The Wisdom Wall

98 quotable lessons, heuristics and mental models. Every one is playable at the moment it was said. No fortune cookies allowed.

Everyone Marc Andreessen (276)Ben Horowitz (250)Benedict Evans (184)Martín Casado (172)Alex Rampell (140)Chris Dixon (111)Steven Sinofsky (98)Balaji Srinivasan (89)Margit Wennmachers (69)Vijay Pande (65)Scott Kupor (56)Peter Levine (55)Anish Acharya (55)Connie Chan (51) Best Newest Oldest

“this is not a magic to discover drugs, because the hard part of drugs has always been candidates. Not candidates. It's always been efficacy and safety. The candidates have, since the eighties, have been able to develop more than we could test. It's human patients, and it's very, very, very hard.”

Steven Sinofsky, Aug 25, 2026

“this middleware layer, it's always, always very unstable. It looks great in a network hierarchy diagram of the OSI levels of networking, but it's just never that stable.”

Steven Sinofsky, Jul 7, 2026

“the universal truth for enterprise software is the, the most difficult thing to do that happens to be the dumbest is to attempt to just compete head on with, with an existing category. And, and by head on, I mean, not just the same category, but doing it the same way. The biggest opportunity right now is always, always…”

Steven Sinofsky, Jul 7, 2026

“And this, the thing that's not different about AI, and that agents don't fix, that nothing fix, is that any enterprise of a thousand people or more, or that's older than 10 years, is just a mass of stuff that's sitting there waiting to be integrated. And, and you can't just say it's gonna integrate. AI actually doesn't…”

Steven Sinofsky, Apr 28, 2026

“their fear is, like, unleashing, not just the agents themselves, but humans to do integration. Because you put, People creating new integrations. And you just say, please break my system of record.”

Steven Sinofsky, Apr 8, 2026

“Also, to build on your point earlier, like, about distribution, and the reason that distribution is not the advantage that it used to be is because It's already exists on seven billion phones.”

Steven Sinofsky, Sep 24, 2025

“About two thirds of the time, the big company says, wow, the leader is really expensive, but we have our magic distribution beans. So we're gonna, we're gonna pick the number two or number three. That's like way, way cheaper and get it in a fire sale. And of course that never, ever, ever works.”

Steven Sinofsky, Aug 8, 2025

“tooling itself is never a really huge business because you have to have it. And so it's sort of this, well, if you have to have it, then there's going to be, there are going to be many alternatives and there are going to be some low priced ones, some high priced ones, but the people that want to have the predominant…”

Steven Sinofsky, Aug 8, 2025

“What China is trying to do is commoditizing our strength. And so the, the, the release of a bunch of open, pure open source, open weight models coming from China is specifically designed to go after a rigid or complacent American view of AI, which is, you know, cloud hosted by a few big players, you know, closed source”

Steven Sinofsky, Aug 8, 2025

“And if you can't do that, then your ability to actually automate that task isn't going to exist because there's no economic incentive to just be, hi, I'm the headless, faceless, nameless, low price mortgage leader is not really a business.”

Steven Sinofsky, Jun 27, 2025

“And that, and whether it was, you know, that or all the database programming languages like, um, Delphi or PowerBuilder, you know, these are all in algorithmic sense, they were all constant improvement. Like just, they added a constant factor, like plus seven onto programming. None of them changed the mathematical…”

Steven Sinofsky, Jun 27, 2025

“The strength of Microsoft is that you never have to be best. You just have to be included.”

Steven Sinofsky, Jun 18, 2025

“Apple taught them how to do this. Now, they didn't plan on doing that. But osmosis happens. And they got all these skills”

Steven Sinofsky, Jun 18, 2025

“the reason that it's a thousand dollars, or 1500 dollars, or whatever, is because of the innovation in manufacturing. So all that needs to happen is like another step function change in manufacturing.”

Steven Sinofsky, Jun 18, 2025

“I think it's very, very easy to say China doesn't respect intellectual property, so they can't be part of the world stage, flat out. I mean, they've crushed the pharmaceutical industry that way. You know, what they've done with BYD and Tesla, Arguably pretty rude and stuff like that. But on the other hand, it's just as…”

Steven Sinofsky, Jun 18, 2025

“And the, the rest of the companies are still trying to figure out their, their revenue models, which I would argue was probably premature. And it starts to look a little to me like, hey, let's charge for a web server. And it's like the business of selling, like serving HTTP, not a great business.”

