
49 segments available
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.
Sam Schillace discusses the common misconception that work must be unpleasant and the importance of pursuing what brings joy. He emphasizes that if you find something enjoyable and people are willing to pay for it, you should embrace it fully. This segment highlights the value of aligning passion with career choices and challenges the notion of grinding through unpleasant tasks.
"we tend to undervalue the things we're good at we tend to think work has to be unpleasant and so if something is easy and fun we don't tend to think it's valuable so I think lots of people like gravit..."
In this segment, Sam Schillace shares his impressive background, detailing his role as Corporate Vice President and Deputy CTO at Microsoft, and his pivotal contribution to the creation of Google Docs through his company Writely. He reflects on his extensive experience in leading consumer applications at Google and his entrepreneurial ventures, setting the stage for a discussion on innovation.
"professional growth I always like to spend this time reflecting on what I accomplished the previous year what I hope to accomplish the next year and whether this is the year I look for a new opportuni..."
Sam reveals the story behind the very first Google Docs file, discussing its origins and the technical challenges faced during its creation. He humorously reflects on the evolution of the document and the complexities of migrating data to Google’s infrastructure, showcasing the innovative spirit that led to the development of Google Docs.
"[Music] today Sam thank you so much for being here and welcome to the podcast thank you happy to be here a really fun fact about you is that apparently you have the very first Google doc uh file I don..."
Sam Schillace delves into the concept of disruptive innovation, explaining its significance in shaping the products and technologies we use today. He emphasizes that every new idea initially faces skepticism and resistance, and discusses the importance of embracing new concepts that challenge the status quo.
"yeah if you made the nft of it that would be more more authentic I think than the document almost it's kind of funny that's amazing and it's amazing that it still works that's a testament to I don't k..."
In this segment, Sam discusses the importance of asking 'what if' questions to foster innovation. He contrasts these with 'why not' questions, which often stem from skepticism. By encouraging imaginative thinking, Sam illustrates how this mindset can lead to groundbreaking ideas and solutions.
"is this important to you why do you spend a lot of time thinking about this and then just what are some tools you found to help you and other people think more innovatively more originally it's an int..."
Sam explains the binary reactions that disruptive innovations often provoke—either excitement or rejection. He shares insights on how this reaction can indicate the potential impact of a new idea, using examples from his experiences with Google Docs and other technologies to illustrate his points.
"like an impatient person I'm a creative person I'm a messy person like I just like to create and and explore and find stuff so like disruptive innovation is just seems Seems natural to me but I think ..."
Sam reflects on the current landscape of generative AI and the importance of maintaining an optimistic outlook despite challenges. He discusses how viewing obstacles as opportunities can lead to transformative innovations, drawing parallels to historical examples of disruptive technologies.
"disruptive technology that's an awesome framework basically if it feels like people sort of like Get Some People mostly people don't care some very few people love it or hate it probably not disruptiv..."
In this brief segment, Sam introduces the concept of first principles thinking, emphasizing its role in innovation. He outlines the process of questioning assumptions to achieve breakthroughs, using Elon Musk as a prime example of this approach in action.
"wrong Tesla is a great example SpaceX is a great example where people are like that doesn't make any sense you know and elon's like well what if you could land rockets and reuse them and they get real..."
In this segment, Schillace explains the concept of first principles thinking, using Elon Musk as a prime example. He outlines the steps involved in this approach: identifying goals, recognizing obstacles, and questioning assumptions. Schillace illustrates how this method can lead to groundbreaking innovations, encouraging listeners to adopt a mindset that prioritizes possibilities over limitations.
"basically question every assumption that stands in the way of making this possible so I think elon's a great like the classic example like you can't talk about first principes thinking without quoting..."
Sam Schillace shares his perspective on optimism, describing it as a conscious choice rather than a natural disposition. He argues that maintaining an optimistic outlook is crucial for innovation, as it encourages exploration and experimentation. Schillace reflects on his own career, emphasizing the value of being open-minded and willing to embrace new ideas, even in the face of challenges.
