The web is (arguably) the only tech platform that has been continuously transformed and evolved at a global scale over the last 30 years. How was this possible? What can we learn from the past technical mistakes and successes? Over the years, I have witnesses the emergence of various web technologies. Some were revolutionary, while others didn't pass the test of time. In this article, I dive into the evolution of web technologies from the 1990s to the present. My focus is on the engineering paradigms that marked inflection points in web's history. Those who don't know tech history are doomed to repeat past engineering mistakes.