Steven Sinofsky, Feb 6, 2025

“And, and it's, to me, this is all the equivalent of the browser getting JavaScript. Because once the browser got JavaScript, then all of a sudden you could do anything you needed without going to some standards body or building your own browser.”

Steven Sinofsky, Feb 6, 2025

“in any feature that you do, when someone says, I don't like it, but it's good for, like, less skilled people, Yeah. There's a warning in that.”

Steven Sinofsky, Apr 27, 2019

“because I think that this move to services, people are just having trouble getting their heads wrapped around it, and it's a very natural progression for any company when it starts to reach a mature level, which is, okay, are we now effectively, you know, selling things to our, our quote, installed base enough, and in…”

Steven Sinofsky, Apr 1, 2019

“the reason that there are none of the PC makers, other than Apple in a sense, are successful phone makers, is because they were exactly like Detroit. They, they had a graphics group, they had a peripheral group, they had an IO group, they had a storage group.”

Steven Sinofsky, Jan 2, 2019

“And, the most interesting thing as you mature on the S-curve is that generally what happens is companies go through massive turmoil, And they change their executive staff, and they bring in people who are willing to figure out how to charge your existing customers more money. And milk the company.”

Steven Sinofsky, Jan 2, 2019

“I feel like that's always where big companies fall down, is they think they need an MBA running a P&L for something”

Steven Sinofsky, Jan 2, 2019

“Yeah, I really agree with that, because, like, when you're at a big company, and you're hit with GDPR, like, you, I know exactly how this is going to work. Like, you've got all the subsidiaries, and you know, too. Well, you're paralyzed, because you have to, you do, the EU just spent four years pulling together 28…”

Steven Sinofsky, Jan 2, 2019

“And this is, like, literally the biggest lesson from Microsoft Clippy, which was, like, automatic features and automation are all cool, except they kind of have to be right literally all of the time.”

Steven Sinofsky, Jan 2, 2019

“very rarely is like an algorithm like this secret sauce for a company. Because you could look at what goes on from the outside and pretty much reverse engineer an algorithm.”

Steven Sinofsky, Jan 2, 2019

“custom chips have always been a competitive disadvantage. For a company in particular, they were a very deep competitive disadvantage for Apple when the run rate for Motorola chips went down and they couldn't sustain it. And then they made the same mistake with the power PC chip where that run rate declined and there…”

Steven Sinofsky, Jan 2, 2019

“Cross-platform is a developer thing because no one person is cross-platform.”

Steven Sinofsky, Jan 2, 2019

“startups look at enterprise software and they think about it in terms of startup scale... And that's fine until you have a 100,000 people in 20 countries with different national laws and policies about business expense and all of those, and then you overlay corporate policies and, and the whole thing just, and then…”

Steven Sinofsky, Jul 7, 2026

“this notion of exception handling is just the root of the challenge with, with agents, which is almost everything interesting in an enterprise is an exception.”

Steven Sinofsky, Jul 7, 2026

“Well, certainly network effects outside of a company are extremely difficult for a bunch of clients and security reasons. But, but the biggest network effect in enterprise software is inside of a company.”

Steven Sinofsky, Jul 7, 2026

“That, the way to say it is, algorithmic thinking. Is really, really, really hard for the vast majority of people who have jobs. And, and so the, the easiest way to think about it is if you were to go into any person and ask them to create a flow chart for a particular thing that they have to go do, they would probably…”

Steven Sinofsky, Apr 8, 2026

“This is, the thing that AI is, is an accelerant in building the product. Whereas what, what sass and the cloud did was accelerate getting paid.”

Steven Sinofsky, Sep 24, 2025

“We've changed our view of excellent because we wanted more access.”

Steven Sinofsky, Jun 27, 2025

“you dig in, and you find out like, wow, you're prompting, Although it's English-like, it turns out you're just programming. And you're just programming in prompts.”

Steven Sinofsky, Jun 27, 2025

“the apps that ended up mattering on the internet literally didn't exist. Before the internet. And I think that's what people are losing sight of.”

Steven Sinofsky, Feb 6, 2025

“startups tend to really underestimate the route to market in the go to market for like existing sort of heavy industry”

Steven Sinofsky, Feb 26, 2019

“They, they do, this is part of their execution is to have this complexity, maximize their, their revenue from it, but not surface it to the average consumer who turns out to not really care.”

