Matthew Prince, co-founder and CEO of Cloudflare, shared his journey as an entrepreneur and the path that led to the creation of one of the most essential companies in internet security. From his early fascination with computers to his pivotal role in shaping Cloudflare, Prince’s story is packed with lessons that any aspiring entrepreneur can take to heart.

Early Days and Education

Prince’s love for technology started early. At just six years old, his grandmother gave him an Apple 2 Plus, and instead of just playing games, he dove into programming. While his peers were content being users, Prince was more interested in creating. This curiosity for how things work would later shape his career, though he didn’t take the most obvious route.

After graduating in 1996, he had offers from the likes of Microsoft, Yahoo, and Netscape—names that any tech enthusiast would jump at. But Prince? He passed on them, thinking they weren’t going anywhere. In his words, “pretty stupid.” Instead, he opted for law school, envisioning a life of courtroom debates à la Perry Mason. Sometimes, the path to entrepreneurship takes a few unexpected detours.

The Winding Road to Entrepreneurship

Like many founders, Prince’s journey wasn’t a straight line. After law school, he worked at several startups and even considered teaching at a public school in Chicago. He describes this phase of his career as “wandering in the wilderness”—trying out different things but never quite settling until he returned to what really drove him: technology.

By 2009, things weren’t looking great for Prince financially—his mom was even helping him pay rent. But as we all know, sometimes it’s when your back is against the wall that innovation strikes. It was during this tough period that Prince, along with his co-founders, laid the foundation for Cloudflare. Interestingly, their initial funding came from winning a business plan competition. It wasn’t much, but it was enough to keep the lights on while they worked on something big.

The Birth of Cloudflare

Cloudflare’s origins go back to a side project Prince and his team worked on, called Project Honeypot. This tool was designed to track malicious activity online, and to their surprise, it caught the attention of web admins everywhere.

When it came time to brainstorm a new business idea, Prince’s co-founder Michelle Zatlyn saw the potential in Project Honeypot. Web admins didn’t just want to track malicious actors—they wanted to stop them. That insight became Cloudflare’s mission: to build a better internet by providing security and performance optimization for websites.

Cloudflare’s Rapid Growth

Cloudflare officially launched on September 27, 2010. They started with about 1,000 users. By the end of the first day? They had 10,000. The response was overwhelming, and they weren’t ready for it. Prince and his team hadn’t built in any limits or fail-safes, so when demand skyrocketed, it led to countless sleepless nights as they scrambled to keep up. Growth like that is exhilarating, but it’s also a huge challenge—one many entrepreneurs can relate to.

A Turning Point: Making Encryption Free

One of Cloudflare’s most defining moments came in 2014 when they made encryption free for everyone. A young engineer on the team believed that the future of the internet depended on more encryption and argued that Cloudflare should be the company to lead that charge.

From a business perspective, it was risky. Encryption had been a key feature in their paid services. But from a mission perspective? It was a no-brainer. And it paid off in a big way. Overnight, they doubled the amount of encrypted traffic on the internet, and new signups exploded, jumping from 100 a day to as many as 2,000. Bold decisions like that often separate the good companies from the great.

The Future of the Internet

Prince believes that we’re at a pivotal moment for the internet. He likens the early days of the internet to “Star Wars: A New Hope”—a revolutionary force ready to challenge traditional power structures. But now, he sees the landscape shifting, comparing today to “The Empire Strikes Back,” where various entities are fighting to control and restrict it.

For Prince, the mission is clear: keep the internet open and secure for everyone. He’s committed to ensuring Cloudflare stays at the forefront of that fight, believing that the internet, despite its flaws, is still one of the greatest forces for good in the world.

Advice for Aspiring Entrepreneurs

When asked what advice he’d give to aspiring entrepreneurs, Prince highlights the importance of relationships and networks. In hindsight, he regrets not working for larger tech companies earlier in his career, recognizing that the insights and connections would’ve been invaluable.

He also emphasizes perseverance and frugality. You need resources, smart people around you, and the willingness to fail and try again. And one more thing? Even when you’re leading a successful company, things often feel chaotic from the inside—that’s just part of the ride.

Matthew Prince’s journey with Cloudflare is a lesson in innovation, perseverance, and staying true to your mission. As the internet continues to evolve, companies like Cloudflare will play a critical role in shaping its future, and it’s entrepreneurs like Prince who will lead the way.