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How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

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Jan 11, 2024

Guest

Sam Schillace

In this engaging discussion, Sam Schillace, Deputy CTO at Microsoft and creator of Google Docs, shares insights from his remarkable tech journey. He delves into the evolution of Google Docs, discussing the value of embracing risk and the joy of creative problem-solving. Sam emphasizes the importance of optimism and playful experimentation in innovation, reflecting on Microsoft's collaborative culture under Satya Nadella. He also touches on why asking 'what if' can spark breakthroughs, urging listeners to pursue their passions for career fulfillment.

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ANECDOTE

First Google Doc

Sam Schillace has the first Google Doc, created in C# before Google acquired Writely.
It still works despite multiple backend and frontend migrations, containing a test message and a picture of Edna from The Incredibles.

question_answer

ANECDOTE

Stealthy Migration

Writely's migration to Google's infrastructure went unnoticed, even by Google.
Sergey Brin asked about the migration three days after it was completed.

insights

INSIGHT

Disruptive Innovation

Disruptive innovations are initially threatening because they challenge existing worldviews.
People tend to ask “why not” questions instead of “what if” questions, hindering innovation.

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The Evolution of Google Docs: A Case Study in Innovation

04:00 • 24min

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The Evolution of Google Docs

28:10 • 15min

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The Balance of Innovation: Playfulness vs. Purpose

42:55 • 5min

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Embracing Risk for Innovation and Fulfillment

47:55 • 25min

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Innovative Leadership and Creative Insights at Microsoft

01:13:18 • 9min

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A Culinary Tech Anecdote

01:22:28 • 4min

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Encouraging Innovative Contributions and Engaging with Ideas

Invisible Cities is a novel by Italo Calvino that defies traditional narrative structures. The book revolves around the conversations between Marco Polo and Kublai Khan, where Polo describes 55 imaginary cities he encountered during his travels. These cities are not just physical places but also metaphors for human experiences, desires, and the passage of time. The novel explores themes of memory, place, and the subjective nature of experience, highlighting how our perceptions of cities and the world are shaped by our personal histories and biases. The cities described by Polo are often reflections of his home city, Venice, and serve as vehicles for Calvino's commentary on human nature, culture, and the limits of communication.

Where Good Ideas Come From

The Natural History of Innovation

Steven Johnson

In 'Where Good Ideas Come From', Steven Johnson delves into the natural history of innovation by identifying seven key patterns: the adjacent possible, liquid networks, the slow hunch, serendipity, error, exaptation, and platforms. Johnson argues that innovative ideas often result from slow hunches that develop over time through interactions within 'liquid networks' of diverse minds. He also highlights the importance of environments that facilitate the mixing and mingling of ideas, such as big cities, which are more innovative due to their superlinear scaling of creativity. The book draws on historical examples and contemporary cases to illustrate how these patterns contribute to groundbreaking innovations.

Poor Charlie's Almanack

The Essential Wit and Wisdom of Charles T. Munger

Charles T. Munger

Peter D. Kaufman

Originally published in 2005, Poor Charlie's Almanack is a collection of eleven talks delivered by Charles T. Munger between 1986 and 2007. Edited by Peter D. Kaufman, this book draws on Munger's extensive knowledge across various fields to provide a framework for rational and rigorous approaches to life, learning, and decision-making. It is renowned for its sharp wit and rhetorical flair, making it an essential read for investors, entrepreneurs, and anyone seeking to enhance their wisdom and critical thinking skills.

The wasp factory

Iain M. Banks

The Wasp Factory is a dark and twisted novel that follows the disturbing thoughts and actions of a teenage boy named Frank, who lives on a remote Scottish island. The story delves into themes of identity, family, and the nature of evil, revealing a tragic tale of isolation and insanity. Frank's life unravels dramatically with the return of his unstable brother, Eric, and the revelation of his own complex past.

