Leave Maine, get big: Local musicians talk about the triumphs and pitfalls of hitting the road

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“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.” — Mark Twain

So many immensely talented and nationally loved acts have spawned out of Portland, but seldom do they stick around. From Lady Lamb and Spencer Albee, to Spose and the Mallet Brothers Band, the city and its supportive, vibrant music scene have served as the foundation for many local acts that eventually blew up across the country.

However it can be argued that those artists exploded into success only after they left our slow burning but bright flame of a state and set out for new audiences and artistic challenges. Musicians who have started with humble Maine roots are now vouching for the importance of travel for others seeking a full-time musical career. If you want to play for the masses, you need to stand in front of them.

“There are no bands that are breaking in Maine,” said Jay Bragg, a solo country artist that got his start in Portland. You may know him as one half of the former country band North of Nashville, that took home the 2015 New England Music Award for “Country Act of the Year.” “There are famous musicians that have lived in Maine, but the industry doesn’t pay attention to Maine. It’s a great place to live, hone your craft and raise a family, but if you really want to make music your career, you really have to think way beyond Maine.”

BIGGER DREAMS | Jay Bragg considers himself a Mainer and still plays in Portland often, but he moved to Nashville to pursue greater country music ambitions.

Leaving Portland promotes growth

With the goal of turning his passion for performance and knack for writing into a full-fledged career, Bragg moved to Portland full-time to pursue music in 2003. Impressed by the level of talent in the city, Bragg started making connections and performing the bar-room circuit weekly, like many others do. He was quickly able to trade his landscaping job for nights on stage with his guitar and went through two bands: Cross Fire Inferno and This Way.

“It was like a domino effect,” said Bragg. “Maine was a great training ground.”

Eventually, he formed and focused a new outfit, a duo called North of Nashville, which took Bragg to all the bigger venues, theatre shows, festivals and openers for big country acts in the Portland area. He had found his voice, and sharpened his musical message. But after years of performing for the same faces, Bragg felt like he had reached the ceiling, and there was no where left for him to grow as an artist. It was time to break out of his comfort zone.

“I left Portland because there was nothing left for me there,” said Bragg on moving to Nashville, a Mecca for country music. “I felt like I had achieved everything I could achieve there. The market in Portland is so small.”   

Bragg loves Portland, and is grateful for the incredible and impressive scene that launched him. He said it gave him the foundation to thrive in a bigger city. But it was only after he took the plunge and moved to Nashville that he started to get considerably more famous. For Bragg, marketing himself as a songwriter from Nashville carried more weight than as a songwriter from Portland.

“It was almost like I had to leave for people to notice what I was doing,” said Bragg. “I got so frustrated working so hard, and trying to be accepted by the mainstream of Maine. Moving out of Maine was a decision I had to make. I’m taken more seriously around the country now.”

Now Bragg isn’t discounting the level of talent in Portland, he’s simply suggesting the great local bands that have found their voice should do what he did: hit the road. Otherwise they risk being, what he called, “big fish in a small pond.”

“I feel like Portland is, for the size city that it is, it’s pretty pretentious in terms of music,” said Bragg. “You have a lot of angry and frustrated people out there. That kind of attitude is unique to Portland.”

Some musicians believe that although it’s great for Portland to host so much varied talent, the already shrinking music market is becoming oversaturated with choices, making it extremely difficult for bands both new and established to draw large, sustainable crowds. While supportive, the scene in Portland can be suffocating for some artists, and hidden gems of original acts are being drowned out by cover shows, battle nights, and to put it bluntly, uninteresting and unrefined original shows.

Being good just doesn’t cover it anymore. You have to be exceptional, especially if you’re going to go on tour.  

“Not everybody should be a songwriter; there are some people that should stick to covers, because their original stuff sucks,” said Bragg. “If you’re awesome, you’re going to do just fine and draw an audience. But you need to hone your craft, otherwise you’ll be chewed up and spit out.”

With Portland’s population of about 65,000, how many of those consumers are really going to go out at night to see a middling original band, when there are myriad other entertainment options, from better local bands, to legendary acts like Bob Dylan or Tommy Emmanuel, to even Netflix at home, which is just easier and cheaper?  

The answer is: not many.

If original musicians want their fan base to grow with different faces, and support themselves with ticket sales, they’ve got to find the fans themselves, instead of settling down and expecting them to flock to Portland.

