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'.