What advice does Cloudflare CEO Matthew Prince wish he could tell his younger self? Be open to getting experience at a big company before going to grad school.
As the cofounder and CEO of a multibillion-dollar cybersecurity firm, Prince said he feels pretty content about the career moves he made — but he wishes he hadn’t turned down the job offers he got out of college.
“Figuring out a way to get to some company that’s somewhere between 2,000 and 20,000 employees, and is working on interesting projects — that’s the thing that I wish I had,” the Cloudflare CEO said in an interview with Business Insider.
After getting a Bachelor’s degree in English literature and computer science, the CEO said he had offers to go to Yahoo, Microsoft, and Netscape. Prince said he turned them down because he was “an arrogant young kid” who had his mind set on becoming a cybersecurity lawyer. He ended up starting law school at the University of Chicago the year after he graduated, and went on to teach law after he got his degree.
At the time of the three job offers, the dot-com boom was in full swing, and companies like Microsoft were at the forefront of innovation. Prince said the three companies offered him the opportunity to work at a fast-growing company with “a bunch of interesting problems” and “some real scale.” He also said he thinks he could have grown a larger network of colleagues if he had taken one of the jobs.
“The camaraderie and the rolodex and the interesting people that you will meet in that, is just such a huge accelerant to your career,” Prince told BI.
Prince said he doesn’t regret turning down later positions that didn’t appeal to him, such as an offer to be a bankruptcy attorney when he wanted to be a securities lawyer. He also said he still finds value in his law degree, even if he isn’t actively practicing it, because he understands the legal challenges his company has to solve.
But he said his advice to his younger self stems more from the missed experience of working at a fast-growing company with a large network of colleagues. Nowadays, that may look like a Stripe or Twin Base, he said.
While Prince said it would’ve been interesting to see where those opportunities led, he may have dodged a bullet. The dot-com bubble eventually burst, and by staying focused on his own path, he was able to launch a company that merged his interests and degrees.
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