The resulting single, “Hello, My Ragtime ’80s,” netted me about a hundred fifty dollars in its first month on sale. No life-changing sum, but it was enough to give me hope that it was possible to record tracks, share them online, and have people willingly pay to consume them. This was passive income at its finest. For the very first time in my life, I had the ability to make money in my sleep. I liked that a lot.
Most importantly, the video allowed me to break free of a monster that had held me back for years—a monster that I never spoke of for fear that acknowledging it would render it even more omnipotent.
THE MONSTER CALLED PERFECTIONISM
The most difficult battles we face in life are those we wage within. Self-doubt, feelings of unworthiness, and fear of rejection: This is the trifecta of demons that holds us back from reaching our full potential. We’re not born with these demons; for proof of this, one need only look at how free and uncensored young kids are. By the time most of us reach adulthood, however, we’ve devolved into a tangle of insecurities and negative experiences.
From what I’ve seen and from what I’ve suffered, I’d wager that perfectionism hits artists the hardest. Artists—whose very calling is based on the expression of feeling—tend to be more introspective than your average human being and spend much more time living internally. Releasing a creative project out into the world requires ceding a part of yourself to the world and exposing it to the slings and arrows of external criticism. So, it’s only natural that the artist, aware of the vulnerability and invitation for judgment inherent in the act of creating publicly, would take painstaking care to ensure that whatever is released into the world is as close as possible to “perfect.” If left unchecked, this tendency to obsess and strive for perfection can lead the artist to devote months, if not years, to producing a single flawless creation. The truth of the matter, though, is that our actual creations will never be so perfect as we’ve dreamt them to be; they can only be perfected in the sense that, when released, they exist.
Sometimes, it takes losing control to gain control over this obsession with perfection. That my relatively unpolished ragtime medley went viral so quickly forced me to push past my aversion to making myself vulnerable to other people’s opinions. Initially, the video received a tremendous amount of praise, but as it found its way to more sites and spread across the Internet, it began to garner a hefty dose of criticism, too. The mostly anonymous critics took aim at everything from my homegrown piano technique to my haphazard haircut (to be fair, both were fairly out of control in those days). It seemed bizarre to me that, given all the evils in the world, people would expend so much of their energy vocalizing anger at a stranger who was simply trying to provide them with a few minutes of entertainment, but at least I now had a solid hunch as to why signs reading “Don’t Shoot the Piano Player” were deemed necessary in saloons. If you put yourself on the Internet, be prepared for strangers to fire shots:
“Horrendous, eh?”
“Nice setup, but you should really invest in a metronome…”
“Sloppy as hell.”
And, my personal favorite: “You’re amazing on that piano. Too bad you look like such a douchebag.”
It was uncomfortable at first, reading these cutting remarks, and my initial thought was that I wanted to reply to the critics to defend myself. Thankfully, I was wise enough to understand that engaging in a shouting match with my critics and haters would not a good look make. Surprisingly, much to my relief, the sting of the criticism subsided after a few minutes. Whether that’s because I’d grown a tougher skin lightning fast or found inner enlightenment and peace, I don’t know. One thing I can tell you for certain: Empathy works wonders when dealing with the most brutal kind of criticism. The harshest of the negative feedback I received oozed with the kind of insecurity that had, for a long while, been lodged so deep within me that it had prevented me from sharing my music. I was able to recognize the ugly emotion and the place of fear that it was born from because once upon a time, I, too, had been at its mercy. The only difference was that I’d resisted the impulse to go on the Internet anonymously and be a jerk about it by taking it out on other people. The choice is always there.
In the end, it was the comments that made valid points about my shortcomings as a pianist that were a bit tougher to hear, but even those didn’t seem to affect me much—at least not in the way they would have even a couple years earlier. The video, I came to see, was akin to a snapshot in time, and my performance in it was honest and genuine. By that measure, it was already perfect for what it was. I had no reason to defend it.
