Joshua Schachter, founder of Del.icio.us and an angel investor, shares his journey through the tech landscape. He discusses the evolution of his bookmarking platform from a simple tool to a significant web asset. The conversation dives into the emotional complexities entrepreneurs face after a startup sells, including balancing newfound wealth with personal goals. Schachter highlights the intersection of technology and storytelling, emphasizing the importance of emotional intelligence in investing while drawing fun parallels to his experiences with HBO's 'Silicon Valley'.

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.