MS DOS, every mention
142 scenes across 20 shows · ← back to MS DOS
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Acquired 65
the a16z Podcast 26
20VC 12
How I Built This 10
Founders 8
Lenny's Podcast 6
Latent Space 5
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every year every show Acquired 65 the a16z Podcast 26 20VC 12 How I Built This 10 Founders 8 Lenny's Podcast 6 Latent Space 5 
the Y Combinator Startup Podcast 4 Top Founders 4 
the Official SaaStr Podcast 3 
Big Technology 3 
All-In 3 
In Depth 2 
Cheeky Pint 2 
the Neon Show 2 
the Startup Ideas Podcast 2 
Innovators & Investors 1 
the Knowledge Project 1 
My First Million 1 
the MAD Podcast 1
Verbatim, from the transcripts: passages where MS DOS comes up on Acquired, the a16z Podcast, 20VC, How I Built This, Founders
Is The Future Customer Experience AI Talking To AI? — With Tony Bates
- ▶ 16:59 Tony Bates I feel like on the user interface side of where we are, uh, we're kind of in our MS-DOS moment right now.
How AI Changes the Economics of Innovation
- ▶ 45:09 Steven Sinofsky And he wrote like a DOS program to schedule a doctor's office, which you'd think it's just scheduling.
Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
- ▶ 1:08:17 Rory O'Driscoll I mean, the MS-DOS product, and the classic example is Magnet. 2 times in the scene
“Every small business should run itself” | Lassie with a16z
- ▶ 11:05 Alex Rampell Microsoft DOS worked pretty well. 2 times in the scene
Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
- ▶ 29:59 Rory O'Driscoll IBM licensed MS-DOS, and they should have protected it, and instead, everyone was able to clone it like Compaq.
🔬How GPT‑5 derived new results in theoretical physics and quantum gravity — Alex Lupsasca, OpenAI
- ▶ 39:59 Alex Lupsasca And it had this whole discussion of how, well, I loaded MS-DOS, and it had five floppy disks, and I had to swap my floppy disks.
Replit's CEO On The Only Two Jobs Left In The Company Of The Future · Y Combinator
- ▶ 8:14 Amjad Masad And he was showing me pictures of the software they're using today, which is MS DOS based software.
Why Rule-Breaking Is the Only Rule in Venture Capital | Ashmeet Sidana, Engineering Capital
- ▶ 1:07:00 Ashmeet Sidana You know, IBM lost control of the platform, even though they were the single largest company, and they're the ones who gave the contract to Microsoft, uh, to develop DOS and then eventually Windows.
Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman · 20VC with Harry Stebbings
- ▶ 12:59 Eran Zinman I was building software for, uh, DOS, you know, without interface.
What Mistake Founders Make With A-Players | Matt MacInnis | COO Rippling
- ▶ 55:07 Matt MacInnis We then emerged, obviously, through, like, MS-DOS into Windows, and Windows and the Macintosh interface, sorry, introduced the graphical user interface, which then became an ever-evolving standard from the mid-nineteen-eighty's until the…
Why AI Moats Still Matter (And How They've Changed)
- ▶ 31:54 Alex Rampell Like their very, very first products, they were not Microsoft Office, it was not DOS. 2 times in the scene
Seeing The Future from AI Companions to Personal Software
- ▶ 3:44 Eugenia Kuyda And so we started thinking, we got obsessed with this metaphor that the current chatbots are really the Microsoft DOS era for AI interfaces, and that there will be some sort of a Windows Mac OS moment.
- ▶ 24:18 Eugenia Kuyda How is it possible that we have this godlike technology, yet we pass around these text prompts, which is almost like Microsoft DOS commands, but worse, because at least the commands were, it was like sort of like you could learn them.
Marc Andreessen & Amjad Masad on “Good Enough” AI, AGI, and the End of Coding
- ▶ 54:59 Amjad Masad Uh, in the DOS, uh, in the DOS. 2 times in the scene
- ▶ 55:24 Amjad Masad So a lot of time I just spent it in DOS and writing batch files and opening games and messing around with that.
Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings
- ▶ 48:08 Mike Cannon-Brookes If you look back to Adobe or Intuit, well, they had to navigate DOS, to client server, to Windows, to the internet, to mobile, to all these things.
OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
- ▶ 6:27 Rory O'Driscoll IBM was the old school company that set them up by doing that famous DOS licensing deal, right?