Starting your first tour

Sam Chandler has been studying and practicing music for 12 years now. He studied at University of Southern Maine, and has been a fixture of the music scene for seven years, originally with a band called Theodore Treehouse. Now he plays piano for a new project called The Up and Ups, a band with an explicit goal to leave Portland one day. For this new band, Portland will serve as a nice home base to write and record, but they’ll focus the majority of their stage time elsewhere.

“Portland is a safe place for a musician to learn, but it’s important to take the next step,” said Chandler. “I’ve never really enjoyed oversaturating Portland. I like to play there every once in awhile. But I get this feeling, every show, it’s like I’m playing for all the other Portland musicians. And while I love them all, and that we all support each other, I want to reach beyond that. I want to play for regular people, and I want to be played inside people’s homes. I don’t want my work to be a Portland secret.”

He continued, with a joke: “It’s like there’s the same $20,000 that just circulates around the same Portland musicians in the scene.”  

So should more local acts travel more, like some of their more renowned predecessors?

Well, Chandler is. He’s currently in the middle of organizing what he called “a big experiment,” his first ever major tour. Nothing’s set in stone yet, but Chicago and Philadelphia are on his radar, not just as places to tour, but potential places to live. In the past, Chandler’s reason for not touring is similar to that of many other musicians: a little thing called life got in the way. Getting every band member, with their individual lives and schedules, on the same page is the first daunting, tour-related obstacle.

Before a musician goes on tour, there are compromises to consider for the sake of going on tour. Chandler and his bandmates from the Up and Ups pondered this question: What am I going to give up for the sake of the band? The dream of going to grad school? Starting a family? Settling down and being financial stable?

“You have to ask these questions and take risks,” said Chandler. “I’m well aware that this first tour is going to be lots of gigs with some people and some with barely any people. When I get home, I’ll be financially worse off, than when I left. But I’ve accepted that.”

Chandler said he’s not worried about the trip, but rather, expectant and mentally prepared for certain obstacles.

“Touring is not for everybody,” said Chandler. “...it’s a lifestyle.”

The Hardships on the Road

Indeed touring doesn’t come without hardships, anxieties, trade-offs, obstacles, dangers and financial hurdles. Many bands that tour out of Portland are lucky to break even by the end of the journey. Some get robbed on the road. Some get stranded. Some are stuck playing to empty rooms in unfriendly towns. Almost all are left sleeping in dingy hotels or cramped vehicles. It can be a discouraging, sketchy, sleepless, back-breaking affair. It’s no wonder that Will Bradford, the local veteran songwriter and frontman of the anti-genre band SeepeopleS, said that often times a band’s first tour is their last.

“It’s tough out there,” said Bradford during a phone interview on his way to a gig in Georgia. “The first tour, can really be a wake-up call for bands. You really have to approach it with an open mind. Shit will happen.”

“It can be a real drag,” said Jay Bragg. “I’ve had guys on the band that quit, they just didn't want to be on the road anymore, they got anxiety about it. It’s a grind.”

Bradford’s words of caution might echo louder, when you consider his exhaustive music experience. Both as a solo singer/songwriter and as a member of his wild-n-eclectic alternative pop/rock band SeepeopleS, Bradford has 20 years of work, thousands of road miles and days of stage time under his belt. Throughout his career, Bradford has had plenty of low moments on the road, but thankfully now enjoys the perks of a booking agent, and enough love scattered throughout the country to organize successful tours.

“It’s a beautiful thing to have, friends and connections in place in a city that’s not your home,” said Bradford.

Later in the interview he said, “It’s really tough these days. I feel bad for bands that are just trying these days. It’s harder than it used to be.”

It’s harder than ever for musicians to make a buck, and further their craft free of stress, but it’s simultaneously easier than ever to get their work out there thanks to the Internet and new technologies. Back in the day getting an album recorded and distributed was the best way for a musician to support themselves, but now the Internet has made the process easier, but with less actual payoff. From abysmally bad to superbly excellent, you can find music everywhere, leaving musicians in the industry wondering how to make an impact, stay true to their originality and also make some dough. Think how easy it is to upload to YouTube, BandCamp or Facebook, and market the shit out of a track or compilation, but how hard it is to reap any actual benefits or money from the social media interactions. Views and likes are nice, but they don't exactly translate to ticket sales. True, long-lasting fans and connections are forged on the road.

Take Bradford for instance; he didn’t get where he is today, easily. Before his meaningful musical connections were solidified, he had to put his 10,000 hours in, refining his sound, testing what works and performing on stages and in festivals in every state in America, except Alaska, Hawaii and “one of the Dakotas.”

