Jesse Terry’s No Rules Zone

Traveling troubadour Jesse Terry talks with Pollstar about how he has no rules when it comes to songwriting.

As a young artist, Terry would fit right in with the songwriters of the 1960s and ’70s.  Listening to his music, it’s easy to imagine hearing his songs on the radio in between cuts by Bob Dylan, James Taylor, Jackson Browne and Joni Mitchell.

But these days artists can’t wait for radio or for record label A&R agents to “discover” them.  And Terry has stepped up to the challenge, embracing a DIY lifestyle that includes him and his wife Jess driving across the country, conducting business and playing gigs. 

Pollstar caught up with the Berklee College Of Music grad as he and his wife were spending a couple of days off visiting friends in Newark, Ohio, as well as using the down time to work on new material. A friendly, down-to-earth man, Terry talked about his career, his new album Stay Here With Me, his musical heroes and how to make a marriage work when you and your spouse are on an endless road trip together.

Photo: Jess Terry
Bluebird Cafe in Nashville, Tenn.

The bio on your website says “the road is home” for you and your wife, Jess.  Do you have a home base, if only for your mail?

My mail is going to Arizona for now.  We’ve been on the road since June.  This is the second time we’ve done this crazy kind of road trip.  There’s no full-time home base at the moment.

You’ve opened for many established artists such as Paula Cole, Darrell Scott and Marty Balin.  Do you think your music is for all ages or do you feel that it’s for the more mature music fans, ones who have lived a while and have experienced life’s ups and downs?

I see a lot of different ages at my shows.  I think I’m in the mid-20s and up in demographics, with folks who like lyrical music.  I think that tends to attract a slightly older crowd.  A lot of my heroes are older.  I’m not scared by that.

Who are your heroes?

Jackson Browne, Neil Young, James Taylor, Levon Helm.  I do love Ryan Adams and Jason Isbell … a lot of my peers, a lot of the folks I play with.  For me it starts with those classic singer/songwriters of the ’70s and late ’60s, and The Beatles.  That’s what I was raised on.

Many of the artists you mentioned emerged during a time when singer/songwriters were all over the radio.  Do you think it’s more difficult now for an artist such as yourself to present new music and build a career?

Yes and no.  I think it’s easier to be able to make a living. I think it may be harder to make a huge living because … there are so many more artists these days and I think … venues and audiences may be a little smaller for most people out there. But it’s larger because there are so many artists.

My dad was an artist.  If he didn’t get a record deal, he couldn’t make a living. It’s exciting that I can make a living as an indie artist, book my own shows, do a lot of my own promotion, sell my CDs and fund my records.  Those were things that weren’t options for people 20, 30 years ago.

I think the attention span was longer. … Nowadays you have to have content constantly coming out and constantly be touring. … Even if you’re giving away a free download in your monthly newsletter, you really have to be out there. … Giving away free content may be a little different than the glory days of the major labels.

Is all your business – CDs, booking, merch – self-contained and handled by you and your wife?

It is.  I have a wonderful lawyer and wonderful reps at SESAC and lots of great friends in the business.  But as far as an official booking agent, I have folks who are helping me in the U.K. and Europe.  As far as the States go, we’re pretty much a two-person show right now.

We’re pretty busy. It’s amazing. We got to tour Europe this year.  We got to spend so much time together, which we love. … It’s been a great thing, a great chapter.

Working together, traveling together, spending more time together than many couples experience during the first few years – do you have any advice on how to make a marriage work?

Luckily we love each other.  We have a lot of respect for each other. … There are so many things I have learned over the course of our marriage.  We’ve been on the road together for close to two years. That’s like 24/7 being together.  So you learn a lot. It’s almost like a condensed marriage, almost like you’ve been married for 10 years. 

I’ve learned to listen.  I’ve learned to breathe if I’m frustrated … and think about what I’m going to say before I say it. …  [She says], “Make time.” This is an endless job, especially if you don’t have a booking agent or a manager.  I have an amazing publicist, Mike Farley (Michael J. Media Group), who has done so much for me.  He’s worked three records for me.  So many blessings have come in because of me working with Mike.  He’s a fantastic guy.

Even so, at the end of the day … there are still a million other shows to book and a million other emails to answer.  I’ve learned I have to shut it down for at least an hour or two and totally devote that time to my wife.  We’re always together but there’s a big difference between working for 14 hours next to each other, and taking your wife out for frozen yogurt or a movie.  It’s the little things. … She’s not very high maintenance.  She just wants a coffee date, a bagel and my phone off.