OpenAI's NEW AI Agent Builder Replaces n8n & Zapier
- ▶ 22:16 Greg Isenberg And it's the equivalent, I'm old enough to remember, using MS-DOS
Taste is your Moat (Dylan Field of Figma)
- ▶ 9:07 Dylan Field I think we'll look back on this era as like the MS-DOS era of AI, and the prompting and natural language that everyone's doing today, I think is just sort of like the start of how we're going to create interfaces to explore it in space.
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
- ▶ 34:35 Marc Andreessen Inclusively, and the IBM team was like, all right, this is ridiculous, and they went back up to Seattle, and they told Gates, if you can't find us an operating system, uh, the, the, the deal for the interpreter is off, uh, and Bill said,… 2 times in the scene
How Bill Gates Works
- ▶ 58:56 David Senra It says, Bill and I were willing to forego per copy royalties if we could freely license the DOS software to other manufacturers. 3 times in the scene
Inside Google DeepMind: AGI, Robotics, & World Models Explained - Demis Hassabis
- ▶ 14:24 unnamed speaker Sounds like using a computing analogy, we're kind of in the seventies era PC DOS kind of.
Booz Allen CTO: AI in Government, Autonomous Driving, Quantum's Promise
- ▶ 12:19 Alex Kantrowitz We get the sense that the government is running on Windows 95 and like the nuclear, uh, processes are like in basically running on MS DOS.
How AI is reshaping the product role | Oji and Ezinne Udezue
- ▶ 45:28 Oji Udezue Otherwise DOS will be the biggest operating system.
How 80,000 companies build with AI: Products as organisms and the death of org charts | Asha Sharma
- ▶ 19:51 Lenny Rachitsky The way Nick described it is, uh, we're in the MS-DOS era of, uh, of ChatGPT and there's a way, which is interesting.
Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)
- ▶ 1:09 Nick Turley ChatGPT feels a little bit like MS-DOS.
- ▶ 50:07 Nick Turley I, I still feel like ChatGPT feels a little bit like MS-DOS. 2 times in the scene
Dylan Field: Scaling Figma and the Future of Design · Y Combinator
- ▶ 0:06 Dylan Field It feels intuitively like we're in the MS-DOS era of AI right now.
- ▶ 21:00 Dylan Field Yeah, I think that it feels intuitively like we're in the MS-DOS era, uh, of AI right now, and that, you know, if you look back 10 years from now, everyone's gonna go, can you believe that we just had this chat box?
Steven Sinofsky & Balaji Srinivasan on the Future of M&A, AI & Tech
- ▶ 55:17 Steven Sinofsky And when IBM came out with the PC and Microsoft came out with DOS, part of that consolidation was due to the 2 times in the scene
Are AI's Economics Unsustainable? — With Ed Zitron
Navigating Startup Success: Insights on Venture Capital, Market Disruption, and Mentorship
- ▶ 10:27 Sriram Sundararajan Um, as consumers, we are in our lives today using a certain level of automation, and you can think of this evolution as being very similar to when the PCs actually had Microsoft DOS and Windows evolve over time that helped enhance…
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson
- ▶ 58:57 Andrew Wilkinson You don't need to learn punch cards and basic programming because, or MS DOS, because we all have keyboards and mice.
The Steve Ballmer Interview · Acquired
- ▶ 8:06 Ben Gilbert Before the IBM PC and before DOS, can you catch listeners up who weren't around at that time?
- ▶ 11:54 Ben Gilbert And so the licensing of Microsoft DOS, which didn't even exist when IBM approached you about licensing some things, is the single greatest business deal in history.
- ▶ 15:16 Ben Gilbert But what ended up happening after all these years, and I imagine it only took a few years to see it play out, was IBM sold a ton of IBM PCs, and DOS was the operating system.
- ▶ 15:30 Ben Gilbert And then everybody else adopted DOS because all the application makers, all the software vendors, were targeting DOS as the platform, and so Microsoft sort of accrued a huge amount of benefit.
- ▶ 16:43 Steve Ballmer There were plenty of people who ran MS-DOS who were actually not IBM compatible because they didn't do a compatible BIOS.
- ▶ 19:45 Ben Gilbert You end up shipping DOS.
- ▶ 31:49 David Rosenthal Not DOS.
- ▶ 31:50 Steve Ballmer Not DOS.
- ▶ 31:51 Steve Ballmer DOS was always sold to OEM.
- ▶ 33:53 Steve Ballmer And, you know, we had DOS and windows and whenever talking to Cutler about coming here, he says, I don't want to work any toy operating systems.
