Sam Schillace
Deputy CTO & CVP, Microsoft. On 2 shows, 2 appearances. The Shows tab opens the full record on each.
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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.
2shows
2appearances
43statements
7resolved
5supported
2contradicted
71%fully supported
Everything Sam Schillace said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Schillace: Google Docs has become a complicated, bloated version of Microsoft Office
“To be honest, like, I'm a little bit sad at the state of Gdocs these days because I think they're losing sight of the idea that, you know, they're kind of turning it into Office and like making it very complicated to use again. And I find lots of things broken…”
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: Failing early is better than failing late in technology
“Failing on the early side, you at least have a chance to, like, course correct, right? Because if you don't spend all your resources and burn out completely, you can keep going, and maybe the world catches up to you, or maybe you make the world catch up to you…”
Schillace: There is no prize for being pessimistic and right in tech
“There's not really much of a prize for being pessimistic and right about these things. Ok, you get a ribbon. Who cares? The prize is for being optimistic and right.”
Schillace: You cannot short broad technological revolutions
“You can't go short on, like, technical, technological revolution, right? You can't, like, short solar or some crazy shit like that. It tends to be wrong. We tend to figure stuff out over time. You know, at best, you're right for a little while, and eventually …”
Schillace: AI tooling will expand engineering ambitions rather than shrink team sizes
“Programmers are definitely going to get more effective. We're going to get more agentic programming tools. So you're going to get higher and higher leverage, but I don't think it's going to make the team smaller. I think it's just going to make the ambitions b…”
Schillace: AI will make creating pixels free, radically altering software applications
“I have the suspicion that the nature of applications is going to change radically in the next five to 10 years. And so I think, you know, this idea that just in the same way that the internet made the distribution of information essentially free, AI, generativ…”
Schillace: Many businesses will be disrupted because their models rely on pixel expense
“I think there are lots of businesses out there that don't fully understand that they're predicated on the expense of creating pixels. And so similar disruption is in the works.”
Schillace: Engineers should think with AI models but plan with code
“The easy way to understand this is when I say you should think with the model, but plan with code because the models are, they're stochastic and fuzzy. And so if you want something reliable, you should build kind of a scaffold around it in code, something exec…”
Schillace: High-value LLM applications work like a cryptographic trapdoor
“The things that work well with LLMs have this shape almost like a cryptographic trapdoor. There are like things where it's started work for the human to create the work, but easy for the human to validate the work. Those are the things that tend to have high v…”
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: Waiting for tech to get easier guarantees too much competition
“The mistake people make the most is, you know, they'll be like, well, that's a cool idea, but it's really hard. Let's wait three years till it's easier. When it's easier, there'll be a million people doing it and there's path dependencies in there and stuff li…”
Schillace: Enterprise software de-emphasizes UX once it clears the CIO's checklist
“There's less of an emphasis on end user experience, I think in the enterprise space, because once you're kind of over the line where the CIO says, okay, that's on the checklist of things that your software does, anything above that doesn't really matter very m…”
Schillace: Durable AI value will accrue to trusted personal data holders
“So that's kind of where that durable value will wind up being, I think, over time. It's kind of the holders of the data and the companies that we can trust to, you know, hold that data and trust to give us the right answers are probably where their value is.”
Schillace: Physicians paired with AI diagnostic tools perform worse than AI alone
“There's a study I saw a while ago that compared like an AI based system, AI only physician only and AI plus physician An AI plus physician did worse than AI only. The physician kind of dragged the AI down because they didn't trust it.”
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: Successful software projects feel slightly out of control
“Most of the successful software projects I've seen Have the same feeling of sort of slightly out of control, but not too much of a disaster as chasing a three year old down a slight incline in a park.”
One line per show, most statements first. The link opens Sam's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 IN DEPTHLEDGER | Deputy CTO & CVP, Microsoft | 1 | 22 | 100% 3/3 | full record on In Depth → |
 LENNY'S PODCASTLEDGER | Deputy CTO & CVP, Microsoft | 1 | 21 | 50% 2/4 | full record on Lenny's Podcast → |