Wednesday December 16, 2015

• Going Pro

I initially resisted writing too much about putting my focus and attention on my band, Airplane Mode. Partially because I didn’t feel I owed anyone an explanation, but mostly because I thought it was self-explanatory. But I’ve heard enough questions and incorrect assumptions that I wanted to offer up some clarity on what I’m doing and why.

* * *

In 2009 I started work on a little side-project startup called Coathangr that we described as “Twitter for pants”; a microblog specifically for posting photos of what you were wearing. The hope was that people would begin seeking each other’s council on their sartorial choices. My partner on this project was my friend (and eventual next-door neighbor) Jay Graves, who was a web developer when we started out, but later went on to become the CTO of a large iOS development company.

It was just the two of us, and my design skills really just boiled down to a rudimentary understanding of Photoshop accumulated over years of downloading and playing with pirated copies. Coathangr never grew beyond maybe a couple thousand users — Twitter was already Twitter for everything. But we loved the project, and we knew deep down that there was potential to turn it into something much better. We worked hard. We spent nights and weekends trying to make it better. We put money into printing t-shirts and stickers to give away, and even sponsored a fashion show. It all meant something to us. We were building something bigger behind the scenes.

My day job was at a software company run by an odd hybrid of jocks and tech-types. The core team of developers held the keys to everything profitable, and management had lost too many staring contests to have any real authority over engineering. It was a weird sort of Lord of the Flies culture where the nerds had become the bullies, and anyone they didn’t like was left on the sidelines at best, or passive-aggressively harassed into submission (or quitting) at worst.

When my co-workers found out what I was working on in my spare time, it didn’t take long for Coathangr to be overrun with throwaway accounts whose sole purpose was to reply to every user photo with the cruelest comment possible. All of the accounts had, of course, originated from the office’s IP address.

I had no proof beyond the network connections, so I couldn’t call out any one person. Not that it would help anyway — any complaints would be met with a chorus of snickers and denials. I silently deleted the comments and blocked the IP. It meant I couldn’t connect from the office anymore, but the problem stopped.

A year later, Coathangr was acquired by an iOS shop and I switched over to working on app design full-time. I was so happy to leave the old job that I never even went back to pick up my stuff.

* * *

I got my first guitar when I was thirteen years old. A birthday gift from my dad, kicking off a brief window where his life-long absence was placed on hold. It was a piece of shit Teisco Del Ray with machine heads so rusted that I could barely tune the thing. (I nearly gave up playing guitar because it was so hard to turn them — I didn’t realize this wasn’t normal until a year later.)

I was terrible at first, of course, but I kept picking up copies of Guitar World and reading about my heroes. People like Kurt Cobain, Billy Corgan, Kim Thayil, Dave Grohl, Dean DeLeo. I read stories about how they got started, how they wrote their songs, and how they saw the world. These were people — mostly young men — taking their stress and anger and turning it into something positive. I liked that.

The energy of early ‘90s rock spoke to me, and I wanted to do what they did. Not because I thought it would get me chicks, or make me cool (playing guitar did neither of those things for me in high school), but because I wanted to make noise and have fun. I read tablature and learned riffs, accidentally studying the craft of writing hooks. It was the best therapy I could hope for.

I didn’t fit in in middle school or high school. Maybe race played a role, but it mostly felt like a musical divide. My school had a large black and hispanic population, and my peers at the time were mostly listening to stuff like Snoop and Dre. I was fascinated by the rawness of it, but the music didn’t speak to me the same way that Nirvana and Stone Temple Pilots did. When I grew my hair out to look more like the guys on the cover of Guitar World and Spin, the kids at school started calling me gay. (I guess they had never seen an actual gay person.)

A year in, I had given up on finding anyone to start a band with me. Nobody else at school played instruments, and they certainly didn’t want to start an alternative rock band with the fat white kid with long greasy hair. Playing music was my own. It was an escape.

When I was 19 my first real girlfriend ended our relationship by cheating on me. I dealt with it by picking up my guitar and writing music for the first time. They were simple songs with a predictable structure and overwrought lyrics, but they were my songs. It made me feel empowered at a time when I otherwise felt helpless.

Those songs would become the foundation of my first band, Karma Ghost. That band was my entire life for a few years, and while finding any kind of success with music was always a struggle and I doubted myself constantly, I was happier than I had ever been. Music was, still, the most consistent friend I’d ever had.

* * *

I used to do a podcast called Unprofessional. The premise was that we would bring on interesting guests and talk to them about anything except work; a premise invented when my co-host Lex Friedman couldn’t get clearance from his day job to do a tech podcast.

At first we brought on our friends from the tech industry — a natural fit, and frankly a cheap way to boost downloads — but slowly we managed to lure in guests from our personal lists of heroes. Folks like Jonathan Coulton, Susan Orlean, Dave Coulier, Ophira Eisenberg, Sean Nelson, Jay Clifford, and Joshua Malina. Jesse Ventura once came on the show to rant (at length) about the government’s use of fluoride to control our thoughts. It was fun.

