Topic: Macromedia

Adam Curry recounts his financial history during the late 90s and early 2000s, including a $50,000 seed investment in Ask Jeeves that briefly ballooned to $65 million. He describes "burning money in the air" by flying helicopters and building a data center in Amsterdam. Despite the eventual market crash, Curry expresses no regrets about his "punk rock" approach to the dot-com era and his subsequent transition into podcasting.

The career of Kevin Lynch is traced from Macromedia to Adobe and finally to his new role as VP of Technology at Apple. The hosts question why such a high-level integration expert would move to Apple unless a major technological shift regarding Flash or video was planned.