The Life Story of Michael Dell
- ▶ 18:26 David Senra They chose DOS for Microsoft and Intel, uh, they were such a huge and powerful company, such an American institution.
Epic Systems (MyChart) · Acquired
- ▶ 50:01 David Rosenthal And to that point, there is no DOS yet.
Vizio: William Wang
20Product: How Scale AI and Harvey Build Product | Why PMs Are Wrong: They are not the CEOs of the Product | How to do Pre and Post Mortems Effectively and How to Nail PRDs | The Future of Product Management in a World of AI with Aatish Nayak
- ▶ 18:56 Aatish Nayak It's the command line starting point of this new frontier, like the MS-DOS was, you know, way back when.
Agents, Lawyers, and LLMs
- ▶ 23:58 unnamed speaker When MS-DOS first came out, you were just typing into a terminal to move things around.
Fabien Pinckaers, CEO @Odoo: The Billionaire Founder Who Doesn’t Care About Money | E1259 · 20VC with Harry Stebbings
- ▶ 1:13:55 Fabien Pinckaers MS-DOS, Dr.
The AI Coding Agent Revolution, The Future of Software, Techno-Optimism | Amjad Masad, CEO, Replit
- ▶ 2:06 Amjad Masad You know, uh, for example, a DOS or like a UNIX command line is a form of a REPL.
Samsara’s Rise to Vertical SaaS Leader and $1B+ ARR with Samsara's CEO and Co-Founder
- ▶ 33:54 Jason Lemkin Maybe it runs on MS-DOS, but they're there.
How to write a book with AI [step-by-step guide]
- ▶ 12:34 Greg Isenberg You can just, like, fire up your, you know, Microsoft 3.1, or whatever it's called, it was called, and, and, or MS-DOS, or whatever, and just, like, start playing around.
Microsoft Volume II: The Complete History and Strategy of the Ballmer Years (Audio) · Acquired
- ▶ 34:14 David Rosenthal It sounds like reality is a lot like the DOS acquisition.
- ▶ 34:26 David Rosenthal Was that the same thing as Microsoft DOS?
- ▶ 2:04:25 Ben Gilbert During the DOS era, Microsoft's productivity apps did not get real adoption in DOS, which is crazy.
Marc Andreessen on Inventing The Internet Browser (How We all Access the Internet)
- ▶ 1:53:01 Marc Andreessen Um, you know, which is the same, um, you know, which is the same, um, uh, you know, the same thing that Microsoft did originally licensed DOS way back when.
Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
- ▶ 21:57 Jason Lemkin And the other thing that happens if you run from competition, especially sometimes in vertical SAS, um, because you can find a lot of categories in vertical SAS where the competition is SAP or Excel or paper or like some DOS application…
Microsoft Volume I: The Complete History and Strategy of founding through Windows 95 (Audio) · Acquired
- ▶ 1:44:46 David Rosenthal And thus, DOS is born.
- ▶ 1:44:49 Ben Gilbert Which, of course, later, they would drop the queue and call it DOS, the Disk Operating System.
- ▶ 1:45:38 David Rosenthal And so he, with the rest of the team, he's part of building DOS, taking his initial work and turning it into real DOS.
- ▶ 1:46:08 David Rosenthal This is DOS.
- ▶ 1:46:10 David Rosenthal Now, look, one programmer wrote a quote, quick and dirty operating system, and Microsoft bought the license to that and adapted it into DOS.
- ▶ 1:46:21 David Rosenthal Seattle Computer Products definitely did not write DOS as DOS becomes.
- ▶ 1:46:25 David Rosenthal It's not like Microsoft bought all of DOS for 75,000 dollars.
- ▶ 1:46:33 Ben Gilbert So, Microsoft would eventually generate billions of dollars on DOS-based products.
- ▶ 1:46:51 Ben Gilbert But my God, 75,000 dollars to buy DOS to get this whole thing started for, I mean, until Windows 95, all of the Windows operating systems were DOS based.
- ▶ 1:47:58 David Rosenthal Okay, so now they've got the operating system, they've got QDOS, or DOS, in place to license to IBM.
- ▶ 1:48:54 Ben Gilbert 45,000 dollars for DOS.
- ▶ 1:49:18 David Rosenthal Every copy of DOS that IBM sells, either included as part of systems that they're selling, or they're free to charge independently for DOS, whatever amount they want, Microsoft gets zero dollars.