Steven Sinofsky, Jan 2, 2019

“I think that that's really important, especially in the startup world, because there's this tendency, you know, if you're a startup and you work in a particular space, and then you just hear an announcement from a big company, that they're working on something. You apply, like, oh my god, it must be important.”

Steven Sinofsky, Jan 2, 2019

“And what Apple is able to do is the bet that they've made is that we have a platform that's made up of a set of APIs, a Unix operating system kernel, these ARM chips that have all of these sensors and capabilities. And it turns out the thing that they do uniquely is they can take that platform and then Take the 80% of…”

Steven Sinofsky, Jan 2, 2019

“it's very difficult if you're a big successful organization to stand up and tell the outside world the thing you love, And the thing that's all the business is not the thing we're going to worry about anymore. And you, you can't do that. Like that's the, that is the literally the innovator's dilemma.”

Steven Sinofsky, Jan 2, 2019

“Cause they're, they're actually no one doing that. All of those Are on the back of their S curve, and they're in sustain mode, and the last thing they're going to do is rewrite them”

Steven Sinofsky, Jan 2, 2019

“The neat thing about being a giant company is that within the company, there is a million ideas floating around and a million prototypes, and, and the process by which they go through this funnel and, and come out, that's what makes a company unique and, and their proprietary advantage, and I think Apple has…”

Steven Sinofsky, Jan 2, 2019

“it turns out all those things people said in the, the eighties when mice came out about like, it's kind of detached from what I'm doing. And it's this level of indirect. It turns out it's very true. And if you've, if you didn't force yourself to experience it as your first computing, it doesn't appear natural at all.”

Steven Sinofsky, Jan 2, 2019

“Yeah, it's worth actually just highlighting for folks, like, exactly how that works, because in the startup world, that doesn't often make a lot of sense. You're like, wow, you raise capital, you build a company, but what, what these people are doing is they're tapping into this whole elaborate ecosystem of…”

Steven Sinofsky, Jan 2, 2019

“you might think you could pick a special part, like, you could pick the best four K camera available, and think that that will be sustainable, but it'll be sustainable for, like, 10 minutes. Because that, that camera will be everywhere, or the capabilities in that camera, and so you really do have to build a…”

Steven Sinofsky, Jan 2, 2019

“the interesting thing is for each of those, they, they, they didn't sell like the first people to buy minis weren't the people who bought all the mainframes. They were all the people who didn't buy the mainframe. And for the people who bought, like, the PCs, they weren't all the people who bought everything that came…”

Steven Sinofsky, Jan 2, 2019

“going back historically, like things that were killer apps are always like in hindsight. Like, it's not like you, you knew right away that your PC was going to be good at making greeting cards or balancing your checkbook. It took decades for, for those things that, that really surfaced.”

Steven Sinofsky, Jan 2, 2019

“the wave of skepticism is really fixated on this, to me, on this notion that the, the watch needs to do everything the way that your phone did it. And, and so, like, that, that problem is that is never how a new device category evolves. Like, in fact, it, by definition, doesn't do everything the old one did. And what…”

Steven Sinofsky, Jan 2, 2019

“That math is very much a, a leading edge indicator of what the market might be interested in.”

Steven Sinofsky, Aug 25, 2026

“The only incumbents are only interested in what the other incumbents are doing. Microsoft is worried way more about what Amazon and Google are doing than anyone in a startup space.”

Steven Sinofsky, Aug 25, 2026

“One of the things that happens in technology shifts is nobody understands exponential when it's happening.”

Steven Sinofsky, Jul 7, 2026

“the most sticky thing you could do is actually collect money from a customer. And if you're collecting money, it turns out it's really, really hard for them to stop sending you money.”

Steven Sinofsky, Jul 7, 2026

“in enterprise software, the two most frequently used features exist in no enterprise software natively. It's export to Excel and export as CSV and or PDF you pick.”

Steven Sinofsky, Jul 7, 2026

“AI might be the first time that inside a company search can actually provide immediate value.”

Steven Sinofsky, Apr 28, 2026

“humans have been a bottleneck In tapping the past 25 years of software capabilities.”

Steven Sinofsky, Apr 8, 2026

“also don't, I keep thinking, do not discount the local compute engine as being a release valve for all of this.”

Steven Sinofsky, Apr 8, 2026

“We're at the 64 K IBM PC era of the microcomputer.”

