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Jazz Pianist Greg Spero, A New Breed Of Record Exec, At Vanguard Of Big Changes In Music Industry

Greg Spero
Courtesy of Tiny Records
Greg Spero premieres new content each month on WRTI's Live Sessions page.

Piano players tend to be a cerebral, intellectually inclined sort. They are to jazz combos what pitchers are to a baseball team: enigmatic, mad scientist types who not only eschew orthodoxy but seem to have a reflexive aversion to it. They are both of this Earth and not, speaking our language but on a slightly different frequency, tending to be somehow left-brained and right-brained, type A and type B, fantastical and innovative, yet incisively, maddeningly logical.

When you take a look at pianist Greg Spero’s headshots, you first notice the kind of unruly mop of kinky dark curls suggestive of this heady, pragmatically eccentric, geek-chic archetype. Talking to him reveals that these superficial suggestions aren’t altogether baseless; he conveys an erudition that belies his age (36), communicating with the kind of professorial exuberance that turns young university lecturers into campus rock stars.

As an interviewer, you suspect you’re talking to the smartest guy in the room—and you know for sure if it’s just the two of you. But, in the manner of all really bright people, he doesn’t bludgeon you with it; he just sort of lets his other-levelness reveal itself, which it does pretty quickly. Spero’s mind, rather than being strained by a surfeit of ideas, actually hums along most comfortably in overdrive.

Then you hear him play and his music forces you to recalibrate your assumptions and premises somewhat. Though he may express his ideas in the manner of an intellectual, the ideas themselves may be born less of the head and more of the soul.

Musician and Unlikely Industry Disrupter?

In early 2020, at just 35, Spero started a record label, Tiny Records. In May 2020, Spero and Tiny launched the Tiny Room Sessions; each Friday, the label releases a new video of music recorded in its cozy Los Angeles studios. And every month since April of this year, one of those Tiny Room Sessions has premiered on WRTI’s NPR Live Sessions page—and will continue to do so, as they say in the world of fast-food advertising, while supplies last. [NOTE: It makes for a sort of fun coincidence that the home of the Tiny Room has partnered with the home of the Tiny Desk (NPR), but know that the Tiny Desk Concerts and Spero’s Tiny Room Sessions are, in fact, two distinct series.]

If that seems like a lot of musical output; if you worry that Spero and Tiny won’t be able to produce enough repertoire, enough variety, you should know this about Spero: he’s actually earned one of the most egregiously misused cliches in all of music journalism; he is a musical omnivore.

First, there’sSpirit Fingers, a Spero-led quartet whose 2018 self-titled debut Downbeat described as “a taut, lyrical style of fusion that falls somewhere between Return to Forever and solo Jean-Luc Ponty.” Which makes sense; Spirit Fingers’ drummer, Mike “Blaque Dynamite” Mitchell has played for years with Return to Forever co-founder and recently named NEA Jazz Master, bassist Stanley Clarke. Meanwhile, the group’s latest, 2020’s Peace, featuresLive Sessions-alum Jonathan Scales (steel pans) as well as Spero’s fellow Chicagoan Greg Ward (alto sax), on an album where Downbeat’s Philip Freeman recently—and memorably— described Mitchell as “…assaulting the kit like it’s done him some personal offense….”

Spero also plays—at least during the Tiny Room Sessions— with the entire roster of acts that cohabitate under the Tiny banner, which, incidentally, makes room for a lot of talented, different-sounding artists. Like guitarist Joe Marcinek, whose “Bella,” a comparatively straight-ahead tune with a Latin feel reminiscent of the Jim Hall songbook, premiered on Live Sessions back in June.

But so far, the most electric—and electrifying—of Tiny’s submissions have been from the Spero-led quartet Anthropoda. If you’re finding that your swag has been dragging, check out “Wanting,” “Green Light,” and, the latest, “Careless.”

Anthropoda is a propulsive force, foregrounded in contemporary instrumental hip-hop and R&B and drawing life from the Rhodes-heavy, funk-and-gospel-inflected music of jazz’s electric period. Every instrument, most especially Spero’s piano, is played as a percussion instrument. And with infectious, circular hooks, each tune establishes a strutting groove that builds velvet-coated tension.

Which makes sense, given Spero’s eclectic discography and a taste in collaborators that doesn’t so much transcend genre as disregard it. The son of musicians, Spero’s played with jazz icons like Arturo Sandoval and Buddy Rich; he’s also toured with and written music for pop and hip-hop acts like Halsey and The Weeknd. Just as likely to be influenced by Radiohead as Miles Davis, the one-time keyboardist for the Miles Electric Band actually cut a record proving exactly that, with 2010’s Radio over Miles.

