Episode #55: From Justin.tv to Claude Hacks: Lessons in Tech, Money, and Security
In this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to explore the financial and technical foundations shaping today’s AI and cloud economy, from the staggering scale of CapEx and depreciation schedules to the sustainability of investments by Microsoft, Meta, OpenAI, and Anthropic. The conversation traces historical precedents like the fiber boom, Google’s rise, and the pivot from Justin.tv to Twitch, leading into a discussion of venture capital shifts, IPO trends, and the enduring importance of the “rule of 40.” They also examine Cloudflare’s emerging role…
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