Whose idea was it to embark on what appears to be a perpetual road trip?

It was my idea at first.  We met in the South Pacific in 2010.  She’s from New Zealand.  I booked this tour, our very first tour when we were in Australia.  I had no idea what I was getting into.  I had to sell a few guitars to make that first tour work.  I continued to tour and she got real jobs … in New York City [as well as in] in Nashville.  Our time apart became too much for us.  She called me one day and asked if she could quit her job and move back into the car.  I thought about it for a few minutes and said, “Absolutely.”

We’re still trying to figure out how to do that. I’m really lucky that I can make a living and keep us afloat but it definitely comes with its share of financial success and it’s not easy to keep it going.  But I have a lot of faith that it will keep on growing.

Any kids?

Not yet, but that’s in the plans.  The goal right now is to play and get as far as we can, then start a family.  At the same time I don’t buy into that whole concept that once you have kids, have a family, that it’s all over and you have to play the local tavern every Saturday night.  I’m sure they’ll come out with a hybrid Winnebago at some point … I’m sure I can fit a couple of kids and a couple of dogs in there. Jess and I are OK that our life is unconventional.

It sounds as if you and Jess have seen more of America than most of us see in our entire lives.

Yeah. … I went to Berklee College Of Music and I got a publishing deal two months out of college, in Nashville, which was really a dream come true.  I was pretty much in Nashville for the majority of five years straight. I wrote five days a week and I didn’t see a lot of the country.  Then touring, camping on the California coast, seeing the Grand Canyon for the first time … we really try to make it an adventure.  It’s not necessarily a vacation but if there’s a chance to drive through Yosemite, we drive through Yosemite.  We make every effort to enjoy it and take in those amazing things.

About spending your Nashville days writing five days a week – at that time were you writing for yourself or for other artists?

I had the publishing deal for five years.  I always wrote for myself as an artist, but I did give it my all to write for other artists and I focused on that for at least the first two years. … almost to a point where it was negative because I was maybe chasing stuff that wasn’t me.

I learned over the years that I needed to be 100 percent who I was, and the money and the other things would … always come to me after I’d written from a place of truth and not a place like, “Let me get a big old cut by Kenny Chesney.”  I’ve never had any success with that kind of mindset.  And I haven’t had that mindset for many years.

If we can get a peek into a songwriter’s life, how do you pitch a song to another artist?

There are a lot of different ways that can happen.  There are song pluggers for every major publisher and some songwriters even hire their own independent song plugger. … It seems to me [these days] that most cuts are secured by writing with the artist or having some connection to the artist, whether it’s through a producer or through their publishing company. It’s become pretty political, I think. … I do think some amazing songs get cut and I would love to work on that in the future.  Most of my success, lately, has come through film, TV and commercial placements. Placements I’ve gotten from the last record were CW’s “Hart Of Dixie,” … Lufthansa Airlines, [and] PBS’ “Roadtrip Nation.” …

“Hart Of Dixie” was awesome.  They played 3:30 seconds of a song.  The show got picked up again, it will go into reruns and Netflix and that’s really cool and great exposure. [There are] other placements that allow [me] to continue and make records.  That’s exciting in a whole other way.

Are you able to mentally divorce yourself from the business of your career so you can concentrate on songwriting and performing?  Or are there times when you’re trying to write a song but end up thinking about the balance sheet or closing a deal?

I never think of that.  I’ve done this for a while and I think … reading too many articles about what a film/TV supervisor is looking for – I think that kind of thinking can be dangerous. It’s chasing a trend and by the time you’re done with that record that trend might be over. You need to go with your strengths and with what you love.  That’s why there is pedal steel on the record.  I’ve been advised in the past that pedal steel can color everything as quote/unquote “country.”  Even though pedal steel has been used in a million recordings, including [Neil Young’s] “Heart Of Gold” and other beautiful recordings. … It’s one of my favorite instruments. … I think of myself as an artist first.  I do exactly what I do on a record and then see where it fits after that.  That’s my philosophy.

What is the creative process like for you?  Do you begin with a lyric, a melody, or a chorus?

There are no rules for me.  I usually have a whole bunch of titles written down and those become songs.  I look at those titles when I have a great melody.  I tend to write a lot in gibberish and sometimes vowel sounds become a hook.  I try to keep that very open and not have the editor going on while writing a song. I think that’s very important.

