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Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 1)

Posted on Monday, Nov 28th 2016

Dan Stewart is a 1M1M entrepreneur. Read how he has navigated his way to an inflection point that has brought him to the cusp of 4x growth in 2017.

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?

Dan Stewart: My family moved around quite a lot as I was growing up. I rarely stayed in a school for more than a year. That took me from West Virginia and Chicago, down to Florida.

Sramana Mitra: Where did you do your college?

Dan Stewart: I went to the University of South Florida in Tampa.

Sramana Mitra: By that time, you were settled in South Florida?

Dan Stewart: We had lived in the Tampa Bay Area when I was about 10 years old. I liked this area. We moved back again when I was in high school. My parents moved to Kuala Lumpur shortly after I finished high school. I stayed to attend USF.

Sramana Mitra: What did you do in college and then what did you do when you came out?

Dan Stewart: I was fortunate. I got a scholarship for college. I majored in Theater and minored in Business. My intention in college was to become a writer. I thought I’d become a playwright or a novelist. That was my childhood ambition. I started being an entrepreneur when I was seven. It sounds bizarre. There’s a magazine called Boy’s Life that you get if you’re a Cub Scout.

I wanted something and the way to get that thing was to sell greeting cards door to door. I started doing that with Boy’s Life magazine back in 1997. What I realized as I was finishing college was that I really loved business. I wanted to learn how to become self-employed eventually. I had a few service jobs bartending and waiting tables.

Eventually I became an assistant manager. I got my first real corporate sales job working for GTE Directories, which was just a great place to be. It was the mid-90’s. The Internet had not killed the yellow pages yet. I got to work with entrepreneurs every single day. It was a great place early in my career to see what life was like for people in different industries.

Sramana Mitra: How long did you do that?

Dan Stewart: I was there for almost four years.

Sramana Mitra: That brings us up to?

Dan Stewart: I started there in late 1995. I left at the end of 1999.

Sramana Mitra: What happens in 2000?

Dan Stewart: I opened my first company and sailed after 90 days.

Sramana Mitra: What was the company?

Dan Stewart: It was called Inner Strength. The idea was that it would be a sales training company. I had gone from being a pathetic sales representative at GTE to be one of the best. From all my experience of moving around as a kid, I made some connections that were useful in building rapport. That really helped boost my sales performance. What I didn’t recognize was that, at 28 years of age, I didn’t have the credibility to be hired by companies to teach their salespeople to sell more effectively.

Sramana Mitra: When you look back, that’s the primary reason why this company didn’t succeed?

Dan Stewart: That plus I didn’t know what I didn’t know. I really was not prepared. I didn’t put my life in a place where I had any option except to replace my $130,000 income almost immediately.

Sramana Mitra: It took much longer to get there.

Dan Stewart: It did.

This segment is part 1 in the series : Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper
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