Best of Bootstrapping: Bootstrapped with a Paycheck to $15M

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In 2018, GreenPal Co-founder Gene Caballero shared a fantastic story of a founder duo bootstrapping with a paycheck, growing from $5M to $15M in one year, with a virtual team of freelancers. Your classic 21st century internet business. No outside financing whatsoever!

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Gene Caballero: I was born in Lima, Peru. My dad’s side of the family are all entrepreneurs. My grandfather had his own propeller business. We made propellers for boats. My dad actually has that business now. I’m the black sheep. I’ve gone into the technology side as opposed to the manufacturing of propellers.

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Best of Bootstrapping: Bootstrapped with a Paycheck to $7M ARR

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This conversation with AIScreen CEO and Co-founder Nikita Sherbina is a classic bootstrapping story with a very small team to serious revenue.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Nikita Sherbina: I was born and raised in Ukraine. I moved to the United States about six years ago without knowing anything about this land.

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Best of Bootstrapping: Bootstrapped an AI Chatbot Startup with a Paycheck

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

It took CoRover CEO Ankush Sabharwal and his co-founders two years to launch their first customer, The Indian Railways. During this time, the founders held on to their jobs, diligently fulfilling their responsibilities while also pursuing their dreams.

Sramana Mitra: Let’s go to the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Ankush Sabharwal: I come from a remote district in India in the extreme north – Rajouri. I was brought up there. My family moved to Jammu. I did schooling there. For Masters, I’ve done Software Engineering.

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Best of Bootstrapping: Solo Entrepreneur Bootstrapped with Paycheck to $15M+

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SoPost Founder and CEO Jonny Grubin started as a solo entrepreneur, bootstrapped with a paycheck, and had built a $15M+ revenue global business with a small amount of funding when we spoke last year. Excellent story!

Sramana Mitra: Let’s go to the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jonny Grubin: I was born in London but moved to Newcastle when I was three. My dad is American and my mom is from the UK. I grew up in Newcastle and started on my entrepreneurial journey at a pretty young age. When I was studying for my high school exams, I kicked off and ran a range of entrepreneurial ventures of my own.

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Best of Bootstrapping: Entrepreneurial Couple Bootstrapped an E-commerce Business

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Nomad Lane Co-Founders Kish Vasnani and Vanessa Jeswani bootstrapped to multi-million dollars in revenue selling a private label product before quitting their jobs. In this story, you also get to see the nuances of running successful (and not so successful) crowdfunding campaigns. Very interesting journey and insights.

Sramana Mitra: Let’s go back to the very beginning. Where are you from? Where were you born, raised, and in background?

Kish Vasnani: I was born in Jaipur, India and moved to the US when I was about one year old. I grew up around the Atlanta area and finished school there. I moved to New York to help a friend of a friend start a software company, which was also bootstrapped. We were able to sell that to Thomson Reuters. I had the itch again to go out on my own. Very candidly, I was also fired from a couple of other jobs over the course of two years.

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Bootstrapping an AI Chatbot Startup with a Paycheck: Ankush Sabharwal, CEO of CoRover (Part 6)

Sramana Mitra: Your friend gave you some money and gave the money back. What other financing has happened?

Ankush Sabharwal: My two friends who joined as co-founders gave me money. We took angel funding just before IRCTC went live. Then we got funds from Canbank VC. Now we will be announcing a fund raise.

Sramana Mitra: What is the total amount of funding so far?

Bootstrapping an AI Chatbot Startup with a Paycheck: Ankush Sabharwal, CEO of CoRover (Part 5)

Sramana Mitra: How much money did you make this way – from advertising?

Ankush Sabharwal: It’s more money than we would have made through subscription.

Sramana Mitra: Really?

Ankush Sabharwal: There are four million users on the website and more in the app every day.

Sramana Mitra: Traffic volume was very large. You just created a way to monetize that traffic for both of you.

Bootstrapping an AI Chatbot Startup with a Paycheck: Ankush Sabharwal, CEO of CoRover (Part 4)

Sramana Mitra: You were working at Ultisource when you negotiated with Indian Railways?

Ankush Sabharwal: Yes. In the appraisal cycle when I was about to quit the company, I got the highest rating. I was Group Manager that time. When you’re the manager’s manager, you hardly get the highest rating in appraisals.