I came away from the whole experience with the perspective-shifting realization that I’d spent a good seven years—precious time that could have been used to create—in perfectionist limbo, rationalizing to myself that I just wasn’t ready. Experiencing the criticism that I’d been shielding myself against for so long showed me how little it actually mattered. I vowed to continue to think of each new video as another snapshot in time, nothing more, and I’m proud to say I’ve kept that promise to myself.
If there’s one lesson you take away from this story of my unexpected YouTube stardom, I hope it’s this: You will never feel “ready” or “comfortable with” putting your work out there. It is so important to make peace with and internalize this idea. If you’re a musician and you’ve just written a song that you’re on the fence about, the best time to record it is right now. If you’re a filmmaker and you want to make a movie but don’t have the best equipment, the best time to begin making it is right now, with whatever equipment you can get your hands on. If you’re reading this and have a feeling that this might apply to you, set my book aside, get up, and go do whatever creative project you’ve been putting off—you guessed it—right now.
Despite my glimpse of twenty-first-century Internet fame—a harbinger, I hoped, of more good things to come—I still struggled to create consistently and courageously at that point in my life. I was tired of feeling like fear had power over me, though, and so I made a rule for myself: Whenever I was having trouble working up the gumption to create something, I simply set a deadline for its completion and told my newfound fans about it, so that they’d help hold me accountable and follow through with it. I continue to put the rule into action to this day, and I urge you to do the same if ever you’re feeling stuck. It’s not unusual for me to announce the release of an album days or sometimes weeks before it’s ready to go. Declaring deadlines helps me stay the course because to delay or cancel a release would mean disappointing my fans. The perfectionist monster in me still rears its head every so often, but my desire to never disappoint those who’ve put their trust in me is a much more powerful motivator.
My follow-up videos didn’t create as much of a stir as that first medley did, but they were pivotal in my establishment of a new working format. I found that having concise, memorable titles was absolutely crucial; I needed to be able to describe each video in a way that would compel my prospective viewer to think, “Yeah, I’d be interested in seeing that.” I learned that the medleys and nostalgia-inducing content were being shared like crazy, and so with the goal of creating even more of them, I teamed up with my saxophone-playing friend from college, Ben Golder-Novick. He was a brilliant improviser with a quick ear who, like me, appreciated a bit of silliness in his music; back in school, we were known for mashing up jazz standards with ’80s riffs, Dave Matthews songs, and Wu-Tang Clan instrumentals. I’d gotten it into my head to do a “Nintendo Jazz Odyssey” video, and inviting Ben to collaborate with me on it felt like a no-brainer. Together, we developed and recorded jazz versions of popular Nintendo game soundtracks and synced them to video game footage. When the finished product went viral, I felt like I’d struck gold—if “striking gold” means getting a small blurb in Nintendo Power magazine, a feat that no doubt would have filled nine-year-old me with limitless awe and reverence. I breathed easy, knowing that with the success of this second video, I was safely out of “one-h
it wonder” territory.
EMBRACING CHANGING TECHNOLOGY
The social media landscape was rapidly changing just as I was beginning to find my footing in it. New sites and blogs dedicated to content curation were appearing daily, and social media platforms like Twitter and Facebook were gradually becoming more influential than traditional media. It was disorienting but exciting, and I saw in the chaos a real opportunity to make a name for myself as a musician for the social media age. In an uncharacteristic burst of organization, I made a spreadsheet of press contacts for all the media outlets that had shared my videos: College Humor, Today’s Big Thing, Digg, Reddit, BuzzFeed, 22 Words, The Daily What, The Awesomer, Huffington Post… the list went on. Every time I went live with a new video, I would blast a link and a short note to all these outlets, hoping that even just one of them would run with it. In the process, I noticed that when one of the bigger websites ran a feature on something, all the smaller outlets would soon follow suit. Determined to make the most of this trickle-down effect, I put myself in the shoes of the editors and did my part to craft attention-grabbing headlines for them that could be quickly cut and pasted, in case they chose to write me up. The strategy seemed to work pretty well; and while I never actually met any of the editors who shared my videos, I felt like we developed a solid, chummy rapport by email, despite my blatant self-promotion.
