Are you talking about Todd Waters? Otherwise link source. It's pretty rare for someone to want that lifestyle unless they've already involuntarily experienced it previously. Todd had started trainhopping when he was in high school.

I know of one other individual who is a millionaire and has a mansion he sleeps in, but during the day appears to be homeless and pushes a cart around cleaning up cans and trash. He's beloved by his local community (very nice man and generous tipper). He also experienced living on the street involuntarily previously and got an inheritance.

https://newscut.mprnews.org/2017/07/todd-waters-mission-was-to-make-people-homesick-for-their-freedom/index.html

Waters was a “hobo” who proudly noted in 2012 that he’s been arrested about 70 times jumping railroad cars out of St. Paul for parts unknown and known. He was also a millionaire.

“My life went south after my wife ran off with a bartender to Arizona. I sold everything I owned and hit the ‘first thing smokin’, running away, then after a year or so, drifting where ever I damned well pleased. I got off ‘the road’ after a few years to settle down,” he wrote on Hobo Times. “That lasted about three weeks. I was homesick for ‘the road’. I returned to ‘the road’. That lasted a few months until I got homesick for settled society. That lasted until I got homesick for the road again.”

Somewhere along the line, he got in the advertising business, made a lot of money, and lived in a million-dollar home on Lake Minnetonka.

Todd’s childhood friend, Bill Martin, once asked him why he would leave the comfort and security of his family and his Lake Minnetonka home every summer for 40 years to live the hobo life, with no money and no phone, exposing himself to danger, dodging the law and sleeping out in the elements. He replied, “It’s the freedom I feel.” The more risks he took, and the less he had in his pack, the more he was free to experience.

While Todd rubbed shoulders with the wealthy, prominent and powerful, the people he probably respected most for their guts and straightforwardness were hobos. So before hiring account executives for his agencies Waters Advertising, Waters & Company and WatersMolitor, Inc. he sometimes asked candidates to hit the streets and panhandle. He insisted that the people he worked with be brave, and know how to close a sale.