“One of the most important things for me, is that you get to go and get new ears, a new audience,” said Bradford. “That really makes you understand your music.”

Bradford’s advice to those looking to start their own tour? Just go out and do it.

“Trial by fire,” said Bradford. “You’ll have more anxiety about never trying it.”

It seems that a fulfilling life and/or memorable experiences begin at the end of one’s comfort zone.

A Maine bluegrass band tours Europe

Coverstory Tricky Britches Dubrovnik

Which brings us to the Tricky Britches, a four-piece acoustic, bluegrass folk band. They're a testament to the notion of breaking out of one’s comfort zone. This band has the answer to the begging question: “How do you emerge into a new market when nobody knows who you are?”

This energetic band of vagabonds started in an unconventional way: They formed, came up with a band name and a first album as a means to busk around the country. They would embark on a DIY tour, before they made the slightest kind of name for themselves. That is, unless you count repeat shoppers at the local farmer’s market, who might remember their fiddles.

“Our motivations right out the gate were to travel,” said Tyler Lienhardt, who plays violin and sings for the band. “We completely bypassed the conventional route and managed to make it work. And it’s still working.”

So they packed their gear and instruments into a four-door sedan and hit the road without a clear set of destinations in mind. On that first tour, the Tricky Britches would end up playing in Kentucky, Tennessee, New Orleans, Texas, New Mexico and the Rocky Mountains, crashing with people they met on the street or in campgrounds and burning money as soon as it was earned. The cross-country trip was not only self-sustainable, but it served as free advertising for the band.

“Busking was still kind of a novelty to us,” said Lienhardt. “We were amazed that we were making money that way.”

Then the Tricky Britches returned to Maine, amped up from their adventures and successes on the road. They would play private parties, BBQ’s and weddings back here in Maine, while they saved up for their next travel experience. Then in the summer of 2010, they kicked it up a notch, and flew to Europe to tour in the same, “fly-by-the-seat-of-their-pants” style.

“At this point it started to become this feasible reality that we could turn this into a business,” said Lienhardt. “That trip was a huge learning experience.”

After arriving in Europe, the strategy was to roll into a new town, find the central square or park and jam like crazy, with posters and CD’s advertising who they were. They would continue with this confidently loud strategy as they snaked their way from Ireland, Scotland and England, to the Netherlands, Germany, Norway, Italy and eventually to Eastern Europe. With a method of playing intensely during a “power hour,” when foot traffic was at its highest, the Tricky Britches were able to organically book shows all over Europe.

“Eventually people would gravitate towards us,” said Lienhardt. “We would find a place to stay, or play that night, and sometime make money.”

Coverstory Tricky Britches London 2010

Lienhardt recounted some of his favorite memories from the Euro tour. After one gusto-packed power-hour in Venice, the Tricky Britches raised enough money in an hour to treat themselves to a lavish, three-course, five-star Italian dinner, right next to the canals.

“Meanwhile we’re like in ripped jeans and T-shirts,” recalled Lienhardt. “It was surreal to be a vagabond and treating ourselves to a fancy meal in Venice.”

Other highlights included being the house band for a concert in the medieval castle city of Dubrovnik, playing a folk festival in Norway and booking a full-fledged, paid tour through Ireland.

“The Irish love us,” said Lienhardt.

More recently, the Tricky Britches did the same thing in Hawaii. They started just playing on the beach or in coffee shops, and eventually fans and venue owners would take notice. Next thing they know, they’re getting their plane tickets paid for by the University of Honolulu.

“The whole island of Oahu knows who we are now,” said Lienhardt. “We can pretty much book any venue we want out there. But we had to just be there in person and play the music.”

The Tricky Britches are a living example of how a band can make it work on the road if they’ve got the genuine talent, patience and courage to give it a shot. Because of their travel experience, they’re better musicians, with a better understanding of how to work as a unit, deal with stress and adapt their play-style to a diverse crowd. They also walked away from their travels with an invaluable sense of self-efficiency.

“Touring does improve your skills in the sense that you’re completely focused on music,” said Lienhardt. “All of the other distractions of your real life are removed. It’s kind of mentally cleansing.”

The Tricky Britches are playing their internationally loved bluegrass tunes in Maine for the whole summer. Summers in Maine can be very profitable for fun bands with performance chops. But next year, they might go to Hawaii, or Europe, or “somewhere completely different.”

Not all good musicians tour

Now before the pitchforks get raised over this article, let’s consider a very ubiquitous reality: touring is not for everybody, and that’s okay.