The sophisticated ear will no doubt discern reverent nods to the fusionists of the ’70s and the Native Tongues cooperative of early ’90s, jazz-influenced hip-hop groups. And it’s no stretch to proclaim that Anthropoda, along with Jazz is Dead—the album series produced by Adrian Younge and Tribe Called Quest’s Ali Shaheed Muhammad—are at the vanguard of this particular “crossover” aesthetic.

But when speaking about, and especially to, Spero, one feels compelled to put a word like “crossover” between quotation marks; there’s the sense he finds it a cringeworthy, media-contrived concept most helpful to promoters and record labels and least resonant with musicians.

What may seem counterintuitive, though, is why a jazz musician with Spero’s convictions would want to become, for lack of a better appellation, a record exec.

“It’s a really good question that speaks to an even bigger question,” answered Spero. “One of the things that I’ve held as a tenet throughout my life is looking where I have some unique value to give. That goes back to having talent for piano, so I spent a ton of time building that because that seemed to be the unique value proposition that I had to offer the world.

“But right now in the arts—and maybe music especially—the world is changing drastically. The advancements in technology have transformed the landscape in which we do commerce and consume information in a way that changes so many opportunities for so many people, often for the better. [The recording industry] is changing massively and it’s being democratized; it’s giving more opportunity for people, with fewer gatekeepers, to get into the creative space and make a living and thrive.

“Because of this change in the landscape, there’s a massive opportunity to help people thrive and to help good music rise up.”

Foregrounding ‘Good Music’

Good music. That’s the operative phrase. Not good jazz music or good funk or hip-hop or pop. Just good music.

Talking to Spero, one allows one’s self to daydream of a much less strictly stratified musical ecosystem, where a term like “crossover” holds much less meaning because the island fortresses of genre are far less fortified and, instead, thought of as far more fluid, more malleable—or, perhaps, not even thought of at all.

Tiny, an imprint of Ropeadope Records focused on featuring emerging artists and ensembles from a variety of stylistic backgrounds, has proven a faithful manifestation of Spero’s ethos so far. The goal, at least of the Tiny Room Sessions, is ambitious yet pretty simple: to showcase the chemistry between all genres and jazz. That’s why you’re just as likely to find music there from electric bassist MonoNeon—the Nas, Thundercat, and Prince collaborator whose original work has been compared to that of John Cage—as you are from the combo of soul-pop chanteuse Carolyn Samuelson and folk band The Heartstrings Project.

Describing a collaboration as I just did, with style signifiers like soul, pop, and folk, feels like an indispensable part of how we must talk about music if we wish to actually communicate anything to other humans; all of us are hardwired to discriminate and classify, to draw distinctions, to place groups, people, and the methods by which we live, work, and entertain ourselves into separate bins. The most intelligent species yet, we’re limited enough to require artificial distinctions as a kind of Tums to aid in cognitive digestion.

And yet, the “good music” concept. Maybe we’re making things way too complicated. Then again, maybe what we’re seeking through music, while eternal, is too grand, too abstract to communicate in any other way.

“I don’t discriminate in music,” Spero says earnestly. “I think a lot of people are trained to discriminate in life and music and they don’t even know that they’re doing so. An amazing country song or an amazing classical or an amazing hip-hop composition or an amazing jazz composition—they all have the same basic tenets if you distill it down: melody, harmony, rhythm, use of motifs, and all these little micro-factions to…tell a story.

“But all these words we put together are all metaphors for things we can’t really describe in any other way than playing the great music. All this chunking of the metaphors that we can relate to other things we understand—they all point to a center, but it’s sort of like looking for God: whatever makes great music at its centerpiece, you can’t describe it in anything other than metaphors.”

How to Make Change Work for You? The Key, Spero says, is Not Resenting It.

Among the things one can know, however, is that when speaking with Spero, there are few clichés and little empty small talk. Like Larry David, he does you the courtesy of elevating the conversation. And music is often just a jumping-off point.

This is the same guy who speaks with a visionary’s zeal about the game-changing potential of NFTs (non-fungible tokens) and the extent to which such innovative new concepts might change for the better the paradigm of how the music industry interacts with both consumers and artists.

Any notion that supremely talented musicians cannot be savvy, intentional entrepreneurs is upended by the idea of Greg Spero. Democratization of the music industry and good old-fashioned American capitalism—guiding the best music and most talented artists to the top—are not mutually exclusive concepts to Spero; to him, the former begets the latter.

“It’s not that hard to do as long as you’re smart about it,” says Spero of managing a record according to his tenets of his paradigm-shifting brand of capitalism. “If you can come to terms with things like ‘the music itself is free.’ Smart artists like Chance the Rapper have known that for five, seven years.

