202. The del.icio.us Story With Joshua Schachter

Brian McCullough introduces the episode as a deep dive into the history of the internet, with a focus on his interviews with early internet pioneers. He explains the origins of this podcast as part of his broader work, including his book 'How the Internet Happened'. He mentions that this episode features one of the original guests, Joshua Schachter of del.icio.us, and notes the long history and influence of the show, with nearly 300 hours of content and millions of downloads.

Josh recounts his first exposure to the internet before the web, through USENET, bulletin boards, and early messaging systems like Zephyr. He vividly describes his initial encounter with mosaic web browser while at Carnegie Mellon, which he vividly remembers as the first time he saw a graphical web interface, predominantly with images, marking the beginning of his deep involvement with web development.

Josh discusses creating Mimple in 1998 as an early link blog or bookmark tracker, emphasizing its role in personal and group memory. He explains how he developed tagging initially for organizing links across various projects and later for public sharing via his tool Muxway, a precursor to delicious, which enabled tagging and visual representation of links. These systems played a key role in early web content organization.

Josh details how he transitioned from Mimple and Muxway to developing delicious in 2002-2003, aiming to help users organize and share web links via tags. He highlights the social features like following other users and subscribing to tags, emphasizing delicious’ role in shaping early social bookmarking and collective knowledge sharing. He reflects on the site's explosive growth, its technological challenges, and the beginnings of its influence on later social media.

Brian inquires about the commercial aspects; Josh explains how delicious grew rapidly without traditional marketing, attracting VC interest. He discusses raising funds, scaling issues, and the eventual acquisition by Yahoo, triggered by the company's rapid growth and market interest. Josh shares insights about the internal struggles at Yahoo, the company's culture, and how these affected the product’s direction and his experience.

Josh discusses the ambiguity around what 'Web 2.0' actually meant, viewing delicious as a pioneer in user-generated content, tagging, and social bookmarking. He talks about the influence of delicious and early web ideas on modern media, social platforms, and user interaction. He reflects on how foundational concepts like tagging and personal memory systems continue to influence technology and web design.

Josh shares his ongoing experiments with art, racing, robotics, and software development. He mentions his involvement in prototyping new ideas, indicating his deep interest in the future of technology, creativity, and physical computing. He also notes his role as an investor and his efforts to build or revive innovative projects, hinting at ongoing engagement with cutting-edge tech.

Josh recounts his experience advising the TV show 'Silicon Valley', including scenes and actor interactions. He offers reflections on dealing with corporate culture, startups, and the importance of focus and execution over office politics. His anecdotal insights aim to help new entrepreneurs understand the complexities and realities of tech innovation and corporate environments.