In fact it’s important to mention, that every musician interviewed for this story feels that way. They only stress the importance of travel in a music career if you fall into at least two of these four categories: You’re actively trying to get more fans, you’re trying to get famous, you’re trying to test yourself in front of new crowds/situations or you’re trying to support yourself full time with music.

No one here is doubting how tough it is go on tour, or the fact that for some bands, with lower ambitions, it’s simply not worth the trouble. Some local bands, like the indie-rock outfit Johnny Cremains, or the stoner-rock band Murcielago, would love to tour, but are unable to make it a feasible, financially sustainable reality because of the demanding nature of their second life.

“Touring is not for everybody,” said Lienhardt from the Tricky Britches. “It’s only for people with a long-term mindset. Just doing a tour, by itself, is not worth it.”

“There’s a lot of bands in Maine that are super talented, that would do great all over the country, but for whatever reason, they would rather be a big fish in a small pond,” said Bragg. “I’m not going to say that that’s the wrong way, because it all depends on what you want to do.”

Perhaps Maine’s own “Sasquatch of Soul,” Lyle Divinsky explained it best.

“It’s all a matter of what you want to do and what you’re going for,” said Divinksy. “If you want to play original music in a sustainable band, touring is the thing that you need to do to open up markets. But if you like covers and playing in different outfits, you can definitely make money here in Maine, especially in the summer.”

Divinsky’s been localized a lot, and has been a constant fixture at the Portland House of Music. But he also has traveled quite a bit: from festivals in the Midwest, to the streets of New York City. In a way he’s got the best of both worlds, in terms of a music career: he’s able to fill venues close to home consistently, and travel a great deal as a new member of the highly successful, Denver-based funk band, the Motet.

Next year, Divinsky departs to Miami, Fla., where he’ll embark on a “Jam Cruise,” with 41 other bands. On the cruise ship, they’ll perform for guests as they journey to Ocho Rios, Jamaica. With all those creative people, playing music in an intimate, yet exotic setting, the Jam Cruise will be an inspiring and formative experience for Divinsky. He said he’s guaranteed to become a better musician because of it.

Coverstory LyleDivinksy PhotobyJeremyScott

“I’ve spent a lot of time in the local music market, I’m really excited to get out, and experience different scenes and different situations,” said Divinksy. “I’ll probably move soon, but I’ll still be coming back up to Maine, playing 10-15 shows a year. My family’s here, and there’s no better place in the world.”

You’ll find plenty of Portland-based musicians without any desire to leave the state because they love the community too much. Or they’re just content with writing, arranging, recording and performing for the same people. To a certain degree, one can sharpen their musical skills anywhere. For bands like the eight-year-old, new-timey Welterweight, who have a monthly residency at Blue and the Dogfish Bar and Grille in Portland, life on the road isn’t worth forsaking their families and full-time jobs. They don’t travel out of state and they hardly play past 11 p.m., a performance schedule completely in line with their ambitions.

“Yeah, we’re not actively trying to make this our profession,” said Doug Cowan, from Welterweight. “For us, the more comfortable we are, the better we play. And we strive to perform as good live as during our best rehearsal.”

Instead Welterweight members just enjoy the stability of living in one place, and having the opportunity to play their instruments in front of people.   

“We’re happy as a stay-at-home band,” said Cowan. “Bands grow up and settle down musically, and this is a good place to settle down. But we don’t want to be a Dad band, we want to be a cool Uncle band.”

Coverstory Welterweight

So who should risk-it-all for life on the road?

No one. Or everyone. It just depends on one’s level of ambition.

In the end, the only things that dictate whether a band or a musician should embark on a tour, are the size and intensity of their talent, career goals and wanderlust.

If you’re a musician with dreams of making it big, performing and recording full time, and having your original songs playing on radio shows from New York to Hawaii, breaking out of the bubble of local comfort is a necessity. No matter what the creative pursuit is, travel nurtures it and helps it flourish. Travel imbues a person with fresh perspectives, new skills and an interesting, far-from average life.

According to many musicians who have “made it,” touring (still) is a key to a musician's growth, popularity and success overall. It’s not the only key, but it’s a vital one.

Unless you’re perfectly content with working from your living room, lugging your gear through the same five to six venues, playing covers, performing for the same people, and attending the same annual festivals, it’s time to branch out of little ol’ Maine. If one’s art is actually worth the time, it could and should be appreciated anywhere.

Last modified onThursday, 02 June 2016 14:33