Sam Schillace (Microsoft deputy CTO, creator of Google Docs)11 January 2024

How to be more innovative

5Frameworks

15Insights

Episode overview

Lenny Rachitsky talks with Microsoft deputy CTO and Google Docs creator Sam Schillace about disruptive innovation, optimism, experimentation, and career choices. Schillace explains how Writely's collaborative editing value emerged through hands-on exploration and why polarised reactions can signal genuinely consequential products. They also examine generative AI as a platform shift that could make software more dynamic, intentional, personalized, and agent-driven.

Key ideas

Replace reflexive “why not” objections with “what if” questions that explore the valuable world a disruptive idea could create.
Strong love-and-hate reactions can indicate that a product is genuinely disruptive, while broad indifference often signals incremental change.
Optimism is a deliberate working posture: make experiments cheap, try ideas quickly, and remain receptive to surprising failures.
Product adoption depends on total user value exceeding every source of effort, including discovery, onboarding, learning, and habit formation.
Use concrete North Star projects to learn emerging technologies; stubbornly pursuing a real goal teaches more than unfocused experimentation.
Extraordinary career impact often comes from leaning intensely into work that feels unusually natural, enjoyable, and valuable to others.
Generative AI may transform software from fixed applications into personalized, stateful agents that understand intent and dynamically produce interfaces.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Self-Mastery4 steps

Guilty-Pleasure Career Bet

Find the thing you feel guilty getting paid for, do the hell out of it with intensity, and take non-linear risks.

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Innovation3 steps

North Star Exploration

Turn aimless tech-tinkering into learning by chasing an arbitrary-but-real goal and being stubborn about reaching it.

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Innovation3 steps

The Love-Hate Disruption Test

Gauge whether an idea is truly disruptive by how polarized the reactions are, not how positive.

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Strategy4 steps

User-Value Thermodynamics

Users are lazy; adoption only happens when total value delivered exceeds total effort spent, ideally by 10x.

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Innovation4 steps

What-If Before Why-Not

Evaluate a disruptive idea by imagining its upside first, then treat the objections as your build list.

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People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 19

Sam SchillaceMentionscurrently he is Corporate vice president and deputy chief technology officer at Microsoft
“today my guest is Sam scache”
▶ Watch at ~0:30approx.
Brett BersonMentionsit's first rounds podcast by Brett Baron he interviews a lot of operators
“a big thank you to Brett Bon for making this introduction”
▶ Watch at ~1:30approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“thank you happy to be here”
▶ Watch at ~3:30approx.
Sergey BrinMentionswhen I was at Google the thing I took away most from any review and Lariat survey
“three days after that Sergey was in a meeting with me”
▶ Watch at ~6:00approx.
Steve JobsMentionsSteve Jobs is just uh the bar he held for the company and for technical talent and for excellence was not uh wavering.
“I found this quote from Steve Jobs just reminding us that everything around us was designed by some person”
▶ Watch at ~10:00approx.
Nate TorkingtonMentionsmentioned
“Nate turkington over at Riley like was this super huge early provide early booster for it”
▶ Watch at ~11:30approx.
Elon MuskMentionsWhether you like him or not, Elon, this is similar to his um if you watch him, he has sets these really ambitious goals
“elon's like well what if you could land rockets and reuse them and they get really cheap”
▶ Watch at ~14:30approx.
Eric SchmidtMentionsmentioned
“I had to threaten either sue him or haul him in front of Eric Schmidt”
▶ Watch at ~35:00approx.
Michael ArringtonMentionsmentioned
“Michael Arington like this another funny rly story is that like we had I had a breakfast with Michael Arrington”
▶ Watch at ~38:00approx.
Warren BuffettMentionsWarren Buffett who's outstanding arguable genius
“Warren Buffett and Charlie munger's whole philosophy is when you find an advantage just go huge”
▶ Watch at ~57:00approx.
Charlie MungerMentionsHis words and documents were assembled into Poor Charlie's Almanack.
“Warren Buffett and Charlie munger's whole philosophy is when you find an advantage just go huge”
▶ Watch at ~57:00approx.
Seth GodinMentionsSeth is an absolute Legend he's published 21 books including 18 International bestsellers
“Seth Goden has this really important advice that's always stuck with me”
▶ Watch at ~1:01:00approx.
Satya NadellaMentionsDiscussed as Microsoft's CEO and as a leader with a strong appetite for learning and refining mental models.
“I think very very highly of Sacha or I wouldn't be there”
▶ Watch at ~1:13:30approx.
Kevin ScottMentionsKevin Scott at Microsoft who's like been really a just an amazing champion for for MCP
“Kevin Scott who I work for is one of the smartest he's probably the smartest person I've ever been fortunate to work directly with”
▶ Watch at ~1:16:00approx.
Italo CalvinoCoinedmentioned
“there's this book called Invisible Cities by Italo calino”
▶ Watch at ~1:17:30approx.
Steven JohnsonCoinedhe has written 14 books he's a New York Times best-selling author and speaker
“where good ideas come from like Stephen Johnson I really like that book”
▶ Watch at ~1:18:00approx.
Iain BanksCoinedmentioned
“this very intense and disturbing book called The Wasp Factory by in Banks”
▶ Watch at ~1:18:00approx.
Gary OldmanMentionsmentioned
“my guilty pleasure is watching Gary Oldman be a completely disgusting over the hill British spy in uh slow horses”
▶ Watch at ~1:18:30approx.
Dave BesbrisMentionsmentioned
“I Dave bezus I interviewed him when he came in in and I asked him that question”
▶ Watch at ~1:20:30approx.

