Building HubSpot to a Unicorn: Dharmesh Shah’s Amazing Entrepreneurial Journey (Part 1)

Dharmesh discussed his entrepreneurial journey with candor, humility, and generosity. Wonderful conversation.

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Sramana Mitra: We will start at the very beginning of your journey. Where did you grow up? What kind of upbringing and what kind of circumstances were you raised in? I know you come from a part of India that is particularly entrepreneurial.

Dharmesh Shah: I was born in a small town in Gujarat. When I say small, I mean really small with no paved streets, no traffic lights, no hospitals. I was born at my mom’s family house with the help of a midwife. I lived my early years in a town not that far away. If you had talked to any of my family or anyone that knew me, I would have been the least likely to start a company. That was not my personality. I was a very quiet kid. It was surprising to many that I would wind up being an entrepreneur.

My childhood was relatively modest. The house that I grew up in didn’t have a TV and didn’t have hot running water. We had to heat the water. It was modest. My dad came over on a student visa in the United States. He came alone because that’s how immigration worked back then. My mom and I stayed in India for a little while. I spent some time here in the States and in Canada.

Right in high school, the entire family moved back to India for a couple of reasons. One is that my grandfather passed away, so we wanted to support my grandmother. I had two siblings at that time. We left Canada and went back to India. I enrolled in high school there. I did a couple of years of undergrad in Mechanical Engineering. You get to choose based on what your score is and that was the best engineeringish thing I could get into. That’s what I did.

While I was an undergraduate, my parents moved back to the USA. I came to visit them during the summer of my second year in college. People had always told me, “You really like Math. You should check out this computer stuff.” Running a computer in India is expensive because you have to have an airconditioned room. It has to relatively clean. I never got a chance to touch a computer while I was in high school or undergrad. I came here and my family was living in Indiana.

Nearby, there was Purdue University. They had summer classes on Introduction to Computers. This was the proverbial love-at-first-sight moment. Even though I had not packed any of my things, I didn’t go back. I enrolled myself that fall into undergrad Computer Science. I was fortunate to find that love early on. I’ve been in computer software for most of my professional life.

Sramana Mitra: You did the University of Alabama for Computer Science and you did an MBA at MIT?

Dharmesh Shah: I started at Purdue. I transferred to Alabama. I finished my degree at Alabama Birmingham and then did my MS at MIT. 

Sramana Mitra: That brings us to what year?

Dharmesh Shah: That catches us up to 2004.

Sramana Mitra: Something happened in between, right? So you must have done something else?

Dharmesh Shah: I did two startups. One in the mid-90’s. I was 24 at that time. My co-founder was 17. We didn’t know anything about business or startups. This was in Birmingham, Alabama which is not the startup center of the universe by any stretch of the imagination. This was an early lesson. We automatically assumed that entrepreneurship requires this deep well of knowledge. It’s helpful to know things but back then, there was no internet.

Sramana Mitra: I had to make so many mistakes to learn the basics which we can now teach in one hour. 

Dharmesh Shah: In a way, it’s much harder for entrepreneurs now than it was then. Then nobody knew anything so you weren’t expected to know much if you were a first-time entrepreneur. Entrepreneurs today have it a little bit harder because there’s so much material out there. The expectation is that you have, at least, absorbed some of the materials that are available.

My first startup was an enterprise CRM in the financial services sector. It was self-funded. I was the founder CEO of that for a little over 10 years. I sold it to a much bigger financial services company. Then I decided to go back to grad school. That’s what happened.

This segment is part 1 in the series : Building HubSpot to a Unicorn: Dharmesh Shah’s Amazing Entrepreneurial Journey
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