“Nobody will know what the hell goes on in my mind from the music, but for me it feels like I'm naked.”

Since the 1975 release of his seminal ambient record Discreet Music, Brian Eno has been creating “generative music.” The producer builds generative systems by feeding sounds through algorithms in software of his own design. The string of resultant music is endless and ever changing, subject to the software's infinite permutations. 

In creating his 2017 record Reflection, Eno spent weeks listening to the output, examining its interplay with life in various situations and then adjusting it to his liking – before committing to the iteration that eventually became the LP. "It's a lot like gardening," Eno wrote. "You plant the seeds and then you keep tending to them until you get a garden you like."

Six years later, as alarming developments in artificial intelligence have us oscillating between bouts of awe and existential despair, it’s worth revisiting the idea of Eno’s generative music. He showed us there can be healthy points of interaction between human and machine, and the collaborative output can be beautiful. Can we hone in on that balance as we move forward?

That hope was on my mind when I spoke with Milo Lombardi, the artist known as Nifty Sax who guides the music non-fungible token (NFT) accelerator Nifty Music. When the pandemic crushed live gigging and the livelihoods of millions of musicians – including his own – the Italian artist seized an opportunity to explore blockchain technology as a means of building a new revenue stream, becoming an early music NFTs pioneer.

In time, his experiments evolved into full-blown roadmaps – guides that have been customized to kickstart the web3 careers of many an intrepid artist. Today Nifty Music’s drop structure and four-tiered approach is a tried-and-true method oriented around education, community building and generating actual sales, and it all started with a genesis project that tied “human generative music” to the technical underpinnings of the blockchain. 

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Lombardi is the child of opera lovers and amateur vocalists, so he was always encouraged to pursue music. By age 11 he was already at conservatory, diving into the rigors of theory and classical training. Eight years later he left the academy a talented saxophone player and started building a career in music.

His path has included stints as jazz quartet leader, musical theater director and sideman for funk and “entertainment bands” that played music from the seventies – “all this kind of stuff where saxophone is needed,” he told me recently. 

But when the pandemic hit, all of his work suddenly dried up. He was forced to reckon with a grim reality: “I've never done anything else,” he said. “I never had any other job, so I'm useless at other stuff.” 

To make ends meet, Lombardi started composing music to sell to advertisers – something he’d done in the past. Then he came across NFTs and saw visual artists selling their work using interesting – and lucrative – mechanics. 

“When I saw that artists were selling art, I thought, why not music?” he said. “This seemed like something similar where I could sell music, but I could actually make the music that I wanted to make. I didn't have to make some random, cheery music for advertising. But nobody was selling music [this way], so it was a bit of a gamble.”

His genesis project was grounded on a wild idea – to generate songs by an “algorithm” via music programming (i.e. the aggregate of Lombardi’s 25 years of study and musical experiences) stored in “human wetware” (i.e. Lombardi’s brain).

“I thought the best way to do it would be to just let go of control and let my training take over,” he said. “Because I studied so much music, there's so much in [my brain] that can be accessed – basically there is a structure in there, an algorithm. But I didn’t have the key, so the key was the psychedelics. I just had to relinquish control, let go and see where it went.”

Using psychedelics, Lombardi channeled his streams of consciousness, planting seeds of ideas and gardening them to some tacit end. The effort resulted in a hundred unique recordings. “It opened up a lot of doors that I normally wasn't checking out. It was really, really vulnerable because some of those pieces are very weird and kind of revealing,” he said, “which is ridiculous – nobody will know what the hell goes on in my mind from the music, but for me it feels like I'm naked.”

Each of the hundred tracks was minted onto the Ethereum blockchain as a unique 1:1 NFT. “I was releasing one every single day, which would've been a good idea if I had already a bit of a following,” he admitted. “But I started the Nifty Sax account with zero followers, so I literally started to release music every day to zero followers.”

Little by little, people started to take notice and the project started to garner attention. “I did a few podcasts where people were curious about it – they were like, ‘oh, you're making collectible music. How does that work? How can you collect music?’ Somehow people still didn't understand that, because it was basically the ‘right click save’ argument,” he said, referring to the skepticism that NFTs’ hold actual value, given that someone could simply create a copy of a digital image with one click. 

“‘Oh, if I could listen to the music, why would it be collectible? Why would I buy it?’ [they asked],” he said. “It's just so ingrained into people's minds that music was free.” 