Resources · 30

MicrosoftMentionscompany · Bill Gates and Paul Allen
“currently he is Corporate vice president and deputy chief technology officer at Microsoft”
▶ Watch at ~0:30approx.
GoogleMentionscompany · Google
“which was acquired by Google and became the foundation for what is now Google workplace”
▶ Watch at ~0:30approx.
Google DocsCoinedsoftware · Google
“Sam is most known for basically inventing Google Docs with this company rightly”
▶ Watch at ~0:30approx.
Google WorkspaceMentionssoftware · Google
“became the foundation for what is now Google workplace which currently has over 1 billion active users a month”
▶ Watch at ~1:00approx.
Google VenturesMentionscompany · Google
“he was even a VC at Google Ventures for a time”
▶ Watch at ~1:00approx.
BoxMentionscompany
“he's also founded six startups was senior vice president of engineering at box through their IPO”
▶ Watch at ~1:00approx.
Google MapsMentionssoftware · Google
“including parts of Gmail Maps Automotive groups reader and more”
▶ Watch at ~1:00approx.
GmailMentionssoftware · Google
“including parts of Gmail Maps Automotive groups reader and more”
▶ Watch at ~1:00approx.
WritelyCoinedproduct · Sam Schillace and co-founders
“rightly was the company that did Google Docs”
▶ Watch at ~4:00approx.
The IncrediblesMentionsfilm · Brad Bird
“there's a picture of Edna from The Incredibles pasted into it”
▶ Watch at ~5:00approx.
Computer History MuseumMentionsplace
“the Computer History Museum wants to curate it”
▶ Watch at ~5:30approx.
ChatGPTMentionssoftware · OpenAI
“you look at something like chat TPT where like the entire world is like this is amazing or this is terrible”
▶ Watch at ~12:00approx.
TeslaMentionscompany · Tesla, Inc.
“Tesla is a great example SpaceX is a great example”
▶ Watch at ~14:30approx.
SpaceXMentionscompany · Elon Musk
“Tesla is a great example SpaceX is a great example”
▶ Watch at ~14:30approx.
TechCrunchMentionswebsite · Michael Arrington
“we were like I think like one of the first 10 articles at TechCrunch”
▶ Watch at ~38:00approx.
Poor Charlie's AlmanackUsesbook · Charlie Munger
“I'm reading uh Charlie monger's Almanac which just came out through strip press”
▶ Watch at ~56:30approx.
GPT-4Usessoftware · OpenAI
“when I started with Microsoft started working on on gp4 with Microsoft in like September of last year”
▶ Watch at ~1:03:30approx.
Semantic KernelCoinedsoftware · Microsoft
“started me down this Rabbit Hole of thinking about building the semantic kernel which we built”
▶ Watch at ~1:04:00approx.
Infinite ChatbotCoinedsoftware · Sam Schillace and Microsoft
“and then building infinite chatbot which was next”
▶ Watch at ~1:04:00approx.
GeminiMentionssoftware · Google
“when um Gemini came out all the Press take was like oh it's not that different from gp4”
▶ Watch at ~1:08:30approx.
BardUsessoftware · Google
“use chat GPT use all use Bard and all these things”
▶ Watch at ~1:09:30approx.
ChatGPTUsessoftware · OpenAI
“use chat GPT use all use Bard and all these things”
▶ Watch at ~1:09:30approx.
OpenAIMentionscompany
“Kevin and Sai made a bet on open AI you know a few years back”
▶ Watch at ~1:16:00approx.
Invisible CitiesRecommendsbook · Italo Calvino
“I like there's this book called Invisible Cities by Italo calino”
▶ Watch at ~1:17:30approx.
Where Good Ideas Come FromRecommendsbook · Steven Johnson
“the business advice one is probably where good ideas come from like Stephen Johnson I really like that book”
▶ Watch at ~1:18:00approx.
The Wasp FactoryRecommendsbook · Iain Banks
“the other one I I recommend to people with some caution is this very intense and disturbing book called The Wasp Factory”
▶ Watch at ~1:18:00approx.
Slow HorsesRecommendstv show · Will Smith
“my favorite one right now my guilty pleasure is watching Gary Oldman be a completely disgusting over the hill British spy in uh slow horses”
▶ Watch at ~1:18:30approx.
Monarch: Legacy of MonstersMentionstv show · Chris Black and Matt Fraction
“I'm actually having a little fun with like the Retro monster stuff like monarch and stuff like that”
▶ Watch at ~1:18:30approx.
Scavengers ReignRecommendstv show · Joseph Bennett and Charles Huettner
“have you seen scavenger rain scavenger rains scavengers rain okay you love it it's on HBO it's incredible”
▶ Watch at ~1:19:00approx.
Sunday Letters from SamCoinednewsletter · Sam Schillace
“I have a substack which is Sunday letters from Sam that I write a letter roughly every Sunday”
▶ Watch at ~1:25:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 5