We had a pretty good setup. I handled editing and production, and Lex lined up sponsors. The show never made a ton of money, but we loved doing it, and we even got invited to do live episodes in amazing places like Dublin and Melbourne.

When Lex left the show in late 2013 I was suddenly tasked with sponsorship duties. But I had no connections, no mojo, and no way to convince anyone that the show could still pull in an audience. It was rough.

Just then, by sheer coincidence, some friends with extremely popular podcasts were looking for someone to handle sponsorship for them, and I offered myself up as the guy to deal with it. I started a little company called Standard Broadcast to handle the money, and used their connections and influence to pull in sponsors. Unprofessional was too small to sell well on its own, but I figured I’d have more luck bundling it with bigger shows.

The best part is that it was all behind the scenes. Standard is a sponsor management system, not a podcast network. Nobody needed to know that I was selling ads to pay my bills, and this way there wouldn’t be a big, weird, public kerfuffle if someone decided to move their show elsewhere.

For nearly a year it was my secret shame. I still went around and gave conference talks as an iOS designer, but the truth was that I hadn’t designed anything in a long time. Standard didn’t take up all of my time, but business was good enough that there wasn’t much point in taking on the kind of design contracts I had worked on previously, and it’s no secret that making a sustainable living on the App Store is incredibly difficult. I was a designer by reputation only.

* * *

Last year I made a video called Podcast Intervention about the overabundance of white-men-talking-about-tech podcasts in the Apple community, and our overall reluctance to try anything new. I had been working on podcasts just long enough to recognize that the trend wasn’t breaking, and I thought that perhaps I might be in a position to spur some positive change.

When the video came out, it was immediately misunderstood. Unfollows, sub-tweets, whispers, and passive-aggressive shots from people I respected. Many had assumed I was picking on this person or that person, not realizing that the vast selection of people I could have been referring to was exactly the point. But nuance is tough, and if I’m being honest I think a few of those white men are still holding a grudge.

The response from inside the bubble was disappointing at first, but when the conversation finally turned introspective it seemed like we might find some positive change: Myke Hurley’s excellent Inquisitive podcast sought to find depth beyond Apple news headlines. Mark Bramhill’s Welcome to Macintosh is a very polished show, documenting the history of the Apple developer community. I hoped we could forge a community more accepting of new ideas and new voices.

Still, a year later, it’s hard to come up with a great example of an Apple community media project not run by white men, and many of the most successful white men are now on three or four different podcasts. It starts to feel like “software development” is more of a podcast category than an actual career.

* * *

My first band didn’t break up so much as it deflated. We were a three-piece, and the first sign of trouble came when the bass player and drummer started dating each other. They promised me it would be fine, but anyone could guess how that would play out.

To their credit, their breakup wasn’t even the problem. Well, not exactly. We still went to practice every week and got along just fine. Some awkward pauses here and there, but our drummer had some social-skills challenges that made this a not-uncommon occurrence anyway.

It wasn’t really a problem until our bass player brought a date to a show.

The drummer responded to this by pounding a bunch of drinks, getting into his car, speeding away from the venue, pulling over, getting out, and punching a telephone pole as hard as he could, shattering his hand.

Like I said, challenges.

And that was that. I had to choose between them, and while she had done nothing wrong, the bass player was still the newest member with the least musical experience. So we waited for the drummer’s hand to recover.

When his hand did finally heal, Mister Drummer succumbed to the worst of musician clichés: he borrowed money from me and disappeared. I didn’t see or hear from him again until years later.

Through all of this, I had just begun a relationship with a woman who, it turned out, had some fairly significant health problems. Rather than seeking out new bandmates or writing new songs, I spent my time and energy with her. As things got a little worse, I took time off work to help her through radiation therapy. Whenever money got really tight, I sold some of my music gear. And every time I did, I felt that part of me die a little bit.

It certainly wasn’t her fault. It was me, not her, that held me back. I thought that growing up meant being responsible and putting away unrealistic dreams. I thought I needed to make more money and focus on my career in order to be a good boyfriend.

When the relationship ended five years later, I finally picked up my guitar again.

* * *

When it became clear that Standard was stable and operating on a surplus, I decided to try my hand at producing something new. I met with a dozen or so people to talk about interesting projects, and a few of them even moved into production. My criteria was simple: it had to be an interesting, realistically sustainable, novel concept for a podcast or video produced by someone who was either not part of the Apple community in-crowd or had something genuinely new to say.

This has mostly gone very well. I’ve put microphones and cameras in the hands of some very talented people who are either producing quality content already or are very near launching their shows. There are never any guarantees of success, but I felt good helping talented people try new things.

At about this same time I was talking with my friend and Airplane Mode bassist Joe Cieplinski about our difficulties finding a drummer. We had just recorded a quick bit of music for the intro to a new podcast by our friend Jim Dalrymple, with Joe and I handling the production and all of the instruments ourselves. The results were good enough that I suggested to Joe that, hey, maybe we could just record an album by ourselves.