"that equation over my career I wish I had been more open-minded and more more optimistic and more willing to try things and more more focused on Poss possibilities rather than problems and so I'm just..."
In this segment, Schillace discusses the importance of user value in product development. He asserts that successful innovations must address real user needs and simplify their lives. Schillace critiques the tendency of product builders to focus on their own passions rather than the end user's perspective, highlighting that true adoption comes from delivering significant value.
"you know going back to this idea of like all the all the um the good ideas look bad at first right so that's okay so that's a that's a first principle like that's a sort of fundamental thing of you're..."
Sam Schillace emphasizes the necessity of experimentation and learning from failure in the innovation process. He shares insights on how to approach product development with a mindset that welcomes mistakes as opportunities for growth. Schillace encourages listeners to adopt a habit of trying new things and being receptive to unexpected outcomes.
"to like get it on its feet and see how it feels it's like kind of a form of optimism right like you know if you're super pessimistic be like ah even that's not worth it like two days is a waste of tim..."
In this segment, Schillace introduces his motto of 'getting to the edge of something and fucking around.' He explains how this approach fosters creativity and innovation by allowing for quick experimentation. Schillace advocates for sharpening tools and minimizing friction in the development process to encourage exploration and discovery.
"completely wrong when you actually try it out and you have this quote I think in one of your newsletter posts talking about building Google Docs you describe it as just around yeah kind of get to the ..."
Sam Schillace discusses the significance of user-centric design in product development. He highlights the need to reduce friction in user experiences, drawing from his early experiences with Writely. Schillace explains how minimizing barriers to entry can lead to greater user engagement and adoption, reinforcing the idea that convenience is key to successful innovations.
"this like oh it's not working but why isn't it working well that's kind of interesting like with brok here we've done stuff like that and some of the things the projects I've got going in Microsoft um..."
In this segment, Schillace reflects on the challenges of evaluating new technologies, particularly in the context of crypto. He emphasizes the importance of identifying real user value and warns against getting caught up in hype. Schillace shares his criteria for assessing the viability of new ideas, advocating for a focus on tangible benefits for users.
"wasn't really a lot of business to be built and then things kind of entered winter time is there anything you've learned that gives you a signal that let's keep working I'm going to stay optimistic ab..."
Sam Schillace explores the concept of user laziness and its impact on product adoption. He explains that users prioritize convenience and ease of use, which can significantly influence their willingness to engage with new technologies. Schillace discusses the dynamics of value addition in products, noting that substantial improvements can lead to rapid adoption, while minor enhancements may yield slow growth.
"yeah so I think the lesson there is truly understand if the value is real versus like the sounds really cool or you think a lot of like would you want it I think as a nice exercise there we pick on po..."
In this segment, Schillace shares strategies for creating low-friction user experiences. He recounts his experience with Writely, where minimizing barriers to entry was crucial for user engagement. Schillace emphasizes the importance of making it easy for users to try new products, highlighting that reducing friction can lead to higher retention and satisfaction.
"the end user at all and like if there's one thing I've learned about product you know particularly in the consumer space just kind of in general is like people are just lazy about stuff and like don't..."
In this segment, Schillace reflects on the competitive landscape between Google Docs and Microsoft Office. He explains the strategic trade-offs made during the development of Google Docs, focusing on ease of use versus feature richness. Schillace illustrates how Google Docs disrupted the market by prioritizing user experience over extensive features, ultimately leading to its success despite initial resistance from established players.
"what I think of as you're describing this is uh Exel Microsoft Excel had a billion toolbars and buttons and options which allowed Google Docs essentially to come in with a much simpler experience now ..."
Sam Schillace shares the early days of Google Docs, detailing the serendipitous discovery of collaborative editing. He recounts how the team initially built the product as an experiment and quickly recognized its potential. Schillace emphasizes the importance of being open to new ideas and the role of optimism in overcoming challenges during the development process.
"being Google like you know so like they survived it like you know they survived they did a good job surviving the challenge like it's you know um we have all the users now but they have all the money ..."
In this insightful discussion, Schillace explores the duality of being a product builder. He emphasizes the need for a strong mission while remaining flexible to feedback and market signals. Schillace articulates the challenges entrepreneurs face in navigating pushback and the importance of maintaining an optimistic outlook to foster innovation and creativity.
