An Interview with Jesse Terry

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Jesse Terry’s seventh album, When We Wander, is the first he wrote since becoming a parent. So it’s no surprise the family theme courses through many of its 12 songs. His music career has been a family project ever since he became a full-time touring artist a decade ago.

The stage had been Jesse’s home for a decade. He plays around 150 shows a year, from Bonnaroo to the Philadelphia Folk Festival, the 30A Songwriters Festival to AmericanaFest. When the pandemic canceled concerts and delayed the album’s release, he pivoted to performing online and found a strong new connection to his fans, who had helped fund his albums all along. “My musical tribe has always been there for me,” he says with gratitude.

Though recorded in 2019, the songs off the new album click with fans online too. He and his band recorded When We Wander live in the studio, a first for his career. “I wanted to try that Jason Isbell, Chris Stapleton, Neil Young approach to live recording, prioritizing emotion and raw performances over perfection. I loved that experience.” Recorded live, the album resonates especially with the intimacy and community spirit of the online shows.

If you would like to learn more about Jesse Terry or his new record, When We Wander, you can take a trip over to his website and dig in. Once you’ve done that, enjoy this interview with Jesse. Cheers.

Bio courtesy of

Jesse, thank you for taking the time to speak with us. This last year has been rough. How are you holding up?

Yeah it’s been challenging at times. It was especially scary at the beginning because everything was so new and uncertain. My wife lost her job, too and I had no idea how my fans would respond to online shows. To be honest, live-streamed shows were never appealing to me. I began those as a means of survival. I remember my dad telling me in March 2020 that I might have to get a “real job” to get through this. That was much more terrifying to me than learning how to play online concerts! Because I knew he was simply telling the truth. My dad is a cool dude and a fellow full-time musician, and he’s always been super supportive of my music. So he wasn’t speaking as the stereotypical “get a real job” parental figure – he was just speaking as a father.

Luckily, we’re still here making music a year later with so many great things coming up and live touring back on the horizon. My fans have been unbelievable in the last year, and I’m immensely grateful.

Tell us about your backstory. What was your musical gateway? 

My parents were musicians and actually a duo until they divorced, so I was always around music. And I really loved what they played on the turntable. It was a pretty diverse mix but I remember The Beatles being in heavy rotation, along with Michael Jackson, James Taylor, Emmylou Harris, Bruce Springsteen, Marvin Gaye, Joni Mitchell, Linda Ronstadt, Neil Young, Jackson Browne and everything in between.

I originally went to school for fine art, and I avoided being a musician for as long as I could. I think I perceived music as hurting some of the relationships in my life, namely my parents, so I think I shied away from it as a career choice. I always loved music so much, and I spent a lot of time recording vocals in my father’s recording studio, but I never took it farther than that. 

When I had a bad leg injury around age nineteen, my mother lent me her old Yamaha acoustic while I was on the mend, and that was it for me. The high of creating a song was like nothing I’d ever experienced before. After a year of playing guitar around the clock and learning how to write songs, I dropped out of art school and eventually enrolled into Berklee College of Music at age twenty-one.

As an artist, who are some of your earliest and most important influences? How did you develop your signature sound? 

I loved The Beatles, but James Taylor, Neil Young and Jackson Browne were probably the most important early influences for me. Something about that confessional, emotional, transparent and personal style of songwriting really resonated with me and affected me. I was sent to several institutions and reform schools early in my adolescence and James Taylor’s music was one of my biggest comforts during that time. I was also reading JT’s various biographies and I feel like he’d already walked in my shoes. So that was a big comfort for me, knowing that I wasn’t alone.

Later on, when I started writing my own songs, I was able to draw from my own experiences and be honest about them, largely because of that influence from James, Neil, and Jackson.

Let’s talk about your new record, When We Wander. How did it come together? Tell us about the recording process. 

I was talking to my long time friend and producer Neilson Hubbard and asking him how he was capturing such magic in his recent recordings. His answer was recording everything live. This is certainly not a new concept, but everything in music seems to come full circle. Once we had the technology in music to keep things super clean, folks really dove into that pristine recording approach where everything is so separated. And don’t get me wrong, some amazing records were made that way and many more amazing records will be made that way moving forward. But it was great to explore recording in a truly live way, singing and playing at the same time and reacting to the band in real-time. For a perfectionist like myself, it was a real revelation to be completely in the moment and not have the time to overthink things. There’s an emotion and vibe that we captured on this record that is different than my other projects. Not better or worse to me, just different. I think exploring other ways to create music just makes you a better artist overall. 

