AI, Google Docs, and the messiness of innovation, with Microsoft Deputy CTO Sam Schillace

·44 min·4 clips

Sam Schillace predicts the next few years will focus on AI applications, not just better models.

The episode features an interview with Sam Schillace, deputy CTO at Microsoft and author of 'No Prize for Pessimism'. Host Todd Bishop introduces Schillace, who explains his book's thesis against pessimism in innovation. Schillace discusses how younger generations face barriers like social media's curated success, hindering messy experimentation. He recounts the story of Google Docs, starting as a prototype in 2005 with technical challenges like collaboration and browser limitations. Schillace describes selling to Google and the difficult transition to their infrastructure. The conversation shifts to AI, where Schillace compares it to the early internet era, noting overreach and misapplication. He details his work at Microsoft on AI tools like the Semantic Kernel and 'infinite chatbots', including issues with 'hate bots'. Schillace emphasizes AI's need for better tooling and applications, predicting a focus on experience over models. He explains concepts like RAG and RLHF, sharing anecdotes about AI quirks. The episode concludes with Schillace's view on AI creating user value through semantics and meaning.

As heard by us

GeekWire treats this as a practical conversation about AI work, platform shifts, and the hard rebuilds behind them.

GeekWire frames the conversation with Microsoft Deputy CTO Sam Schillace as a clear look at where AI work is heading: applications, plumbing, experience, and the discipline of choosing problems carefully.

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Why you'd press play

If AI plumbing sounds more useful than AI theater, this one speaks your language.

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