"you know useful app so it's a I think it's a good little counter example of like that optimistic pessimistic perspective we were talking about like you we could easily have missed that idea easily hav..."
Sam Schillace speculates on the future of document technology, critiquing the current focus on replicating traditional formats. He discusses the evolution of documents in the context of AI and collaborative tools, suggesting that the future lies in dynamic, interactive formats rather than static documents. Schillace's insights highlight the ongoing transformation in how we create and interact with digital content.
"just not seeing opportunities there's a lot of hard work for sure there's a lot of stuff that you can read about and best practices of doing iteration and user testing and user interviews and really l..."
Sam discusses the shift in expectations for collaboration with technology, predicting that future applications will need to allow for seamless interaction and customization. He reflects on the limitations of current applications and the need for a more dynamic approach to user experience.
"still like a creating stuff at the bottom of this linear artifact but the next step that we're working on now is just making that Dynamic where you just like come to something and you talk to it and i..."
In this segment, Sam shares his philosophy on balancing play with purposeful development. He emphasizes the importance of having clear goals while experimenting with technology, illustrating how this approach can lead to valuable insights and innovations.
"remember it for me and bring it back later and you know all that stuff so that was a long digression but I would just like you know you're kind of asking about features and functionality and I feel li..."
Sam recounts his experiences with early technical challenges while developing Google Docs, including the complexities of asynchronous programming. He highlights the importance of adaptability and problem-solving in engineering, showcasing how overcoming obstacles can lead to significant advancements.
"bare metal in the Dom and there were bugs like when I went to Google like I had to write this um little Network stack at the bottom of of the JavaScript that like in in theory XML HTP you could interr..."
Sam discusses the importance of experimentation in engineering, advocating for a culture that embraces risk and failure. He shares insights on how playful exploration can lead to innovative solutions and the necessity of maintaining a sense of curiosity in technology development.
"of our little our little hacks to get this working I love it this episode is brought to you by atrs many of you already know atfs as one of the top tools for search engine optimization it's used by th..."
In this segment, Sam explains his strategy of setting 'North Stars' to guide innovation efforts. He emphasizes the need for clear objectives while experimenting with technology, illustrating how this focus can lead to meaningful advancements and valuable insights in product development.
"engineer you just want to work on interesting things and work on the technology before you find a problem that it's solving it feels like with this example it was you just think this is a cool technol..."
Sam reflects on the role of play in fostering creativity and innovation in technology. He discusses how a playful mindset can lead to unexpected discoveries and the significance of allowing engineers to explore ideas without the pressure of immediate results.
"it's kind of interesting too because like that system already it's produced a bunch of good insights one of them is it's kind of complicated and hard to debug it it's this asynchronous system of stoch..."
Sam shares his personal motto about learning from mistakes and the necessity of embracing failure in the creative process. He discusses how this mindset can lead to growth and innovation, encouraging others to adopt a similar approach in their work.
"it's just like what the worst thing that can happen even the early days of rightly like the very I mean we had a goal from the beginning the beginning was like can I write a word processor in the brow..."
In this segment, Sam discusses the importance of thinking ahead and being open to new possibilities. He reflects on generational differences in attitudes toward risk and innovation, encouraging a more optimistic and proactive approach to problem-solving.
"perspective sometimes so Sam the renaissance man of all languages add more like it but yeah mention of things I wanted to follow this thread a little further around being good at these what if questio..."
Sam Schillace discusses how a lack of unstructured playtime in childhood can hinder creativity and experimentation in adulthood. He reflects on his own experiences growing up, emphasizing that the ability to mess around and explore without strict boundaries is crucial for innovation. Schillace argues that the fear of failure can stifle creativity, and he encourages embracing mistakes as part of the learning process.
"didn't do extracurricular I was just like a weird nerd at you know having to be good at math and so I think there's that as well like if you're highly curated where you've spent a lot of your life thi..."
