From the Major Leagues to the Big Leagues

Barry Zito AKA Drake Holloway has enjoyed a stellar life, with an unexpected transition. After a 15-year career playing Major League baseball, he went on to follow his lifelong dream of pursuing a music career; including graduating from Recording Connection in 2022. I sat down with him to discuss life, career, family, his music, and the program.

How did you first become interested in music?

I came from a musical family. My father was a road conductor [music conductor] for Nat King Cole back in the late 50s and 60s. My mother dropped out of UCLA to run off and sing with Nat King Cole, as part of this backup group called The Merry Young Souls. That’s where they met. So, it’s in my blood.

And how’d you decide to start pursuing music as an adult?

I was a professional athlete for 15 years, and I started playing guitar on the side when I was 21, which is a little older to come into an instrument. I learned Dave Mathew’s entire catalog like most people learning in that time. I learned John Mayer, Incubus, then got into jazz. It was important for me to learn the exact way to play things. My approach was to slowly work through all the music that I loved.

Can you explain this Barry/Drake name duality?

Barry Zito is associated with my baseball career. My father was coming up as an Italian in New York in the 40s as a piano player. He couldn’t get jobs with his immigrant-sounding last name, so he adopted the stage name, “Drake Holloway.” I have adopted it to keep these two worlds separate. I also use it as my producer name. It’s helped me foster a stronger music community.

Let’s hear a bit more about “Barry,” give us the rundown on your baseball career.

Like I said, I played for 15 years. I won a Cy Young Award my second year, which is the pinnacle award for a pitcher. I had the chance to be a part of a couple of World Series teams. I signed one of the biggest contracts ever given to a pitcher and ended up retiring in 2015.

That’s an insane run for an athletic career! Isn’t that about three times the average time span?

Definitely. They say the average career is about 3-5 years. In anything we do our best as long as we can. Sports is a little different because you can finish a successful career pretty young. There’s plenty of time to get into something new.

There’s something kind of audacious about transitioning from one career that millions of people dream of, to a second career that millions of people dream of.

“Audacious,” yea, I love that word. The thing is, people who don’t know me think, “Oh, this guy just decided to become a musician.” But the truth is I had a deep musical inheritance. I had been studying music for about 15 years and had a deep knowledge of music theory. I took music classes at Berklee and read every book there was on songwriting. Once I retired I wrote songs for three years on Music Row here in Nashville, before getting into production. It wasn’t, “What am I gonna do for the rest of my life? Why not music?” The truth is music was always my first love.

Can you tell us more about the transition?

I came to Nashville to play Triple A, which is one level under the major leagues. I didn’t really want to play in the Minor Leagues after playing in the Major Leagues for 15 years. But, it forced me to rediscover my love for the game before I retired. There was less pressure. While in Nashville a local newspaper did a story on me, and I said in it that, “I’d love to write songs in Nashville before I go back home to California.” The creative director of ASCAP, a guy named Robert Filhart, read that article and reached out to me the next night. He said, “I just read your article, I’d love to chat on the phone.” I sent him a few songs, we ended up talking and he asked me if I’d ever heard of Mike Reid. I hadn’t, but he explained that Mike was a four-time pro bowl NFL player in the 70s who’s now in the Songwriting Hall of Fame. He thought I could be the next Mike Reid. I guess he liked what I’d sent him, and he instantly believed in me. He took me under his wing, and put me in rooms with other emerging writers.

Do you see any benefits to pursuing music when you’re a bit older?

I think the benefit came from living life. I’ve had a lot of good experiences and a lot of bad experiences, which gives me a lot to draw from as a songwriter. Heartbreak and emotions like love and joy and grief don’t necessarily pertain to an age, but I do feel I have more to draw from than some younger folks.

What are you working on these days?

I have my own studio, which I built out of my home. I’m also a producer for Song House here in Nashville. I work with my own group of artists that I’ve met along the way. I have a lot of irons in the fire, which is common for producers.

What are your favorite genres to work in?

I grew up with jazz, funk, soul, hip hop, and r&b and all that. For me too, pop music is my love, my pride, my joy– it’s what I’ve always wanted to do. I think writing and producing country music, which I still do, really helped from a sonic and groove standpoint with pop.

I can tell that your family is super important to you; we had to schedule this around parent/teacher meetings and other fatherly duties. How is balancing your career with family life?

For me, I’m a guy that had a great mom and dad. I’ve watched a lot of documentaries on the most successful musicians- the David Fosters, the Quincy Joneses- and one thing I’ve gathered is there’s a cost to become what they became. The cost was their family, their children. I’m not willing to give that up. I have big dreams, but I’m not willing to sacrifice my kids. I don’t want to turn 80, and say, “Man, I’ve killed it, but I don’t know what my kids’ childhood was like.”

How did you discover Recording Connection?

I contemplated going to Belmont when I retired from Baseball. I talked to a lot of people, and they all agreed that going the formal route wasn’t the right move for me. Friends in town, who were musical engineers, advised me that I should be educating myself. I had taken multiple classes at Berklee, but RRFC made sense for me because of the mentor component. I had realized that a mentorship is the only way to get where you want to be as a producer. I ended up getting paired with Ric Web and it was really incredible to be mentored by him.

It seems like you and your mentor have maintained a great relationship post-graduation.

We have! He’s just so helpful. He just came over to my studio and helped me with drum recording, which can be daunting at first. We’ve been collaborating with a younger artist in town. There is still a great relationship there.

Do you have any advice for someone thinking about entering the program?

I would say that you have to get as much out of this thing as you can. It’s not that much time, but it could make a huge difference in the trajectory of your career in the music business. You have to take it seriously.