Producer, songwriter, manager, entrepreneur, and self-proclaimed “Waldorf lifer” Jeremy Skaller ’90 (TWS) sat down with John Graham ’97 (KWS Alumni Association) for a conversation about artistic decisions, meaningful musical experiences, and why failing uphill is the only way to live. A piano player turned Producer, Skaller started his songwriting career as a founding member of several bands. Later, he became a successful entrepreneur in the music industry as a co-founder of Orange Factory Music (OFM), the production team that brought Cash Money Records and Cultural Icon, the artist Jay Sean to the forefront of the global musical stage. OFM has also produced, remixed and/or written for many artists including Nicki Minaj, Lil Wayne, Yoko Ono, and Fabulous. To date, as a Publisher, Producer, Manager, Writer and Label owner, Jeremy via his companies The Heavy Group and Orange Factory Music, has sold over 75 million records worldwide.
In the mid-’70s to early ’80s Skaller attended Kimberton Waldorf School and then also attended Waldorf schools in Germany, Scotland, and Canada where he graduate from the Toronto Waldorf School in 1990. He currently lives in Los Angeles, California.
Your career has so many layers, so many stages, it’s as if you’ve already lived multiple career lifetimes. How and when did you get a big break?
You know it’s funny, it’s kind of the opposite. I never got a big break really, it was always more about failing and learning from each failure. I like the idea of “failing uphill” because I think that accurately describes my life and career. Each loss only fueled me with the energy to continue walking upwards, or taught me a valuable lesson, not to be repeated (hopefully)… in that way, each failed moment has moved me “Uphill.”
I will say that working really hard allowed me to be in the right place at the right time. I remember having the opportunity to work with Yoko Ono in the early 2000s, and of course, she was such a legend, it was extremely intimidating to be working with her. But at the same time, I learned from that experience that I have something to offer that even legends need; I found my place. But I also learned a lot from the experience of being completely dirt poor in New York City, and having to choose whether to buy a bagel and walk to the studio or forego breakfast to instead buy a bus ticket across town. It was either/or in those days and there was no external pressure, it was just me against the city. I had to put pressure on myself to get better and be better. I had very supportive parents of course as well, and they probably wouldn’t have let me starve…but I never REALLY told them how dire it got at times.
But success did come, and you have the resume to show for it! Tell me how you look at success.
You know, I’ve worked with big artists, and I’ve helped them be “commercially” successful for sure. But success for me is about being creative and helping other people be creative. It’s about making a difference through creative-to-creative empathy. Let me give you an example. When I was shopping for Jay Sean, an Indian singer from England, all the major US labels could not or would not commit to the idea of an Asian Popstar. It was too unknown, too risky (in their estimation). He didn’t fit the profile of what they thought could work in America. But together, along with him, we pushed harder because we knew deeply that the stereotypes and racial biases. in the Music Industry needed to be challenged, and now was the time. There had to be some representation and Jay was the one to start it. We finally found the right Label for Jay Sean (Cash Money/Republic Records), and he blew up because of talent, determination, and lots up Failing uphill moments…just because the industry wasn’t ready, doesn’t mean that the market wasn’t! There are always ground-breaking artists, and Jay Sean is one of them. Jay is the first South Asian (or Asian of any kind) to have a #1 Billboard single in America.
Tell me about your own journey into music as a child.
My father is a piano player, and I started playing at a young age. I was pretty serious about it for a while. I also had incredible musical experiences at Kimberton, from Kimberton onwards. My class teacher Gerry LeDolce challenged me to expand my comfort zone, so instead of just playing the usual Recorder, I played piccolo and then Alto, and finally the Bass recorder with the class. He intuitively knew that he needed to push me or I would have been bored. His insight is not lost on me 40 years later. Mrs. Karp was the orchestra teacher, and she was just amazing. I have so many memories of her. One of the most impactful was when I was supposed to play the song “Wish upon a star” on the piano for class recitals. I wanted to jazz it up of course… I was always pushing. But instead of any of the other responses that many teachers might have given, I remember Mrs. Karp just being joyful at my desire to be a little disruptive and hence, creative. “Do it differently,” she told me, “I’ll support you.” It’s those kinds of early support moments that give Creatives like me the confidence to do what I do now. I felt completely safe exploring my creativity. She also told me at one point, you’re not a French Horn player, you need a Trumpet in your hands. And she was right! She knew music, and she knew her students.
I also had incredible music teachers at Kimberton that encouraged creativity! How about musical experiences in your later years?
There were so many. But a couple of teachers really stand out. In Toronto, David Willkenson was my homeroom teacher and he didn’t just encourage me to learn guitar, he wanted to jam with me. I think that was the first time I started to see myself as an artist, not just a player. That level of support absolutely helped me feel safe to start writing songs, which in turn led to me starting some bands (most of which didn’t do much) and then finally having an actual career with my band Belizbeha. (We toured for years sometimes doing upwards of 150 shows per year for many years in a row!) Also, my choir teacher in Toronto, Dorothy Haller is just a phenomenal musician. I mean really world-class. Instead of letting me sing in the bass section (which is where I wanted to be), she put me in the tenor section where I really had to learn to use my upper range. This was another “failing uphill” moment because I was pretty terrible as a tenor at first, But that switch forced me to develop a muscle that I would not have otherwise developed. Mrs. Haller also knew, long before many others that my talk about becoming a Lawyer was nonsense. She knew, even before I did, what journey I was about to embark on.
What else in your Waldorf experience informs your decision-making today as a music industry insider?
I am a Waldorf lifer. I attended Waldorf schools all around the world, finally graduating from The Toronto Waldorf School. My parents were quite engaged with Anthroposophy, so I also experienced something of an immersive home life in that world.
An important idea (certainly not an original one) that I often share, is that ”Art informs Art.” By that, I mean that our experiences with other art, informs and amplifies the creativity in our own sphere. At Kimberton, like all Steiner schools, we had these sorts of artistic experiences on a daily basis. Painting, Handwork, Sculpture… etc. All of these artistic pathways served to inform me of where my music would eventually end up taking me. They also allow you to see things from different angles and perspectives. For example, I find that I am well informed when talking about visuals (music videos or photo shoots) because I understand color and composition. It’s just inside me now. It’s that cumulative exposure to all of these arts as a child that gives me a level of comfort across so many mediums.
Recently, there was a memorial zoom-gathering for Helge Rudolf, one of the founders of the Toronto Waldorf School, and almost everyone who attended brought a piece of handwork that they had created with her. I was so moved by this. The arts have a legitimate and positive physiological effect on us, that in my case they have helped me to remain healthy, mindful, and constantly evolving as a musician and as a result, also as a person.