Hot Take09:00

Better to Be Optimistic and Wrong Than Pessimistic and Right

Sam argues engineers are fundamentally pessimistic — they see everything as a problem to be solved — but he's concluded he has lost far more by being pessimistic than by being optimistic too early. His mantra is that there's very little prize for being pessimistic and right, especially in a moment of rapid change. Optimism, for him, is a deliberate choice rather than a personality trait.

Engineers 'come into the world broken,' seeing everything as a problem
Sam has missed out more from pessimism than from early optimism
There's almost no reward for being 'pessimistic and right'
Optimism is a conscious habit, not his natural disposition

“it's much better to be optimistic and wrong than pessimistic and right”
Sam Schillace · 09:30

#optimism#mindset#innovation

Hot Take22:00

Why Crypto Never Passed Sam's 'What If It Works' Test

Sam spent a lot of time genuinely stress-testing his own skepticism about crypto, checking whether he was just reacting to something that threatened his identity. He never found a 'what if this works' scenario that produced real value — even in the best case, the user outcomes felt dystopian rather than desirable. He concluded the pessimism was justified.

Sam deliberately checked whether he was reacting from threatened identity
His test: 'what if it works — how valuable is it?' Crypto failed even best-case
He couldn't name a single thing valuable to him as a user
Conclusion: sometimes the pessimism really is justified

“what if it works like then I have to run upsc on my personal finances that sounds dystopian I don't want that”
Sam Schillace · 22:30

#crypto#skepticism#user-value

Hot Take55:30

Do the Thing You'd Feel Guilty Getting Paid For

Sam pushes back on the belief that work has to be unpleasant to be valuable — we systematically undervalue the things we're good at. His advice: find the thing you'd feel guilty getting paid for and do the hell out of it, as hard as you can. The most impact you'll ever have comes from that flow state where you can't quite believe you're getting away with it.

