My first Linux distribution was Mandrake 7. After a few months, unsatisfied with the experience, I found out about Gentoo and Portage. The idea of having running a system that was fine-tuned to my hardware intrigued me, so I decided to try it. That was 10 years ago.
I downloaded the Stage 1 Live CD and ran it off my main box. I loved its colorful framebuffered background, and the way it simply dropped you in a terminal. We didn't have desktop virtualization back then, so I had to read the docs on my brothers PC and go back and forth between his computer and mine.
With my very little experience with Linux, I hardly understood the commands I was typing in. Somehow I made some progress. I managed to partition the hard disk (burning the bridges - as the say), chroot into the boostrap environment, and use portage to update my system. I remember setting my CFLAGS with the most unstable options possible ( -O3 for everything, obviously), compiling GCC three times, and then beginning to slowly compile all the essential packages.
Finally, I reached the crowning moment of the installation: configuring my first kernel. Unfortunately, I made a mistake somewhere between "make menuconfig" (I went through each option!) and installing LILO, and was rewarded with my first Kernel Panic, and a bricked system.
After several failed attempts, I managed to get a working system and log in. I remember the great sense of achievement. It still was less challenging than whipping up an LFS system, but - what a ride!
I later abandoned Windows, became a Linux system administrator, converted an entire webfarm (80+ servers) to Gentoo, started a career as a web developer, and became lazy. Today, I am happy with Xubuntu on my desktop, and CentOS on my servers.
On #gentoo, denigrators would often link to https://web.archive.org/web/20050217094757/http://funroll-lo... (now a spam site) and laugh about all the pain and time to get that 0.02% increase in overall system performance.