Joshua Schachter, the founder of del.icio.us and a key figure in Web 2.0, shares his journey from creating one of the first social bookmarking sites to becoming a successful angel investor. He reflects on the early web, discussing the challenges of content creation and user engagement. The conversation dives into the evolution of social sharing and the impact of venture capital on media platforms. Schachter also addresses the hurdles of startup life, including data privacy and tech transformations that shaped the modern internet.