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Bootstrapping

Best of Bootstrapping: Bootstrapped Art.com First, Raised $30M Later

Posted on Wednesday, Oct 4th 2023

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

Art.com Co-founder Josh Chodniewicz bootstrapped for 10 years before raising a $30 million first round of funding. Read on to learn more about his journey.

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

Josh Chodniewicz: I was born in New Jersey. I am the oldest of seven kids. My parents had seven kids in nine years.

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

Posted on Tuesday, Oct 3rd 2023

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

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: Serial Entrepreneur Bootstrapped Three PropTech Ventures

Posted on Friday, Sep 29th 2023

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

LuxuryProperty Founder Jason Hayes has worked at the cusp of real estate and digital marketing for 35 years and built three successful ventures. All of them are bootstrapped, organically grown, capital efficient businesses.

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?

Jason Hayes: I’m speaking to you from Dubai. I was born in the UK, brought up in Sri Lanka, and I’ve spent time living and working in the Barbardos and California. I’ve been in Dubai for nearly eight years now. I consider myself a global citizen.

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Best of Bootstrapping: Solo Entrepreneur Bootstrapped to Over $5M

Posted on Thursday, Sep 28th 2023

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

Ukrainian entrepreneur Vladimir Gendelman started as a solo entrepreneur in Detroit and has bootstrapped a $5M+ niche e-commerce company called Company Folders.

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?

Vladimir Gendelman: I was born and raised in the former Soviet Union in Ukraine. We came to America when I was 16.

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Best of Bootstrapping: Bootstrapped an AI-Powered Security Startup to $10M+

Posted on Wednesday, Sep 27th 2023

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

Osprey Security CEO Rohit Anabheri has effectively used the Bootstrapping Using Services technique to bootstrap an AI-Powered Enterprise Security venture to mid eight figure revenues. In that process, he has turned down offers for Venture Capital. I believe, in Artificial Intelligence and Machine Learning, currently, Bootstrapping Using Services is one of the best ways to find problems to solve and build successful companies.

Sramana Mitra: Let’s start by introducing our audience to yourself and then we’ll come to the Osprey Security journey in a moment. You are a serial entrepreneur, yes?

Rohit Anabheri: That is correct.

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

Posted on Tuesday, Sep 26th 2023

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+

Posted on Monday, Sep 25th 2023

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

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: Bootstrapped Using Services to $26M and a Fabulous Exit

Posted on Tuesday, Sep 19th 2023

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

When we spoke in 2021, Founder CEO Vamsi Kora had bootstrapped Gathi Analytics to over $26 million in revenue in four years and exited at a fabulous multiple. Much to learn from his journey.

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?

Vamsi Kora: I’m from south India, from a village in Rajamundry, which is very close to the Bay of Bengal. I did Mechanical Engineering. Right after it, I went to have one of the very few well-paid careers at that time. I couldn’t afford to come to the US. So I went into merchant shipping and roamed around the world for about three years. I made two and half rounds around the equator.

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