Interview with Brandon Ross (@flyguy_connection)


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path? 

I remember being a kid growing up in Chicago, playing sports, and making music. I always told my parents that I was gonna be a rapper when I got older or a basketball player, so in grammar school, I played JV basketball, in high school. I played basketball, even went to Sauk valley CC to continue my basketball career and writing music at the same time, but after my freshman year in 2009 at that point, I said my career in music is what I need to be pursuing and from that point, it was music for me 24/7 365 I began to put more and more time and money into my craft which I might say has taken me some time but it’s taken me all across the world in a 10yr life span, which has gotten me streams and followers from all over the world.

Can you share the most interesting story that happened to you since you started doing this? 

Okay, I remember back in 2016, just a young me 26 at the time, about to release my 3 mixtapes. I got a mysterious call from a guy named Teddy C, he was an A&R at this digital marketing firm… he called me and was like “is this Brandon Ross aka b. Ross” I said yeah! He said hey man I’ve been peeping your videos on YouTube and I feel we can do some business together and I said “How do I know this is legit” he did I tell u what this is so legit to the point I’ll fly out to Chicago and meet you in person… I said okay fine, but I thought the whole thing was a scan, 2 days later he calls me and said “I’m here let’s link” I said okay cool, we met at the airport… talked business over, did the deal and I began to travel the world with my music opening up for big acts such as Future, Lil Durk, Juicy J, Migos, etc.. even got a major feat from Epic Records artist Zoey Dollaz. 

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

I can just keep working on your craft as much as possible because it’s gonna be that day that u least expect something to happen.

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? 

Yes, Again His name is Teddy C Money, “GTMG” he’s an A&R, his experience in the music industry guided my career into a level that he only knew I could achieve, he’s made me a core artist, he’s polished my career and guided to a point where there is no looking back. 

How have you used your success to bring goodness to the world? 

I’ve used my success to show the up incoming artist that you can be successful at the Indy level of music.

Do you have a favorite “Life Lesson Quote”? Can you share a story of how that was relevant to you in your life? 

My life lesson quote would have to “strive for something, even if it’s not what u expected at least you tried” it’s better to try and fail than to fail and not try at all.

How can our readers follow you on social media? 

My social media pages are all open Ig:



Brandon ross 

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Brandon Ross (@flyguy_connection)

Kyle Christopher Cobb (@therealkcobb)