cut his teeth at an internet travel agency for the next 4 years Then joined IBM with Tivoli and then Perceptive He stepped into the world of tech sales… … All while keeping his side hustles, what were they?
His first startup idea (Biz #2) was an online dating site called Single To Taken inspired by an article about the success of Plenty of Fish Tope realized early on that he simply didn’t have the technical or product skills to build the platform, so he pivoted to ecommerce instead
His ecomm idea (#3) was ProjectorSpot (selling projectors online), but low margins made growth difficult YardSteals (#4) was similar, but in the Home and Garden nice with a focus on grills – the same problems cropped up again So Tope decided on a few key factors for #5
1) It had to be software, since the margins were incredible 2) He had to have a passion for it 3) It needed a growth channel he could really understand (the last 2 used SEO) It took a few more years of sales jobs before he found that magic combination while working at Dell
At the end of 2012, he realized how much time it took to get scheduled with a prospect💡 Dozens of emails going back and forth each day for a single meeting Existing scheduling software sucked. Calendly was born! …but Tope did not know how to build software.
So he did the classic first time entrepreneur thing: he outsourced it overseas. This was a disaster. It took 1+ year to build and he put all his life savings into it. in 2014, he almost lost it all…
His dev team was in Ukraine and they were going through violent riots. Undeterred, he flew into Kiev and stayed with his team through the riots making sure they shipped. That risk paid off with a top notch product and during his time there, they cracked something special…
The “Upside Down Funnel” – or said differently, the inherent virality in the product. I send you a calendly and its like marketing and product built into one. Tope was building a social network + software, he calls it the “Instagram of Scheduling.”
Whenever someone sent a link, they shared the product along with their schedule – UX was the #1 goal The MVP was so good, the CLIENTS of beta users asked if they could roll it out to their entire 80+ team Individual users turned into departments and then whole companies ➰🚀
By the time they launched publicly, Calendly was already a scheduling favorite with schools for parent teacher conferences The viral design of the app has not changed, and it’s popularity at @ATLTechVillage and on Twitter that led to their only investment for the next 7 years..
Trying to raise from the Southeast with almost no revenue meant the Sand Hill gang wouldn’t take a second look Thanks to an A+ product, Calendy secured a $350K seed round from Atlanta Ventures in April 2014 – just enough to keep going and launch a premium version in July 2014
Then they began adding $25K in ARR every month They began building new automations and integrations to start boosting paid conversions By the end of 2015, they had tripled growth and were adding $75K ARR every month and broke $1MM ARR The were already profitable.
Growing $1MM to over $70MM meant increasing profits – without increasing the price for everyone In 2017, they released a Pro plan for 50% more for Salesforce users And 2018, Calendly narrowed focus to their 6 most profitable customer segments and have stuck with them since
Since then, the company has bootstrapped to over $70MM ARR and 10MM+ monthly users How? By staying maniacally focused on ease of use, a strategy that fed the viral experience built into the core of the scheduling app
In January, Calendly raised $350MM at a $3B valuation. $200M will be used to give liquidity to the team and early investors… On track to hit $100MM ARR later this year, this bootstrapped giant is growing too fast to even consider an IPO yet! Tope’s Net Worth is >$2BN!!
Lessons Learned from Calendly’s Founding 1) Solve a problem you have 2) Passion and grit WIN 🚀🥊 3) Ease of Use + Great Experience = organic growth In 2020, Calendly grew by 75%. The app’s description and value prop is the same as it was in the original 2014 seed announcement
Enjoy this? Follow me @jspujji for more stories on “Bootstrapped Giants,” DTC, Growth Marketing and entrepreneurship!!

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