• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
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
Down Arrow Button Icon
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.

Read more from Fortune

  • This entrepreneurial couple cashed out their 401(k)s and sold a $126 million company—now, they run a U.K. soccer team
  • Trump’s 25% tariffs are backfiring and threatening Gen Z’s trade career aspirations—putting car manufacturing jobs in peril
  • Gen Z women are being sold a risky dream: the realities behind ‘investing’ in designer bags like the Hermès Birkin
  • Like Tim Cook and Gen Z, AEG’s top exec eats the same lunch most days and wears the same outfit
  • Warren Buffett reveals the unique education strategy he took in school—and eventually paid off with a $170 billion fortune
  •  

    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.

    At the Fortune Workplace Innovation Summit, Fortune 500 leaders will convene to explore the defining questions shaping the workforce of the future—delivering bold ideas, powerful connections, and actionable insights for building resilient organizations for the decade ahead. Join Fortune May 19–20 in Atlanta. Register now.
    About the Author
    Preston Fore
    By Preston ForeSuccess Reporter
    LinkedIn iconTwitter icon

    Preston Fore is a reporter on Fortune's Success team.

    See full bioRight Arrow Button Icon

    Latest in Success

    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025

    Most Popular

    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Fortune Secondary Logo
    Rankings
    • 100 Best Companies
    • Fortune 500
    • Global 500
    • Fortune 500 Europe
    • Most Powerful Women
    • World's Most Admired Companies
    • See All Rankings
    • Lists Calendar
    Sections
    • Finance
    • Fortune Crypto
    • Features
    • Leadership
    • Health
    • Commentary
    • Success
    • Retail
    • Mpw
    • Tech
    • Lifestyle
    • CEO Initiative
    • Asia
    • Politics
    • Conferences
    • Europe
    • Newsletters
    • Personal Finance
    • Environment
    • Magazine
    • Education
    Customer Support
    • Frequently Asked Questions
    • Customer Service Portal
    • Privacy Policy
    • Terms Of Use
    • Single Issues For Purchase
    • International Print
    Commercial Services
    • Advertising
    • Fortune Brand Studio
    • Fortune Analytics
    • Fortune Conferences
    • Business Development
    • Group Subscriptions
    About Us
    • About Us
    • Press Center
    • Work At Fortune
    • Terms And Conditions
    • Site Map
    • About Us
    • Press Center
    • Work At Fortune
    • Terms And Conditions
    • Site Map
    • Facebook icon
    • Twitter icon
    • LinkedIn icon
    • Instagram icon
    • Pinterest icon

    © 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
    FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


    Latest in Success

    Premium card perks are ‘designed to create a win-win-win for everyone’ but customers are paying with heavy annual fees and data
    Personal FinancePersonal Finance Evergreen
    Premium card perks are ‘designed to create a win-win-win for everyone’ but customers are paying with heavy annual fees and data
    By Catherina GioinoApril 30, 2026
    5 hours ago
    Girl reading in a library
    SuccessEducation
    Public schools in Texas banned cellphones. One district has already seen 200,000 more library books checked out
    By Preston ForeApril 30, 2026
    5 hours ago
    Bill Perkins, founder of Skylar Capital
    SuccessWealth
    Multimillionaire hedge fund manager Bill Perkins says money should ‘drive your fulfillment while you’re alive’—so he’s spending it all before he dies
    By Emma BurleighApril 30, 2026
    5 hours ago
    teri
    BankingBanks
    Exclusive: America’s largest Black-owned bank launches podcast with mission to unlock hidden shame holding back generational wealth
    By Nick LichtenbergApril 29, 2026
    23 hours ago
    Emma Grede, who helped found the $5 billion Skims empire, rejects ‘celebrity CEO’ label: ‘I’m a CEO who’s done so well you know my name’
    SuccessEntrepreneurship
    Emma Grede, who helped found the $5 billion Skims empire, rejects ‘celebrity CEO’ label: ‘I’m a CEO who’s done so well you know my name’
    By Cheyann HarrisApril 29, 2026
    1 day ago
    Lloyd Blankfein, former chief executive officer of Goldman Sachs
    SuccessCareers
    Former Goldman Sachs CEO: Ivy League geniuses aren’t always the most successful—This overlooked skill is key
    By Emma BurleighApril 29, 2026
    1 day ago

    Most Popular

    Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
    Success
    Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
    By Preston ForeApril 27, 2026
    3 days ago
    Google Cloud revenue is now 18% of Alphabet's business. Is this the beginning of the end of Google's search identity?
    Big Tech
    Google Cloud revenue is now 18% of Alphabet's business. Is this the beginning of the end of Google's search identity?
    By Alexei OreskovicApril 29, 2026
    20 hours ago
    ‘They left me no choice’: Powell isn’t going anywhere—blocking Trump from another Fed appointee
    Banking
    ‘They left me no choice’: Powell isn’t going anywhere—blocking Trump from another Fed appointee
    By Eva RoytburgApril 29, 2026
    1 day ago
    Jamie Dimon gets candid about national debt: ‘There will be a bond crisis, and then we’ll have to deal with it’
    Economy
    Jamie Dimon gets candid about national debt: ‘There will be a bond crisis, and then we’ll have to deal with it’
    By Eleanor PringleApril 29, 2026
    1 day ago
    ‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
    AI
    ‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
    By Sasha RogelbergApril 28, 2026
    3 days ago
    With no end in sight, Trump considers new options in Iran war—including the ‘Dark Eagle’ hypersonic missile
    Big Tech
    With no end in sight, Trump considers new options in Iran war—including the ‘Dark Eagle’ hypersonic missile
    By Jim EdwardsApril 30, 2026
    12 hours ago