Steven Sinofsky, Jun 27, 2025

“can they transform the way they think to something new? Because that's really where the disruption is going to happen.”

Steven Sinofsky, Jun 27, 2025

“the real thing that Apple needs to do is figure out what model is going to be tuned to run on their unique hardware on the edge and their unique offering or constraint, depending on, of privacy and how that plays out.”

Steven Sinofsky, Jun 18, 2025

“they can't understand that these paradigms where, where like the liabilities either don't matter or just become features.”

Steven Sinofsky, Feb 6, 2025

“because the, the best, the best feedback loop to build a great platform for other people to use is to be building apps.”

Steven Sinofsky, Feb 6, 2025

“When you make a bold bet, like, there's always someone who is going to say, I could have fixed it. Just give me more time.”

Steven Sinofsky, Apr 27, 2019

“Frank and Ollie were like, you want the box. And we're like, we do. Yeah. They're like, because every character needs a stage. And, and this allows the character to exit and enter with grace because otherwise it would be like an alien and it would just disappear.”

Steven Sinofsky, Apr 27, 2019

“I honestly believe in hindsight that the, sort of, the boldness of out front retiring him, as opposed to, like, just secretly cutting him and pretending like he never existed. Or it never existed. I keep saying he, but there's no gender. Uh, I think that contributed to the, sort of the, the burgeoning cult status.”

Steven Sinofsky, Apr 27, 2019

“underneath every, what, there are probably, you know, a very, very small number of people at a very, very smaller number of companies that understand all the complexity that could go into delivering Apple Card. That complexity, Apple is, is erasing.”

Steven Sinofsky, Apr 1, 2019

“they don't have to get nine hundred million people for every service. And they can aspire to that, and they can measure that But there's some point where it becomes a very good business and a very great value proposition, even for people who don't have them, to know that they can get them.”

Steven Sinofsky, Apr 1, 2019

“you don't prematurely bundle things, because then you really don't know if you're successful or not.”

Steven Sinofsky, Apr 1, 2019

“And again, this was something Apple pioneered very early when they made upgrades to the Mac operating system free. They realize that that turns out to be a better business if you just make owning, being part of the ecosystem great.”

Steven Sinofsky, Apr 1, 2019

“they all are dealing with the next parts of why you go to CES, which is these ingredients that sort of bubble up, and then they take about the same amount of time for a big company to act, and they all show up with it at the same time.”

Steven Sinofsky, Feb 26, 2019

“really nobody wants to make smoke alarms, because that's like super easy and massive liability. Like, it's, it's like a scary business to enter. And plus, you have to know all the fire codes all around the world.”

Steven Sinofsky, Feb 26, 2019

“The, the big lesson I do think that people should definitely walk away from as founders is to again, remember that it's not just the shiny product, but boy, managing distribution, managing pricing, understanding how you bring things to market, um, and do so is, is, is much about innovation as like what code and what…”

Steven Sinofsky, Jan 2, 2019

“The US just chose not to make laws and regulations that are nearly as all encompassing as these EU ones. But often what happens is it's just better to just pick that as the standard by which to do, because it's, it's the higher bar to, to the higher threshold.”

Steven Sinofsky, Jan 2, 2019

“So I think that, that, you know, for any startup, a key thing is there's probably a good chance that, that the company has a process around the service going down, and the reality is they need the same kind of checklist, process, call list, pagers, alerts, in case of being notified by a breach, which might actually not…”

Steven Sinofsky, Jan 2, 2019

“a good rule of thumb is if you can sign on to your product, Then you're collecting private information, because you have that key, and then everything associated with it is private.”

Steven Sinofsky, Jan 2, 2019

“Right, which is, for startups, a super interesting point, because it means, like, if you take the lead from the big companies in what to do, you'll see that all of them, they have the resources to, like, do everything five times.”

Steven Sinofsky, Jan 2, 2019

“something with three sets of parentheses in it, it's likely to have a bug in it just because it has three sets of parentheses in it.”

Steven Sinofsky, Jan 2, 2019

“there's something about a mechanical device That produces answers that makes the human brain ascribe way more authority to it than there necessarily should be.”

Steven Sinofsky, Jan 2, 2019

“the truth is, is that the, the org is as much a product of a company as the product.”

Steven Sinofsky, Jan 2, 2019

“it's really important to keep in mind that you, you can't really take one thing that a company does and then extract from that, like, oh, this is how we're going to operate.”

