Best of Bootstrapping: Leveraged Domain Knowledge and Bootstrapped to $15M

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Ernie Bray, Chairman and CEO of AutoClaims Direct (ACD), leveraged his domain knowledge in auto insurance claims processing, and built a robust, sustainable business. When we spoke in 2015, he was using a virtual workforce strategy to scale.

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

Ernie Bray: I was born in a small town in Central California called Porterville, California. It’s a farming community. My dad was a teacher. My mom stayed at home and took care of us. I grew up in a small town environment.

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Best of Bootstrapping: Bootstrapped to Exit from Oklahoma

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How often do you hear of a successful entrepreneurship story out of Oklahoma? Well, meet Robin Roberson, Co-founder of WeGoLook. This is our conversation from 2015. WeGoLook was acquired by Crawford & Company in 2017.

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

Robin Roberson: I was born in Oklahoma. I was raised, primarily, on a farm. There were about 12 kids in my class. I didn’t know much about the outside world other than what was there in town. I started my entrepreneurial journey in the second grade making yarn belts on the playground. I was able to talk a few of my friends into making them with me. We had quite the distributorship going with yarn belts until the Principal shut us down. When he asked us to stop making yarn belts, I started making Christmas tree ornaments to sell. He shut that down too.

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Best of Bootstrapping: Bootstrapped a Freemium Business Using a Paycheck

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Aytekin Tank, Founder and CEO of JotForm, is a Turkish entrepreneur who bootstrapped his company with a paycheck. When we spoke in 2015, he was using a freemium business model, and a virtual team strategy to scale.

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

Aytekin Tank: I was born in Istanbul. I spent my childhood moving from city to city since my family worked for the government. Constantly having to adapt and make friends instilled in me an appreciation for different cultures and meeting new people. We have offices in San Francisco and in Turkey. We have remote workers in 20 countries.

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Best of Bootstrapping: Peruvian Entrepreneur Bootstrapped to $200 Million

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We hear a lot from Indian and Chinese entrepreneurs. We hear some from Europeans. But thus far, not as much from Latin American entrepreneurs. WEI President Belisario Rosas is Peruvian, and is also interested in fostering further entrepreneurship in Latin America. This is our conversation from 2015.

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

Belisario Rosas: I was born in Lima, Peru.

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Best of Bootstrapping: Bootstrapped in New Zealand, Scaled in the U.S.

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I have always said that you need to bootstrap your way to validation and traction. ProjectManager.com Founder Jason Westland did just that, and built a robust company from New Zealand. Read on, it’s a fabulous story from 2016.

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?

Jason Westland: That’s further back in time than I expected. I’m from New Zealand in the Southern Alps. My first job was managing a project of 25 people. I was 22, just out of university. I was in project management until around 15 years ago when I became the General Manager of a software company that grew fast. I was inspired to start my own business based on reporting to a Board that I learned a lot from. This is the third business that I’ve started.

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Best of Bootstrapping: Bootstrapped with Services from Houston

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Identity Automation Founder James Litton built an identity management software company from Houston and then went upmarket. Here is our conversation from 2016.

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 circumstances?

James Litton: I am a native Houstonian. I’m a rare breed. I was born and raised in Houston. In terms of circumstances, I think I’m from your quintessential American middle-class family.

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Best of Bootstrapping: Bootstrapped Using Services from Pune, India

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Services companies are easy to bootstrap, but often, they grow slowly in the beginning. How do you accelerate? This discussion with Mindbowser CEO Ayush Jain is about the levers of acceleration.

Sramana Mitra: All right, Aayush, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, what kind of background?

Ayush Jain: I was born and raised in a city in India called Agra, which is famous for the Taj Mahal. I was born into a middle-class family; education was the focus of the choices that our parents made. They always made sure that we were in the best of the schools possible. I did an integrated post-graduation course in computer science and management from Gwalior. It was a unique program, where you learn both tech as well as management. In introspection, it was a great program and it was a good experience.

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Bootstrapping Using Services from Pune: Mindbowser CEO Ayush Jain (Part 6)

Sramana Mitra: Can you give me an example of a Lego block that AI has enhanced? What was the Lego block and what did AI do to enhance that Lego block?