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Meet Jay Psaros of Jay Psaros Singer/Songwriter

Today we’d like to introduce you to Jay Psaros.

Thanks for sharing your story with us Jay. So, let’s start at the beginning and we can move on from there.
Well, the brief long version would go as follows: I’ve always had an interest in music. What started as tinkering around on guitar and piano as a young kid eventually turned into a full fascination with music in high school. Through high school and several years after, I was playing in bands as well as playing the role as “The Minstrel” at Boston’s (since closed) famed dinner theater Medieval Manor.

Throughout this time, I began taking an interest in writing, recording and making albums. During this transition, I was living in Vermont commuting between Burlington and Boston picking up gigs along the way throughout the region. New England has a robust music scene and I found music served a great vessel for not only creativity but for making friends and developing lasting relationships along the way.

After several years of scurrying about the region, I decided to relocate to Boston where I wanted to apply to music school and start a career as a Singer/Songwriter. It came as a big hit when I wasn’t accepted to music school. At this time, I was working more or less professionally as a musician but viewed music school as a turning point which would help propel me to where I wanted to go. As with so many people in a creative field, art is something that they are pulled to do, that they would be doing no matter what circumstances lay ahead of them. I felt the same for myself in regards to music. Still working odd jobs and as well as various music gigs, I decided to start making my first album.

This was a process I fell in love with. I loved the idea of crafting a song from nothing, and beginning to build its recorded vision, one microphone, sound, idea and cut at a time. I knew this was something I wanted to work hard at being surrounded by. Creative people in creative environments making musical projects. Since that wonderful time period of discovery, I’ve really just kept exploring and never looked back. I’ve had the great privilege to create several albums, of my own as well as producing for others. I’ve been blessed to have shared the stage with some of the country’s most prominent acts ranging from Boz Scaggs to Ziggy Marley.

I also own and operate a small “record label” which provided gig opportunities to local artists, produces video and photo content for musicians, as well as providing insights to establishments looking to develop a music program. I’m happy in that I am surrounded by creative people, doing creative projects and that my income does come from music-related endeavors. I’m thrilled to be in a position to keep making and performing music. Of course, the challenges change, setbacks occur many expectations go unmet.

However, I keep using the past to reference lessons that often seem, cliche although truly universal.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Ha! Well, I think anyone trying to create something whether it will be a business or an artistic project will all have their fair share of challenges. I need to remind myself of how fortunate I am to be doing what I am doing. There are people out there that have it far worse than I do… and often my trials and tribulations, when compared, feel dull to what many people go through in life and career. That being said, in music, there are constant challenges.

The music business is one of the most challenging career paths. The record industry has been in collapse and large streaming platforms (although helpful to a large degree) have put record sales at all time lows. It’s a great but scary time to be working as an independent artist. Of course, I’ve had my pivotal challenges but to me, the most challenging aspect is nature of a musicians schedule. We are constantly communicating with a large variety of people with a large variety of schedules, under a large variety of circumstances. Musicians are largely a community of the self-employed.

Because of this, things are constantly in flux as we, as “independent contractors” are always working our schedules to fit our client’s needs, which can vary drastically from a wedding ceremony to a late night party at a club. This inconsistent schedule is perhaps equally as freeing as it is challenging. It’s a lot of juggling but when you get in the flow, it feels like a really good place to be!

Jay Psaros Singer/Songwriter – what should we know? What do you guys do best? What sets you apart from the competition?
I primarily work as a Singer/Songwriter. This encompasses many different elements within itself. Some nights, I’m performing original music for crowds that come to see, well, original music. Other nights I’m paid to provide atmosphere and simply play and sing various covers to create a vibe. Many times, it can be a mix of the two. I love writing songs, but in regards to work and a career, I believe that having your own original content leaves room for an unlimited ceiling.

Gigging to play cover music at weddings and restaurants etc is certainly a great way to make a living as a musician although there is somewhat a cap on what you can generate for income that way. Being connected to original material of your own as well as others offers not only an immediate stream of extra income but provides a potential for greater success. Outside of the performing and songwriting aspect, I do several other things within the music industry.

Several years ago I created PB and Jay Records. Initially, I had the idea to create a traditional record label, in a sense but given the changing landscape and the local market, I eventually found a niche in working with singer-songwriters, creating albums with them as well as great video/audio content. Developing the content for a handful of singer-songwriters eventually left me with access to an “in-house” body of work. Gigs of my own eventually turned into booking and consulting positions helping businesses develop live music programs to suit their needs.

Over the past several years our clients have included The Boston Harbor Hotel, Bertucci’s, The Envoy Hotel, The Burlington Marriott and several other locations big and small. At our peak season, we book upwards of 180 acts per month, primarily in the singer/songwriter genre. I’ve found this to be a very rewarding process as providing an opportunity for others has helped forged some wonderful relationships within the community. It feels good to be able to get other songwriters like myself paying gigs that help them support their being and their art.

As a company, this is perhaps what I’m most proud of. In terms of what sets me apart from others, it’s hard to say. There are so many creative people out there doing similar things and I’d hate to think that any “one thing” I’m doing puts me “apart” from my peers. I do, however, think that I have a great network and deep insight into the local singer/songwriter scene as I find myself on “both sides of the fence.” I often get asked from booking agents who is doing what, and from singer/songwriters what booking agents could help them with certain gigs or what not. It’s good middle place to be in!

What is “success” or “successful” for you?
Success to me has always been a pretty simple bottom line, which is to support myself from what I love to do. There are times when I feel close to this success and other times when I feel far away. There are times when I have a great run of shows. Where I’m playing my music to good audiences who are there to appreciate and admire live original music.

Other times, if shows are slow it can feel like all I’m doing is booking for a few venues and playing gigs where people aren’t primarily there for the music. I think that perhaps my ultimate success would be to make a comfortable living solely off of my original material for a substantial amount of time. In many regards, I feel I’ve met some of my personal criteria in that I am making a living from the music industry.

I will continue to strive for my ultimate success, which is to make a living solely off of my original material.

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