Jon Weisberger

Hillbilly music, one record at a time

Jon Weisberger was born in Ohio and went to high school in Rochester, New York. Rochester had country radio, but he came from an academic family and had no connection to the people listening to it, so he found the music on records. One of the first he bought was Flatt and Scruggs at Carnegie Hall. He still uses the old term for the field he fell into: hillbilly music.

In the late 1970s, living in New York City, he came across a Red Allen record called Live and Let Live. Around the same time he moved to Cincinnati, where Allen was from and playing. Southwest Ohio was a bluegrass town on the scale of Baltimore, built by decades of migration out of Kentucky and the upper South, and he found two audiences there. One was working class and hardcore. One had come by way of the folk revival. By background he belonged to the second.

"I just really liked the hardcore music, and so that put me in with the more working class crowd."

A mailing list turns into a writing career

He joined his first bluegrass band around 1980. In 1990 he quit thirteen years of software engineering on mainframe computers and spent the decade at home in Cincinnati. That is when the playing got serious, four and five and six nights a week, in a band called Union Springs with mandolin player and singer Dwight McCall, later of J.D. Crowe and the New South.

He also signed on to BGRASS-L, the bluegrass listserv Frank Godbey had started at the University of Kentucky in 1991. A few hundred people were on it, a lot of them working in the business. Weisberger had time and opinions, so he posted constantly about records he heard and shows he went to. Ken Irwin of Rounder Records was reading. Around 1995 Irwin asked him to write a magazine piece on Rounder's twenty-fifth anniversary, and Bluegrass Unlimited started sending him records to review. That became ten years of liner notes, something like 140 albums' worth, and three IBMA writing awards, the last of them shared with Sam Bush in 2023 for Radio John: The Songs of John Hartford.

Nashville, and never one paycheck

At the end of 1999 Aubrey Holt asked him to play bass in the Wildwood Valley Boys, his son Tony's band, on Rebel Records. They toured. Afterward Weisberger went back to local dates around Cincinnati and could not make a living at it, so he moved to Nashville at the start of 2003 and Chris Jones hired him for the Night Drivers. He stayed sixteen years, on bass and harmony vocals, through seven albums. He joined Roland White's band in 2004. From 2006 to 2018 he co-hosted Hand Picked with Del McCoury on Sirius, then in syndication, then on SiriusXM's Bluegrass Junction.

"I didn't make even 50% of my income from any one source."

Backing into songwriting

He wrote his first song because a Cincinnati label owner told Union Springs he would cut their record if they brought original material. He was in his forties. Co-writing came after the move to Nashville, and it stuck. He has now written with close to 150 different people, and the credits run to nearly 200 cuts.

Writing with the artist solves a problem he never had to learn to solve. He does not pitch songs. Several of his co-writes with Billy Strings are on Home, including "Away From the Mire." "California Sober," written with Aaron Allen and Strings, was recorded by Strings and Willie Nelson and nominated for a Grammy. "A Hard Life Makes a Good Song," written with Jeremy Garrett, is on the Infamous Stringdusters album Laws of Gravity. "Autumn Leaves Don't Fall" is a co-write with Thomas Cassell. IBMA gave him the first Songwriter of the Year award in 2012, and he won it again in 2025.

"With co-writing, you look for productive relationships where people's strengths balance each other out."

The desk job that is still a music job

In 2018 Asheville Music Publishing brought him in as a writer and a partner to build a bluegrass catalog. Then the label asked him to do A&R part time, then full time, which meant leaving the band. He moved to Brevard, North Carolina in 2019. Mountain Home is small for the record business and large for bluegrass, about thirty artists and a staff of a dozen. He does artist relations, writes press copy, produces, and sometimes ships CDs out of the warehouse.

The producing has settled into large collaborative projects, more by accident than design. He co-produced Roland White and Friends: A Tribute to the Kentucky Colonels with Ty Gilpin in 2018, and Bluegrass Sings Paxton, an album of Tom Paxton songs sung by bluegrass artists, with Cathy Fink. He produced the Bluegrass at the Crossroads sessions, one of which, a cut of Earl Scruggs's "Ground Speed," won an IBMA award in 2021. He is the A&R person for Sister Sadie, whose album No Fear was nominated for a Grammy.

"I feel very well recognized."

The streaming argument

Weisberger is the one who speaks up when a post goes around saying streaming pays artists nothing. His point is not that the complaint is wrong. It is that the transaction changed shape. Selling a CD at the merch table feels like being a musician, but economically it is retail, and once you have the money you have all of it. Streaming pays a little every time somebody listens, and keeps paying. Past roughly 1,200 streams of a track it passes what the sale would have paid.

So: sell merch for cash flow, because a CD is only one kind of merch and not a good one. And pay for a subscription rather than listening on the ad tier, because a paid stream pays more.

"Think of your recorded music revenues as your retirement plan."