Jason Walsmith on the Realities of Indie Music, Storytelling, and Saying Yes

The Nadas Co-Founder and Des Moines Music Legend Joins Maxwell's Iowa CoffeeCast

Sitting down with Jason Walsmith of The Nadas for this episode of Maxwell’s Iowa CoffeeCast felt like catching up with an old friend—one who happens to have a lifetime of stories about life on the road, the evolution of independent music, and the eternal tug-of-war between cynicism and optimism.

I recently saw Jason play before Chip Albright’s intimate show at XBK, and he told a story that stuck with me. It was about a conversation with Chip, who had asked him for advice on making a living as a singer-songwriter based in Iowa. Jason, having spent decades navigating the industry’s shifting tides, didn’t sugarcoat his response.

"I basically just told him the reality of what it's like to try to make money with music as an independent person these days," Jason recalled. "I answered every question with brutal honesty. And at the end of it, I said, ‘Here’s all the reasons why this is a bad idea. But you absolutely should do it. No doubt about it.’”

That moment, to me, summed up so much about Jason’s perspective—someone who has seen it all, who knows the hard truth, but still believes in the power of chasing a creative life.

The Journey from Folk Duo to Iowa Music Icon

Jason’s journey into music wasn’t necessarily planned, but looking back, it feels like it was inevitable. Growing up in Des Moines, he was involved in choir and sang in church, but it wasn’t until college that he picked up a guitar and started playing in earnest.

"I wrote one song in high school—it was called The Parrot Song," he laughed. "I didn’t really know how to play guitar yet, but I was a big Jimmy Buffett fan, and I just thought, 'I should have a guitar on the beach.'"

That early fascination with singer-songwriters shaped Jason’s musical sensibilities. While attending Iowa State, he started going to live shows at local bars and coffeehouses, seeing regional musicians like Rob Lumbard and Larry Myer. That’s when he had an epiphany.

"I realized you didn’t have to be famous to write songs and play music," he said. "There were these artists—people like Greg Brown and David Wilcox—who weren’t household names but were making a living touring and playing for real audiences. That’s when I thought, ‘I can do this.’”

That mindset led him to form The Nadas with Mike Butterworth, and they built a following the old-fashioned way—gig by gig, song by song.

"We were just this little folk duo playing anywhere we could," Jason said. "We learned songs off mixtapes, we played every bar in Ames, and eventually, we started getting real shows. That was our training ground."

The Evolving Business of Music

Over 30 years, The Nadas have played hundreds of shows, recorded multiple albums, and built a devoted fan base. But the way artists make a living has changed dramatically.

"Back in the day, we sold records. That was a big part of it," Jason explained. "Now, the economics are different. Streaming doesn’t pay much, touring is expensive, and you have to be creative in how you make it work."

That need for reinvention became especially clear during the pandemic. When touring shut down, Jason and his wife started the I'll Play Anywhere Man tour, traveling the country in a camper van and playing backyard concerts.

"I had to get out of the house," he said. "We just put it out there—if you’ve got a backyard and some friends, I’ll come play. I did a hundred shows in a year and a half. It was an awesome adventure."

That tour led to an unexpected sponsorship from a camper van company that loved what they were doing and wanted to support it financially.

"It was this really organic, authentic partnership," Jason said. "They weren’t trying to turn me into a jingle guy. They just wanted to help. And that’s one of the new ways musicians can make a living—real partnerships with businesses that believe in what we do."

The Magic of Storytelling

One of Jason’s hallmarks, both as a solo artist and with The Nadas, is the way he connects with audiences through storytelling.

"Sometimes the story before the song makes people invest in it more," he explained. "If they hear why I wrote it, what inspired it, they’re already engaged before the first chord even plays."

I asked him if he ever worried about repeating stories for the same audience.

"Not anymore," he said. "When I was younger, maybe. But now I think about all the times I saw my favorite artists tell the same stories, and I loved it. It felt like an inside joke, like I was part of something."

That relationship with an audience is what makes live music so powerful, especially in intimate settings like house concerts.

"For me, that’s where the magic happens," he said. "A small group of people, all really listening, sharing that energy. You can feel when it’s working—it’s like electricity in the room."

Advice for Young Musicians

As someone who has spent decades in the trenches of independent music, Jason has plenty of wisdom for younger artists trying to find their way.

"My advice is in a song called The Other Side of the 45," he said, referencing a track from The Nadas’ latest album Come Along for the Ride. "One of the lines says, When they ask, just say yes. That’s it. Just say yes. Play anywhere, take the opportunities, and don’t overthink it."

He also emphasized the importance of simply showing up.

"Take your guitar everywhere," he said. "People will ask you to play. And when they do, say yes."

The Future of Music in Iowa

As our conversation wrapped up, we talked about the local music scene and whether there’s a renewed energy in Des Moines.

"I feel like the train is coming back," Jason said. "And I feel like I’m on it."

That’s the perfect way to sum up Jason Walsmith—an artist who has seen it all, who knows the ups and downs of the industry, but who still believes in the power of music, the importance of saying yes, and the magic that happens when a song connects with the right audience.

And as long as there are people willing to listen, Jason Walsmith will keep playing.

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LISTEN to my coffee conversation with Jason on Spotify below, or CLICK HERE.