Bobby Jaggerjack: An Independent Artist Pursuing Authenticity and Navigating The Rap Game

Welcome to another captivating episode of HipHopEargasm, where we delve into the minds and journeys of remarkable musicians. Today, we have the pleasure of sitting down with the multi-talented artist Robert, widely known as Bobby Jaggerjack. Hailing from the vibrant city of Cleveland, Ohio, Bobby has carved a unique path in the world of entertainment, wearing many hats, from recording artist to actor, model, comedian, podcaster, and more. What sets him apart is not only his diverse skill set but also his unwavering dedication to his craft. In this exclusive interview, we'll unravel the story of his musical odyssey, and his trials and triumphs, and gain valuable insights into how he's navigating the ever-evolving music industry. Join us as we dive into the world of Bobby Jaggerjack and discover the essence of his unapologetically authentic approach to his art.

HipHopEargasm: Could you kindly introduce yourself and recount how you ventured into the realm of music?

Bobby Jaggerjack: Hello, I'm Robert, aka Bobby Jaggerjack, and I'm an independent recording artist, songwriter, actor, model, comedian, podcaster, and, amongst other things, the sole creator, owner, and operator of both my record label (Lucky Libra Records) and publisher (Lucky Libra Publishing) from Cleveland, OH.

I include these titles as a representation of the fact that my focus in entertainment is all-encompassing, even though I started as and am primarily a recording artist. I'm one of those rare cases where you have an individual born to be in this industry who has the fortitude for it but hasn't put all the pieces together. For me, there are only two things I lack: a budget to make more of the moves I'd like to make and enough exposure to ensure that my music's success is self-sufficient, and I don't have to worry about it because I've built up enough of an organic fan base.

I'm currently working on those two things. I'm a shrewd businessman, and I apply everything I've learned when it comes to solidifying the foundation of my brand and marketing my material in general. I'm the one who manages all of the fine details without outsourcing anything because it's the best way to learn.

I even own the federal trademark for my pseudonym "Bobby Jaggerjack" across multiple international and domestic classes. (even though it took over a year for the process to complete, I managed every single step, did the research, taught myself how to do it, and, without consulting any legal counsel, could do it all alone.) There are many other things I've done, but for simplicity's sake, let's say that every single last thing a label would do for the development of their artists and the solidification of their brand, I've done 100% by being lonesome.

HipHopEargasm: What ignited your pursuit of a musical career?

Bobby Jaggerjack: My interest in pursuing a career in music and entertainment arose because I needed to find a healthy way to deal with some of my issues. Combining that with my genuine love for hip-hop music and my ability to put words together akin to a fucking thesaurus, I decided to pursue music as a no-brainer for me. Having a goal that I was dedicated to seeing accomplished gave me discipline that I needed to improve as well, and it ended up keeping me out of not all but a lot of trouble that came across my doorstep.

HipHopEargasm: In what words would you characterize your unique musical flair and the primary genre with which you identify?

Bobby Jaggerjack: I genuinely embody the spirit of what hip-hop is supposed to be. I respect and pay homage to those who came before me while forging my legacy in the process.

HipHopEargasm: Could you recount some of the trials you've encountered as a burgeoning artist in the music field?

Bobby Jaggerjack: Many trials have come up over the past 10+ years during my journey as an artist. Some have to do with the fact that I've always been limited in resources, even though my skills and aspirations have no ceiling. Others are more focused on my character and instances where I didn't immensely value my worth as a creator, and my lack of effort during those times would be proof enough of me feeling that way.

Unless you've personally pursued the same things under similar circumstances, I find it difficult for others to understand the toll it takes mentally when sacrificing everything that "makes sense on paper" in order to see the goal of becoming a successful artist through to the end. That's also been a struggle of mine. The consensus is that you can only do so much as one individual, but how do you even begin to build a team of trusted compatriots to take along on your journey if they need help understanding the value of the process?

HipHopEargasm: To date, what would you consider your most noteworthy accomplishment or significant milestone in your musical journey?

Bobby Jaggerjack: For my most noteworthy accomplishments to date, I'd reevaluate my introduction and note that when I created my record label as well as my publishing company, I hadn't realized the value of what I was doing entirely until it was finished. The fact that I'm in control of my career and destiny as an artist unequivocally without having to ask the permission of another within itself is a significant accomplishment.

HipHopEargasm: How do you navigate the ever-evolving landscape of the music industry, particularly in your role as a fledgling artist?

Bobby Jaggerjack: Simply put, I'm me! What I mean by this is that I haven't, nor am I willing, to make any sacrifices or compromises that would belittle my character in exchange for being given an easier path to success. This sets me apart from many peers because I can't be bought. I'm willing to take the long way toward my goals, regardless of how long it takes, because I truly understand the value of being patient and doing things right for me! I'm also trying to "get on," if you will (the monetary aspect of my success) so that I can disappear! Many artists in the rap industry these days, for whatever reason, seem to be hell-bent on being in the spotlight, and with that comes the drama, the trouble with the law, the street beefing, and other goofy shit that we keep seeing, and with me, it's the exact opposite. I want to build enough resources to take care of myself and the people I care for while staying as far out of the way as possible.

HipHopEargasm: To what extent has technology contributed to shaping your music and professional trajectory?

Bobby Jaggerjack: I'm adaptable, and having to do everything by myself teaches me everything I need to know, regardless of what direction the industry goes. Change doesn't intimidate me, so I tend not to be affected by it. I can run the majority of my enterprise musically from behind a computer screen. It's second nature at this point, so I need help to single out a list of things tech has helped with.

HipHopEargasm: How do you gauge your success as an artist, and what objectives are presently occupying your focus?

Bobby Jaggerjack: If I'm able to make enough money to take care of all of my necessities and occasional wants, then I'm happy with where that point lies. I don't have an exact idea of what success looks like in the end for me, past just being able to provide a life for me and mine while doing what I love. Hell, that within itself is what I classify as success. I'm also a genuine lover of the art form and roots of the rap game, so if I gain the respect of the hip-hop community as well as those same pioneers who inspired me to do this all in the first place, that will reinforce that I'm succeeding by my own standard. I'm not really that complicated, guys!

HipHopEargasm: What counsel would you extend to budding musicians who are embarking on their own journeys within the industry?

Bobby Jaggerjack: There are many things I could say to an upcoming artist, but they would mostly be coming from a place inspired by my own experiences, and there isn't a "one size fits all" approach to any of this, so I suppose trying to impart that to them would be one thing. I'd also say, Be YOU! We live in a time where so many people want to be someone they aren't and live the lives of others, but that's not how life works. You'll probably achieve the best results by being true to yourself, and there aren't too many ways for me to cut that one. 

Educate yourselves on the process from scratch. Even if your aim as an artist is to "get signed," don't underestimate the importance of educating yourself on how the business works. The industry isn't geared in favor of the artist, so educating yourself on how things work behind the curtain is one of the few things you can do to protect yourself against being taken advantage of.

Also, compromise is satisfactory if you're comfortable with yourself afterward. Still, don't compromise on anything that'll keep you up at night or shortchange you in the long run. Try not to let money be your only focus, as it has a tendency to blind you to what's essential. Just be mindful, because this is your life we're talking about.

Connect with Bobby Jaggerjack on Instagram

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