Privately owned aircraft are referred to as "that hole in the sky into which the money goes."
... and may be your coffin.
I worked with one of the cofounders of Intuit. He has what he described as the "Honda Accord" of helicopters. If someone worth many hundreds of millions only has an average helicopter, you probably need many tens of millions for a small helicopter.
I'd say that an R44 is the "Honda Accord" of helicopters, and they're around $500k brand new. With a net worth of hundreds of millions, I'd expect that he went for something safer (with a turbine), like a Bell Jetranger.
You don't even need a $500k net worth to afford a Cessna. Most guys I know that have them are firmly middle class. They have to make some compromises on houses and cars, but it's worth it to them because they love to fly.
Somebody was asking about this on Reddit (/r/flying I think) a few months back. Short answer is that the FAA does not take kindly to receiving payment if you don't have a commercial license, and if you do then there's better work out there than Uber-for-cessnas.