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SuccessCareer Advice

CEO of $40 billion Cloudflare wishes he had taken a job offer at Microsoft or Yahoo before going to law school

Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
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Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
Down Arrow Button Icon
April 25, 2025, 11:41 AM ET
Matthew Prince gestures
Gen Z has regrets over their degree—and Cloudflare CEO Matthew Prince agrees that he would have been successful sooner had he put off college and gone straight to work in Big Tech.David Paul Morris/Bloomberg via Getty Images
  • Billionaire founder Matthew Prince has three degrees to his name, but admits the path he took to get there could have been easier had he spent time in Big Tech expanding his networking instead.

For Gen Zers early in their career, Cloudflare CEO Matthew Prince has some advice: don’t underestimate the power of networking.

While the 50-year-old executive is by all means one of the most accomplished in the cybersecurity world as the founder of a $40 billion firm, he just revealed that had he gained experience and made connections in Big Tech, his success may have come a little easier.

“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 Business Insider.

Instead of saying yes to a job offer from companies like Microsoft, Yahoo, and Netscape during one of the most interesting times in tech—the dot-com boom—he went straight to law school at the University of Chicago after graduating with his bachelor’s degree in English and computer science.

“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,” he said.

And while Prince does not regret going back to school at all, it’s a viewpoint that’s increasingly hard to find among graduates. Some 51% of Gen Z report their college degree was a “waste of money,” in part due to the skyrocketing cost of tuition as well as the ever-changing job landscape. 

Fortune reached out to Prince for further comment. 

Tech founders have mixed feelings on the value of higher education

Prince is, by all means, an embracer of higher education, having later gone on to teach law and obtain his MBA from Harvard Business School (where he met Cloudflaire co-founder Michelle Zatlyn). 

While he may sound like a unique case among tech leaders, considering big names like Mark Zuckerberg, Bill Gates, and Sam Altman are famously known for dropping out, getting multiple degrees is not uncommon.

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  •  

    Fellow cybersecurity CEOs, like Broadcom’s Hock Tan and Palo Alto Networks’s Nikesh Arora, also both have at least three degrees, which likely helped them land the roles they have today.

    On a Sequoia Capital podcast, Arora described his mantra as goal-driven.

    “Ideas are not good enough,” Arora said. “You got to have a plan and a North Star. You have to have resourcing that you can sort of execute at the plan.”

    And while every Fortune 500 leader may have differing perspectives on the value of degrees, the data doesn’t lie: they are broadly financially worth it, especially if the right major is picked.

    A bachelor’s degree in business will pay for itself after just eight years, and current graduates can expect to earn lifetime earnings of over $8 million, according to the Education Data Initiative. For computer science degrees, the return on investment (ROI) is even greater—the degree pays for itself in five years and earnings of over $10 million.

    Join us for a virtual Fortune 500 Europe C-suite conversation, in partnership with Syndio, on mastering workforce decisions and pay transparency in the age of AI. Built for global and regional HR leaders, this session, moderated by Fortune editor Francesca Cassidy, will take place Wednesday, March 25, at 2:30 p.m. GMT (10:30 a.m. EDT) and feature senior HR leaders from Hilton and Syndio. Together we'll explore how CHROs are using AI to drive smarter pay decisions, manage regulatory risk, and strengthen workforce trust. Register now.
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    Preston Fore
    By Preston ForeSuccess Reporter
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    Preston Fore is a reporter on Fortune's Success team.

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