Cloudflare CEO Matthew Prince Regrets Turning Down Big Tech Jobs Out of College, Advises Younger Self to Gain Industry Experience

Cloudflare CEO Matthew Prince reflects on his career decisions and shares insights on what he wishes he had done differently after graduating from college. In the late 1990s, during the height of the "internet bubble," Prince had the opportunity to join Yahoo, Microsoft, and Netscape—three major companies at the forefront of innovation and technological development. Instead, he opted to pursue a career as a cybersecurity lawyer. Prince, who studied English literature and computer science as an undergraduate, received job offers from these prominent companies. However, the young and, in his own words, “arrogant” Prince was convinced of his path to becoming a cybersecurity lawyer, leading him to enroll in the University of Chicago Law School. After obtaining his law degree, Prince became a law professor before eventually leveraging his legal and technical expertise to co-found Cloudflare, now a multibillion-dollar cybersecurity and performance company. Reflecting on his decision, Prince acknowledges that joining a large tech company right out of college would have provided him with invaluable exposure to a rapidly growing industry and a wide network of colleagues. Such experiences, he emphasizes, are crucial for career development, as they can significantly accelerate one's professional growth and help build a rich and diverse network of connections. Prince highlights the camaraderie and personal connections he could have formed, noting that the value of working with intelligent and interesting people is immeasurable. Although he avoided the potential fallout of the tech bubble burst, Prince believes that a stint at a major tech company could have given him more hands-on experience and a broader perspective on the industry. For young professionals entering the workforce, Prince advises taking a thoughtful approach to career choices. He recommends considering positions at companies that are actively growing and have a team size ranging from 2,000 to 20,000 employees. These environments, Prince argues, offer the best of both worlds: the opportunity to explore a variety of roles and projects, and the chance to collaborate with a diverse group of like-minded individuals. However, Prince also notes that he does not regret turning down job offers that did not align with his career goals. For example, he declined a position as a bankruptcy lawyer when he was aiming to become a securities lawyer. His legal education, he maintains, has been incredibly valuable in understanding the complex legal challenges that companies face. This unique blend of legal and technical knowledge ultimately enabled him to co-found Cloudflare, a company that seamlessly integrates both. Prince's advice extends beyond the immediate benefits of working at a large company. He emphasizes the importance of building and leveraging a professional network. While he acknowledges that startups and small companies can offer valuable experiences, the platforms and resources available at large tech firms are unparalleled. These opportunities can help young professionals grow faster and lay a solid foundation for future ventures or leadership roles. Industry experts agree that Prince's insights are highly relevant, particularly in today's competitive tech landscape. Experience at a large tech company can provide a strong foundation, helping young professionals not only to develop their skills but also to forge connections that can benefit their careers in the long run. Founded in 2009, Cloudflare has grown into a global leader in cybersecurity and performance services, and Prince's career trajectory and success story serve as a valuable reference for aspiring tech professionals. In summary, while Prince's path to co-founding Cloudflare was driven by his unique blend of legal and technical expertise, he encourages young graduates to consider the advantages of early career experience at large, dynamic tech companies. Such opportunities can provide a springboard for professional growth and a robust network of connections that are essential for success in the tech industry.