HeyJaredStewart Squared
Stewart Alsop III reviews a broad range of topics with his father Stewart Alsop II, who started his career in the personal computer industry and is still actively involved in investing in startup technology companies.
- Indexed episodes, last 90 days
- 12
- Latest publication
- Sep 24, 2026
- Audience
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- Earliest in this view
- Jul 9, 2026
Latest episodes
Episode #108: Cybersecurity vs. Existential Risk: What Anthropic Won't Tell You in Their IPO (opens the original)
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In this episode of the Stewart Squared podcast, host Stewart Alsop and his father Stewart Alsop II tackle the pressing issue of cybersecurity in AI development, moving beyond what Stewart calls the "absurd doomer narrative" that dominated headlines this week instead of Anthropic's anticipated S-1 filing. The conversation ranges from zero-day vulnerabilities and the evolution of network security to the existential risks posed by foundation models, including the recent Hugging Face incident where
Episode #107: $2 Trillion, No Debt: Anthropic's Answer to SpaceX's Risk Factors (opens the original)
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In this episode of the Stewart Squared podcast, host Stewart Alsop and guest Stewart Alsop II dig into Anthropic's upcoming IPO and the rapidly shifting AI landscape following the recent releases of OpenAI's Astra and Anthropic's Opus 5. The conversation explores how both models have reached a level where it's becoming difficult for even intelligent people to evaluate their capabilities, with OpenAI leaning heavily into visual computing and 3D graphics while Anthropic focuses on language and mat
Episode #106: The $30 Trillion Question: Inside Anthropic's Audacious IPO Play (opens the original)
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In this episode of the Stewart Squared podcast, host Stewart Alsop and guest Stewart Alsop II tackle Anthropic's upcoming IPO and what it means for the broader tech landscape. They compare it to SpaceX's recent public offering, examining how Anthropic's projected $30 trillion in potential revenue stacks up against current performance and whether the company can sustain its growth amid mounting customer frustration with usage limits and pricing. The conversation ranges from the mechanics of SPACs
Episode #105: Beating OpenAI at Their Own Game: Our Case, and the Filing That Settles It (opens the original)
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In this episode of the Stewart Squared podcast, host Stewart Alsop III and his father Stewart Alsop II dig into the unprecedented AI infrastructure buildout happening across big tech, with Google raising $85 billion in equity and floating bonds to fund data centers while questions mount about whether this mirrors the dark fiber overbuilding of 2001. They analyze the diverging paths of Anthropic and OpenAI, with Anthropic's revenue reportedly hitting a $65 billion run rate—now surpassing OpenAI—w
Episode #104: 36,000 Companies, One Metric: What DPI Did to Private Equity (opens the original)
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In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his father Stewart Alsop II to unpack how private equity, venture capital, and growth equity have evolved—and possibly converged—since the 2008 financial crisis. They explore how massive liquidity injections in 2020 fueled a PE buying spree, why the distinctions between investment categories are blurring as everyone gets measured by the same metrics (DPI—distributions per investment), and whether the whole system i
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