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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\u2019s 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:

\u2022 The journey of building Google Docs

\u2022 The importance of taking risks, embracing failure, and finding joy in your work

\u2022 The importance of asking \u201cwhat if\u201d questions vs. \u201cwhy not\u201d

\u2022 Why convenience always wins

\u2022 How, and why, Sam stays optimistic

\u2022 Inside Microsoft\u2019s culture

\u2022 Why you should solve problems without asking for permission

\u2022 Early-career advice

\u2022 Why \u201cpixels are free\u201d and \u201cbots are docs\u201d

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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:

\u2022 LinkedIn: https://www.linkedin.com/in/schillace/

\u2022 Newsletter: https://sundaylettersfromsam.substack.com/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Sam\u2019s 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\u2019s 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:

\u2022 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

\u2022 Edna Mode: https://disney.fandom.com/wiki/Edna_Mode

\u2022 Sergey Brin\u2019s profile on Forbes: https://www.forbes.com/profile/sergey-brin/

\u2022 People Who Were No Smarter Than You: https://medium.com/thrive-global/people-who-were-no-smarter-than-you-4e1c88c3fee6

\u2022 Nat Torkington (O\u2019Reilly Media): https://www.oreilly.com/people/nathan-torkington/

\u2022 How Tesla Has Shaken (Not Stirred) Established Carmakers\u2014and 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/

\u2022 First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

\u2022 Ashton Tate: https://en.wikipedia.org/wiki/Ashton-Tate

\u2022 Learning by Doing: https://www.linkedin.com/pulse/learning-doing-sam-schillace

\u2022 Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/

\u2022 How do we make sense of all of this?: https://sundaylettersfromsam.substack.com/p/how-do-we-make-sense-of-all-of-this

\u2022 Steve Newman on LinkedIn: https://www.linkedin.com/in/stevescalyr/

\u2022 Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-schmidt-02158951/

\u2022 Michael Arrington on X: https://twitter.com/arrington

\u2022 TechCrunch: https://techcrunch.com/

\u2022 \u201cHello, Computer\u201d scene from Star Trek: https://www.youtube.com/watch?v=hShY6xZWVGE

\u2022 Writely\u2014Process Words with your Browser: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/

\u2022 Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

\u2022 Poor Charlie\u2019s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

\u2022 Calvinism: https://en.wikipedia.org/wiki/Calvinism

\u2022 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

\u2022 AI isn\u2019t a feature of your product: https://sundaylettersfromsam.substack.com/p/ai-isnt-a-feature-of-your-product

\u2022 Introducing Gemini: our largest and most capable AI model: https://blog.google/technology/ai/google-gemini-ai/

\u2022 Invisible Cities: https://www.amazon.com/Invisible-Cities-Italo-Calvino/dp/0156453800

\u2022 The Wasp Factory: https://www.amazon.com/WASP-FACTORY-NOVEL-Iain-Banks/dp/0684853159

\u2022 Where Good Ideas Come From: The Natural History of Innovation: https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380/

\u2022 Slow Horses on Apple TV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

\u2022 Monarch: Legacy of Monsters on Apple TV+: https://tv.apple.com/us/show/monarch-legacy-of-monsters/umc.cmc.62l8x0ixrhyq3yaqa5y8yo7ew?mttn3pid

\u2022 Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

\u2022 2023 Mustang Mach-E: https://www.ford.com/suvs/mach-e/

\u2022 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.