Meet Caleb Jerome Morales | Musician, Creative Entrepreneur

We had the good fortune of connecting with Caleb Jerome Morales and we’ve shared our conversation below.

Hi Caleb, can you walk us through the thought-process of starting your business?
If we are the products of the environment in which we are raised, and I could distill my environment down to three key elements – my parents, education, and community – starting my own business was an inevitability that I pondered for my whole life. Entrepreneurship was perpetually in the zeitgeist, only amplified by the rise of social media, the development of ideas such as conscious capitalism, and for musicians, the growth of streaming platforms. My environment showed me, both by example and explicit education, that owning a business is a practical and realistic goal as long as one retains a positive attitude and a passionate tenacity.

Starting with my parents, my father is a veteran car salesman who has consistently posted national record volume each year for three decades, and my mother is an entrepreneur who, in her latest success, has grown the number one English language Italian magazine on the internet by traffic. They showed me firsthand the power of betting on and investing in yourself.

The next element was my educational background, especially university. I studied Marketing & Entrepreneurship at the University of Florida from 2012-2016. At the time, entrepreneurship programs were a rare commodity in universities, and UF’s was number one in the nation. I was surrounded by dozens of students who had started multiple businesses by the age of twenty-two and hundreds of students eager to engage in think tanks, startups, and mock business plans. It was an irreplaceable, practical 360 degree education, within and outside of the lecture hall.

Lastly, I grew up between the Hialeah/Miami Lakes and Cooper City/Davie communities. Especially in the former, most of my friends’ parents were also entrepreneurs, running their own businesses from industries like home improvement to private medical practice. For the early years of my life, I was under the impression that, eventually, everyone runs their own business. While that perspective was certainly a flawed, childlike point of view, it did wonders for building my can-do attitude!

While it took me until 29 years old to officially start my first business, a modern take on a “record label,” it was something I thought about deeply for at least a decade. Growing up playing music from five years old, I obsessed over the music industry for virtually my whole life, absorbing its history, its inner workings, its business models (or lack thereof), and its key job functions. I observed as the industry changed dramatically with the evolution of the internet and social media. I mulled my fit and whether there would ever be a place in it for me while building a career in Consumer Packaged Goods (CPG), a superficially opposite yet deeply parallel industry. I cut my teeth in CPG at the world’s largest media measurement company, absorbing how multi-billion dollar companies achieve and maintain success at scale, then downshifted into a boutique competitor to learn how a fiery upstart might do business differently.

Armed with these experiences and the unique understanding of how to do business at different scales, last year, I knew I was ready to finally embark on the adventurous path of the entrepreneur.

In the current musical landscape, the barriers to entry have been lowered, democratizing streaming platforms and other media to the masses, but only those with a strong entrepreneurial focus and an efficient business model can sustain through the turbulent conditions of said landscape.

While I am currently at the starting line of this industry, I am confident that over time, I will be able to deliver my unique, story-forward, genre-agnostic music to those who crave a more intentional style of music.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
My musical journey began at five years old when I began training as a classical pianist. While the structure was great for my overall music education, each year during my annual exams at the University of Miami, I felt like I fell further and further behind compared to the seemingly preordained future concert pianists. By ten, pop and contemporary music felt like a great outlet for my musical desires while significantly lowering the skill bar required to perform competently.

I learned early on that while pop music was easy to play and create, making and differentiating great pop music was incredibly difficult. Anytime I heard great singers like Mariah Carey and Usher or great lyricists like Jason Mraz and Sara Bareilles, it felt as though they had magical powers. On top of that, breaking into pop music seems like a game that prefers young artists who are easier for big wigs to control and lock into predatory contracts. Thus, I made it my goal to pursue pop music independently and withhold professional ambitions until I was in a position of personal advantage.

The choice was not always easy, and I struggled for years to find my voice. Despite my natural inclination to pick up instruments – in high school, I learned to play over ten – my singing voice eluded me. For a pop artist, this is the death knell, as the voice is the entry point for listeners into your song. While not everyone can play or relate to a given instrument, all can empathize with the human singing voice, and thus, it is the single most important element of pop music.

