When he was a teenager, all Kevin Milton could think about was hopping on his motorcycle and traveling across the United States. His part-time jobs while in high school got him a serviceable bike and the summer after his senior year was spent on a cross-country trip that included a stop at the annual rally in Sturgis, South Dakota. Money was a big concern, so he took his chances with one-star accommodations near Sturgis.
Keeping a merely “serviceable” bike rolling gave him the kind of real-world experience that can get you jobs – which is exactly what he found at a popular bike shop back home. Kevin’s wanderlust wasn’t anywhere near fulfilled, so the job was just a way of paying for his frequent road trips. The following May he rolled off to Myrtle Beach Bike Week – and was able to move up to 2-star hotels in the Myrtle Beach area.
While in Myrtle Beach, Kevin met the beautiful Robin Finnegan, who just happened to live a few miles away from Kevin’s home in Virginia. Life moved quickly and within a couple of years they were married, had two kids and Kevin was managing that bike shop. Time for a “spring break” trip to Florida – this time taking advantage of 3-star places to stay near Orlando.
In the evenings, Kevin started working with his tech-friendly brother-in-law on a web site devoted to weekend bikers. It didn’t produce enough cash (yet) to live off of, but it did come in handy when Kevin and Robin celebrated their fifth anniversary with a weekend at a 4-star hotel in New York City.
Luck, timing and enthusiasm helped make that original web site into the most popular online biker destination in the world. Meanwhile, they expanded their “web empire” to include a variety of travel and sports-related web sites. Life was good – and only got better a few years later when a “major web company” bought it all for $250 million. An appropriately extravagant celebration followed at The Royal Hawaiian Waikiki, one of the 5-star hotels in Hawaii.
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