Matthew Prince, the co-founder and CEO of Cloudflare, a cybersecurity firm valued at $40 billion, recently reflected on his early career decisions, expressing a notable regret: not accepting job offers from major tech companies like Microsoft before pursuing law school. In an interview with Business Insider, Prince admitted that as a young graduate, he was "an arrogant young kid" focused on becoming a cybersecurity lawyer, leading him to decline offers from Yahoo, Microsoft, and Netscape. Instead, he enrolled at the University of Chicago Law School and later taught law.
Prince believes that gaining experience at a large, fast-growing company working on "interesting projects" would have been invaluable. He emphasized the benefits of such an experience, stating, "The camaraderie and the rolodex and the interesting people that you will meet in that, is just such a huge accelerant to your career." He advises young professionals to consider roles in companies with 2,000 to 20,000 employees to build a robust network and gain exposure to large-scale challenges.
Despite his success with Cloudflare, Prince acknowledges that early exposure to a large tech company could have accelerated his career trajectory. However, he also recognizes that his path allowed him to build a company that aligns with his interests and education.
It's important to note that while Cloudflare has experienced significant outages in the past, such as the incident on October 30, 2023, caused by a misconfiguration in their deployment tool, (blog.cloudflare.com) the largest-ever Windows outage was actually caused by a faulty software update from CrowdStrike, affecting approximately 8.5 million devices globally. (en.wikipedia.org) This incident highlighted vulnerabilities in Windows' handling of third-party security software, leading Microsoft to consider enhancing the security of its operating system. (ft.com)
In summary, Matthew Prince's reflections underscore the value of early career experiences in large organizations and the importance of building a strong professional network. While Cloudflare has faced its own challenges, the company was not responsible for the major Windows outage attributed to CrowdStrike.
Source: Times of India Why CEO of $40 billion company that caused biggest-ever Windows outage wishes he had joined Microsoft before going to law school - The Times of India