Streaming – the industry’s bid to recapture some of the immense value that was being lost to platforms like Napster and The Pirate Bay – is responsible for formally cementing the notion that music should be free or almost free. But streaming really hasn’t been around that long – perhaps the cement’s not completely dry and on-chain music can help resurrect our accepted pre-streaming, pre-piracy reality that music shouldn’t be free. “It was exciting for me,” he said, “the fact that I felt like I was at the beginning of something really big and I just wanted to surf the wave and stay afloat as long as possible.” 

Lombardi did more than stay afloat. He started dreaming bigger, enlisting a developer friend to help him start building a marketplace around this new technology, and he got to work on his second project, Spheres, a collection of solo saxophone music expressed in 55 unique, audio-reactive tokens. Minted in September, 2021, Spheres was one of the first projects to blind mint single-instrument music as ERC-721 tokens and use rarity metrics. It sold out in less than 12 hours, earning Lombardi 30,000 Euros in a single night.

Read more: Oh La La Wants to Aggregate Music NFTs — Are Musicians Ready?

“Of course it didn't happen overnight – I was working right up to it for like six months, but still…” he said. “So I thought, ‘let's do one part of the marketplace that was going to be like an agency. Let's do just that first – we don't have to do the marketplace. We're gonna help [artists] out and create the project with them, making sure that it's set up in a way that will be successful as far as we know, like we put really everything we know into it. And yeah, those projects were successful – they were insanely successful.” 

Alongside co-founder Robin Spottiswoode – whose artist name is WeiZ – Lombardi turned the project into Nifty Music. Leading web3 artists like Rae Isla, Josh Savage and Violetta Zironi have all since sold out releases through the platform, using their strategies to launch bespoke projects that became the bedrock of their on-chain careers.

Isla’s Rocks and Zironi’s Moonshots are examples of the fully custom, built-from-scratch releases built through Nifty Music Pro, the organization’s premium offering. “We get together every week and we figure out a way to make it happen,” Lombardi said. “We create the project around the artist’s personal brand and the music – to make sure that that will be the foundation of the artist's career in web3.”

Beneath Nifty Music Pro are another three layers: a music NFT marketplace (yet to be released to the public), an academy designed to educate curious artists on the culture and mechanics of on-chain music, and the floor drop – tradable music NFT collections they call “digital vinyl” that help artists build small communities of highly engaged collectors.

Scaling these efforts, though, is difficult. For the time being it’s still a manual process managed entirely by Lombardi and Spottiswoode. And as they continue to build and begin to explore partnerships that will help expand Nifty Music, they continue to deepen their perspective on how the blockchain will ultimately affect the music industry.

Lombardi sees two potential futures. “One is that this will be completely disruptive,” he said. “We're not gonna be calling them music NFTs anymore. It's just making music and it's gonna be web3 for everyone. That's possible.

“But as things go on,” he continued, “I feel like this is going to be something that’s more geared towards niche music that doesn't really have a space in the normal economy, because maybe it's weird – maybe it doesn't hook you in the first 10, 30 seconds.

“The more time I spend in web3, the more I see it going that way because I see already we are starting to race to the bottom,” he said. “So this is more like a safe environment for weird music – this little garden of weird creatures.” 

To varying degrees, both outcomes are improvements. Option two is clearly a smaller shift, but still significant. Streaming platforms categorically devalue the weirdos. Few people are going to listen to Karlhein Stockhausen or John Zorn or LaMonte Young on a regular basis – their music is challenging and often dissonant, and that’s the point. Stream counts shouldn’t dictate the value of their music.

Without LaMonte Young, there’s no Velvet Underground. Without Velvet Underground, no Sonic Youth. Without Sonic Youth, you probably don’t get Nirvana. You get the point. Zoom outward from any artist you love and you’ll eventually find a cadre of influential weirdos who made them more interesting. We owe them a great debt – all those pioneers who grant creative license by doing something yet undone, so that the artists that come next have more expansive territory to wander.

Count Lombardi amongst that group. By going first, he created precedence and a path to follow. Even if ultimately the result is a garden for weirdos, that’s a win. But perhaps we can dream bigger – maybe an entire forest of fiddling folk next to tree-lined raves where theater punks write symphonies for hundreds of guitars and psychonauts channel the cosmic fidelity of their own subconscious. A place where the Eno acolytes sew generative seeds of sound, tending them into chordant gardens of their own algorithms, teeming with rich, bizarre musical life, endless and ever changing.