Great pic.
Bike is an Indian. It has the sprung front forks, and is a v-twin with inlet-over-exhaust valves, it still has pedals and rather plain mudguards so its circa 1910 to 1913 or so. Could just be an export model, which had a slightly different arrangement of back brakes ?
So someone who knows their Indians should be able to pick the exact years and model. Someone who knows their cars could probably pick the year and model of the car in the background, and say if its Italian or USA - the car is about the same era. Its interesting that "Indian' is not visible on the tank, the logo was usually quite prominent.
P.S. In 1913 and 1914 , Indian was manufacturing in excess of 30,000 bikes per year, so was by far the worlds largest motorcycle manufacturer (or Motocycle, as Indian called them). And did a huge volume of export business.
Opethiselps.