What Does “We Are All Musicians Now” Actually Mean? [WAAMN Prologue]

My favorite fintech startup founder explains.

This is the weekly installment of my new book, We Are All Musicians Now. To make sure you don’t miss future serializations, subscribe here. Below you’ll find the Prologue. Enjoy!

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In 1997, 12-year-old me walked into a Blockbuster on 56th Street and First Avenue and emerged with the first three albums purchased with my own money: Sublime’s self-titled album, the Titanic soundtrack and Puff Daddy’s classic No Way Out. One of my favorite tracks on the latter was “Been Around The World,” which sampled the David Bowie classic “Let’s Dance”—and introduced me not only to the Thin White Duke, but to the very concept of sampling.

I soon came to realize how often musicians borrow, so it’s only fitting that I’m now sampling the phrase “We are all musicians now” from my dear friend Jon Bittner. We served as co-business managers of the Yale a cappella group Out of the Blue—no, it was not like Pitch Perfect; yes, I’m a big nerd—and the experience kicked off my fascination with the intersection of business and music. We toured from Texas to Tribeca so we could fund the production of our 2005 album No Pun Intended. After a grad school detour to Harvard’s physics program, Jon founded the bill-sharing app Splitwise, which now boasts tens of millions of users (I’m an investor).

When I say we are all musicians now, here’s what I mean: the vast majority of professionals find themselves in sectors affected by major disruptions that arrived first in the music business. The shift from physical retail to online sales, for example, shuttered the aforementioned Blockbuster decades ago (it’s now a TD Bank)—and the music industry was among the first to experience the unimaginable speed and transformational power of the internet. 

When Jon says we are all musicians now, he has something a little more specific in mind. His experience is informed by years spent running a consumer internet startup, raising nearly $30 million from firms such as Insight and Greylock. During that time, he pitched dozens of venture capital outfits who grew increasingly interested in working with celebrity investors and entrepreneurs (as much for their social reach as the connections and expertise they bring when it comes to courting consumers, as I wrote in my recent book, A-List Angels).

“Music is one of the most interesting and earliest cases on the internet of trying to monetize fame, monetize fans, and this imbalance between the sort of influence and power that people have versus how easy it is to charge for things,” Jon explains as we stroll the Blackstone Boulevard in Providence, the city where he founded Splitwise. “Everyone on the internet figured out you need to have something good and free to share.”

Jon and I walk this route whenever I come to visit him in Rhode Island, usually meandering along in the dark while peppering each other with half-formed ideas. The Blackstone, as it’s known locally, has been the site of many conversations about the premise that we are all musicians now. According to Jon, that idea came to him after reading my 2011 Jay-Z biography Empire State of Mind (the newly-updated “Billionaire Edition” came out several weeks ago). The book made Jon realize how much of Jay-Z’s success came from parlaying his musical achievements into all sorts of other businesses—and what that meant for everybody else.

To Jon, Jay-Z’s story—and the story of musicians as a group—offered a path through one of the great dilemmas of the consumer internet: how do you get people to pay for something that feels like it should be free? 

In a way, this is a trick question. Jay-Z’s music has always been available in some places for free (from radio to Napster and beyond), but the name recognition that came with it helped him bank much more on the road—and land nine-figure checks when selling controlling stakes in his clothing line and champagne brand.

One might say his earnings from actual music over the years are much like a startup founder’s salary: insubstantial compared to the potential long-term benefits of ownership. “Fuck rich,” Jay-Z declares on the song “No Hook” from the American Gangster album. “Let’s get wealthy.” Of course, there’s no business without hits, and that goes for musicians and startup founders alike. 

“Music is very memetic, in terms of earworms, beats, and hit songs,” Jon says. “I think the internet and music are driven by memes in a similar way. Something is either viral or it isn’t. It’s fickle and hard to engineer … one lesson, as I have understood it for Splitwise, is to keep experimenting on something until you find that the thing that people want to share organically.”

Similarly, my whole Substack enterprise won’t work unless I can capture that same sort of energy. The free weekly posts are like my version of radio, serving to whet the appetite of my readers and hopefully convert them to paid subscriptions for the weekly installments of WAAMN, something like an exclusive fan club with benefits like concert presales. But, like Splitwise, it won’t scale unless I can find that viral element.

“It just feels like everything follows music,” says Jon. “Music business journalism in particular … has been a window into startup land and what’s going to happen in the consumer internet. And I don’t know what that implies for the next ten years of business on the internet. But it does feel like, to the degree that everyone in Gen Z wants to be an online content creator, we are all musicians now.”

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