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Rising Star ToBy On the Five Things You Need To Shine In The Entertainment Industry

An Interview With Jason Sheppard

I think I would want everybody to check up on at least one other person in their life daily. You never know what we’re all going through and especially for those who like to shoulder the burden and keep it pushing, they need that acknowledgement the most.

As a part of our series about rising music stars, I had the distinct pleasure of interviewing ToBy.

Blending elements of modern rap music and indie rock, L’Esprit follows a narrative and a character that is loosely based on ToBy himself and is his most personal work to date. The album deals with heavy topics such as depression, anxiety, grief, lost romance, and self-doubt, all while presenting catchy and memorable tracks that will get stuck in one’s head with ease.

L’Esprit, which translates to The Spirit, is also an ode to ToBy’s late grandma who passed away from cancer in 2020. ToBy was extremely close to his grandma, as she helped raise him and always supported his musical journey when others in ToBy’s life did not (ToBy’s parents were immigrants from Haiti and did not understand why anyone would want to be a rapper for a living. ToBy’s grandma had to talk to them to get them to understand his passion). After receiving news of her cancer diagnosis in 2019, ToBy decided that he needed this record to pay tribute to the woman who helped him so much over the years. You can hear her voice on the record as a narrative guide, which was taken from a six minute convo ToBy recorded with her shortly before her passing.

Thank you so much for joining us in this interview series! Can you tell us the story of how you grew up?

I grew up in between Miami and Haiti. My grandmas were always singing and playing piano in the house, so I was exposed to music pretty early. My dad had an eclectic taste in artists, so I was listening to Simon and Garfunkel and Pet Shop Boys growing up. I went to school and hung out with my best friend who was always in a band and when I started writing he became my first producer/engineer. Eventually, I ended up moving away to LA to pursue my career.

Can you share a story with us about what brought you to this specific career path?

It was a culmination of things, but when I was in High School I got into a pseudo rap beef with another kid, and we ended up sending diss tracks to each other through SoundCloud. I eventually realized I loved writing music so much and kept doing it till it became my life.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I had an opportunity to open for ScHoolboy Q in 2013, and I took it thinking that it would be a make or break career move. My friends and I ended up selling a bunch of tickets to secure our spot, but when we got to the venue they put us on first at like 5 P.M. (an hour after soundcheck) and we got to play for like 7 minutes to an empty room. ScHoolboy Q didn’t perform till like 1 in the morning, and absolutely nothing came from that experience. I learned that if it sounds too good to be true, it probably is and to move with more skepticism in my business dealings.

You have been blessed with success in a career path that can be challenging. Do you have any words of advice for others who may want to embark on this career path?

I think the hardest thing for a lot of people is continuing. If you want to pursue this, you have to be okay with saying yes to it every day, otherwise you’re going to have a hard time and may quit on yourself before you get anywhere. These things take time and effort, and no one’s path is written in stone. People are going to surpass you or fall off, but you can’t think about it, you only have to worry about yourself and what you’re doing to progress.

We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?

I think back to being a kid and gravitating to characters, artists, or figures who looked like me or came from similar backgrounds and seeing them as proof that it was possible for me to do the same one day. I think being able to see yourself represented in media and across the board can help alleviate some fears and doubts that come up when you decide to take it upon yourself to chase the same goal.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

I really only have 3 to be honest,

  1. I wish somebody told me there were going to be days when this would feel like a choice. I always took for granted the fact that I liked art and music but on the days when it gets really hard, I had to keep in mind that if I wanted to move forward I had to make the decision to do so myself.
  2. I wish somebody would have told me that an investment in myself would be more beneficial than trying to find a quick route to the top. Not only that, but I would have taken the pursuit of music knowledge and production much more seriously earlier, and who knows where I would be now.
  3. Lastly, I wish I was aware of how expensive making music would be at the start. I managed to find ways around the really costly things, but it really is like running a one-man company sometimes, and that comes with all the costs.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Feed your muse. We aren’t flowing wells of uninspired creativity, all of our ideas come from somewhere, and usually it’s from the observation of other engaging art forms. Read a book, go to a museum, people watch, siphon the art from the surrounding life, and you’ll always have an idea.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I think I would want everybody to check up on at least one other person in their life daily. You never know what we’re all going through and especially for those who like to shoulder the burden and keep it pushing, they need that acknowledgement the most.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I would say there’s a laundry list of people who took time out of their life to invest in me or teach me something that put me in my current position. I’m extremely grateful to my best friend and long time producer friends SMLE who always answered any production questions I had and taught me a little about writing music on my own. Furthermore, I really believe in the “teach a man to fish” mentality.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them.

I would have to say Donald Glover. I have so many things to ask him about how he navigated this industry and set himself for all the groundbreaking media he’s making. Not only that, but I also feel like he has a good taste in coffee for some reason.

How can our readers follow you online?

I am @itstobyseason on all platforms, at this point you can google “ToBy Season” and I’ll come up.

What are some of the most interesting or exciting projects you are working on now?

I’m already writing my next music endeavor and working on some exciting film ideas outside my music.

This was very meaningful, thank you so much! We wish you continued success!



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