Will and his partner started with a somewhat flawed business idea, but has successfully built up to a $50M company.
Along the way, pivots had to happen, and are still happening. Interesting study in customer-driven strategy.
Sramana Mitra: Let’s start at the very beginning of your journey. Where were you born, raised, and in what kind of circumstances?
Will Fleming: I was born in New York City and moved around a bit as a child. The first lengthy stop was my grade school years. That was probably, in retrospect, the beginning of my entrepreneurial journey. Although of course, I couldn’t know it at that time. One of my favourite entrepreneurial memories of the grade school years was when I was 9 years old. There was a magazine I got called Boy’s Life. I found an advertisement at the back of the magazine and I wrote to them to receive a whole bunch of flower seeds.
The arrangement was that I could then go and sell the flower seed. If I didn’t sell a certain number, I needed to return them. If I got over a certain number, I got to keep the rest of the money. There I was—a nine-year-old going door to door, selling some sunflower seeds. I started with neighbors and people who knew me. I expanded in concentric neighbourhoods. Looking back now, that sounds crazy but it was actually a lot of fun.
Sramana Mitra: Also for a nine-year-old, that was great training in selling.
Will Fleming: Even more than the selling, I think it was probably the initiative and a bit of self-confidence that came at the end of it, and the willingness to chart my own path. I remember one of the things that intrigued me about selling these flower seeds was that my other friends would go through, what seemed to me, an awful lot of work to be really uncomfortable and sit out in the hot Atlanta sun and maybe sell a cup or two of lemonade. I liked the idea of earning a little bit of income but that seemed to be a really long hard way to generate not very much.
Sramana Mitra: You had a better business model.
Will Fleming: It was just a different business. I was also sitting there thinking, “How can I put up a lemonade stand? We’ve got three kids on the block with a lemonade stand. That doesn’t make sense.” I needed to do something different. I did that till I was 11.
Sramana Mitra: What did you do after high school? Did you go to college in the Atlanta area?
Will Fleming: No, when I was 12 years old, we moved to the middle of the United States. The middle of the midwest – Omaha, Nebraska. I grew up as a midwesterner, which is a great place to grow up. After high school, I went to college in a small liberal arts school in Southern Minnesota. After that, I worked for a few years for a financial consulting firm before seeking my MBA, which I did at the Wharton School at the University of Pennsylvania.
Sramana Mitra: What year did you finish Wharton?
Will Fleming: 1990.
Sramana Mitra: What did you do after that?
Will Fleming: My first job after that was working in international trade. I was with a consulting firm that was housed within a major law firm. It was really interesting to be exposed, indirectly, to law firm life and, very directly, to the consulting business. It was while working in the consulting business that one of my classmates from business school sent me a business plan and said, “I have a really rough draft of a business plan. I need you to review it. Buy a plane ticket. Come to Florida. Let’s spend the weekend talking about this.” I did that. Very shortly after that, I moved to Florida and I have been a full-time entrepreneur ever since.