We’d start out by recording demos at home, and see if we could use those to attract a drummer and keyboard player. Worst case, we’d just end up doing the full record ourselves. And hey, what if we documented the whole process? Like a poor man’s Sonic Highways. We could make little videos and do a podcast.

And then it clicked. This was exactly the kind of project I’d been wanting to produce. And it just happened to align with a dream I’ve had since I was 12 years old.

* * *

When Airplane Mode launched I felt like I undersold it. To most people who follow me or read my blog I’m either an app designer or a guy who makes videos about design-related things. So when I say, “Here’s a new podcast about my band,” it’s easy to see why people would think that this is another side-project.

Working on song demos with Joe got me fired up in a big way, ushering in a creative energy I hadn’t felt in a decade. I realized that if I wanted a chance at being taken seriously, I needed to start taking things seriously. More of my free time went into music, and thanks to our partnership with Hover — our first-round sponsor for the podcast — more of my time went into all of the things that make music work as a business.

As the weeks went by and the band did more new things, I kept posting them to Twitter. As a result there has been a steady, marked decline in followers since then. In fact, any time I post something about Airplane Mode, at least a couple of people unfollow within an hour.

To be clear: I don’t blame them. Our interests no longer aligned in a way that kept them engaged. People who followed me expecting to see design talk and Apple commentary are welcomed to unfollow me when I change focus. Music is a tough business, and art is subjective. I don’t need or expect for everyone to like what I make.

Airplane Mode had become my primary public focus. Given that, and with so much time having passed since my last paid design gig, it seemed disingenuous to continue billing myself as a designer. So I outed myself as a professional musician.

* * *

Reaction has been interesting. Some people got the impression that I had abruptly quit the app business to go chase some naive dream of being a rock star. There have been whispers that “this won’t last”. Some people I’d count as friends have taken to joking about it behind my back. One of them even bought an Airplane Mode t-shirt and had it shipped to another friend — apparently as a gag gift. This friend unfollowed me a few days later.

But we’ve also made some new friends, found new followers, and have started building an audience outside the tech industry. People have written to us, thanking us for telling our story the way we do, saying that it has inspired or emboldened them to try new things or chase dreams.

What we’re trying to do is difficult. It’s hard to find an audience, it’s hard to book shows, it’s hard to sell songs, and it’s hard to get anyone who knows us from the software world to see us anything more than a novelty. And that’s exactly why I chose to say, in no uncertain terms, that I am a professional musician. Not because this is how I pay my bills (it isn’t — so far every penny we’ve made has been reinvested back into the band), or because it’s my only job (it isn’t — I still run Standard Broadcast), but because I want to hold myself accountable for this. I want it to be a matter of public record that I’m trying something big. I want it to be really goddamned hard to walk away. I want the shame of giving up to outweigh the difficulty of success.

This time, I’m doing this thing for real. No excuses. No more letting other people’s judgements or expectations hold me back.

Airplane Mode is a brand-new indie rock band from New York City. Our first recording is only a few months old, and the current lineup has only existed since October. Hell, we haven’t even played a show with all four of us on the same stage yet. But in that time, we’ve released 9 episodes of our podcast, put out a 7-song EP, played shows in three different countries, put out two music videos with tens of thousands of views, and lined up sponsorship deals — a minor music business innovation — which will take us through March of 2016.

It would be insane for me to claim that we’re destined for success, but I feel really good about what we’re doing and how it’s all coming together.

When I have to do things like set custom MX records to get our email hosted on Google apps, or when we build a custom iPad app to drive the click track for our set list at practice, or when I design our logo and branding in Photoshop, I’m thankful for every job I’ve done in the last ten years.

But long before I was a UNIX admin, a sales engineer, a designer, a podcaster, a YouTuber, or a content producer, I was a musician. And the truth is that I’m allowed to be all of those things. Or none of them. It’s my choice.

It’s absurd that I’ve let other people define me at all.

* * *

There will always be excuses for procrastinating. There will always be responsibilities. There will always be easier wins. There will always be jerks, bullies, and nay-sayers; people who don’t understand, or think that other people’s dreams are stupid.

Twenty one years ago I picked up a guitar for the first time and set out to learn something new, despite what the cool kids were listening to.

Ten years ago I let a single personal relationship define me, and tried too hard to be an adult while my band collapsed around me.

Six years ago I started work on a project I loved, and I was almost passive-aggressively bullied into giving it up by the cool kids, whose own dreams were limited to what seemed immediately attainable.

I’ve wasted too much time worrying about what other people think. I’m done conforming to someone else’s standard of “adult”, and I’m done trying to be one of the cool kids. This is my story, and I get to decide what happens next.

Going pro with music has been, and will continue to be, a slow gradient. I’m not turning my back on anything, least of all the many, many great people I’ve met in the app business, and I still have my hands in a few projects. I’m just going to try something else for a while. The one thing that has ever really made me happy.

Wish me luck.