I don’t have a certain rule about how I do things except that … I can’t remember writing lyrics for a whole song before [writing the] melody.  I feel like the lyrics and the melody have to be a perfect marriage.  I can’t imagine the lyrics coming first without that melody. I’m not sure I can capture magic by setting lyrics to music after the fact.  That melody, for me, dictates so much what that song is about, where it fits.

And sometimes a poem can become a lyric.  Jimmy Webb’s great song “The Moon Is A Harsh Mistress” almost reads like a poem.

Can you only write when inspired, or can you say, “At 3 o’clock I’m going to write a song.”

Sometimes the inspiration will come after you have sat down, even if when you first sat down you had no inspiration.  Sometimes the guitar, the music and melody can give you inspiration.  I think if you’re a writer you need to write and sit down to work, just like anybody else going to work.

Regarding writing plus running the business of making music, can you still play and sing merely for the joy of making music? 

I shouldn’t say it’s never [like] work.  It’s work to drive, to book, to promote.  For me, it’s never work to play guitar and sing.  That’s what keeps me going.  There are a lot of other jobs that I could have picked that were sure things and paid better salaries.  If singing songs and playing guitar ever felt like work, I don’t think I’d do it anymore.  But I can’t imagine that ever happening.

Let’s talk about the future.  Now that you’ve released your third album, Stay Here With Me, how far are you into creating the next LP?

I’m just starting to get things together.  I have so many ideas for records I want to make.  I was in a rock ’n’ roll band while in college.  They’re still dear friends.  They live in this house in Los Angeles. It’s all wired, they have a great studio setup.  I’d love to make a record with my old buddies and rehearse like a band. It really reminds me of Neil Young’s Harvest.  Those guys are geared more towards Tom Petty and Bruce Springsteen. I’d love to do a project for them.  I definitely want to continue working with my producer, Neilson Hubbard.  He’s been unbelievable for me.  I’d love to do an acoustic record, maybe like a trio record.  There are so many different things, I think the songs will dictate it.  Hopefully, I will be able to make a couple of records in the next year or so.

Are most of your performances solo gigs, or do you have a backing band?

About 90 percent of my gigs are solo gigs.  I like to think of myself as a troubadour.  I’m traveling around playing to folks all over with just an acoustic guitar, telling stories and singing songs.  I have an amazing band in New York City and I really treasure those full-band shows in the city. … It does happen sometimes but I haven’t gotten to the point where I can squeeze the whole band into a van.

You have a full band on your albums – is it a challenge to take those songs from the album and strip them down for solo shows?

Not at all.  They were all created from the acoustic guitar with the exception of one song on the new record that I wrote with a piano player – Angela Kaset.  So bringing them back to the acoustic is usually no problem at all.  That is part of the reason I would like to make an acoustic record, a stripped down record.  Something that sounds a bit more like my traveling, solo-acoustic shows.  I think a lot of my fans have asked for that and I want to give it to them. I think that’s a cool thing. If you can keep an audience engaged for two sets with just a guitar, vocals, stories and songs … that’s a high compliment.

Were you the one in high school who brought a guitar to parties and played?

I wish.  I would have had a lot more girlfriends.  I was a fine artist in high school.  I did a lot of singing but my parents were musicians and I think I rebelled against that as long as I could.  I didn’t pick up the guitar and writing songs until I was almost 19 years old. … I always loved music. It was always the thing that got me through … comforted me … probably saved my life.  But until I actually wrote a song I didn’t get bit by the bug.  After I was bitten I quit art school and that was it for me.

So what caused you to write that first song?

I’m not sure.  I had an injury. I think I had a broken leg … something serious.  My mom lent me her old Yamaha guitar.  I started playing and learning James Taylor songs and Beatles songs … and before I knew it I wanted to create something. After writing that first song … people were like, “It’s not so bad.” It was an incredible feeling of expression and healing.  I realized I absolutely needed it.

Did you write that song strictly for yourself or were you already thinking about entertaining people?

It was for myself and [songwriting] definitely heals me and keeps me sane.  But without the interaction from other people and without the feedback from other people and the connection [with them] there wouldn’t be any allure to it for me.  Just sitting in my bedroom and writing songs, that wouldn’t do it for me. That’s why I’m out on the road all the time, playing for folks and talking to every person I can meet, trying to have some connection with them and make some kind of impact on their lives.

What advice can you offer someone who’s trying to write their first song and is thinking about making music a career?