In this segment, Schillace shares his personal motto, 'from error comes virtue,' highlighting the importance of viewing mistakes as opportunities for growth. He explains that taking risks and being willing to fail is essential for achieving extraordinary results in one's career. Schillace encourages listeners to adopt a playful mindset and iterate on ideas, even if they initially seem foolish.
"much less of an ability and willingness and skill set about around experimenting to the point of failure like making making fool of yourself like having bad ideas I send like stupid emails to sachcha ..."
Sam Schillace contrasts the traditional linear career path with the pursuit of extraordinary outcomes through risk-taking and creativity. He reflects on his own unconventional journey, emphasizing that true impact comes from doing what you love with intensity. Schillace encourages individuals to seek out roles that align with their passions and to embrace their unique skills, rather than conforming to societal expectations.
"good skill to have like I it's it's a saying I took on this year and I really really like it as my I never had a personal motto before I think it might be my personal motto like virtue from airor amaz..."
Schillace discusses the significance of finding joy in one's work and how it can lead to greater success. He shares insights on how to identify tasks that bring happiness and fulfillment, urging listeners to pursue careers that feel rewarding. Schillace reflects on his own experiences managing people and discovering the joy of collaboration, emphasizing the importance of being open to new opportunities.
"I I feel like I always tell people like I think I mean I I I I pitch this because I've observed myself and thought about like what has been successful in my career it's not it's not a thing everybody ..."
In this segment, Schillace advises listeners to remain open to unexpected career opportunities that align with their interests. He reflects on his journey of self-discovery and the importance of recognizing one's unique contributions. Schillace emphasizes that while not everyone can pursue their passions immediately, it's crucial to pay attention to what brings joy and fulfillment in work.
"this but it's super cool anyways right like I think that's the that's the career thing that makes sense to me at least that's what I've done you know who knows like it's all luck sometimes so it's har..."
Sam Schillace shares his philosophy on the importance of pursuing work that feels enjoyable and fulfilling. He encourages listeners to identify roles that resonate with their passions and to embrace their unique strengths. Schillace reflects on his own experiences and the privilege of being able to focus on work that excites him, while also acknowledging the challenges many face in finding such opportunities.
"often have to make compromises but I still think it's worth paying attention to right when you're working like what makes you happy what is the stuff that you feel guilty for getting away with what li..."
Schillace discusses the transformative potential of AI in the software industry, emphasizing that AI is not just a feature but a foundational element of future products. He shares insights on how AI can disrupt traditional business models and create new opportunities. Schillace highlights the importance of building applications that leverage AI as a core component, rather than treating it as an add-on.
"just going to do the best I can at being a waitress at this place I'm just going to do the best at greeting people entering the Apple Store absolutely yeah I think that's absolutely right like I I thi..."
In this segment, Schillace explores the concept that AI will make digital creation more accessible, likening it to how the internet revolutionized information distribution. He discusses the implications of AI for content creation, suggesting that the barriers to producing high-quality digital assets will diminish. Schillace encourages listeners to consider the future possibilities of AI in transforming industries and creative processes.
"I think both of those are are really are really true like I so I'm like what I'm working on is I most of the industry right now is focused on when you talk about somebody who's working in AI it's some..."
Sam Schillace invites listeners to ponder the future of AI and its potential to revolutionize various fields. He poses thought-provoking 'what if' scenarios regarding the capabilities of AI, such as enhanced planning and personalization. Schillace emphasizes the importance of curiosity and exploration in driving innovation, encouraging individuals to think creatively about the possibilities that AI presents.
"on it hard being hard to distribute information 25 years ago but like you can see this already with things like just images right like you know two years ago if you wanted a piece of digital art you h..."
Schillace reflects on the parallels between the current generative AI landscape and past technological shifts, such as the rise of the iPhone. He emphasizes that while the foundational ideas are emerging, significant engineering and development work is still required to fully realize the potential of generative AI in transforming software and business models.
"spend a lot of time talking to that agent like it's like you know what would you do if you imagine you're like the richest person in the world you've got a hundred of the best people working for you a..."