Yet, for 25 years of my life, I did not have a voice worth listening to. I played countless open mics to sour faces and negative comments. It took a decade of ego dissolution and suggestion before I would pursue vocal coaching, and when I finally did, I trained with the best. Kevin Michael Murphy, co-founder of NYC Vocal Studio and Broadway performer known for his run on The Book of Mormon, taught me to sing in a very physical and holistic fashion. He showed me the relationship between one’s fitness and one’s vocal control, a message that resonated with me, as I do fancy myself a fitness junky. Through his unorthodox teachings, I gained not only the skills to break through a lifelong plateau, but also, the tools to pursue the vocation to the elevation of my voice. Now, five years later, I am starting to receive consistent compliments on my voice for the first time. This was my signal to pursue my musical career now with more fervor and belief than ever before.

Despite the years struggling to find my voice, I found strength and resilience in a natural ability to write strong, layered, and visual lyrics. I dedicated myself to becoming a great writer. I set a goal and mantra for myself in my high school AP English class – “one day, my lyrics will be taught in schools around the world.” This is where my art sets itself apart. While there are a handful of great lyricists in country, rap, and other styles of music, strong and poetic lyrics very rarely break through in a catchy, hook driven pop song. In my perhaps controversial opinion, pop music by nature appears to self-sanitize, sacrificing lyrical specificity and intention in favor of broadening its audience to its ultimate outer limits.

Pop music is fun, catchy, and repeatable, getting “stuck in your head” when at its best. It is a liberating and expansive mode of music that gives itself a chance to reach a broad audience through great melodies and hooks. And now, in the renaissance of independent music, great songs have an opportunity to break through to caring audiences when strategic approach combined with resonant messaging meets a stroke of luck.

With all my passion, energy, and love, I am working to build a fun, nostalgic, playful brand of story-forward, genre-agnostic pop music that audiences will enjoy reading as much as they enjoy hearing. Beginning in June, I will release a new song every two weeks on Fridays, working towards a goal of bi-weekly song releases for two years.

Finally, I aspire to be remembered for leaving behind a positive musical and digital footprint, for contributing a catalog of hundreds of songs and poems worthy of academic study, and for advancing the songwriting tradition. Until then, I have a lot of work to do, and I hope that all reading this consider walking alongside me on this journey!

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I love this question! Having lived in Miami for most of my life, with some additional time living in Chicago and New York, I think I can offer a unique perspective here. Miami has changed so much over the past thirty years, so an ideal week as a tour guide (a role I have been able to play a few times!) would need to balance a mix of the old and the new. Food, sights and entertainment are such important parts of that, so that’s where I will focus.

Food: to me, nothing can connect you to an area faster and more comprehensively than a good meal. Assuming that we can eat out five times during our vacation week, there are five essential themes that we would need to check off: “The Old Miami,” “The New Miami,” “The Locals’ Spot,” “The Beach Spot,” and “The Culture”.

The Old Miami – Mandolin Aegean Bistro. My favorite restaurant of all time in Miami was off 29th and 2nd, I believe, and was called Morgan’s. It was a brunch and lunch only spot built into a classic southern colonial home with two floors, a huge outdoor patio, and tropical foliage. When they sold the property to a condo developer, I was devastated, but a recent trip to Mandolin filled that gaping hole in my heart. Mandolin is just up the street from the old Morgan’s site and offers a similar “backyard” style ambiance, with a beautiful tropical canopy shading your top tier Mediterranean dining experience. The quality of food was so magnificent that I was instantly transported to Mykonos. The ambiance is one that is becoming scarcer in Miami with property values skyrocketing out of the reach of most, and the shift from single family homes to towering condominiums. While twenty years ago, this was a vibe achieved in the Hialeah backyards of most Cuban kids’ abuelas, for transplants and young families alike, this may be the last public connection to “The Old Miami.”