- ▶ 1:50:12 David Rosenthal To own DOS and to own their languages and license it and them to anyone else they wanted at any price on any terms.
- ▶ 1:55:36 David Rosenthal Now, before we talk about the clones, this is really just a footnote because, of course, all the incentives are aligned for IBM to push DOS as the operating system for the PC.
- ▶ 1:56:03 David Rosenthal They don't have to go with DOS.
- ▶ 1:56:05 David Rosenthal Consumers can choose between DOS, sixteen-bit CPM.
- ▶ 1:56:37 David Rosenthal And DOS, which was developed specifically for the PC, is the best way to run it, is only 60 dollars.
- ▶ 1:56:49 David Rosenthal Their hardware for the PC by selling DOS, because they don't have to pay Microsoft any of that, and they've set up the incentives that, like, obviously everybody's gonna choose DOS.
- ▶ 1:57:09 Ben Gilbert One is, we're simplifying and calling it DOS.
- ▶ 1:57:11 Ben Gilbert It was PC-DOS, which is different than MS-DOS, which would get licensed to other computer makers.
- ▶ 2:01:10 David Rosenthal But yeah, Compaq, all these other clone companies that get started, Microsoft licenses DOS to all of them, importantly, critically, on a per machine sold basis.
- ▶ 2:19:43 Ben Gilbert No, these are DOS applications.
- ▶ 2:30:39 unnamed speaker Microsoft Word comes out for DOS.
- ▶ 2:30:54 unnamed speaker We're gonna do that for DOS.
- ▶ 2:31:00 unnamed speaker So they actually ship a mouse tied to the application that's not a part of DOS.
- ▶ 2:32:15 Ben Gilbert You're starting to see truly divergent cultures at Microsoft between the systems group, which is currently making DOS and will soon make windows or soon partner with IBM or soon do something else that we're getting into here in the next…
- ▶ 2:34:32 David Rosenthal You know, Lotus and the world back in the command line interface where you've got these programs running on top of DOS, that is like a completely foreign concept.
- ▶ 2:39:47 David Rosenthal It's just a graphical interface on top of DOS.
- ▶ 2:39:56 Ben Gilbert In all of their early marketing, they referred to it as Windows, a graphical operating environment that runs on the Microsoft MS-DOS operating system.
- ▶ 2:40:26 Ben Gilbert Obviously here, Microsoft knows they need to evolve DOS.
- ▶ 2:41:47 David Rosenthal This was bad, and so IBM wants to find a way to evolve the PC ecosystem back to being more IBM proprietary, and they're gonna make Microsoft come along for the ride here, and the way that they're gonna do this is with the next generation…
- ▶ 2:43:18 Ben Gilbert This is such a crazy part of the story to me because we just talked about how Microsoft discovered this amazing business model and with everyone needing to license DOS from them, they're taking over the world and they're becoming the…
- ▶ 2:47:54 Ben Gilbert I mean, DOS and the applications were both great businesses by 87.
- ▶ 2:48:56 David Rosenthal Open PC ecosystem that you can have a really good, true multitasking, good UI, graphical user interface running on top of DOS.
- ▶ 2:49:08 David Rosenthal So, Windows one point O and Windows two point O only ever achieved five percent penetration of the DOS installed base.
- ▶ 2:49:58 David Rosenthal It accommodates existing DOS applications, and it makes you believe that it belongs on a PC.
- ▶ 2:58:13 David Rosenthal Because developers were targeting DOS at this point.
- ▶ 2:58:33 Ben Gilbert At this point, they were still installing DOS, or some people were actually installing nothing and requiring users to put operating systems on.
- ▶ 2:59:13 David Rosenthal You could pay us, you know, a license fee for every machine you ship with DOS installed on it, or DOS and Windows.
- ▶ 2:59:27 David Rosenthal We'll give you a cheaper per unit deal, because you're gonna ship DOS on everything.
- ▶ 2:59:31 David Rosenthal DOS is the standard, and we want Windows to be the standard, and Windows is gonna be the standard.
- ▶ 2:59:35 David Rosenthal We'll make it more economically attractive to you, give you a lower per unit rate, if we just kind of change the terms and say, instead of every unit you ship with DOS or with Windows, every machine you ship, period.
- ▶ 2:59:58 David Rosenthal So if you do that, you'll be paying us for every machine, whether you ship DOS or Windows on it or not, but you're gonna ship DOS and Windows anyway.
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