These videos of mine that they so graciously helped to hype ranged from a sepia-toned Jersey Shore trailer (I realize this is the second time I’ve referenced Jersey Shore; rest assured, it will not be the last) that played over a ragtime treatment of an EDM song; to a beatbox flute and electric piano mashup of Notorious B.I.G.’s “Big Poppa” with the Harry Potter theme; to a five-minute sax-and-piano medley of the Pulp Fiction soundtrack. The only commonality among all three was their vaguely jazz- and pop culture–oriented vibe. I was primarily preoccupied with pushing the creative envelope to see just what was needed to gain traction and go viral. To learn what worked, I did what a lot of business people refer to as “A/B testing,” although I had never learned that term, so at the time I didn’t know there was an official, alphabet-inspired name for what I was doing. As far as I was concerned, I was just going through the same meticulous motions I’d once undertaken to figure out jazz piano: trying a bunch of different combinations of ideas, seeing which combinations got me closer to my desired goal, and continuing to innovate from there. I experimented with video length (three minutes or under seemed to be the sweet spot for most attention spans), titles (jamming in oft-searched terms helped to get views but only when the content was actually related to those terms), and lighting (uploading certain videos in black and white or stylizing them in old-timey filters helped dress up the videos but only as a once-in-a-while thing). None of my methods were too scientific or precise; really, I just paid attention to the feedback I received—the non-insulting, constructive feedback, that is—and responded accordingly.
I hadn’t quite put all of my music career eggs in the YouTube basket… yet… but at the same time, I was meeting with enough success on the platform that I didn’t even think twice before dropping the idea of starting school for physics that fall. Something exciting was brewing—I could feel it. I was playing a great deal more piano gigs on the regular, and I was starting to make a bit of money on them by leveraging my online following to book higher-paying venues. My favorite gig was a weekly slot I secured for myself at Robert Restaurant in Columbus Circle, where I was paid handsomely (in money and in free food) to perform three hours of whatever solo piano pieces I wanted. It was a life I could get used to, and I wasn’t the only one who was pleased with the way things were going.
“This is the most lovely place! I always dreamed you would play in a place like this,” my mom exclaimed after my dad took her to New York City to hear me perform at the restaurant. She was beaming with pride.
The restaurant became yet another laboratory for me, and I used it to explore the concept of musical mashups: combinations of different songs that share similar themes. I developed a go-to format for my weekly sets at Robert, sticking to pure jazz in the first hour; a mixture of jazz peppered with a bit of classic rock in the second; and in the third and final hour, a no-holds-barred mashup assault on the senses that ventured into the edgier terrains of gangsta rap, ’90s television themes, and beyond. The restaurant staff played a sizable role in my set planning, often slipping me hand-jotted notes filled with ideas. “Mashup Aerosmith and Music Theatre,” one requested. “‘Girls Just Wanna Have Fun,’ but sad,” another read.
That the restaurant was located on the top floor of the Museum of Arts and Design meant that celebrities passed through frequently, and whenever they did, I would try to incorporate them into the show—usually without their consent. When Alan Alda came in to dine one evening, he did so to the tune of the theme from M*A*S*H* played in fourteen different styles. At the end of the night, he graciously tipped me a twenty, and I responded by playing the theme once again as he made his way to the elevator, as exit music.