The New Miami – Mila. While it is difficult to see the erosion of Miami’s historical fabric, the development has brought some good, if overrated dining experiences. One that is fully worthy of its praise while connected to a hub of Miami’s bygone era, Lincoln Road, is Mila, a delicious Asian Fusion rooftop restaurant that offers tasteful house music and fire dancers alongside the tapas style dining experience. Celebrity sightings here are extremely common; last time, I saw Shark Tank’s Kevin O’Leary!

The Locals’ Spot – Kush by Stephen’s. Outsiders may never know the importance Hialeah plays in Miami’s story, yet even most insiders do not know of Stephen’s, a deli hidden away in East Hialeah in an area they have half-heartedly tried to rebrand as the Leah Arts District. Corny gentrified naming conventions aside, Stephen’s has all the fixtures of a traditional Crown Heights deli complemented by not-so-subtle Cuban modifications reflective of its Jewish-Cuban founders. Headlined by their flagship “Jewban” sandwich, a pastrami substituting take on the original Cuban sandwich, there is truly no other place in the world where you’ll find some of these dishes, and no places in Miami where you’ll find these prices anymore.

The Beach Spot – This is much less about the food and more about experiencing the beach in a way that jives with your personality. Beach picnics are a classic South Florida experience, and Publix subs are easily the picnic staple of choice. South Beach, especially south of 5th, is surprisingly wonderful almost all times of year outside of Spring Break, Hollywood and Dania Beach offer a more laid back experience, Hobie Beach and Virginia Key are unique beach experiences with city views, and Matheson Hammock is a once-but-never again destination with a chance of bull shark or saltwater croc encounter!

The Culture – this is your obligatory Cuban/Latin American restaurant that completes any trip to Miami. Most travelers choose Versailles due to its name and proximity to MIA, but any La Carreta or Las Vegas is a great choice for their reliability and omnipresence. The most important thing here is to avoid the Cuban restaurants in the tourist traps because they will be overpriced and mediocre. Good Cuban food is easy to find – you just have to go to the suburbs!

For entertainment beyond food, there is so much to do, but there are three things that I would put above all the rest.

Heat game – Miami has garnered a reputation from its cold Northeast rivals as a poor sports’ town, but a single Heat game will disprove that instantly. Yes, folks do arrive late, but it’s not due to apathy, rather, a lack of public transportation. So plan to arrive early and find city parking. Pro tip, the Heat tend to save their best for after February, so count on the most exciting games being in the Spring.

Clean Cut show – Clean Cut is far and away the best local band, and they often play at the Heat games, so if you’re lucky, you can do both in the same night. Their unique funk sound and epic medleys of your 2000s radio favorites like Ja Rule and Nelly will keep you dancing all night, especially when they are posted at the coolest bars around town.

Thalatta Estate & Deering Estate – I have a very specific image in mind when I think of “Old Miami,” and while that aesthetic can be found in a number of places like Coral Gables, the two estates are publicly accessible and scarcely known. Thalatta Estate specifically is a great place to bring a yoga mat or picnic blanket and simply hang out. So if we’ve spent all our energy eating out, dancing to Clean Cut, and chanting “Let’s Go Heat,” this is a great place to end our trip and reflect on all the fun we had.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My shoutout is dedicated to my lovely mother, Lisa Morales, who has played so many roles in my entrepreneurial development. Firstly, she was my piano teacher, fostering and growing both my love of music and my skill. In high school, when I proffered applying to Berklee College of Music and University of Miami’s Frost School of Music, she wisely encouraged me to explore the more well rounded option of business, knowing that I would continue an independent study of music while developing a more versatile career path. Around that time, she started her public relations business, Allegory PR, often taking my siblings and me to her meetings in Midtown Miami, where several of her clients were based. This demonstrated the power of hard work and determination, while doubly showing us that, with adequate preparation and planning, you can be a successful business owner and a great parent simultaneously. My mother is an inspiration, a teacher, and of course, an essential emotional support base without whom none of my endeavors would be possible.

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