Chapter 1: The Nostalgic Revival of Turntable.fm

Typically, the first email I encounter each morning doesn't elicit a dramatic reaction. However, receiving a message stating, "Hey! I plugged in the Turntable servers" certainly did. It was from Billy Chasen, the original founder and CEO of Turntable, and it contained a password that I eagerly entered into my browser. Turntable.fm was akin to the Clubhouse of its time—a platform with social features that captured the joy of shared experiences in a fresh way while revitalizing a familiar concept.

As music transitioned into the digital realm, it paradoxically became isolating. While having access to a vast library of music in the cloud was a significant advantage, it came at the cost of communal enjoyment, transforming it into a solitary endeavor. The shift was not due to consumer preference but rather the constraints of DRM, negotiations with record labels, and financial factors. Turntable quickly reintroduced the concept of listening parties, and it was an absolute blast.

In the spring of 2011, links to join sessions were circulating among friends. "Come join me here now!"—that was the invitation on a late Friday night as a group of enthusiasts spun classic hip-hop tracks from our youth. Gradually, more people joined in, culminating in Union Square Ventures leading a funding round, which also saw me becoming an angel investor in this exciting new platform.

The digital music landscape had shifted to a more solitary experience.

Despite the excitement, the business model struggled. Record labels were hesitant to foster collaborative discussions, and the team often lacked a unified direction. Eventually, Turntable ceased operations. Over the years, Billy and I maintained a loose connection, witnessing each other's journeys and adventures. He has always had an uncanny ability to anticipate needs and transform them into products—sometimes just a bit too early. However, the bonds formed during such enjoyable projects tend to endure beyond the startup's life. (Interestingly, my connection with Sahil also stemmed from Turntable. He was a young talent who had just developed Pinterest’s mobile app, and we made a concerted effort to recruit him for Turntable. Despite our best pitches, he opted to pursue his own vision, which ultimately became Gumroad. It's indeed a small world.)

Occasionally, Twitter threads pop up, filled with nostalgia for Turntable and other long-lost products that have yet to find adequate replacements (RIP Google Reader). While someone might suggest a collaborative playlist tool, none could replicate the unique magic of Turntable.

Now, I find myself enjoying the nostalgic ambiance of the iconic "I ❤️ the ’80s" room, reminiscent of those earlier days. It feels inviting, warm, and lived-in—the hallmark of a quality consumer product. While some startups grapple with achieving product-market fit, Turntable had it, disappeared for nearly a decade, and has now revived itself with the same appeal. Incredible!

What lies ahead? Will Turntable evolve into a "company" once more? Is this merely a fleeting period of joy before server costs become unmanageable or the code starts to falter? The uncertainty is part of the excitement. Right now, it's like 2011 all over again, and I'm eagerly waiting for my chance to DJ again. Time to bring back my monkey avatar!

Chapter 2: The Future of Turntable.fm

Section 1.1: The Digital Music Landscape

The evolution of music consumption has led to an increasingly solitary experience, even with vast libraries at our fingertips.

Subsection 1.1.1: The Rise and Fall of Turntable.fm