At the time I first met Bob I had my first business location on Maui selling tickets and tours at the corner of Front and Hotel Streets at the Pioneer Inn in downtown Lahaina. At that time (early eighties) I had already been in business almost a decade and I knew just about all of the activities on island and all the owners. At that time there was a somewhat out of character hotel up off the highway in Lahaina called the Travel Lodge. This is where Bob had his first location. He had purchased a series of bikes which he kept outside there and rented them out to visitors for day use. I personally didn’t see that business as being one that was destined to be a terrific success but that didn’t deter Bob from coming over to visit me on the corner where I sold tours to elicit my assistance in helping him rent his bikes. I just never saw bike rentals from that location as having a big market. On one of his visits to see me he brought over a brochure which described his bikes, gave rates for renting them for a day or half day etc. and then at the very bottom he had a small bullet point with the words “Bike Down Haleakala Crater”. I asked him what he meant by that and he said he just put it down as an afterthought on the brochure but that he thought it would be a great activity to take bikes up to the top of the mountain and then just coast them down. I remember discussing the concept with one of my original employees that day and coming to the consensus that it sounded like an activity that could have its dangerous side if not properly safeguarded but still held the notion that the idea did have merit because the idea of gliding down 38 miles of roadway to sea level without peddling was a compelling thought. Well sure enough, some months later I saw Bob driving up and down Front Street in Lahaina with a specially designed truck built to house a bevy of bikes that would be used to cruise down the crater. In fact, Bob liked the term “cruising” so much that he actually named the company Cruiser Bob’s Downhill.
At some point a couple of weeks later I heard that Bob had taken his first group down the hill. It became a sensation pretty quickly and within a couple of years there were four or five companies all going up the mountain and taking bike trips down filled with island visitors. Today the industry is much more heavily regulated by the government but it has become one of the staple activities people have come to recognize and put on their ‘to do list’ when visiting the island.