We undervalue what's easy and fun, assuming valuable work must be unpleasant
Find the thing you feel guilty to get paid for and pursue it at full intensity
That work doesn't have to be hard — the best case is that it isn't
Peak impact comes from the flow state of 'getting away with' doing what you love

“you should go do the thing that you feel guilty to get paid for if there's a thing like that and do the hell out…”
Sam Schillace · 55:30

“the most impact you'll ever have is where you're in that mode where you're just like in the flow”
Sam Schillace · 56:00

#career#advice#flow

Hot Take1:02:30

AI Isn't a Feature of Your Product — Your Product Is a Feature of AI

Sam argues you can add some value by bolting AI onto an existing product, but the transformative value comes from apps and solutions that wouldn't work at all without it — products that treat AI as a true platform. He inverts the usual framing: rather than AI being one feature among many, the product itself becomes downstream of AI's capabilities.

Bolting AI onto an existing product adds only marginal value
Massive value comes from products that can't exist without AI
Treat AI as a true platform, not a feature
The framing inverts: your product becomes a feature of AI

“AI isn't a feature of your product your product is a feature of AI”
Sam Schillace · 1:02:30

“really transformative massive value will come from building apps and solutions that won't work at all without it”
Sam Schillace · 1:03:00

#ai#product#platform

Hot Take1:04:30

Just as the Internet Made Distribution Free, AI Will Make Pixels Free

Sam sees AI driving a giant disruption in software analogous to how the internet made distributing information free. Producing pixels — UI, images, software output — is currently expensive, requiring programmers and infrastructure, and many businesses are predicated on that cost. AI will collapse it, the way image generation already replaced the Photoshop-skill pipeline with a plain-language request.

Internet made distribution of information free; AI will make pixels free
Producing pixels today is expensive — programmers plus infrastructure
Many businesses are predicated on pixels being costly to produce
Image generation already shows the shift — 'a cat riding a bike' vs learning Photoshop

“I think the way that the internet made distribution of information free I think AI is going to make pixels free”
Sam Schillace · 1:04:30

#ai#disruption#software

Explainer· 3

Explainer11:30

A Polarized Love/Hate Reaction Is the Signal of True Disruption

Sam explains that a product's impact shows up in the shape of the reaction. A bell curve of indifference and mild dislike means an incremental product. But when a small group loves something intensely and others want it to 'die in a fire,' that polarization signals genuine disruption — as with early Google Docs and later ChatGPT. He notes the haters can even outnumber the fans for a long time and it doesn't matter.

Modern indifference and mild dislike = incremental, non-disruptive product
Intense love plus intense hatred = a truly impactful, disruptive product
ChatGPT ('amazing' vs 'terrible') is a clear example of the pattern
Early Google Docs had haters outnumbering fans for a long time — that's fine

“the entire world is like this is amazing or this is terrible and there's like not a whole lot in between”
Sam Schillace · 12:00

“for a long time the haters outnumbered the people who were fans”
Sam Schillace · 12:30

#disruption#product#signals

Explainer25:00

Adoption Follows 'Thermodynamic' Rules — and Friction Is Hidden Cost

Sam frames adoption almost like physics: add a little value and adoption creeps; add a lot and it explodes (ChatGPT). But builders forget the whole system around their feature — the user has to hear about it, remember it, learn it, build a habit, and get past sign-up friction. To win, the total ease gained has to exceed the energy spent, ideally by 10x. On Writely they cut friction so hard they didn't even ask for an email at first.

