Matthew Prince, the CEO of $40 billion company Cloudflare wishes he had joined Microsoft before going to law school

Cloudflare CEO Matthew Prince has said that he would advise his younger self to gain experience at a big company before pursuing graduate school. Speaking as the co-founder and head of $40 billion dollar cybersecurity firm, Prince said he’s largely satisfied with his career choices but regrets declining job offers straight out of college. After earning a Bachelor’s degree in English literature and computer science, Prince reportedly received offers from Yahoo, Microsoft, and Netscape. However, he turned them down, admitting he was "an arrogant young kid" focused on becoming a cybersecurity lawyer. He instead enrolled at the University of Chicago Law School the following year and later went on to teach law.

In an interview with Business Insider, Prince said: “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.”
During the period when he received the three job offers, the dot-com boom was at its peak, with companies like Microsoft leading innovation. Prince noted that the offers would have allowed him to work at a fast-growing company with "a bunch of interesting problems" and "some real scale." He also noted that accepting one of the roles may have helped him build a larger network of colleagues.
"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 added.
However, Prince said he doesn’t regret declining later job offers that didn’t align with his interests, like a bankruptcy attorney role when he wanted to pursue securities law. Yet, he highlighted that his law degree remains valuable, even though he doesn’t practice, as it helps him navigate the legal challenges his company faces.
Meanwhile, his advice to his younger self comes from missing the experience of working at a fast-growing company with a broad network of colleagues — something like a Stripe or Twin Base today, he continued.
While Prince thinks it would have been interesting to explore those opportunities, he acknowledged that he may have avoided trouble. The dot-com bubble eventually burst, and by following his path, he was able to build a company that combined his interests and education.