Patrick Clinger

Sometimes that has meant writing software. Sometimes it has meant designing systems, growing a business, building an engineering team, or helping someone become more capable and confident in their work. The tools and scale have changed considerably over the years, but the impulse has stayed the same: I see something that could exist or work better, and I want to help make it real.

I started building websites in 1996, when I was thirteen years old. I met another kid named Brian in an IRC chat room, which is a sentence that could only have come from a particular era of the internet. He introduced me to HTML, and I was immediately hooked.

The first website I was paid to build earned ten dollars. The client, Lisa, mailed me the money, and Brian and I agreed to split it evenly because he had helped me. Mailing a letter cost thirty-two cents at the time, so I sent him exactly $4.84 through the mail. We divided everything, right down to the stamp. Shout out to Brian H.

I spent about eight hours building that site. It was not exactly a promising hourly rate, but that did not matter. I had made something on the internet, someone valued it enough to pay me, and I could not stop thinking about what else might be possible.

My parents were both computer programmers, although they did not teach me how to code. Their influence was less instructional and more atmospheric. Computers never felt mysterious or inaccessible in our house. Building with them felt like something I was naturally supposed to explore.

HTML eventually stopped being enough. I wanted websites to do things, not just display information, so I taught myself Perl by reading whatever I could find online. Matt’s Script Archive was a major source of inspiration. I remember uploading one of my first scripts through FTP and receiving nothing but an “Internal Server Error.” It took me roughly two months to discover that files needed the correct permissions set with a strange little command called chmod.

That experience captures much of how I learned: try something, fail, search, experiment, get frustrated, and eventually understand enough to move forward.

I created several websites and tried many business ideas. Most did not work. One of my earliest projects, Web-Authoring.com, combined web-development advice, directories of free online resources, and affiliate links. I later sold the domain for a few thousand dollars. It was encouraging, but HostedScripts.com was the first project that felt like a real success.

Launched in early 1999, HostedScripts offered tools that website owners could add to their pages without needing to program them themselves. It included message boards, guestbooks, mailing lists, polls, form mailers, password protection, download tracking, and other interactive features that are easy to take for granted today. I had a business partner who helped with development, and together we saw the service grow rapidly.

By my sophomore year of high school, hundreds of thousands of requests were flowing through software I had helped build. I monetized the traffic through online advertising and spent most of my time outside school programming, shipping features, troubleshooting servers, and trying to understand how to keep the growth going.

Toward the end of 1999, I began building ProBoards. It officially launched on January 1, 2000, while I was still in high school.

At the time, people could talk through services such as AIM and ICQ, but creating a lasting online community was considerably harder. Running a message board usually required technical knowledge, hosting, installation, and ongoing maintenance. ProBoards gave people a free and accessible place to hold sustained conversations, build relationships, and create communities around nearly any shared interest.

The service became profitable almost immediately. During my senior year of high school, it generated roughly $72,000 in gross revenue. Over the years that followed, more than four million forums were created on ProBoards, serving tens of millions of users. It became the largest free forum-hosting service on the internet and, for many people, an important part of their online lives.

I wrote the original software and managed the early infrastructure, but as the company grew, my role expanded with it. I defined the product roadmap, hired and led the team, worked with advertising partners, managed the business, supported customers, dealt with accounting, and learned how to operate increasingly large and complicated systems.

ProBoards was entirely bootstrapped. There were no investors and no established playbook. I had to learn nearly every part of building a company by doing it, usually after discovering that I did not yet know what I was doing.

I made plenty of mistakes along the way. My early code lacked the structure, testing, and discipline I would expect today. I was also not naturally a good manager. At one point, I micromanaged too much, focused too heavily on the work itself, and did not pay enough attention to the people doing it.

I was fortunate to have employees who were willing to give me direct and honest feedback. More importantly, I was willing to hear it. That feedback changed how I approached leadership. Over time, I learned to delegate, listen more carefully, create room for autonomy, and pay closer attention to what people needed in order to grow.

Empathy has since become one of the qualities I value most in leadership. Technical judgment matters, but engineering is ultimately a human activity. Effective leaders have to understand the person on the other side of the conversation. They have to assume good intent, create psychological safety, communicate clearly, and help people succeed rather than simply measure their output.

That responsibility becomes especially important when circumstances are difficult. When COVID arrived, advertising spending dropped sharply, and because ProBoards was funded primarily through advertising, the business was immediately affected. I reduced my own pay first and told the team what I had done. We ultimately recovered quickly, but I remain proud that we kept everyone employed. I believe that when leaders benefit during the good years, they should also be the first to absorb the impact when conditions turn against them.

VerticalScope acquired ProBoards in 2021. I was happy with the outcome and stayed for nearly two years to help ensure a smooth transition. Selling the company closed a chapter that had defined more than two decades of my life and gave me the opportunity to take on new challenges.

Since then, I have held senior engineering-leadership roles at several companies and am currently a Vice President of Engineering at Raptive. I enjoy entrepreneurship and startups, but I also value working with larger teams. Human connection matters deeply to me. I like mentoring, coaching, improving organizations, and helping people see possibilities in themselves that they may not yet recognize.

I have also continued building. I created BidFilter after seeing the damage caused by malicious and disruptive advertising, including ads that unexpectedly redirected users away from the sites they were visiting. I wanted a durable technical solution, so I built technology to identify, analyze, and block those ads.

I still write software regularly. Coding has remained a passion throughout my career, even as my responsibilities have expanded into architecture, business strategy, organizational leadership, and executive management. Today, AI and software agents are allowing me to experiment and deliver at a pace that would previously have been difficult for one person. I find that enormously exciting, although I also believe that developers need to understand what these systems produce rather than blindly trusting code they cannot evaluate.

Much of what I know came from experimentation, failure, books, colleagues, employees, and other people who were willing to share what they had learned. Books such as The Manager’s Path, The Phoenix Project, and Clean Code have influenced my thinking, even where I disagree with parts of them. I believe there is considerable value in learning from someone else’s experience without feeling obligated to adopt every one of their conclusions.

That is part of why I write now. I have accumulated lessons about programming, scaling systems, entrepreneurship, engineering leadership, AI, and the realities of building products over long periods of time. I want to contribute some of those lessons back in the hope that they help other engineers, leaders, and founders make better decisions or see a problem from a different perspective.

My career was never the result of a perfect plan. It came from trying many things, watching most of them fail, learning what I could, and continuing until something worked. Even after finding success, I continued making mistakes and changing how I worked.

I am still building. I am still learning. And I expect I always will be.

I live in Southern California with my wife and our two young children.