Small value = slow adoption; large value = explosive adoption
Builders overweight their feature and ignore the surrounding effort cost
Hearing, remembering, learning, habit-building, and sign-up are all friction
Net value must exceed effort — aim for ~10x better than what it costs to use
Writely deferred asking for an email until ~2 minutes of use to kill friction

“when we did uh rightly at the beginning we didn't even ask for an email address because it was such a novel thing we didn't…”
Sam Schillace · 26:30

“it has to make your life a lot better hopefully a really a lot better like 10x better than what you spend to use it”
Sam Schillace · 27:30

#adoption#friction#product#onboarding

Explainer49:30

Why Sam Thinks the Younger Generation Is More Pessimistic

Sam has puzzled over why students today seem less energetic about solving problems than earlier generations. He traces it to a reduced willingness to take risks and fail: filtered content presents rare five- and six-sigma successes as normal, living 'out loud' makes failure feel more painful, elite kids grow up highly curated with everything needing a reason and output, and children stopped being allowed to play unsupervised. The through-line is that you can't succeed if you're afraid to embarrass yourself.

Filtered content presents rare extreme successes as the norm
Public/'living out loud' life makes failure feel more painful
Elite kids are highly curated — everything must have a reason and output
Loss of unsupervised childhood play reduced tolerance for experimenting to failure
Core skill: being willing to make a fool of yourself and fail

“you see a lot of filtered content and that filtered content presents low probability events like five and Six Sigma events as though they were…”
Sam Schillace · 50:30

“you cannot succeed if you're afraid to fail”
Sam Schillace · 52:30

#risk#failure#generations#mindset

Story· 3

Story04:00

The Very First Google Doc From 2005 Still Opens Today

Sam still has the original document from before Google Docs existed — a 2005 test file written in C on rented Windows servers in Texas, later ported to Java on Bigtable, then Spanner, with the front end rewritten twice. Despite all those back-end and front-end migrations, no user data was ever lost. The document is just him messaging a colleague about whether collaborative typing was colliding, plus a pasted image of Edna from The Incredibles.

Started in 2005 in C on three rented Windows file servers in a Texas data center
Migrated to Java on Bigtable, then Spanner, front end rewritten twice — nothing lost
The content is just a note to Steve testing whether collaboration was colliding
The Computer History Museum wanted to curate it but the live doc can't really be preserved

“we moved all the data over in big table and we we didn't lose anything like we never lost anybody's stuff”
Sam Schillace · 04:30

“it is the old Google doc from like October of 2005 or something like that”
Sam Schillace · 05:00

#google-docs#history#migration

Story06:00

They Moved All of Google Docs to Google's Infrastructure and Nobody Noticed

When Writely migrated onto Google's infrastructure, the team put the site into read-only 'maintenance mode' for eight hours on a Sunday, moved all the data, and brought the new system up. Days later Sergey asked when they'd migrate — and Sam had to tell him it was already done. The only person who spotted it was a blogger in Germany who noticed the IP address had changed.

Migration done quietly in an 8-hour Sunday read-only window
Sergey Brin asked when they'd move over — days after it had already happened
The only detection was a German blogger noticing an IP address change
Sam values doing high-stakes engineering changes invisibly to users

“oh yeah we did it this weekend no one noticed some blogger in Germany like noticed the IP address changed and that was it like…”
Sam Schillace · 06:30

#google#migration#engineering

Story28:00

Google Docs' Innovator's Dilemma: 'We Have All the Users, They Have All the Money'

Sam describes deliberately stripping features to make Google Docs zero-install, easy, and collaborative against an Office incumbent that was asymptotically adding low-value features. They even cut too much — students demanded word count early. It was a textbook innovator's dilemma: a small product chipping away from the bottom of a market the incumbent didn't understand. Microsoft survived it well; Google took the users, Microsoft kept the money.

Deliberate tradeoff: zero-install and collaboration in exchange for far fewer features
They cut too far — word count was an early demand from student users
Classic innovator's dilemma: chipping from the bottom of a neglected market
Outcome: Google took market share, Microsoft kept the revenue

“we took a bunch of market share but they kept all the money basically”
Sam Schillace · 30:30

#innovators-dilemma#google-docs#microsoft#strategy

Takeaway· 4

Takeaway10:30

When People Call It a 'Toy,' You've Probably Built Something Real

Sam says every new idea looks dumb at first — but so do genuinely dumb ideas, so it's an imperfect signal. The tell he listens for is dismissive language, especially the word 'toy.' If people can't muster a better criticism than 'it's just a toy,' that's often a sign the thing is actually real and threatening.

