Chris Gladwin is a true business builder. It is his craft. He has now launched four startups, including one which raised $100M and sold for over $1B.
During our time on the DealMakers podcast, Gladwin shared his incredible journey of building multiple businesses. Including what’s keeping you from the funding you seek, how a business that doesn’t go as planned can still achieve a great exit, and how much you need to raise for a software startup.
Plus, we gain his insights on market timing, what it’s like to sell your company to IBM for big bucks, and the secret to creating a successful product and business.
Let Your Entrepreneurial Spirit Out
Chris Gladwin was born and grew up in OH. Growing up in the midwest was about going to school, mowing lawns, and getting good grades.
He still recalls one guest speaker who was a musician. When asked how he wrote songs, he said “You just have to learn to let them out. If you’re really a songwriter, they’re inside of you.”
Chris’ inner artist was an entrepreneur, and he has certainly learned to unleash that and express it. Moving to Boston to attend MIT was certainly instrumental in this, and preparing him for startup life.
Boston was a big new world. It provided a global perspective in terms of innovation. He also found that while he might have been the smartest kid in his high school, he was now just one of many smartest kids from schools all over the world. That means you can’t afford to coast. You have to work hard.
Right out of school Gladwin went to work at Martin Marietta, and then Zenith Data Systems. He worked and learned the hardware business better than anyone else.
So, while he was still young and inexperienced in business, that enabled him to spin Cruise Technologies out of the company as his first big venture-backed startup.
Don’t Get Stuck On Your First Company, Your Third Or Fourth Can Be Even Better
Chris’ adventures certainly show why you shouldn’t get hung up on your first venture. Many entrepreneurs think it is the end all be all of their existence.
Yet, he has proven that not only can you turn what some may consider a failed startup into a great outcome, but you can keep snowballing that into something greater.
You learn a lot on the way, especially from the struggles.
Cruise Technologies was in the middle of the 90s battle for end-user computer architecture.
They were behind all but one of the major wireless or mobile clients in the market. Intel and Microsoft won that battle thanks to their giant size.
Though Chris still managed to sell the company to Motorola.
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