The Arts

After putting music career on hold early in his life, Riverhead developer goes back to his roots by forming rock band

In the late 1980s, Raymond Castronovo would bounce around from club to club in Manhattan with his friends Tom and Mike, performing a mix of rock ‘n’ roll with a punk flavor.

They called themselves, RayTomIx.

To this day, Mr. Castronovo says he enjoys bands like Green Day that harnessed some of that punk music he played back then in his early 20s.

Their band appeared destined for big things and Mr. Castronovo envisioned a career in music for himself. A few record labels expressed interest in having the band record for them, he said.

But life quickly took a different turn.

Mr. Castronovo’s wife was pregnant. They had married young and life was coming at them fast.

“Those Italians in Brooklyn did that,” he said with a laugh.

He thought what a career in music would be like — an industry with no guarantees — and how touring would conflict with raising a family.

He decided to put music on hold. In the back of his mind, he knew an opportunity would be there at some point in his life to turn back to his passion. When? He couldn’t say for sure.

His wife gave birth to a boy, the first of their two children, and Mr. Castronovo, who had quickly realized college wasn’t for him, shifted his focus to gaining real world experience in the construction industry. His father was a native of Sicily and had worked with a talented group of bricklayers who were more like artists, Mr. Castronovo recalled.

Developer Raymond Castronovo formed the band StreetWise. (Credit: Courtesy of StreetWise)

He landed a job at a big construction company and after grinding a few years, the owner approached him and offered to teach him how to run the business. His career took off from there and he went on to found his own construction business. For about 20 years, he’s had a satellite office in Riverhead, where’s he been active on a number of different projects and was a member of the Riverhead Business Improvement District. He currently has a pending development project downtown for a four-story building on McDermott Avenue that would replace the small home that was once his first office on the East End.

Now 55 and living in Laurel, Mr. Castronovo sees his time in the construction industry winding down, and in music winding up. He always kept up his guitar playing and he always focused on staying in good physical condition, knowing one day music could be a second career.

“I kept my mind stimulated, just because if the opportunity came, I wanted to give it everything I got,” he said.

That opportunity finally came in the last couple of years.

Mr. Castronovo had purchased a building on the corner of Second Street and Roanoke Avenue about seven years ago. He used the second floor for his office and the third floor featured a ballroom with a dance floor and disco lights. He decided to transform the space into a rehearsal studio.

He spent about a year and a half working on music, and reaching out to people in the industry to slowly work his way back up. He found a vocal instructor in Manhattan, Deric Rosenblatt, who had been teaching Broadway stars and other artists to help train him.

“I reached out to a couple major record companies and they welcomed me in and then I reached out to the owner of the [recording studio] Hit Factory [in Brooklyn],” he said.

After researching record companies, he realized he could be better off starting his own record company, which he called DayQuest Records. 

“I said, I’m going to be the first guy I sign up,” he said.

Mr. Castronovo performs at The Suffolk Theater in May. (Credit: Courtesy of StreetWise)

From there, he formed the band called StreetWise. As lead vocalist and guitarist, Mr. Castronovo leads the seven-member band that performs a variety of music. He pieced together a talented group of professional musicians, featuring Joe Martinez on bass, Heather Simon on backup vocals, Dave Keyed on keyboards, Seal Vellure on guitar, Carl Obrig, who lives in Calverton, on saxophone and Linda Mackley on drums.

Mr. Castronovo always had a natural ability with music, not only to play, but to write it as well.

“I never studied it, it just came natural,” he said.

He got to work writing and arranging songs, some of which had been in the works for several years, and others that he started from scratch. In 2021, he released his first album called “Crossing Bridges.” The album cover featured a black and white photo of the Brooklyn Bridge with the World Trade Center in the background.

“I grew up in Brooklyn and always looked at the Brooklyn Bridge,” he said.

A second EP released this year is called “The Other Side” with an album cover showing Manhattan on the other side of the bridge.

| See more on Instagram, Facebook |

StreetWise performed many of those songs Friday evening in Riverhead as the featured act for the latest Reflextions: Art in the Park event in Grangebel Park. His music can be found under StreetWise on streaming services like Spotify and Apple Music. In an interview Friday, Mr. Castronovo recounted his journey as he awaited his bandmates to arrive for a rehearsal ahead of the show.

“I want to make the world happy,” he said. “I want to share our music and our stories with the world and make it so this can be my next career and help out these musicians that are backing me up.”

When asked about the genre of their music, Mr. Castronovo says it can be hard to classify. He told one radio station he was going to invent his own genre.

“I said, I’m going to call our music, music stew,” he said, saying how songs draw on inspiration from different genres of music, from B.B. King, to Eric Clapton to The Rolling Stones.

In May, StreetWise performed at The Suffolk Theater as part of a benefit for the Leukemia & Lymphoma Society. He had been diagnosed with leukemia about 18 years ago, he said. The event raised about $42,000, he said.

Looking ahead, StreetWise plans to start performing more live shows. Mr. Castronovo still thinks about how things could have been different had he pursued music from the beginning.

“It would probably have been a struggle,” he said. “It worked to my advantage that I went this road. … It was a lot more lucrative than being a musician. … It’s a long shot to become a star. It is. It’s a lot of work and if that don’t work, later on in life, it becomes tougher.”