On May 19, 1903, Horatio Nelson Jackson was in San Francisco on business. His primary residence was in Vermont where he had been a physician. Following a bout with tuberculosis he spent time in California and in May of 1903, having given up the practice of medicine three years earlier, was returning from Alaska were he had overseen some gold mine investments.
While at the University Club he overheard a group of men talking about the new horseless carriage – in their opinion it would never be able to make a cross-country trip. Horatio thought otherwise and boastfully wagered $50 claiming he could make the trip in less than three months. The wager must have seemed impetuous since Horatio did not own an automobile, and likely had very little, if any, experience driving one.