Byron Isaacs and Peter Cole form their own doctrine in Lost Leaders.
In the late ’90s, two self-described “jazz refugees” from the New York jazz scene—Byron Isaacs and Peter Cole—longed to write rock songs. While they loved the vibrant jazz scene in New York and the music they were making, the two friends decided to collaborate on a side project. They called themselves Lost Leaders, “a double pun, a reference to us both being solo singer-songwriters attempting to co-lead in some kind of blind-leading-the-blind fashion, and a ‘loss leader’ because the project only ever had a vague promise of ever paying for itself.”
Decades later, Lost Leaders are returning to the Hudson Valley this month for a double co-bill with rising indie singer-songwriter Ginger Winn at two iconic venues: a sold-out show at The Falcon in Marlboro this Saturday, Nov. 15 and the following week at Park Theater in Hudson on Friday, Nov. 21.
Like many greats, both Lost Leaders and Winn’s careers blossomed in Woodstock—just generations apart. Their first album was originally written as a group of songs by the two longtime friends while Isaacs was playing in Woodstock when Helm started the Midnight Rambles. Isaacs played in the house band and eventually Helm’s band, leading him to play on multiple Grammy Award-winning albums. When no one else was using the studio, the two were invited to live and record at Helm’s barn for a few weeks. Their first gig was opening a Midnight Ramble with Helm himself.
In the early 2010s, both Isaacs and Cole went off to have children, playing in separate projects. Cole toured with the beloved band Lava Baby and became a professional audio engineer. Isaacs was spending so much time in Woodstock that half the year he was upstate and the other half he was in Brooklyn. After “hundreds of Rambles” and various bands—Isaacs was also one of the six founders of the legendary Americana band Ollabelle with Amy Helm—Isaacs found himself invited to the studio to play on the upcoming record of an undisclosed band that Simone Felice was producing, which turned out to be The Lumineers.
Isaacs met the band cold in the studio when they were just beginning to record Cleopatra, riding off the success of “Ho Hey,” the song that would catapult their career and propel the pop-folk Americana genre. Shortly after, he was asked to join their touring band and has been touring the world with them ever since.
The Lumineers have a long history in the Hudson Valley. Since 2015, they’ve been recording their albums at David Baron’s Sun Mountain Studios in Boiceville, The Clubhouse in Rhinebeck, and Utopia Studios in Bearsville. When they released their album Automatic earlier in 2025, the music video for the lead single was filmed at Bearsville Theater in Woodstock. They even played an acoustic secret show at Dreamland Studio in Woodstock for an Amazon Songline special.
Isaacs may be touring the world next year—some stops include New Zealand, Australia, Japan, Singapore, India, and South Africa, to name a few—but the Hudson Valley has been Isaacs’ “musical home” since the 2000s. So when The Lumineers took a break in 2023, it was a natural choice for Isaacs and Cole to return to record upstate.
They added a new, younger band—including Isaacs’ nephew Will Bryant on keys and Marlboro’s Lee Falco on drums—two accomplished Hudson Valley musicians in the locally beloved band The Restless Age, the latter doubling as the owner of The Falcon in Marlboro.
Isaacs commented on the longevity and success of The Lumineers: “No one can come up with a reason why it keeps growing,” but he offers a well-thought-out perspective. “They knew why they were doing it and the reasons they weren’t. When a band becomes a business, it’s trickier. They steered clear of the homogeneous effect. A lot is riding on you delivering consistently, which makes people repeat themselves artistically. They have not done that. Every record, they make bold, aesthetic changes. It’s very smart. They’re not playing into the typical fears that people play into when they realize they have a lot of people depending on them,” he summarizes, recalling an interview where David Byrne once said, “Success is a creativity killer.”
However, both Baron and everyone he works with seem to be immune. He’s a stationary presence in the top percentage of producers creating viral hits not only with The Lumineers but with a new wave of pop-folk talent too: Noah Kahan, Michael Marcagi, Jade Bird, Vance Joy, Matt Maeson, Nolan Taylor, The Felice Brothers, and Ginger Winn.
Winn worked with Baron to release her debut album Stop Motion in 2024 and was immediately picked up for a West Coast tour with the Gipsy Kings, opened for Gail Ann Dorsey at Opus 40, and created the first-ever waterfall-side concerts at the enchanting Woodstock Way Hotel with her label and creative partners Keep Good Company Records.
Their approach has blended sound and vision in all aspects of the creative process, including concerts and music videos, with Ginger winning laurels and awards in film festivals, including the Rhode Island International Film Festival for her short film 8:48, inspired by 9/11, which was also screened at the National September 11 Memorial.
She abandoned her plans to move to New York City when she felt inspired by the local creativity and found a large extended family of collaborators in the Hudson Valley.
Winn and Isaacs met after the first album release concert while Isaacs was recording Automatic with The Lumineers, connecting over a shared experience of the musical boot camp that is recording at Baron’s Sun Mountain Studio. Bryant, Isaacs’ nephew, also played in Winn’s band. Both Bryant and Falco played at the album release the following year for her sophomore album Freeze Frame in June of this year. The release led to an article in Spin magazine’s special 40th anniversary issue.
Presented by Catskill Crew, a local newsletter showcasing “the best of the Catskills” to over 40,000 subscribers, the pair of shows are a collaboration of old and new—a combination of Hudson Valley legends and the next generation of talent.
“It was an obvious decision for Catskill Crew to team up with Keep Good Company Records to showcase these incredibly talented artists and bring folks together for two nights at two iconic venues,” founder Michael Kauffman said.
Matt Baoine, co-founder of Winn’s label Keep Good Company Records, said, “Our name is our mission statement, and these two special nights are the embodiment of it: a circle of artists, places, and friends born out of the creative current flowing through the Hudson Valley.”
Winn agrees. She describes the shows as a love letter to everything she loves about the Hudson Valley. “These two shows with Lost Leaders feel special for a lot of reasons. I’ve never shared a stage with them before, but I admire their dedication, songwriting and energy. Both venues have a mix of vibe, sound, and space, so the music will really transcend. These two nights mark the end of the best year of my life, and I can’t think of a better way to close out 2025 than making music with some of my favorite people.”
Though Isaacs never formally lived in the area, he has certainly made music that has become a part of it. “It’s a homecoming for me,” he states.
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