Every new idea looks dumb at first — but so do actually dumb ideas
The more disruptive an idea, the dumber it feels initially
Listen for dismissals like 'it's a toy,' 'it's stupid,' 'I don't get it'
'Toy' is a strong signifier of something real people can't otherwise argue against

“if you hear people saying something's a toy that's often a really good signifier that it's actually something real and threatening”
Sam Schillace · 10:30

#innovation#disruption#signals

Takeaway22:30

Users Are Lazy — Only Real User Value Wins

Sam's root principle is that everything comes down to significant user value. People are lazy and cynical at heart; nobody adopts something because it's friendly, nice, or has a pretty logo. If you can't point at real user value, no amount of marketing dollars or articles will save the product.

It's all about user value — everything else is noise
People are lazy and only care whether something makes their life better
Marketing spend and articles can't rescue a product with no real value
Convenience wins because users won't expend effort for weak payoff

“users are lazy right we're all lazy we don't really care that much at the end of the day”
Sam Schillace · 22:45

#user-value#product#adoption

Takeaway53:00

Sam's Personal Motto: 'From Error Comes Virtue'

Sam describes himself as a maker with poor motor skills who makes mistakes constantly — and then figures out how to turn each mistake into something good. He adopted 'virtue from error' as his personal motto this year, the first he's ever had, and says the more he repeats it the more he likes it. It captures a whole disposition toward creating from your own mistakes.

Sam constantly makes mistakes as a maker and turns them into virtue
'Virtue from error' is his first-ever personal motto, adopted this year
He frames mistakes as raw material to be creative with, not failures to hide
The more he repeats it, the more it resonates

“I have this personal motto which is like from error comes virtue”
Sam Schillace · 53:00

#motto#failure#creativity

Takeaway1:09:30

'Just Play With It' Is Bad Advice — Pick a Concrete Goal Instead

Sam disagrees with the common advice to just play with AI. The best way to learn a new technology is to pick a concrete thing to build with it — even a goofy or arbitrary goal — and be a little stubborn about reaching it. 'Mess around for an hour' isn't a goal; 'build a GPT that can do this part of my job' is. Aim goals somewhere at least slightly interesting.

'Just play with it' isn't really useful advice for learning AI
Pick a concrete goal — even a goofy one — and be stubborn about reaching it
An arbitrary but real goal beats aimless messing around
Choose goals that lead somewhere at least a little interesting

“just play with it is not really great advice”
Sam Schillace · 1:09:30

“picking in some arbitrary goal and being a little bit stubborn about trying to get yourself to it is a good way to learn stuff”
Sam Schillace · 1:10:00

#ai#learning#advice

Key ideas

Frameworks in this episode

Guilty-Pleasure Career Bet

North Star Exploration

The Love-Hate Disruption Test

User-Value Thermodynamics

What-If Before Why-Not

People & resources mentioned

People · 19

Resources · 30

Insights & moments

◆Hot Take· 5

Better to Be Optimistic and Wrong Than Pessimistic and Right

Why Crypto Never Passed Sam's 'What If It Works' Test

Do the Thing You'd Feel Guilty Getting Paid For

AI Isn't a Feature of Your Product — Your Product Is a Feature of AI

Just as the Internet Made Distribution Free, AI Will Make Pixels Free

✶Explainer· 3

A Polarized Love/Hate Reaction Is the Signal of True Disruption

Adoption Follows 'Thermodynamic' Rules — and Friction Is Hidden Cost

Why Sam Thinks the Younger Generation Is More Pessimistic

❝Story· 3

The Very First Google Doc From 2005 Still Opens Today

They Moved All of Google Docs to Google's Infrastructure and Nobody Noticed

Google Docs' Innovator's Dilemma: 'We Have All the Users, They Have All the Money'

▲Takeaway· 4

When People Call It a 'Toy,' You've Probably Built Something Real

Users Are Lazy — Only Real User Value Wins

Sam's Personal Motto: 'From Error Comes Virtue'

'Just Play With It' Is Bad Advice — Pick a Concrete Goal Instead

Hot Take· 5

Explainer· 3

Story· 3

Takeaway· 4