Love this topic, as I have been a cyclist since 1988.
First ride was a Cannondale with Shimano 105 components. Once I started riding and learning, I decided that was not the bike for me.
Working at a bike shop, I bought a Bridgestone RB1 frame, 1990 model, and built it up with Mavic components, inspired by Greg LeMond's 1989 TdF winning Bottechia rig. It still gets use as a winter/rain bike. This bike is like an old broken in pair of boots. Impossibly comfortable to ride, solid and predictable. This bike could tell lots of stories of when I was younger and had time to spend hours upon hours on training rides.
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When I got into racing, I picked up an Italian rig and built it with Campy Record components. It was a Guerciotti, repainted from its original yellow, here I am at a race circa 1997 (note - I have been dropped here, on a brutal crit course). Lots of races, and lots of aggressive group training rides, often harder than the races I did, were done on this rig. It hangs on a hook in my attic now. I might build a fixed gear rig with it this winter.
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I did a fair bit of commuting by bike when I was in the bike biz, and had a Bridgestone CB Zip built up with drop bars for the task. It was frequently morphing and changing to suit my mood. Here I am after a snowy commute, in my basement workshop in my old house, circa 1998 [date stamp on photo is wrong]:
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In '95 at the West Coast bike show, I met John Slawta, owner/builder of Landshark Bicycles. If you have followed racing since the 80s you might know the name Andy Hampsten, winner of the Tour of Italy in 1988. While his 7-11 team road Huffy branded bikes built by Ben Serotta, Andy's climbing bike was a Huffy branded Landshark built by Slawta. Slawta has a background in art, and it is reflected in some of the paintwork you see on his bikes. Right as I was about to get out of the bike biz, I decided I better get John to build me a frame. The custom bike is built to the same fit dimensions as my RB-1, built with a faster front end and tighter rear end, but not to the extreme, a very race worthy rig, while still being very comfortable and predictable. It's Reynolds 853 steel, filet brazed, which you don't see much anymore. When it came time to paint it, I still had not decided what I wanted him to do. I said "suprise me with a three color fade in purple, red and yellow", and below you see what he did. I had this built for me in '99, and it's been my main ride for pleasure rides, training, and the little bit of racing I still do. Built with essentially the same Mavic set up as my Bridgestone, but with Shimano brake/shifter setup, newer Mavic hubs, and some other bits. It it looking a bit retro on the training rides these days though, gotta say.
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John works exclusively in carbon now, and I had hoped to get him to build me a new rig for my 50th birthday this summer, as I was going to be near his shop in Oregon on a family trip anyway, I thought I would go there and discuss plans. Alas, my finances were not what I felt they needed to be to justify the gift to myself, so that got back burnered - maybe when I turn 55. My uncle, a rider since the 70s, has one of Johns bikes, based on my recommendation, in full carbon. I saw it this summer, and it was amazing, of course, for about $9k, it should be. My uncle's bike is not as flashy as this, from the Landshark Facebook page:
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Ok - sorry for such a long winded post, and all the pictures. But it was nice to geek out on something I am passionate about OTHER than bass and music. I'll leave you with one more picture, my son riding the bike I got for him this spring for his 12th birthday. He is a natural on the bike and I couldn't be more thrilled. Here he is recovering after racing me up a knarly climb on a ride this fall. He won [I let him ;-)].
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