The thing about recording live is that you have to trust who you’re working with. It has to feel great in your headphones to sound great on tape. With this project, I knew that the whole team was the very best, from Neilson to the engineer Dylan, to all of the players and singers on the tracks. And finally, I needed to be at a place as an artist where I had confidence in myself to let go and give everybody great performances. I feel like it was the right time in my career for me to do this. I was ready.

What was the inspiration in songwriting? Is the lyrical content personal? Or are these only
stories, so to speak? What would you compare your music most to? 

I usually feel like I write a batch of songs, and then we evaluate the theme in them after the fact. I just try to write what is powerful and inspiring to me. Usually, that’s personal stuff, but I’m also excited to start writing more character-based songs. Any story or topic that sparks a real emotional connection has the potential to be a great, authentic song. This was the first album I wrote as a father and we realized after the fact that the theme of family and parenthood coursed through the music—so many new emotions there and topics to explore for me. 

I went into the studio with Neil Young’s Harvest Moon as a bit of a blueprint. I loved that instrumentation and feel on that record so much, including the harmonies of James Taylor, Linda Ronstadt, and Nicolette Larsen. I think I’d compare my music to James Taylor, Neil Young, Springsteen, Jason Isbell, and Linda Ronstadt. I’ve really embraced the purity of my voice. Self-acceptance is the most attractive and wonderful thing. I love so many songwriters, including Dylan and Tom Waits, but when it comes to delivering those lyrics, I really look to singers like Ronstadt, Vince Gill, Emmylou’s Harris, James Taylor, and Bonnie Raitt for inspiration. Singers with so much soul in their voices while also sounding incredibly pure.

How about the production side of things? Do you self-produce, or where outside sourced
brought in to help hone the sound? What can fans expect from your new When We Wander?

I’ve started to co-produce some of my upcoming projects since being locked down. I built a home recording studio that I’ve used on a couple upcoming albums so far and I’ve been blown away by the quality of that. It’s been a great silver lining to this time and another thing, along with online concerts, that I never had interest in prior to the pandemic.

But usually, I really enjoy having a producer steering the ship. It’s great to have someone you trust to bounce ideas off of. There are so many things my producers have done for me that I never realized. Crucial things like finding the right key and tempo and making small tweaks to a song structure. Some of those things can make or break a recording. 

Neilson has been my main producer in my career, and it’s been an amazing journey with him. I feel like he’s been there to watch me grow as an artist and encourage me. He’s been one of the most important figures in my career. I’ve been lucky to work with some other fine folks too, but Neilson is special to me. We have two more upcoming projects we’re working on together, set for release later this year. I think fans can expect a new sound from me with “When We Wander.” I’m always striving to grow and get better, but I feel like this album is at another level for me in terms of songs, sonics, and confidence. We recorded this in September of 2019, and the release has been delayed for a while. The fact that I still dig it after all that time speaks volumes to me.

How much of an influence has the COVID-19 pandemic had on your songwriting and on
the overall process and creation of your new record? 

This album was recorded in September 2019, so COVID didn’t have an impact on it, which is great. It was great to have that last bit of innocence together as a band before the world changed. It makes the record really significant and special to me. Even the music videos were filmed in Feb. 2020, so the whole project is like a little time capsule. I’m currently writing new songs for my next original album and I imagine that the impact of COVID will touch my new work. When We Wander was totally spared from that experience.

Let’s shift gears now, live music is usually a huge part of a working artist’s proverbial
machine, but as we know, COVID has disallowed it. What do you miss most about live

I miss so much about it. I miss the simplicity of plugging into an amp and plugging my microphone in, having no worries about internet strength or technology. That feels so simple and so beautiful to me right now. I miss the carefree interaction between me and my audience and the hangs after the shows. I miss the drives and flights with my family and the late-night coffee. I was built for touring and traveling. It’s going to be great to get back to that when the time is right.

One disturbing fact I’ve learned over time is that streaming services don’t pay artists well, if at all. What are your thoughts on that issue? How do we as fans do our part to help? 

