“If nothing goes wrong, then everything has gone wrong.”

That’s the rallying cry of The Mountain Folk Adventure Series, a new Bloomington-based philanthropic organization that seeks to raise money for charitable causes through bare-bones, unsupported adventure travel through some of the planet’s most challenging terrain.

The Mountain Folk’s debut event, dubbed the Mississippi River Run, launches May 5 at Lake Itasca, Minnesota, and ends in New Orleans. Teams of up to four “swashbucklers” will make their way down 2,350 miles of the Mississippi in anything they can find, build, or buy—as long as it doesn’t have a motor. That’s about the only requirement, other than the entry fee of $650 and the commitment to raise at least $1,000 to benefit New Orleans Area Habitat for Humanity.

The Mountain Folk Adventure Series is led by Michael Waterford, a 2004 graduate of Edgewood High School, who went on a working holiday after graduating from Purdue University in 2008 with a degree in tourism and hospitality management. His travels took him to Germany, India, Malaysia, New Zealand, and across the U.S.

Waterford, 27, worked in mainstream resorts like the Four Seasons on Hawaii’s Big Island, but his career outlook changed in 2010 when a friend asked him to take part in the Mongol Rally, an 11,200-mile journey on small motorbikes from the Czech Republic to Mongolia (see Bloom Magazine, “The Ride of a Lifetime,” April/May 2012).

Waterford initially didn’t aim to found his own philanthropic enterprise. He wanted to work with The Adventurists, the U.K.-based organizers of the Mongol Rally, on a U.S. adventure. “But they said America isn’t wild enough,” he says. “That offended me.”

To prove them wrong, and also out of a desire to see parts of his home country he’d never visited, Waterford settled on a Mississippi River voyage to kick off the Mountain Folk series. He says it’ll show the world that the United States isn’t a “sissified, fat kid, couch potato” nation.

“I want to distill our sense of ruggedness,” he says. “It’s still here.”