Sam Schillace is deputy CTO and corporate vice president at Microsoft. Prior to working at Microsoft, Sam started a company called Writely, which was acquired by Google and became the foundation of what today is Google Docs. While at Google, Sam helped lead many of Google’s consumer products, including Gmail, Blogger, PageCreator, Picasa, Reader, Groups, and more recently Maps and Google Automotive Services. Sam was also a principal investor at Google Ventures, has founded six startups, and was the SVP of engineering at Box through their IPO. In this episode, we discuss:

• The journey of building Google Docs

• The importance of taking risks, embracing failure, and finding joy in your work

• The importance of asking “what if” questions vs. “why not”

• Why convenience always wins

• How, and why, Sam stays optimistic

• Inside Microsoft’s culture

• Why you should solve problems without asking for permission

• Early-career advice

• Why “pixels are free” and “bots are docs”

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Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-be-more-innovative-sam-schillace

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Where to find Sam Schillace:

• LinkedIn: https://www.linkedin.com/in/schillace/

• Newsletter: https://sundaylettersfromsam.substack.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Sam’s background

(03:45) The first Google Docs file

(06:45) Disruptive innovation

(10:11) First-principles thinking

(11:00) Recognizing disruptive ideas

(13:17) Examples of first-principles thinking

(15:46) The power of optimism

(19:47) Sam’s motto: Get to the edge of something and f**k around

(21:53) User value and laziness

(24:31) People are lazy (and what to do about it)

(28:36) Building Google Docs

(31:06) The evolution of Google Docs

(37:15) Finding product-market fit

(39:52) The future of documents

(44:57) The value of playing with technology

(47:58) Taking risks and embracing failure

(49:21) Thinking in the future

(53:48) Finding joy in your work

(01:01:20) Just do the best you can

(01:02:34) The transformational power of AI

(01:09:27) Advice for approaching AI

(01:13:07) The culture at Microsoft

(01:16:51) Closing thoughts

(01:17:32) Lightning round

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Referenced:

• Google Docs began as a hacked-together experiment, says creator: https://www.theverge.com/2013/7/3/4484000/sam-schillace-interview-google-docs-creator-box

• Edna Mode: https://disney.fandom.com/wiki/Edna_Mode

• Sergey Brin’s profile on Forbes: https://www.forbes.com/profile/sergey-brin/

• People Who Were No Smarter Than You: https://medium.com/thrive-global/people-who-were-no-smarter-than-you-4e1c88c3fee6

• Nat Torkington (O’Reilly Media): https://www.oreilly.com/people/nathan-torkington/

• How Tesla Has Shaken (Not Stirred) Established Carmakers—and Why It Really Matters: https://www.forbes.com/sites/jenniferdungs/2021/04/23/how-tesla-has-shaken-not-stirred-established-carmakersand-why-it-really-matters/

• First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

• Ashton Tate: https://en.wikipedia.org/wiki/Ashton-Tate

• Learning by Doing: https://www.linkedin.com/pulse/learning-doing-sam-schillace

• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/

• How do we make sense of all of this?: https://sundaylettersfromsam.substack.com/p/how-do-we-make-sense-of-all-of-this

• Steve Newman on LinkedIn: https://www.linkedin.com/in/stevescalyr/

• Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-schmidt-02158951/

• Michael Arrington on X: https://twitter.com/arrington

• TechCrunch: https://techcrunch.com/

• “Hello, Computer” scene from Star Trek: https://www.youtube.com/watch?v=hShY6xZWVGE

• Writely—Process Words with your Browser: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

• Calvinism: https://en.wikipedia.org/wiki/Calvinism

• This Quote from Seth Godin Could Change How You Think About Pursuing Your Passion: https://friedchickenandsushi.com/blog/2021/7/5/this-quote-from-seth-godin-could-change-how-you-think-about-pursuing-your-passion

• AI isn’t a feature of your product: https://sundaylettersfromsam.substack.com/p/ai-isnt-a-feature-of-your-product

• Introducing Gemini: our largest and most capable AI model: https://blog.google/technology/ai/google-gemini-ai/

• Invisible Cities: https://www.amazon.com/Invisible-Cities-Italo-Calvino/dp/0156453800

• The Wasp Factory: https://www.amazon.com/WASP-FACTORY-NOVEL-Iain-Banks/dp/0684853159

• Where Good Ideas Come From: The Natural History of Innovation: https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380/

• Slow Horses on Apple TV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Monarch: Legacy of Monsters on Apple TV+: https://tv.apple.com/us/show/monarch-legacy-of-monsters/umc.cmc.62l8x0ixrhyq3yaqa5y8yo7ew?mttn3pid

• Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

• 2023 Mustang Mach-E: https://www.ford.com/suvs/mach-e/

• Boccalone Salumeria (now closed) on X: https://twitter.com/boccalone

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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