Todd Waters was drawn to two worlds — one of a Twin Cities advertising executive, living a comfortable life on the shores of Lake Minnetonka; the other as “Adman,” a hobo who hopped freight trains and scrounged dumpsters for dinner.

“He was a free-spirited person who lived on one side of the tracks but longed to be on the other side,” said Julianna Porrazzo-Ray, who like Waters frequently swapped her life in Minneapolis for adventures on the rails.

“He always wanted to see what was around the bend,” said Porrazzo-Ray, known on the rails as Minneapolis Jewel. “He took life and said, ‘Let’s have fun. Let’s see what’s out there.’ ”

Now, she said, Adman has “caught the westbound” — hobo slang for those who have died. Waters, of Orono, died July 7 after a long illness. He was 69.

Those who knew him said Waters was as much at ease in the boardroom as he was in a hobo camp, in part because he was gregarious, fearless and creative. Moving between worlds was seamless for him.

In the business world, he was the bearded guy in moccasins who was polished and articulate, said Steve Bakke, a longtime friend and advertising business colleague. “He was the creative force, driving unique ideas that won national and international awards.”

Waters jumped into advertising, starting his own company after he graduated in 1971 from St. Cloud State University and continuing to work for other firms and his own throughout much of his life.

“He lived in a big home on Lake Minnetonka [and] made a lot of money in the advertising business, but you would never know that when you were out on the trains with him,” Bakke said. “He genuinely believed in the value of people. His slogan ... was ‘Everyone matters.’ ”

Waters lived life on his own terms, but never trampled on others and always gave people the benefit of the doubt, said Bakke, who spent four summers riding trains with his friend. “You meet a lot of people on the rails, some who are a little frightening, and Todd was able to break down those barriers partly through the force of his personality and partly because he was just a genuine person,” he said.

Waters was lured to the rails long before he had a driver’s license, hopping a slow-moving boxcar with a childhood friend. The adventure took them a few miles to Wayzata.

In high school, he hitchhiked around Minnesota. Years later, when his first wife ran off with a bartender, he sold his belongings and thumbed his way around the country for a couple of years.

The hobos adopted him, he once told a reporter: “They could see that I was lost and lonely and always hiding in the shadows, and they really reached out to me and made me feel welcome in their community.”

He spent 40 summers riding the rails. He would get the itch to leave as soon as the frost left the ground and the tree frogs began to sing, said his daughter, Alexandra, of Washington, D.C.

It was the freedom that enticed him to be a “sport hobo,” said family and friends. “You could never be late because you had no place to be, and you couldn’t be lost because you had nowhere to go,” said his wife, Dori Molitor. “It was rejuvenating for him.”

He found comfort in the clatter of steel against steel, the sway of a boxcar, the smell of baking creosote on railroad ties. He reveled in the expanse of the prairies, mountains and the night sky speckled with stars.

In addition to his wife and daughter, Waters is survived by a son, Andrew of Boston, and two sisters, Jeanne Elizer of West Palm Beach, Fla., and Lynn Bolyard of Onsted, Mich. Services have been held.