I would say that, just like when you fall in love, you know if you need it.  If you don’t need it, I don’t think it’s the job for someone.  I’m not saying that to discourage anybody.  If they need it they actually have to go after it, stay humble and strive to get better.  And keep your overhead very, very low [laughs].  Don’t get into debt like I did.  Luckily I’m good now and am on the right track.  But to be able to tour, especially in the beginning stages, you need extremely low overhead.

I’m in the same place I was 10 years ago. I’m always striving to get better.  Like Steve Martin says, “Be so good they can’t ignore you.” … I think people will take notice if what you are doing is undeniably great.

“I learned over the years that I needed to be 100 percent who I was, and the money and the other things would … always come to me after I’d written from a place of truth …”

Upcoming shows for Jesse Terry:

Jan. 24 – Port Clinton, Ohio, The Listening Room
Jan. 25 – Bay Viullage, Ohio, House Concert
Jan. 26 – Pittsburgh, Pa., House Concert
Jan. 30 – Greenwich, Conn., Famous Greek Kitchen
Jan. 31 – Clinton, Conn., Chamard Vineyards
Feb. 1 – Barto, Pa., Landhaven Bed & Breakfast
Feb. 6 – Greenwich, Conn., Famous Greek Kitchen
Feb. 7 – Guilford, Conn., Ballou’s Wine Bar
Feb. 8 – Cortlandt Manor, NY  The Music Room
Feb. 11 – Boston, Mass., The Red Room @ Cafe 939
Feb. 14 – Newtown Square, Pa., Burlap And Bean
Feb. 15 – Chester Springs, Pa., The Barn At Fellowship Concerts
Feb. 20 – Greenwich, Conn., Famous Greek Kitchen 
Feb. 21 – New Haven, Conn., House Concert
Feb. 22 – Seaford, N.Y., The Song Box
Feb. 28 – Guilford, Conn., Ballou’s Wine Bar
March 1 – Stowe, Vt., Stowe Mountain Lodge
March 5 – New York, N.Y., Rockwood Music Hall
March 6 – Greenwich, Conn., Famous Greek Kitchen
March 7 – Clinton, Conn., Chamard Vineyards
March 8 – Yorktown Heights, N.Y., House Concert
March 13 – Greenwich, Conn., Famous Greek Kitchen
March 14 – Manhasset, N.Y., The Unitarian Universalist Congregation at Shelter Rock
March 15 – Tarrytown, N.Y., Tarrytown Tunes
March 17 – Dataw Island, S.C., Folk At The Cannery
March 21 – St. Petersburg, Fla., The Hideaway Café
March 22 – Bonita Springs, Fla., Laughing Parrot Tiki Hut
March 28 – Buford, Ga., House Concert
March 29 – Cumming, GA  Sweetwater Café
April 5 – St. Petersburg, Fla., Drifting Under The Stars Concert Series
April 12 – Coral Springs, Fla., House Concert
May 2 – Fall River, Mass., Narrows Center For The Arts (Appearing with Amy Black & the Red Clay Rascals)
May 3 – Blackstone, Mass., House Concert
May 9 – Austin, Texas, Ham Jam Concerts
May 18 – Austin, Texas, Private Function
June 5 – San Francisco, Calif., Soma Loft Concert
June 8 – Summit, Ore., House Concert
June 9 – San Francisco, Calif., Osteria
June 13 – Canberra, Australia, The Clubhouse @ Hyatt Hotel
June 20 – Saratoga, Calif., Blue Rock Shoot
June 21 – Berkeley, Calif., House Concert
July 24 – Bridgton, Maine, Noble House Inn
July 26 – Yorktown Heights, N.Y., House Concert
July 31 – Quechee, Vt., Concert On The Green
Aug. 8 – Blacksburg, Va., House Concert
Aug. 9 – Virginia Beach, Va., Bakers On The Bay House Concert
Aug. 22 – Raymond, Ohio, Bokes Creek Winery
Aug. 23 – Hebron, Ohio, House Concert
Aug. 24 – Avon Lake, Ohio, Barnful Of T unes
Oct. 17 – Lake Schuyler Lake, N.Y., Andrew’s Cot & Crackers
Oct. 18 – Scorpio Center, N.Y., Merrifield Cocnerts
Nov. 22 – Falls Church, Va., The Stone Room
Dec. 13 – Summit, N.J., House Concert

Jesse Terry will also appear as an “invited writer” at the International Listening Room Retreats on Inisheer Island, Ireland Oct. 5-12.

For more information about Jesse Terry, please visit