After several years of playing the bar and restaurant circuit in his native Virginia, Williams decided to head to Colorado to take in the Telluride Bluegrass Festival and get in a little skiing.
"Well, it was primarily wanting to ski and snowboard for free, and play the bars out there at night," Williams told POLLSTAR. "I worked it to where I would play once a week for a very little amount of money and in return they'd give me a free ski pass."
It was during that time that Williams, who got his start playing a country club happy hour in his hometown of Fredricksburg, Va., met up with members of The String Cheese Incident.
Soon, the eclectic singer/songwriter was signed with the band's in-house booking and management firm, Madison House, as well as its label, SCI Fidelity Records.
"It started off slow," Williams explained. "It started off with just booking. It was about 1998, I guess, when Madison House began helping me out with getting some gigs. The big word back then was 'exposure.'
"It was always: 'Exposure, exposure. There's no money in it, but there's good exposure.' So we pretty much lived by that word as our guide for a couple of years."
Williams means that quite literally; he, his wife Emily and Labrador retriever Earl lived for two years on the road as he honed his performance.
"From '97 through 2000, my wife and I basically just did loops around the country," he said, laughing. "We stayed in motels, campgrounds, friends' houses, rest areas, truck stops and stuff like that in all kinds of vehicles."
Things took off for him in '99 with a little help from his friends, when he released Breathe with The String Cheese Incident backing him on the recording.
But Williams is a solo performer and his August release, Home, is his first on which he plays every instrument as a virtual one-man band.
"It's something I've always wanted to do, to go in and play all the instruments," Williams said. "I've never really let myself do it; one, because I've never really felt that confident on all the other instruments and, two, because I've crossed paths with so many fantastic musicians who are monsters in their field and are willing and able to collaborate with me in the studio."
Not that Williams isn't a formidable musician himself. Besides his guitars, including a 10-string ("basically, it's a 12-string with two strings taken off"), there's a whole range of instruments that Williams can pull out onstage or in the studio. Get him talking about his music, instead of the business, and he sounds like a kid at Christmas.
"I play the drums, all kinds of percussion. I recently acquired a MIDI vibraphone. It's got the shape of a vibraphone but has all electronic pads," he explained, enthusiastically. "So, I can get the vibraphone, marimba, xylophone, and all kinds of drum sounds out of it! There's a thing called the theremin. I dabble in the trombone. There's a little bit of piano. ..."
Well, you get the picture.
The other thing Williams talks about with gusto is his newest venture: He has recently launched his own syndicated radio show called "Keller's Cellar: Somewhat Ruleless Radio."
"That came out of the piles and piles of caseless CDs that are around my house and motor home that are in danger of being stepped on," Williams explained. "I wanted to make, like, narrated mix tapes of all my favorite songs off these CDs, kind of like an Internet kind of thing, like a radio show."
A record promoter mentioned that idea to a radio station program director one day and the next thing Williams knew, he had a regular 10 p.m. Saturday slot. Since then, the show has been picked up by seven radio stations and, according to co-manager Nadia Prescher, it was about to double that total at press time.
"It is the coolest thing," Prescher told POLLSTAR. "The radio station idea came about when Keller maybe had one too many days off the road. Keller loves to work.
"This is an artist that I feel so lucky to work with because he makes my job easy. He's got his music and then he's got this fabulous live show that speaks for itself. He's got this great independent spirit, this huge creative vision."
With the business end of being Keller Williams taken care of under one roof at Madison House, he's able to concentrate on his music, which suits him just fine, too.
"I'm very, very, very lucky to have such wonderful folks around me that I completely trust to take care of everything about the business," Williams said.
"Everything is under one roof. It's a young and hungry group of people who are really passionate about their particular music scene that they've helped create," he explained. "It's really a fantastic thing that's going on in Boulder."
And the skiing's not bad, either.