Growing up in Newmarket, making it to Nashville was always Steven Lee Olsen’s dream, and while others saw it as just a dream, he knew it could become a reality.
Now after 16 years writing hit songs for the likes of Keith Urban and Dallas Smith and collaborating with country music giants such as Garth Brooks and Rascal Flatts, Olsen is making another dream a reality. He’ll be making his official Grand Ole Opry debut in the Music City tonight (July 23).
The Grammy-nominated Newmarket native has more than 75 million streams and while it’s been a long journey to get here, he credits the support he received at a young age in the town that he still loves.
“I’ve been really into music from a really young age,” he said. “My mom was a singer and it was one of the things in school that kept me occupied and busy. I was always tapping on stuff and drumming. I wasn’t great at school, but music was something they could incentivize me with, they would let me play drums in the music room during recess if I could keep it together during class.”
When Olsen was about 18, he was working as a used car detailer at a dealership on Yonge Street in Newmarket. After three weeks, one of his co-workers caught wind that he sang and played guitar.
“Before you knew it, I brought my guitar into work and after my shift I was singing songs to her in the parking lot,” he said. “One of the top salesmen heard me, his name was Stephen Lawrence, and he called me into his office … I thought I was getting fired.”
As it turned out, Lawrence himself was a musician and he saw something in Olsen that made him eager to take him under his wing.
“He never had someone show him the way,” said Olsen. “It was sort of like the stars aligning because I owe so much of where I’m at now to that man.”
After that, Lawrence would become Olsen’s manager and buy him his first acoustic guitar, which he still has, and he found the closest (and cheapest) recording studio where the two would write and record a few songs.
“It was the first time I had any music of my own that was recorded, so it was a big deal because I was really doing it,” said Olsen. “We ended up putting together this small EP of songs and he would just make stuff happen and reach as far as he could to get me doing anything.”
The duo’s efforts didn’t go unnoticed, and Lawrence landed Olsen a chance to play in Halifax at the Canadian Country Music Awards new artist showcase about 18 years ago.
“He basically told me to call off work, and I never went back to work, and he picked me up and we drove to the CCMAs,” he said. “I’m sure my showcase was god-awful, but for whatever reason it showed enough promise to land me the opportunity to meet Ron Kitchener and Denny Carr of Open Road Records.”
Kitchener had a publishing company in Nashville, so after a few weeks back in Newmarket, Olsen got a call.
“We were invited to Nashville to write some songs,” said Olsen. “We packed our bags and drove to Music City. It was so exciting knowing every legend on the planet had been in Nashville. We were just two guys from Newmarket trying to make some stuff happen.”
Not long after arriving in Nashville, Olsen was offered a publishing deal.
“It’s never that easy for anybody, and granted, it was a horrible deal; I was making like $600 (Cdn.) a month living in the U.S.,” said Olsen. “The term starving artist definitely applied to me, but it got me to Nashville, so we took the deal.”
From there, Kitchener wanted to manage Olsen’s career, and given Lawrence’s penchant for doing what’s best, they agreed.
“He (Lawrence) never wanted anything from me, he just wanted me to succeed and get the shot he never had,” said Olsen. “So, we moved me here and I still talk to Steve every day.”
Olsen always knew if he could get to Nashville and learn to write songs, that he could make it in the country music industry.
“By nature of doing it and failing a ton of times, I ended up learning and that’s how I’ve been able to stay relevant as a songwriter,” he said. “I’ve been able to write these hits because I’ve stayed a student and I’m so hungry for the knowledge of songwriting so I can better my craft.”
Crediting his passion and love of songwriting for helping him make it, his life experiences have played a major role in him finding his voice as an artist.
“I’m a husband, I’m a father, I’m a brother, there’s a lot of things I put into my music now and it’s authentic,” he said. “I think people are connecting with the real side of me as a human. And, Newmarket is where I spent a lot of my time and it’s what I think about when I’m writing my nostalgic stuff. It’s Upper Canada Mall, it’s Bayview Park, I remember taking the bus up on Mulock when I was supposed to be in math class because I wanted to go buy licorice.”
Olsen said it’s a full circle moment with him making his Grand Ole Opry debut and he wants to use it as an opportunity to inspire others to take risks and shoot for their dreams regardless of where they grow up.
“The best thing I ever did was bet on myself,” he said. “You learn nothing from success, and everything from failure. It wasn’t easy, but I love staying connected to Newmarket because coming from a small town — I don’t think you can even call it a small town anymore — it shows that if you take the risk, you can chase your dreams. Whatever is consuming your mind, that is your purpose and you owe it to yourself to explore it and see how much it feeds your soul.”
With all the doubters throughout his life, and those who didn’t believe he’d even make it to Nashville, Olsen thinks it will make the moment he takes the stage at the Grand Ole Opry even sweeter.
“I realized later in life it was their own insecurities and limitations they put on themselves that made them think that,” he said. “A lot of people told me I couldn’t perform at the Grand Ole Opry, but my wife believed in me and lifted me up. I remember getting the call from my agent and I thought he was joking, and I got choked up. I have so many family members from Newmarket, Barrie and Bradford coming for the show. I couldn’t be more excited, and I’m going to try not to cry.”
