Diego's shipwreck

Every few months I’d meet Diego at the Palo Alto train station and we’d go for a walk, get some dinner, catch up. Diego was impossible to extract from Palo Alto – I can’t imagine him anywhere else, even though I know for a fact he’d once worked at IBM in Westchester, not far from where I grew up, and studied at Drexel, not far from where I went to school.

We’d always time things perfectly. As I’d step off the train I’d see him loping along Alma Street, red sports jersey, who knows what team. Cargo shorts, Vibram shoes. Wraparound sunglasses. I’d wave, he’d nod his head and smile. We’d meet at the corner and he’d greet me in his mellow nasal way: “Well hello.” Meeting up with Diego always felt like a scene out of Ocean’s Eleven.

We’d head up Lytton Street and quickly get into it. For the last ten years Diego had more or less been working on one project, essentially impossible to describe beyond this: a full-stack reimagining of the way information was stored, visualized, and shared. Any given layer of that stack would be an ambitious undertaking by itself, worthy of an entire company. Inventing a distributed peer-to-peer architecture that would do away with the limitations of the cloud. Collapsing email, photos, and calendaring into a single application. Designing a “virtual reality-first” interface that would still work on mobile and desktop. Using blockchain to create a trust system that would solve spam issues and storage costs.

The project had gone through many names, and as Diego prepared to launch, he started calling it n3xt. Other than receiving sporadic help – from a designer in Argentina, a programming buddy, me – Diego worked on n3xt alone.

Not that he wanted to. Diego wanted to build a team, and was frustrated that he couldn’t. I was frustrated too – I wanted to work with Diego, admired him greatly, believed in his vision. But it was too sweeping, too ambitious, too uncompromising. Too intimate. Diego was an artist, and everything he produced – from the prose to the code to the iconography – stemmed from values that were uniquely his. I tried to help, and whenever he’d come up with a direction that seemed like a feasible slice of his vision – a bug tracking system that ran on version control, or a direct-to-audience file-sharing app for musicians – I’d encourage him to pursue it. “Yes, that could work,” Diego would muse. But within days, he’d have floated back to the big picture like a moth to flame.

Jewel, in her elegy for Tony Hsieh, says, “Death is so shocking. I don’t know how other people feel about it, but the brain can’t comprehend why you can’t just call that person anymore, and the heart can’t understand why you can’t just hug that person anymore.” I’ve been missing Diego more and more over the last few months because we are now long overdue for a walk, and my brain and my heart can’t comprehend that there will be no more walks.

Diego’s death, from a heart attack at age forty-something, was at once entirely unexpected and strangely foretold. There was a kind of precarity to his life – living alone, toiling away in isolation, harangued by health ailments.

When I got the news the first thing I felt was shame, shame because he’d needed help and I’d let him down.

The pandemic meant an in-person memorial was impossible, so we gathered to remember him on Zoom. I dropped in to see screenfuls of familiar faces from Ning, the forgotten social networking startup where I’d met Diego. My four years there feel like the plot of a thrilling four-season television series. We had it all – the beautiful and headstrong CEO, boardroom drama, idiosyncratic engineers, a rowdy support team, celebrity customers, viral growth, and of course the antisocial architect – played by Diego – with the algorithm for bringing the world together.

And now we were having our reunion episode.

I figure everyone considers themselves to be Jim Halpert in the dramatization of their work life, but my role was more Halpertian than most. In the early days – this would have been season one – I held an entry-level role on customer support, responding to people who’d forgotten their password and occasionally writing blog posts or FAQs. On the support team we called Diego the Dream Crusher for the effortless way he’d take one of our product requests, long-researched and well-defended, and not only not add it to the roadmap but assure us in no uncertain terms that it would never, so long as he were alive, be considered. Sometimes I’d sit it on intense late-night meetings and hear Diego rail against the emerging consensus: “That will never work,” “Are you kidding?” “Now that’s really stupid.”

Diego could be intimidating. But the thing about Diego was he dismissed ideas, never people. And the ideas he dismissed most were the ones that undervalued people. He was adamant about banning the word “users” from our codebase because it was dehumanizing. Diego was no misanthrope. He only disliked people in the aggregate.

After two years I’d done stints in support, customer success, and marketing – the kind of rotation that some companies design, but at Ning was borne out of chaos. When Diego suggested I work with him as a product manager, I was excited but intimidated. Didn’t product managers have computer science degrees? And he just sniffed in his dismissive way. “I can teach you. It shouldn’t take more than a few weeks.” And basically he was right. Diego taught me what he knew, plainly, without pretense, always assuming that I would figure it out. He told me to read Alan Cooper, Jef Raskin, Don Norman, Amy Jo Kim, Jesse Schell. He challenged me privately and always had my back in public. He believed in me.

It felt very, very good to have Diego believe in me.

So I came to our reunion episode ready to memorialize my private Diego, to reveal the sweetness, humanity, and humor beneath the prickly exterior. But this turned out to be the Diego that everyone knew. For hours people told stories of his mentorship, or how he made them a thumb drive of essential films (the Alien trilogy, Primer) before they packed off for military service, or about the time he tried to set the record for most espressos consumed in 24 hours. His genius was the last thing that anyone wanted to talk about.

What will happen to n3xt?

In Thomas Bernhard’s Correction, the narrator is tasked with organizing the papers of the architect Roithamer, who has died and left behind a massive manuscript describing the unfinished project which was his undoing. The narrator fears going insane himself as he pores over the manuscript.

Reckoning with the unfinished work that Diego leaves behind I find myself touching something like insanity, or at least a big case of vertigo. Ten years of blog posts, YouTube videos, GitHub repositories. Teasers, trailers, introductions, demos. Fragments of an epic vision, never fully realized.

The word that comes to mind is naufragio, Spanish for “shipwreck.” Diego’s English was perfect but let’s remember: even after being naturalized he was still an Argentine. From the land of Borges, that strange mix of the new and the decadent, hope and despair, beauty and death. And so I like to think of Diego’s legacy as un gran naufragio: imposing, inspiring, instructive, cautionary, magnificent, tragic.

Maybe someone will dredge up his work. Or maybe it will sink to the digital depths, becoming an artificial reef, food for others.

What will happen to n3xt? I’m not sure, but I know that the important thing to him was never a particular product, a technology, or even an idea. What Diego cared about was a better way of living: more intimate, more vivid, more humane.

In one of his other unfinished projects, a “blog novel” that he started in 2002, Diego writes:

The street feels surreal every time I arrive in it. Any street. Day or night, out of my apartment or out of the office. Nothing belongs to me, but nothing is distant. The sounds, the people, the asphalt, everything is immediate and close. I want to hold it all in one hand, then hide it in my pocket.

Or toss it away, maybe. As one would do with a penny, one of those that seem to persist in their attachment to pockets.

Throwing something away is the ultimate act of ownership.

Farewell, Diego. Stay close.

Cards: The Power of Cards, Episode 0, ft. Matt


Matt and I spend just about an hour waxing nostalgic on hyper-specific memories of the cards we bought, played, and traded. Featuring:

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