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” — Brought to you by Teal—Your personal career growth platform: https://tealhq.com/lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny | Ahrefs—Improve your website’s SEO for free: https://ahrefs.com/awt Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-be-more-innovative-sam-schillace 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 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.