In this segment, Schillace shares insights on how to approach learning and integrating AI into products. He advises listeners to set specific goals and engage deeply with the technology, rather than just experimenting superficially. He draws parallels to the early days of the internet and emphasizes the importance of staying informed amidst rapid changes.
"new game like fill in start coloring in the blanks right like you know let's go so like I that's that's where I I think we're going and you know that sounded really certain it's probably sounded more ..."
Schillace discusses the current phase of AI development, likening it to the early cloud computing era. He explains that while identifying the initial idea is challenging, once recognized, the optimization and scaling of AI technologies will happen rapidly. He encourages professionals to stay engaged and proactive in this evolving landscape.
"track of all the stuff that's happening um it's kind of interesting because like I remember going just to pick on just to kick crypto's corpse one last time like there was some tweet like at the begin..."
Sam Schillace shares his perspective on Microsoft's culture under CEO Satya Nadella, highlighting the emphasis on humility, hard work, and the presence of talented individuals. He reflects on how these elements contribute to Microsoft's innovative capabilities and its ability to adapt in a changing tech landscape.
"you know it's not there's no magic single bullet to learning this stuff you just have to run it's like it's like how how do I run this Sprint without getting out of breath like you don't like you're g..."
In this closing segment, Schillace encourages listeners to take initiative in building solutions and solving problems without waiting for permission. He emphasizes the importance of energy and creativity in driving innovation, reinforcing the idea that anyone can contribute to building the future.
"it's like there's you know that that doesn't happen by accident either no drama there by the way I would know anything there I hear it's calm from it as possible honestly most under the radar startup ..."
Sam Schillace shares his favorite book recommendations, including 'Invisible Cities' by Italo Calvino, which profoundly impacted him during his travels in Italy. He also discusses the intense psychological exploration found in 'The Wasp Factory' by Iain Banks, and highlights 'Where Good Ideas Come From' by Steven Johnson as a valuable resource for business insights.
"exciting lightning round are you ready I probably not great answer Sam what are two or three books that you've recommended most to other people I like weird book like I like there's this book called I..."
In this segment, Sam reveals his current favorite TV show, 'Slow Horses,' featuring Gary Oldman as a disgraced British spy. He also expresses his enjoyment of retro monster-themed shows and animated sci-fi series like 'Scavengers Rain,' emphasizing his taste for entertaining and visually captivating content.
"the other one I I recommend to people with some caution is this very intense and disturbing book called The Wasp Factory by in Banks which is um probably the creepiest and hardest book I've ever read ..."
Sam discusses a thought-provoking interview question he used to ask candidates at Google: 'How many zeros are at the end of 100 factorial?' He explains the purpose behind the question, which is to gauge a candidate's problem-solving approach when faced with seemingly impossible challenges, highlighting the importance of resilience and creativity.
"don't know I I have like absolute junk food taste when it comes to yeah love creepy creepy monsters and bugs yeah I love it science shooty science things that blow up a lot I'm I'm not very deep uh by..."
Sam shares a humorous story about selling both a company and 200 pounds of blood sausage to Google. He recounts the quirky circumstances surrounding the sale, including the eccentric chef at Google who appreciated the artisanal product, showcasing the unique and often unexpected intersections of the tech and culinary worlds.
"do you like fall over and what was the question again just how many zeros are at the end of 100 factorial in in decimal WR and then why did it get banned I think it got known and like you know somewhe..."
In this segment, Sam reflects on his favorite life motto, 'Virtue from error.' He emphasizes the importance of learning from mistakes and being creative in the face of failure, encouraging listeners to embrace their errors as opportunities for growth and innovation.
"the most right now next question do you have a favorite life motto that you often repeat to yourself find useful share with friends or family either in work or in life virtue from error yeah I think t..."
Sam discusses how listeners can connect with him and share innovative ideas. He expresses his interest in disruptive concepts that challenge the status quo, emphasizing that he is looking for truly unique and interesting projects rather than incremental improvements. This segment encapsulates his passion for fostering creativity and innovation.
"called balone which was a like a Artisan salumi thing in the ferry building and so he'd make blood sausage and stuff so there was this wonderful insane Chef back in the day when Google had like really..."