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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’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”

Some takeaways:

1. The bifurcation of love/hate reactions is a positive sign that you’re building something disruptive. Less strong reactions (like moderate indifference or mild dislike) likely mean you are not building something disruptive.

2. Career success stems from impact, which in turn arises from doing something you’re good at with passion. The key is to find that skill you feel slightly guilty about being paid for.

3. Instead of merely integrating AI as a feature, envision and strategize for a future where AI is a fundamental platform. Embrace the “what if” mindset, preparing for a transformative shift where AI is not just an add-on but an integral component shaping the core functionality of your products or solutions.

Listen now on Apple, Spotify, Overcast, and YouTube.

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

Where to find Sam Schillace:

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

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

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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 fuck 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

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

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

Lenny may be an investor in the companies discussed.