My first bike was a red Schwinn Buddy, with big, solid rubber tires. Very heavy, but I never had to worry about flats! Rode it all over the neighborhood. I was 8 years old, sometime back in the Dark Ages; 1969.
Then we moved to Denmark (that's in Europe somewhere) for a few years, and since cycling is so common there we kids got in the habit of riding everywhere. I rode my third-hand city bike to school, a couple of miles through the farmland, over pretty rolling hills, every day. Even when it snowed or rained. OK, sometimes when it was really nasty I would take the bus, but I hated doing that. Some things never change!
When we moved back here I saved my pennies up and bought my first 10-speed, a Sears Free Spirit or something like that, at the Sears by El Camino and San Antonio in Mountain View. It had smaller wheels than standard as I was kind of short, even for my age. I don't recall if they were 26" or 650c.
Then I saved up even more money and bought a full-size Peugeot UO8, in the Bicentennial year of 1976. I rode my old 10-speed bike to high school and all the way through junior college, with a lot of repairs and mods along the way. I dreamed of getting something really high-end, like a Bob Jackson with Reynolds 531 tubing and full Campagnolo, but could never afford it. All I could afford was reading the bike magazines, books, and catalogs like "Bikecology." I also dreamed of racing... but even then I had Walter Mitty traits and was too intimidated to actually try it. I came close enough that I found San Jose Bicycle Club's number in the phone book, but my fingers hesitated over the rotary-dial phone for many, many years.
I took several years off bikes while I went to SJSU, as working full time and studying full-time left me with... well, no time (and a nasty commute through north San Jose). Then I got a mountain-bike in 1993, after a friend showed me his trick, very custom, built-up mountain bike. I couldn't believe how cool the indexed shifters and suspension fork were. Mine was nothing fancy; a Marin with a solid fork, but I rode it a lot on the trails in the Santa Cruz Mountains and even the Sierras. I mountain-biked once or twice a week, then gradually upped it to 3-5 times a week around 1996 or 1997. That was easy because I worked from home in San Jose and could go whenever it fit into my workday.
I finally got the courage to enter my first bike race ever, in 1996 or 1997. It was a mountain-bike race held in Angel's Camp, in the rain. It was followed by my first visit to The Sea Otter Classic. I was hooked and raced for several years, racing long-gone races like Treeze and Breeze, The Sizzler, the Knobular series and others. Never did much better than mid-pack though. I also got a couple of nicer mountain-bikes; a Santa Cruz Heckler with full suspension, and a Specialized Stumpjumper hardtail. I raced the Stumpjumper in various cross-country races, and the Heckler in a number of downhill races, until mountain-bike racing pretty much died in this area in about 2000.
I got hired by HP in 2002 and started riding to work in Sunnyvale every day, rain or shine, for about 75 miles a week. When we moved to Santa Cruz that went up to about 130-160 miles a week. I had mounted slick tires on my Stumpjumper at first, but that seemed silly given the amount of miles I started putting in on the pavement. So I sold the Heckler and instead bought my Specialized Allez Elite road-bike in January of 2004. When my office at HP moved to Palo Alto my riding increased to about 160-200 miles a week. Plus I started riding centuries and stuff. But I've since cut back some on miles, and now I ride between 110-220 miles a week.
I got back into mountain-bike racing in 2004, getting 6th at The Sea Otter and 2nd at Napa Valley Dirt Classic. That was pretty cool, after my mediocre results from earlier! All those miles on my road-bike helped tremendously.
In 2004 I joined the Santa Cruz County Cycling Club (Team Santa Cruz). Yes, my childhood dream came true! I really went out of control, entering over 20 races, mostly road. I upgraded from Category 5 to Category 4, based on racing volume, but have now upgraded to Category 3, based on points from winning and placing at races. I have also been recruited by Team Bicycle Trip as a sponsored rider for the 2008 season. How cool is that!