Episode 2259: Idealab founder Bill Gross on what's he's learned over the last 20 years

Few innovators have had a better front row seat on the internet revolution than Idealab chairman Bill Gross. Having founded Idealab in 1996, Gross has been a participant in every wave of digital innovation - from Web 1 and 2.0 to Web 3 and today’s AI revolution. He’s also been a frequent speaker at events like DLD, the Munich based annual conference which is celebrating its 20th anniversary in January. And so, having visited Gross at his ultra cool Idealab offices in Pasadena, I asked the serial entrepreneur and investor to reminisce about the last twenty years of tech history. What were his greatest successes and failures? And how fundamentally different is today’s AI boom from the other cycles of innovation that he’s experienced?Bill Gross founded Idealab in March 1996. Bill is a lifelong entrepreneur, starting his first solar business in high school. After graduating from the California Institute of Technology, Bill started GNP Development, Inc., which made a natural language product for Lotus 1-2-3 called HAL. In 1985, Lotus Development Corporation acquired GNP. In 1991, Bill started Knowledge Adventure, an educational software publisher that was eventually sold to Havas/Vivendi. Bill serves on the boards of directors of numerous companies and is also a member of the Board of Trustees of Caltech and the Art Center College of Design. Bill received his B.S. in Mechanical Engineering from Caltech.Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best known broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running How To Fix Democracy show. He is also the author of four prescient books about digital technology: CULT OF THE AMATEUR, DIGITAL VERTIGO, THE INTERNET IS NOT THE ANSWER and HOW TO FIX THE FUTURE. Andrew lives in San Francisco, is married to Cassandra Knight, Google's VP of Litigation & Discovery, and has two grown children.Keen On is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe