Okay, let’s tackle this. So Jack Cummings has experience as a company owner, which is a unique skillset. However, without specific details on his industry, skills, or education, it's challenging to estimate a precise hourly rate. Typically, entrepreneurs with similar experience might charge between $50-$200 per hour, depending on their industry and location. Considering Jack's location in Richmond, Virginia, and his experience as a company owner, I'll estimate a rate around $100 per hour, on the lower end of the spectrum.