Sydney “Syd” Chaplin, half brother to Charlie Chaplin and his business manager.

But it was in aviation where he made history in 1919 when he bought a plane and hired pilot Emery Rogers and thus begun the first privately owned domestic American airline.

Things were looking good for Chaplin, but when the pesky government began requiring things like pilot licenses, he got out of the business.

https://thejivebombers.com/2018/11/04/syd-chaplin-aircraft-corp