Fresh off my first string of YouTube successes, I was antsy to think up additional unique ways of harnessing technology to bring my passion for “vintage” music to new audiences. I learned about Ustream, a streaming video interface that was popular at the time, and began using it to broadcast my piano playing over the Internet. One night, feeling extra inspired to experiment with my set, I brought my laptop with me to the restaurant, placed it on the piano, and spent the last hour of the three taking song requests over the Ustream chat interface. I posted a link to the broadcast on my Facebook page, and before long I had hundreds of viewers writing to me with their requests—while the restaurant’s patrons, unaware of the online concert I was conducting before their very eyes, continued to dine per usual. Well, for the most part, that is. I’ll never forget the night when an elderly patron wandered over to the piano mid-broadcast and stared directly into the webcam at the top of my laptop screen.
“What’s all this here?” he asked, quizzically, gesturing at my setup.
“HEY, OLD MAN,” someone instantly wrote in the chat feed. The old man gave me a confused look. I shrugged my shoulders sheepishly and launched into the Neil Young hit by the same name.
If you had told me back in high school that when I turned thirty I would mostly be playing concerts for strangers on the Internet and making YouTube videos, I would probably have recoiled in horror at this vision of a career gone horribly awry (after asking what YouTube was, of course). However, in reality, I was extremely fulfilled. I had stumbled upon a way to do something I had long dreamed of: turning my background music gigs into genuine concerts with an actual audience. The only difference was that the concert venue existed virtually; the real-life audience only offered occasional applause here and there, punctuated by the occasional confused stare into the webcam as they passed.
Besides the curious old man who’d sauntered over to investigate my setup that first night, no one else at Robert seemed bothered by the streaming sessions I’d taken to hosting—even when technical difficulties and dropped Wi-Fi signals occasionally delayed my start times. The staff knew that something exciting was happening, even if it was a little strange, and often involved ragtime renditions of Rick Astley’s “Never Gonna Give You Up.” I had set up a new laboratory in an unlikely location—at the piano in the corner of the restaurant—and was furiously attempting to redefine the term “cocktail pianist.”
Once, while wrapping up a live session, a diner who’d been watching me all night with amazement strolled over and asked for my card. The next day, he texted me and introduced himself as Kai Tao, former hedge fund president-turned-entrepreneur. Without any further preamble, he invited me to demonstrate what I was doing with interactive music broadcasting at the upcoming TEDxOrangeCoast in Orange County, California. His proposal completely caught me off guard; I’d performed for other people’s enjoyment too many times to count, but never before had I been presented with an opportunity like this—to sp
eak about the inspiration and process behind my music as an innovative artist, not a cocktail pianist—and I wasn’t sure I could handle it. I’d be damned, though, if I was going to forgo the chance to appear in front of thousands of influential people who could help my career. I accepted on the spot and got to work. I had a kernel of an idea, and I needed to make it a reality—fast. I would build my very own customized streaming site (which, in my head, I’d already named Emote CTRL because why not put the cart before the horse), so that I would have some kind of visual to present with my talk. I had no idea what this entailed, but I called a couple friends who did and gave them the timeline for this project. In just a couple months, I’d be boarding a flight to California to give my very first speaking gig as an innovator, despite having no real credits to my name. But imposter syndrome be damned—it was starting to feel like I might be going places.
Touching down in sunny Los Angeles was something of a culture shock. Everyone seemed to simultaneously exude both success and laid-back relaxation. The people were also a lot friendlier than the brusque New Yorkers I’d grown used to. Kai—an enthusiastic natural connector—took me under his wing and brought me around to meet his friends in the entertainment business. At a dinner party the evening before the talk, I was introduced to an entrepreneur named Evan Lowenstein. In what felt like a serendipitous encounter, I learned that he was the founder of the online concert venue StageIt, which had, in large part, inspired the design of the website I’d built for the talk. Evan told me about how he’d gotten his project off the ground and about his previous life as a pop star. He had a twin brother, Jaron, who’d just made the switch from performing to management and was looking to sign up-and-coming talent. Together, as Evan and Jaron, they’d had a massive Billboard hit in 2001: “Crazy for This Girl.” This he revealed to me with zero pretension and total casualness.
Outside the Jukebox Page 6