Context Relevant CEO Stephen Purpura is working on the leading edge of big data — helping companies use their data more effectively. But Purpura, whose company scored $21 million from Bloomberg Beta, Madrona, Vulcan and others earlier this year, followed a career path many of his peers advised him against.

After working at Microsoft, Purpura decided to go back to school, earning a degree from Harvard and studying at Cornell before returning to found his own company. He describes being CEO of Context Relevant as “one of the most exciting things that I could do in my life.”

At Context Relevant, Purpura and his team are leaders in the field of big data and automated machine, exploring a space few other companies have investigated so deeply. Explaining why he loves his position, Purpura says the big idea behind Context Relevant is “to analyze data without hiring an expert.” [1:40]

Though an executive now, Purpura’s focus has always been on the technical. He explains that he wanted to be more than an “empty suit” who couldn’t explain how a product worked. “The only way you can do interesting new things and really explore the space is to get in and do it, he says. He adds: “If you do not understand [the tech], it is really difficult to lead a team effectively.” [6:40]

Before he was a startup CEO, Purpura spent several years at Microsoft, though he knew he wasn’t meant for that environment for long. “At bigger companies I sort of felt stifled,” he explains. As a CEO, “I get more ability to…be my inner child, in the sense that I get to do what I want as long as I can back it up and actually make it happen.” [9:00]

On leaving big companies to pursue further education, Purpura explains that many of his technical peers told him he was making a mistake. “Many people believed it was a blunder for me to go back to school,” he says. But he counts this time as a blessing. “Let’s face it: when you work at Microsoft or when you work in the industry, you sort of get a point of view, and you put blinders on that point of view. And what I was able to do in the middle of my career was redefine my point of view.” [11:00]

When asked if he had advice for other startup founders, Purpura emphasized the importance of being in the right market. He shared a story from an earlier startup where they failed to find a big enough market for their product, from which he ultimately learned that it’s better to find a great solution to a problem in a big market than to focus on finding the right team or the most money. “Even if you have a fantastic team with $100 million in cash, it’s difficult to fix the market,” he said. “If the opportunity is large enough, you will find people who want to work on it” even if you have to bootstrap on the weekends.

Purpura closed the interview with thoughts on life as a founding CEO. He describes his company as “an overnight success story that took 13 years.” “You are responsible for everything and there is nothing going for you,” he says, adding that it’s the hardest job he’s ever had in his life.

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