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From Building Multi-Million Dollar Companies to Revolutionizing Conversational Marketing, A Founder’s Story with Dan Stewart

Dan Stewart is a serial entrepreneur, four-time Inc. 500 Honoree, and the founder of Happy Grasshopper, where he’s helping real estate professionals nurture over 26 million contacts. His company helps real estate brokerages and brands increase headcount and production. Dan helps thousands of salespeople make connections and build relationships with the people in their databases.


Tell us about your childhood and where you grew up?
My family moved around quite a lot as I was growing up and I rarely stayed in school for more than a year. That took me from West Virginia and Chicago, down to Florida. We had lived in the Tampa Bay Area when I was about 10 years old and I really liked the community. We moved back again when I was in high school, and my parents moved to Kuala Lumpur shortly after. I stayed to attend USF, got a scholarship, and 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 before I found my love for being an entrepreneur.


How did you get started as an entrepreneur?
It sounds bizarre, but I started being an entrepreneur when I was seven. 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 it was to sell greeting cards door to door. Years later, what I realized as I was finishing college was that I really loved business and I wanted to learn how to eventually become self-employed. Initially, 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 and the Internet hadn’t killed the yellow pages yet. I got to work with entrepreneurs every single day. It was a great place early in my career to develop and see what life was like for people in different industries.


What is one business lesson you would tell a startup founder?
One business lesson I would tell a startup founder is the value of breaking goals down into smaller components that you can win, at the moment. Now follow me on this. Before you achieve that giant goal at the end of the year, you have to have won the quarter. You have to have won a month. You have to have won the week and the day, the hour and the very moment, okay? So if like me at some point in the past you find yourself turning inward and going, “Oh my gosh, it’s so hard. There are so many obstacles and challenges that are in my way between where I am and where I want to go.“ If you’re having those moments and you’re feeling like you don’t know how you’re going to get there, the answer is to win the moment. You don’t have to win the hour. You have to win the moment, that small moment, the one you’re focused on right now.
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