Best of Bootstrapping: Bootstrapped to $5M, Raised Money Later

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

Founder CEO Josh Millet had bootstrapped Criteria to almost $5 million in revenue before raising funding.

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

Josh Millet: I was born in Toronto, Canada. I have dual citizenship of US and Canada. I came to the States for school 20 years ago and have been here ever since.

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Best of Bootstrapping: Bootstrapped an E-Commerce Startup from Utah

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To succeed in e-commerce today, you need to look for unserved niches with unique products. Learn how KURU Footwear Founder Bret Rasmussen bootstrapped an e-commerce startup from Utah.

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

Bret Rasmussen: I was born in Utah, but my parents quickly moved to Indiana. We actually lived a few years in Italy until I was about eight or nine years old. Then we moved to Taiwan and then back to Indiana. I graduated high school in Texas and then I went to college out west here in Utah. 

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Best of Bootstrapping: Bootstrapped a Niche E-commerce Venture

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

This conversation with Modded Euros Co-founder Sean Dawes from 2019 is a comprehensive discussion on how to bootstrap a niche e-commerce venture with a lean team and effective use of inventory financing. You can listen to the podcast interview here and watch the interview here:

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?

Sean Dawes: I was born and raised in Philadelphia. I haven’t gone too far away from my hometown as my company is based out of West Chester, Pennsylvania, which is 20 or 30 minutes outside of Philadelphia.

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Best of Bootstrapping: Bootstrapped with Services, Raised Money, Acquired by Salesforce

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John Stewart and his co-founder have built MapAnything from Charlotte, North Carolina and Atlanta, Georgia. When we spoke in 2018, he had raised over $40 million in funding, proving that you can build sizable VC-funded SaaS businesses from anywhere. MapAnything was sold to Salesforce in May 2019.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where did you grow up? Give us some early story.

John Stewart: I’m from upstate New York. I’m from a middle class background. My mother was a stay-at-home mom. My father was in the construction business. He was an architect. I went to school in New England for Mechanical Engineering at Worcester Polytechnic Institute in western Massachusetts and graduated in 1997.

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Best of Bootstrapping: Bootstrapped, Raised Money, and Exited from Karnataka, India

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Robosoft Founder Rohith Bhat started a services company in his hometown – a small town on the west coast of Karnataka, India. When we spoke in 2017, fifteen years later, the company was generating $18 million in revenue and had raised two sizable rounds of VC funding. In 2021, TechnoPro acquired Robosoft for $108 million. I find this story exhilarating!

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?

Rohith Bhat: I was born in Udupi, India. It’s a small town on the west coast of the country. Then I went to the local school and university and studied engineering and computer science in 1992. Once I finished engineering, I had an opportunity to go on to work for a company in Japan for Recosoft. I worked for this company for around three and a half years.

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Best of Bootstrapping: Serial Bootstrapped Entrepreneur’s Journey

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

Going against the grain of Venture Capital mania, in 1999, Beyond Security CEO Aviram Jenik started his second bootstrapped venture. When we spoke in 2017, 18 years later, he was still running it. In 2021, Beyond Security was acquired by HelpSystems.

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?

Aviram Jenik: I was born and raised in Israel. I moved to California about 10 years ago. I spent most of my adult life in Israel. I studied at the Technion which is like MIT in Israel. We half-jokingly say that pretty much everyone can say that they went to the top 10 universities in Israel because there are less than 10 universities. I’m an entrepreneur by background. I started my first company, which was bootstrapped when I was about 19.

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Bootstrapping an AI-Powered Security Startup to $10M+ in Revenue: Osprey Security CEO Rohit Anabheri (Part 4)

Sramana Mitra: These two customers that you were able to place the MVPs into pilots with, how long did it take you to turn them into paying customers?

Rohit Anabheri: About three to six months. They wanted to ensure the stability of the platform.

Sramana Mitra: What is the average deal size?

Rohit Anabheri: Six figures.

Bootstrapping an AI-Powered Security Startup to $10M+ in Revenue: Osprey Security CEO Rohit Anabheri (Part 3)

Sramana Mitra: How long did it take you, and what was the trajectory? How many customers did you work with in the beginning? As you started to productize, what was the timeline?

Rohit Anabheri: The first year is always a struggle. It was completely bootstrapped by me and my co-founder.