Posted on Thursday, Mar 3rd 2022
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Dean Guida, CEO of Infragistics, has a real passion for the elegance, simplicity, and beauty of software development. He has built a company celebrating these values.
Sramana Mitra: We will start at the beginning of your journey. Where are you from? Where were you born and raised? Dean Guida: When I was six years old, my mom and dad got divorced. I moved to Miami, Florida. I saw how much my mom struggled to make money for us, When I was eight years old, I just wanted to work. I convinced the maintenance man in the apartment that I was living in to let me do his work. He would pay me off the books.
I have always worked. I have always worked ever since I was eight. I wanted to go out in the world and make money. I worked all the way from then to now. That was a big catalyst for me. When I was 16, people my age were saving up money to buy a used car to take out girls. Instead of doing that, I went and bought an IBM PC. I loved that thing. I taught myself how to program in twenty different languages. I just loved everything about that.
I loved technology. I went to the University of Miami and I studied operations research and deterministic and probabilistic models. While I was at school, I was working for the VP of HR. He had this $8 million a month payroll system and it didn’t work. I told him that I could fix it. He told me, “You can’t fix that. We spent millions of dollars to build that.” I told him, “You don’t have a lot to lose. You are just paying me $3 an hour. What if I could fix this?”
I fixed it and he just couldn’t believe it. I learned that when people give you intrinsic motivations where they say you can’t do things, and then you do it; and you see the glitter in their eyes, you get great feedback from that.
Sramana Mitra: What was wrong with this thing? Dean Guida: There was more than one thing wrong with it. It had a lot of data errors on the front end. It had all kinds of logic areas when it was processing the data. There were so many things wrong with it. It took me a month and a half to fix, but I got it all fixed. I was a pretty big codebase. Sramana Mitra: That is amazing. What happens next? Dean Guida: While I was at the university, I started operating their mainframes at night. Again, I am a geek at heart. I just loved all the machines rolling around and the noise it makes. I worked the graveyard shift, working from midnight to 8 AM. I became friendly with the Director of Operations. He went over to Sea Escape Cruise Line out of the port of Miami.
It was a day cruise. He asked me to operate their mainframe. I operated the mainframes over at the Sea Escape Cruise line. He then asked me to write software to report to the Bohemian officials so that people can get off and go shopping and then get on the boat. I wrote this program and I was really proud of it. They deployed it.
The first day that I deployed it, I get this phone call. They said, “Your program doesn’t work. The passengers are angry. The captain is angry. We are picking you up and we are flying you over the Bahamas.” I was so scared. I was sweating. I get there and there is all this pressure.
I go and look at it, and there’s nothing wrong with the program. They just had a paper jam. It was really easy for me to fix, but they were so worried and nervous that I got to sit on the boat and do nothing. I got to hang out with the captain and relax on the boat. It was another fun and cool experience that I had earlier on.
Our conversation continues
here. This segment is a part in the series : Best of Bootstrapping . Bootstrapping to an Exit . Why is Bootstrapping Important? . How Can You Play this Low-Probability Game Intelligently? . Do NOT Go to VCs as Beggars - Go as Kings . Excess is NOT Required for Success . Bootstrap First and Raise Money Later . Some Bootstrapping to Exit Case Studies . The Buy Side of Bootstrapping to an Exit . Blitzscaling vs. Bootstrapping . Bootstrapping to Unicorns More »» . Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million . Mailchimp Bootstraps to $600M Revenue . Bootstrapping from Arizona to $10 Million . Bootstrapped Basecamp Executes a No Nonsense Strategy . How Under30Experiences Bootstrapped to $5 Million . Bootstrapping with a Paycheck . How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan . Seed Investors Who Like Bootstrapped Businesses . How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million . Bootstrapping with Services . How The Intern Group CEO David Lloyd Bootstrapped to $13 Million . How Passageways CEO Paroon Chadha Bootstrapped from Indiana . How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million . Death by Overfunding . How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+ . How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck . TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage . The VC-Entrepreneur Compensation Disbalance . BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering . Tremend CEO Marius Hanganu Bootstraps from Romania . Gesture CEO Jim Alvarez Bootstraps to $10 Million . SproutLoud CEO Bootstraps to $30 Million from Florida . Tuft & Needle CEO Bootstraps to Over $100 Million . Co-founders Bootstrap Linguamatics to Over $10M from the UK . Ownership Matters . Vainu Co-founder Mikko Honkanen Bootstraps from Finland . Entrepreneur Couple Bootstraps to $10M from Colorado . 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