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Entrepreneur Journeys

Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal (Part 1)

Posted on Monday, Oct 29th 2018

This is a fantastic story of a founder duo bootstrapping with a paycheck, now 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 >>>

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Capital Efficient Entrepreneurship: Neil Vaswani, CEO of Corestream (Part 1)

Posted on Monday, Oct 22nd 2018

Neil has turned a $3M investment into a ~$10M annual revenue company by addressing a cumbersome piece of workflow in benefits management. Read on to learn how.

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?

Neil Vaswani: I was born in New York and lived there for a part of my life. My parents are from India. I did live in India for a while and spent some time in Europe. I went to school at Babson College and then moved back to New York City right around 2000. I started Corestream probably about 2006. >>>

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Building a Fast Growth, Cutting-Edge Insurance Brokerage: Karn Saroya, CEO of Cover (Part 1)

Posted on Monday, Oct 22nd 2018

This is a terrific story of a team that has tremendous expertise in building and acquiring customers for consumer apps, and how they applied that unfair advantage to disrupt a domain (insurance).

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?

Karn Saroya: I’m a Canadian living in Silicon Valley. I was born in Canada in Vancouver. I was born and raised there. I went to Queens and eventually MIT. >>>

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Building a VC-Funded B2C CRM Company From Virginia: Zaius Founder and CTO Spencer Pingry (Part 1)

Posted on Monday, Oct 15th 2018

We love companies that have roots in off-center geographies. Zaius started in Virginia, raised capital in Boston, and has grown to ~500 customers with a $24k average ARR per customer. These are healthy metrics, and for the team in Virginia, accomplishments to be proud of.

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?

Spencer Pingry: I was born and raised in Tucson, Arizona. I lived there for the first 24 years of my life. I went to the University of >>>

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A Kick-Ass Woman Entrepreneur: Cooper Harris, CEO of Klickly (Part 1)

Posted on Monday, Oct 8th 2018

This is a terrific entrepreneurial story of a woman entrepreneur with no technology background who is killing it with a technology startup.

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

Cooper Harris: I’m from the southeast of the East Coast. I was born in Atlanta and I grew up in North Carolina just because my mom is a professor at Duke and UNC. I also studied at Duke.

Sramana Mitra: Where did you do your education? >>>

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From Zero to $3.7 Billion: Jyoti Bansal’s Textbook Case Study of Building AppDynamics (Part 1)

Posted on Monday, Oct 1st 2018

Jyoti started as a first-time entrepreneur trying to do a fat startup. Read how he managed to navigate the chicken and egg, and build a Unicorn-level success. Superb story!

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?

Jyoti Bansal: I was born and raised in a small town in India. >>>

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Scaling to $10 Million: Humanity.com Founder Ryan Fyfe (Part 1)

Posted on Monday, Sep 24th 2018

Humanity.com has operations in San Francisco, Pakistan, and Serbia. The founder lives in Panama. Yet another distributed software company that is scaling nicely.

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?

Ryan Fyfe: I grew up in Canada. I moved around a lot as a child. Both my parents were educators. My mom is a primary school teacher. My dad is a mechanical engineering professor. Through that time, we lived in Belgium, across different parts of Canada, and >>>

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Building Fat Startups: Delphix CEO Jedidiah Yueh (Part 1)

Posted on Monday, Sep 10th 2018

Jed has built two fat startups. This discussion delves into the nuances.

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?

Jedidiah Yueh: The funny thing is, I never wanted to an entrepreneur. I started out as an English major in college. When I was in grade school, high school, and college, I was never interested in technology. I was the guy who always asked my friend to help me set up my computer. >>>

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Bootstrapping a Niche e-Commerce Company to $10 Million: iHeartRaves CEO Brian Lim (Part 1)

Posted on Monday, Aug 6th 2018

Niche e-commerce still produces compelling success stories. Read on to see how Brian built iHeartRaves.

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?

Brian Lim: I was born in LA County. My parents immigrated here to escape communism in China and Cambodia. I grew up very poor. We bootstrapped our company back in 2010 with $100 and turned it into a $20 million a year company. >>>

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Scaling to $10M ARR with a Virtual Company: Fred Plais, CEO of Platform.sh (Part 1)

Posted on Wednesday, Aug 1st 2018

Fred has built a wonderful company with a virtual architecture. Read on to see how.

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

Fred Plais: I was born in the western part of France. I’ve worked at three different companies. I’ve got three kids and a wife, and I now live in San Francisco.

Sramana Mitra: What is your education? What did you study? >>>

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