Sam Schillace
Deputy CTO & CVP, Microsoft · 1 appearance on the record.
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Sam Schillace is Deputy CTO and Corporate Vice President at Microsoft. He previously co-founded Upstartle, creating the web-based word processor Writely which became Google Docs, and served as Head of Engineering at Box.
21statements → 11claims → 4claims resolved → 50%fully supported → 3.9/5average certainty → 2.1/5average debate potential → ≈4.0/5argument clarity, estimated →
2 supported 0 partly supported 2 contradicted 7 not checkable as stated how the 11 claims stand · each chip opens the sources
1 prediction · 10 assertions · 4 opinions · 4 insights · 2 what ifs · every statement was checked. The prediction and assertions are the 11 claims: statements the public record can support or contradict. 4 are resolved, and 7 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.
The record, in short
What the tape says about how Sam argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.
Their most notable supported claim
Schillace: Google Docs won market share, but Microsoft kept the money
“In retrospect, they did fine. Like, we took a bunch of market share, but they kept all the money, basically. So, you know, we being Google, like, you know, so, like, they survived it. Like, you know, they survived. They did a good job surviving the challenge. …”
Their most notable contradicted claim
Schillace: Google treated candidate controversy and single interview vetoes as positive signals
“I interviewed Dave Bezris. I interviewed him when he came in and I asked him that question and his response was, I don't do math next question. And so I failed him. I was the veto and they have this policy where we're friends now, like, They have this policy w…”
Expressed certainty vs assessment result
weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet
How they sound: not measured why? →
We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Sam Schillace on measured tape to publish a rate. This says nothing about how they speak.
Everything Sam Schillace said on Lenny's Podcast that made the record, most notable first. Filter by type, assessment or year in the ledger →
Schillace: Crypto lacks meaningful user value even in the best case
“For crypto, I was always like, well, what if it works? Like, then I have to run OPSEC on my personal finances. That sounds dystopian. I don't want that. Like, I can't think of anything as a user that I think actually, like, is valuable here. Even in the best c…”
Schillace: Most Good Product Ideas Originate from Engineering
“I think a lot of the good product ideas, most of the good product ideas actually come up from engineering.”
Schillace: In five years, software you cannot converse with will feel broken
“I think we're gonna feel the same way about intention and interactivity in our products very soon. Like, if I can't tell something what my intent is and have it configure itself in an intelligent way, have it converse with me, whether that's a device or a piec…”
Schillace: AI will make pixels free like the internet freed distribution
“I think the way that the internet made distribution of information free, I think AI is going to make pixels free.”
Schillace: AI found more use cases in one week than crypto did
“Just to kick cryptos corpse one last time. Like there was some tweet, like at the beginning of the year that I saw that somebody was like, yeah, it took like the AI bros, like a week to come up with as many use cases as you know, crypto came up within that dec…”
Schillace: Giving multi-agent AI systems shared whiteboard memory makes them smarter
“We were trying to get multiple versions of them working together, like multi-agents working together, and we gave them whiteboard Working memory, like as a shared working memory thing to fix this problem, and that turns out to make them much smarter.”
Schillace: Google Docs won market share, but Microsoft kept the money
“In retrospect, they did fine. Like, we took a bunch of market share, but they kept all the money, basically. So, you know, we being Google, like, you know, so, like, they survived it. Like, you know, they survived. They did a good job surviving the challenge. …”
Schillace: Google Docs would have died without legal protections and Schmidt's support
“If I had just been, like, a random Google employee with this idea, and no legal protection, and the CEO wasn't, you know, a fan of the project, it would have died. Like, there's no way it would have made it through that, that negativity, and that pessimism”
Schillace: Believing Gemini's parity with GPT-4 means AI stalled is dumb
“When Gemini came out, all the press take was like, oh, it's not that different from GPT-IV. I guess we're done with AI now. We can go back to bed. I'm like, that is the dumbest possible interpretation of that story.”
Schillace: Google executives wanted to kill Google Docs despite millions of users
“Like in the early days, like we had like, I don't know, a couple million users, five million users. And there were still executives at Google telling me that it was a stupid idea and that it should stop. And like, we shouldn't be doing it.”
Schillace: Writely co-founders initially rejected building Google Docs in browsers
“When I had the idea for Rightly, like, my two co-founders, who were both deep domain experts in both app building and word processors, were like, the browser's never going to support this. It's a bad idea. Let's not do this.”
Schillace: Google Docs collaboration began as an accident before locking was built
“And like, the fact that you could collaborate on them was kind of an accident. Like, they're just like these things on the server. We hadn't built the thing. That would lock somebody out yet. So there was just like, here's a document, like you can edit these t…”
Schillace: Focus careers on effortless strengths rather than unpleasant grinding
“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 You know, very valuable. So I think lots of people like gravitate in this direction of like, let's go d…”
Schillace: Generative AI is in the rapid elaboration phase filling white space
“The zero to one is hard. Like understanding that there's something there at all is the really hard part because you have to be lucky and you have to be talented and you have to look in the right place and like, Do some very hard work, but once you understand t…”
Schillace: Testing candidates with seemingly impossible problems reveals builder resilience
“The reason I ask is not to get to the answer, it's because I just want to see how people react when I give them something that seems impossible and unreasonable. And some people just like back off and, you know, refuse to engage with it. And some people are ju…”
Schillace: Google treated candidate controversy and single interview vetoes as positive signals
“I interviewed Dave Bezris. I interviewed him when he came in and I asked him that question and his response was, I don't do math next question. And so I failed him. I was the veto and they have this policy where we're friends now, like, They have this policy w…”
Schillace: Writely originally ran on C# on three rented Windows servers
“We started off, in, in C Sharp, which is little known, in, you know, our own, there's, like, pre-cloud, so we, like, had three file servers that we rented that were Windows machines in a data center in Texas with a sysadmin in the Philippines running them. So …”
Schillace: Writely migrated onto Google infrastructure during an unnoticed 8-hour window
“When we migrated in to Google, we were very sneaky about it. And we like put the site into quote maintenance mode for eight hours on a Sunday where everything was just read only. And then we migrated all the data and moved everything and brought the new system…”
Schillace: Writely initially let users edit documents without an account or email
“When we did rightly at the beginning, we didn't even ask for an email address because it was such a novel thing. We didn't want any friction at all in the onboarding process. So you could just come in and make a document and start using it without telling us a…”
Schillace: Writely might not exist if founders knew collaboration's difficulty first
“Because if we understood how hard the collaboration piece would have been first, Without understanding that value might have been like, eh, it's not worth it. Like, it's gonna be so hard to solve that problem. It's probably not a, you know, useful absence.”
Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) | Jan 11, 2024 | 1h 6m |