People are making money in different ways and losing money in the ways they made money before. And it’s going to keep going in that direction.
Greg Spero

“Most people are still banging their heads against this wall of ‘I want to sell my record; I want to sell my record!’ But if you can recognize that Spotify is a marketing mechanism now, you can play the Spotify game and use it to aggregate audience and gain fans for something else that you would sell other than the music itself.”

So, then, what is that end game for an enterprising artist cum entrepreneur like Spero, if not just the music itself?

“I’ve been spending a lot of time since Covid hit working on an app for musicians that I believe can make things better for us,” says Spero, who worked in his early twenties in tech and business fields and in his teens had his own web development company. “It’s a new model of commerce that de-risks the content creation process.”

The concept came to him in the midst of hosting a piano channel on YouTube; with tens of thousands of followers, he found himself constantly responding to requests to play certain things and explain certain musical concepts to aspiring pianists. He was putting a lot of work into it and getting a lot of exposure but wasn’t generating much income from it.

“I was like, ‘Why do I struggle to monetize this? The videos are getting hundreds of thousands of views, and YouTube’s giving me like $10 a month.”

Spero figured out that his following was strong enough that fans would probably crowdfund some of what he was posting, but he realized just posting anything he wanted wouldn’t generate the crowdfunding; he’d have to post what they wanted.

“So I put together a mechanism where fans can submit ideas to me—like, ‘I want you to do a video on Oscar Peterson technique, or I want you to do a collaboration with Halsey on a jazz song’— and they upload their money and that money goes to me only after I deliver the video.

“It’s a pretty simple concept but nobody’s done it yet. And it opens up this giant marketplace of things, for any artist, of what their fans actually want from them.”

The way Spero sees it, this flips the currently prevailing model on its head.

“It’s the way people should be doing business in the music industry,” he adds. “An artist shouldn’t be trying to figure out what their fans want, putting in all the thought, investing all the money, doing it, and then trying to go through these over-saturated platforms like YouTube and Spotify to try and get it to them—and make no money. It’s like the worst possible situation for artists.”

Spero’s platform is called weeBid, and you can get a feel for how it actually works by visiting my.weebid.app. According to Spero, it will drastically reduce front-end risk to artists and align most closely to fans’ preferences.

A devil’s advocate might posit a concern that it could dilute individual artists’ creativity, especially those who thrive on improvisation. But, as Spero explains it, it’s not as though the app is a radio request show. One can just as easily request “an album of solo piano improvisations”—which just happens to be one of the ideas currently receiving crowdfunding on weeBid—as one could a request version of “Autumn Leaves” played in the style of Oscar Peterson. As long as it’s within the artist’s repertoire and musical capacity, the sky, in theory, is the limit.

“I truly believe this can change things for artists,” he says of weeBid’s concept. “It allows them to monetize their fans’ desires in a way that sidesteps these oversaturated platforms that aren’t paying people anything right now. But it’s also no detriment to the YouTubes and Spotifys because [musicians] can still put the music out on those platforms…they can still go through their traditional sh*tty deals.”

When Spero and I spoke in July, the app was still in its beta phase and not yet publicly launched on his website. But he encouraged me to share the private link with our audience and shared that some pretty notable musicians have already joined the platform—names like Quincy Jones and Herbie Hancock.

“Just some friends of mine that I’ve brought in,” Spero mentions casually. “People are crowdfunding things for Quincy Jones right now—and he’s into it!”

You’d assume savvy forces like Jones and Hancock are involved, at least partially, because they have an idea of the direction in which industry winds are blowing.

And Spero has plans to further monetize; that’s where the NFT part comes in.

“There’s also some stuff I can’t fully talk about right now,” hints Spero with a shred of I’ve-got-a-secret giddiness, “that has to do with NFTs and actual equity that fans will be able to get in things they crowdfund.

“Stay tuned for that; it’s going to be a really, really cool functionality that will allow fans of artists to invest in a way that they couldn’t before.”

As paradigms change in major entertainment industries, there are billions of dollars at stake and kings to be made. The Quincy Jones for this new age is out there, and it’s not hard to envision that person as a tech-and-business-savvy musician/producer like Spero.

But if Spero really wanted to monopolize all this insight, he’d talk about this stuff less; instead, he’s a pied-piper of paradigm change, inviting the artists he believes in—and all their fans—into a tent he believes will be big enough for all of them.

“People are making money in different ways and losing money in the ways they made money before,” Spero says with the glibness and analytical incisiveness of a senior analyst at Goldman Sachs. “And it’s going to keep going in that direction. So what I encourage artists to do is look toward the future, and don’t get resentful of the changing landscape. Because there’s a lot of money to be made out there if you can think outside the box and work hand-in-hand with the changing environment.”

Matt Silver is a journalist, commentator, and storyteller who’s been enamored with the concept of performance since his grandparents told him as a toddler that singing "Sunrise, Sunset" in rooms full of strangers was the cool thing to do.