This episode explores the parallels between the late 1990s telecom bubble and the current AI boom, focusing on the massive infrastructure investment driving both. Against the backdrop of the Telecommunications Act of 1996, which spurred deregulation and competition, the conversation delves into the rapid growth of digital traffic and the subsequent influx of debt financing into the telecom sector. More significantly, the discussion highlights the role of key regulatory decisions, such as wireless number portability and access charges, in shaping the competitive landscape. For instance, the elimination of access charges for dial-up internet proved crucial for the growth of companies like AOL. As the discussion pivoted to the AI boom, the interviewee draws parallels to the telecom era, noting the similarities in massive infrastructure spending and the emergence of key players. However, a crucial difference is highlighted: while the telecom boom involved a significant amount of debt, the current AI boom is characterized by a greater involvement of established tech giants. Ultimately, the conversation concludes with insights into the long-term value of infrastructure investments and the potential for established cloud providers to dominate the AI landscape.