This is a post by Jesse Pujji. Jessi a serial entrepreneur that lives in the US. He has:
- Bootstrapped to an 8-figure exist with his previous startup, Ampush
- Is currently building GatewayX, a venture studio that he plans to bootstrap to $1B+
- Executive Chairman & Founder of GrowthAssistant.com
- ex-McKinsey Consultant
Guest Author: 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.
Tope Awotona was born in Lagos to a biz family. 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.
They moved in with relatives and set off to realize the American Dream. He went on to UGA at 17 and shortly after had his first biz idea.
He invented a device using optical character recognition to see and count cash. 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. And he also kept up his side-hustles.
And he started building a framework for what he needed his life’s work to be:
1) It had to be software
2) He had to have a passion
3) It needed a growth channel he could understand
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 schedule calls. Dozens of emails for a single meeting. Scheduling software sucked.
And so Calendly was born! But… Tope has no clue how to code.
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.”
The MVP was so good, the CLIENTS of beta users asked if they could roll it out to their entire 80+ team. Then they launched and 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.
Since then, the company has bootstrapped to over $70MM ARR and 10MM+ monthly users
In 2021, Calendly raised $350MM at a $3B valuation.
$200M used to give liquidity to the team and early investors…
Tope’s Net Worth is >$2BN!!