Yeah, I resisted Spotify for a while and stayed pretty old school with vinyl, downloads, and CDs in the car. And I know people are fighting the good fight to make streaming income for artists more realistic, fair, and sustainable. I’m so grateful for that. But I’ve also realized that streaming can be a part of my overall puzzle in my career. I’m a person that pays for Spotify Premium and uses it when I can’t relax at home by the turntable. And I discover great music there. I want folks around the world to discover my music there and then come out to a real live show. You can’t replicate that experience. Maybe when that new fan is at the show, they’ll grab a real live record, which is the best way by far to experience recorded music. You can’t replicate that experience either. Fans can help by coming out to shows and buying those real products that create profit for artists. I think the awareness of streaming rates is good for people to be aware of. To me, it’s mainly a discovery platform and a cool way to reach lots of people. Hopefully, that translates into lots of cool stuff in the real world.

In a world dominated by big business and social media, can artists really, truly get ahead? How do we keep the playing field level so that everyone has a chance to succeed?

Good question. I think the answer is yes, but it is an uphill climb. Fans fuel everything, and if you have enough people that love your work, you can make a great living. But you have to fight for that and find ways for enough fans to discover you. Being famous or successful is a relative term. Do you want to play to sold-out theaters around the world that can seat two hundred to a thousand people? That’s a pretty awesome career right there, even if you’re not a household name. 

I love that folks are finally becoming more aware and proactive about inclusion. It’s not fair to start a race when you’re already behind. I think we need to continue working on being inclusive and continue working on being anti-racist. 2020 and the last few years have shone a light on some dark places. My hope is that the human race will take the opportunity to improve and make changes for the better. We’re at a fork in the road, and people have to make a choice.

Are you into records? Tapes? CDs? Digital? Where do you like to shop for music? What
are a few albums that mean the most to you and why? 

I’m WAY into vinyl and always have been. And I’m not just saying that because of this interview! For a while there we were touring non-stop and I didn’t have access to my turntable or record collection. That was difficult! Last year I finally invested in a new turntable with a great stylus. What a difference that has made in my life. Listening to a perfect album on a great turntable is the way music was intended to be heard. It’s the closest thing we have to the recording studio and the sound that comes out of those speakers. It’s a different experience.

Of course, music is still great on CD or streaming. If the sounds are great, it’s still an awesome experience. It’s just that vinyl is the pinnacle. In normal times, we love finding our local independent record store and shopping there.

There are some records that are always near my turntable because they always create a new world for me. Music has the power to completely shift emotions, which can have a direct impact on circumstances. It’s a powerful force. Pet Sounds, Revolver, Bruce Springsteen Live, and Joni Mitchell’s Blue are never far from my stylus.

Last question. What advice would you have for other artists? How do they stay afloat in
a world that seems to be so abhorrent to creatives?

Another deep question. It’s not easy to do this for a living, but it brings such joy and fulfilment. And during the pandemic I got a great sense of what my music meant to other people, which gave me more sense of purpose and energy than anything. It takes some time to build a career in music, but once you do that I do believe it’s possible to stay afloat and even thrive. I totally reject the notion that artists have to starve. At least not forever. I think the main thing is, you really need to love this work and this job. I had to change my relationship to “work” and how I view it. I’ve fought for this career and have foregone many things to hold onto this dream. So the fact that I’m usually working six to seven days a week doesn’t bother me. Because most of that time is being spent making music, connecting to music lovers, talking about music or sharing my creations with the world. That’s not the worst way to spend a life. It’s also given me the best opportunity to see the world with my wife and daughter. I’m so lucky they are along for the journey.

I don’t take anything for granted, and we’re always making sure we’re ready for the next thing. As online concerts and income there starts to dry up, we’re starting to really focus on re-booking my tour schedule. I know that nothing is assured here and that I need to work hard for everything I receive. But I’m fine with that. I also feel like a steady flow of writing and recording is really necessary these days. Lucky for me, I really love writing and recording. 

I think gratitude is vital for success in all areas of life, along with the clear visualization of goals. After that, I think it’s crucial to be fearless about creating and releasing your art because there are always going to be some people who don’t like it. That goes with the territory. But you’re also going to have lots of people that love it. After all of that gratitude and visualization, it’s vital to do the work and make it happen. That’s the only way I know how to do this.

Interested in learning more about Jesse Terry? Check out the link below:

Dig this interview? Check out the full archives of Vinyl Writer Interviews, by Andrew Daly, here:

Published by Andrew Daly

Since he was a young child growing up on Long Island, NY, Andrew has always loved writing and collecting physical music. Present-day, Andrew is proud to share his love of music with the world through his writing, and the result is nothing short of beautiful: articles and interviews written by a music addict for fellow music addicts. Andrew lives on Long Island and works as a Horticultural Operations Manager by day and runs the Vinyl Writer Music website by night.

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