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

This week on the GeekWire Podcast, our guest is Sam Schillace, a deputy CTO at Microsoft and author of the new book, No Prize for Pessimism, the first title from Microsoft’s new publishing imprint, 8080 Books.

Schillace discusses the importance of optimism in innovation, drawing parallels between the early internet era and the current AI revolution. He also talks about his experiences as one of the creators of Google Docs, and emphasizes the value of tackling difficult, non-obvious problems.

Listen above, and continue reading for related links and takeaways. Subscribe to GeekWire in Apple Podcasts, Spotify, or wherever you listen.

Related links and coverage: 

• Sam Schillace’s Sunday Letters on Substack.
• Schillace’s No Prize for Pessimism custom GPT.
• No Prize for Pessimism on Amazon.
• GeekWire: Microsoft turns a new page in the book business with its own publishing imprint

Top takeaways

Schillace’s background and role at Microsoft: Schillace founded the startup that created Writely, which was acquired in 2006 by Google, where he and his team built Google Docs. He joined Microsoft in September 2021 as a deputy CTO, part of Chief Technology Officer Kevin Scott’s organization.

• Scott and Microsoft CEO Satya Nadella initially gave Schillace three objectives: improving horizontal infrastructure (i.e., across different Microsoft divisions); enhancing Microsoft’s consumer culture and products; and creating another new category of technology, similar to his past work on Google Docs.
• Schillace likes to say he gets to play “mad scientist,” working with his team on a variety of experiments and projects with the potential to inform or contribute to the company’s products.
• He also contributes to the leadership group for Microsoft Windows and Office, offering advice and input based on his past experience and ongoing work as part of the CTO’s office.

Innovation mindset: Schillace says optimism and a willingness to embrace messiness are crucial for encouraging innovation, especially with emerging technologies like AI.

• Groundbreaking technological advancements often come from tackling challenging, messy problems with a “what if” mentality rather than falling into the trap of a “why not” attitude.
• Growing up in a world of curated online experiences and pressure to succeed, younger generations tend to be more pessimistic about technology and less willing to experiment. One goal of the book is to help aspiring entrepreneurs shake this tendency.
• The innovation mindset is particularly relevant in the age of generative AI, where technology’s rapid evolution demands an experimental approach to problem-solving.

Going AI native: Generative AI has the potential to transform technology in a way comparable to the shift from desktop to cloud software, requiring a rethinking of problem-solving and application development.

• While AI models will continue to evolve, much of the opportunity in the next two years will come from building the applications, user experiences, and infrastructure to harness those capabilities within specific domains.
• Developers need to adopt an “AI-native” mindset, looking at existing applications and longstanding problems and coming up with solutions in the context of AI’s emerging capabilities.
• Success in this new world will often be found in the middle ground between the precise rules of coding and the more nuanced, unpredictable nature of AI, or “the tension between chaos and order,” as Schillace puts it.

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Audio editing by Curt Milton.