In this episode, I sit down with mandolinist, composer, and bandleader Jacob Jolliff for a wide-ranging conversation about curiosity, discipline, and building a musical life that resists easy categorization. Jacob is one of those rare musicians who move fluently between bluegrass, jazz, classical, and experimental music without losing his voice in any of them. We begin by talking about his love of variety, why collaboration continues to drive his schedule, and how he follows genuine musical curiosity rather than a rigid career plan. Jacob reflects on touring, playing weekend runs versus more extended tours, and why he’s motivated to say yes to projects while the travel still feels energizing.
A significant focus of the conversation is Jacob’s upcoming classical recording, a mandolin concerto explicitly written for him by composer Jesse Jones. Jacob walks through how the project came together, from a lifelong friendship that began when he was a child to a reunion nearly two decades later, after Jesse had become one of the most respected contemporary classical composers in the country. We talk about performing the concerto with an orchestra, recording the work, memorizing a demanding five-movement piece, and learning the nuanced skills required to follow a conductor while still maintaining musical agency. Jacob explains how the music successfully bridges contemporary classical language with bluegrass sensibilities without feeling like a caricature of either tradition.
We also dive deep into Jacob’s years at Berklee College of Music and the fertile Boston roots scene that shaped a generation of genre-bending acoustic musicians. Jacob reflects on studying with John McGann, the early days of what would later become Berklee’s American Roots program, and coming up alongside players like Alex Hargreaves, Dominick Leslie, Sierra Hull, Julian Lage, Brittany Haas, and others. We talk about why conservatories embracing acoustic and roots instruments have changed the musical landscape and why this moment feels uniquely exciting for mandolin, fiddle, and banjo players.
Jacob shares the origin story of his band, including how his time with Yonder Mountain String Band prepared him to lead a project of his own. We talk about the balance between being a sideman and a bandleader, why the best leaders often have deep experience in both roles, and how empathy grows when you’ve carried responsibility from both sides of the bandstand. Jacob walks through how his lineup evolved, why consistency eventually mattered more than flexibility, and how his current band came together organically around shared priorities and musical trust.
We spend time talking about Jacob’s jazz projects, including his standards recordings and the unusual instrumentation of mandolin, bass clarinet, snare drum, and bass. Jacob explains why learning jazz still feels like learning a second language, how making records can be part of the learning process rather than a final statement, and why exploring multiple genres keeps his playing honest. We also talk about his admiration for musicians who dedicate their lives to a single tradition, even as he continues to thrive as a musical generalist.
We close with a thoughtful discussion about Jacob’s practice routine, discipline, and mindset. He explains why he practices nearly every day, how consistency prevents stagnation, and why regularly confronting technical and musical walls is part of long-term growth. Jacob speaks candidly about the psychological challenges of being a driven musician, the tension between ambition and perspective, and why staying curious ultimately matters more than perfection. It’s an honest, inspiring conversation about craft, patience, and the lifelong pursuit of musical depth.
To learn more about Jacob, visit his website.
Music from the Episode:
Large Garbage Barge (Jacob Jolliff)
Moose the Mooch (Jacob Jolliff)
Sheerson Crosses the Rocky Mountains (Jacob Jolliff)
The Good, The Bad, and the Home-Schooled (Jacob Jolliff)
Stumbling Distance (The 376 Years) (Jacob Jolliff)
Thank you for listening. If you have questions, feedback, or ideas for the show, please email me at
[email protected].