Steven Sinofsky, Jan 2, 2019

“it's a smart management strategy to not goal everybody on everything, because the minute you do that, then you're, you're, Your linear equations are too hard to move people around because having flexibility is both good for the employees and good for the, for the company.”

Steven Sinofsky, Jan 2, 2019

“Because I think that's something that you really need to internalize about these four companies is that they have built platforms, strategies, and organizations that understand how to deal with changes in technology in a way that past generation companies just had challenges with.”

Steven Sinofsky, Jan 2, 2019

“We now build systems that no one understands, and that classic, if I could get a time machine and go back to, like, 1950, I'd invent whatever your favorite product is now, and then you realize you couldn't come up with an iPhone in 1950.”

Steven Sinofsky, Jan 2, 2019

“most new things are, like, 90% old stuff, like, with a slightly different perspective that comes from how you think about, um, the, the collection of things, your own expertise, your own experiences”

Steven Sinofsky, Jan 2, 2019

“the whole thing about AI was always, if you actually could find a practical use for one of the techniques, you cross it off the list of AI techniques, and it's like no longer AI.”

Steven Sinofsky, Jan 2, 2019

“that is like, in a sense, the ultimate reason why all of these things are, are working is basically because of cloud computing, the scale of the architecture of cloud computing, and the internet that brings all that data in.”

Steven Sinofsky, Jan 2, 2019

“Because I, I just don't find them valuable because my view of notifications is I, I want to be able to act on it, and so seeing it and then having to swipe it and clear it and deal with it, I might as well just look at the app and see the badges that tell me which apps to go look at.”

Steven Sinofsky, Jan 2, 2019

“You, you can't really project where the, the whole social norms are going to be. And like when laptops first came out, we had big fights about like whether it was appropriate to bring them to meetings or not, because it was super clear you were focused on whatever was going on in your laptop. And here we are a decade…”

Steven Sinofsky, Jan 2, 2019

“Well, and I think that the, this is one where, where I think people can overstate the need for the cloud side of it, or understate the amount that they can do based, sort of, not really Cloud, but, or clients, but like on a client side way, I mean, if you think about all the things that they could suggest, they could…”

Steven Sinofsky, Jan 2, 2019

“the closer you are to, like, actually helping make the change, in a weird way, it's almost harder for you as an individual to see the changes, because you're mired in all the details.”

Steven Sinofsky, Jan 2, 2019

“and then one day you have, like, someone else's whole vertical integrated into your product, but it's never as good as the separate one. But it might be good enough to keep your customers from jumping and using another product.”

Steven Sinofsky, Jan 2, 2019

“You know, every CEO of every major corporation is now effectively an IT person. Because every company in Software Eats the World is really a software company.”

Steven Sinofsky, Jan 2, 2019

“It also allows IT to focus much less on the deployment and management and scale and reliability and, and security, which of course, the idea of competing with With, you know, the Googles and the Amazons and the Microsofts on security, if you're, you know, an appliance maker in the Midwest, like that's a really, where…”

Steven Sinofsky, Jan 2, 2019

“at the heart, the goal of developing a platform, you know, has the side effect, whether you think it's intended or otherwise, of making cross-platform development harder.”

Steven Sinofsky, Jan 2, 2019

“And so now we've got this, we got to this world where these tools were democratized and it, it, it didn't just Um, make things more efficient. It also defined a work culture.”

Steven Sinofsky, Jan 2, 2019

“today's model where everything is sort of a click away, even apps, which everybody can talk about the headaches of getting all the different apps and stuff, but the friction is very, very low. And your ability to put it on the machine, to get it off the machine is very, very easy, not just because of the store, but…”

Steven Sinofsky, Jan 2, 2019

“Like, what your role as a manager is in a meeting is no longer to be reported to, because frankly, if you want to know, you should just go visit the place that everybody on the team is already using to To keep track of their information. And when you get everybody together, it shouldn't be to argue the pros and cons of…”

Steven Sinofsky, Jan 2, 2019

“clippy ended up being the default, and so that was probably why, and also the absurdity of a paperclip telling you to write a letter.”

Steven Sinofsky, Apr 27, 2019

“what's really happening now is, is the innovation has just moved up the, the stack. And now you're just going to start to see like constellations of, of innovation.”

Steven Sinofsky, Jan 2, 2019
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