One more look at what it takes to build a fat startup. Sunny Gupta discusses Apptio. The company raised a $7 million series A to get started, and then went to raise over $130 million thus far.
Sramana Mitra: Sunny, let’s start at the very beginning. Tell us a bit about yourself. Where were you born and raised? What kind of circumstances? Give us a backstory of the Apptio story.
Sunny Gupta: I was born in India in a town north of New Delhi. I went to school there and lived in New Delhi till I was 19. My father was in the government services. This is in the late ’80s and I didn’t feel, from a career perspective, that there were that many career options. My mom’s family had some history of entrepreneurship. My dad’s family was in the government or in administrative jobs. We grew up in a very modest family – three brothers and I was the youngest one. We were very close. We inherited our mom’s side of the genes on wanting to be entrepreneurs. We always talked about that while growing up. We also had a big culture of debate in our family. My father always encouraged the culture of debate and just asking the next question and the next question.
When I was 19, I wanted to do something different. I didn’t feel that there were any great entrepreneurship opportunities for me in India. I ended up immigrating and coming to study Computer Science at the University of South Carolina back in 1989. The reason I went there is because they gave me a scholarship. My father really couldn’t afford my education that much. My father gave me $2,000 and a plane ticket and said, “That’s pretty much all that I can afford.” There was an American family who my father knew so I could go stay with them for the first six months and save on my boarding. I had enough money to buy my books and barely enough to pay for my food and stuff in the 1st semester.
I finished my Bachelors in three years and did a minor in Mathematics. I worked very hard -50 to 60 hours in a week. I was a resident assistant. I was cleaning dishes, working in cafeterias, and moving houses. I also became an intern to the President of the university. Through scholarships and working hard, I graduated with a 3.9 GPA. That was probably some of the most incredible experiences that I had. Just being out here on your own and not having any funds at your disposal, that fuelled the fire of succeeding and being an entrepreneur while still at college.
From there, I worked at IBM. That was my first job. I worked as a software engineer for two years in Florida. That was an amazing experience. When I graduated out of college, I had a job offer from Microsoft and one from IBM. IBM was offering me a software developer job and Microsoft was offering me a testing job. I felt like I wanted to be a software engineer. I always regretted that decision in hindsight. I felt that sitting in a cubicle every single minute and not interacting with people was not what I wanted to do for the rest of my life. I also felt that my career was developing at a much slower pace. IBM had layers and layers of bureaucracy.
So I joined another software company in Boston. They were called Easel. They were a 300-person software company. That was a great experience. I transitioned my career into software consulting. I wanted to have customer interaction and met with 50 to 60 customers. That really excited me. I was there for two years. Again, I realized that the company was having some problems. I also felt that my career was going to move at a snail’s pace. I was looking for dramatic ways to grow myself and if I’m in the corporate side of the world, it’ll just take me forever.
Back in 1996 was the first time I stepped out and started my own company called Bigger Technology with a couple other co-founders. I was based in Atlanta at that time. In less than a couple of years, we were acquired by a company called Rational Software. It was literally 18 months into the life of the company. We had no venture capital. That was an amazing experience. I ended up moving to Seattle in 1998 and worked at Rational for seven years. I transitioned my career into more of business development. I was leading a big part of business development. I was involved in selling Rational to IBM at that time and worked on some really interesting elements. I felt that I grew up there from a career perspective.