Microsoft, every mention

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every year anyone Ben Gilbert 1015David Rosenthal 995Steve Ballmer 163Ben Thompson 45Brendan Eich 21Jensen Huang 7Emily Chang 7David Senra 6Dara Khosrowshahi 6Mitch Lasky 4

Verbatim, from the transcripts: the passages where Microsoft comes up

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Google Part II: Alphabet (Audio) · Acquired Aug 26, 2025 · 40 mentions

  • ▶ 2:21:12 Ben Gilbert To your point, maybe without Chrome, Bing would have been a serious competitor to Google.
  • ▶ 2:22:28 David Rosenthal Let's go attack Windows.
  • ▶ 2:22:29 David Rosenthal Let's take it to Microsoft where it really hurts.
  • ▶ 2:22:44 David Rosenthal It is wild how much the PC computer operating system market is still dominated by Windows.
  • ▶ 2:22:59 David Rosenthal Windows has like, 70% market share of computer operating systems.
  • ▶ 2:30:15 Ben Gilbert So they end up selling this company to Microsoft, right?
  • ▶ 2:30:20 David Rosenthal Microsoft does end up acquiring the company, but not until 2008, which is the same year that Android launches.
  • ▶ 2:32:10 David Rosenthal Or, you did have OEMs, device makers, who made devices, and then they bought an operating system, either from Palm, which made their own devices, but then also started selling the operating system to other vendors, or the big player was…
  • ▶ 2:32:28 Ben Gilbert As we talked about in our Microsoft part two, this was, you pay Microsoft single digit dollars, and you get an operating system, and
  • ▶ 2:32:43 David Rosenthal And this was a good business for Microsoft.
  • ▶ 2:33:49 David Rosenthal Hey, stop buying an operating system from Microsoft or from Palm.
  • ▶ 2:38:01 Ben Gilbert If they don't buy Android and they don't get started basically in the month that they did, this market belongs to Microsoft.
  • ▶ 2:38:08 Ben Gilbert No, Microsoft.
  • ▶ 2:38:10 David Rosenthal Oh, why do you say Microsoft?
  • ▶ 2:38:15 Ben Gilbert There's going to be a fully integrated player, which Apple was going to be, and then there's going to be an OEM plus licensed operating system, and the model would have just been that Microsoft sells operating systems, a mobile operating…
  • ▶ 2:58:44 Ben Gilbert And before this, Microsoft had a shot.
  • ▶ 2:59:17 Ben Gilbert And three, we aren't Microsoft.
  • ▶ 2:59:22 Ben Gilbert Microsoft managed to suck up all the profit in that entire value chain, and handset makers, you currently make money, so why would you go work with Microsoft who did that to the PC makers?
  • ▶ 3:00:27 David Rosenthal But Microsoft is dead.
  • ▶ 3:02:12 Ben Gilbert Microsoft was dominant in PCs and then lost their dominance in the web era.
  • ▶ 3:03:20 Ben Gilbert Famously, IBM made more revenue than Microsoft for a lot longer than people think.
  • ▶ 3:03:25 David Rosenthal Or even take Microsoft and Windows.
  • ▶ 3:08:08 David Rosenthal It's the same thing as the Microsoft Surface strategy, why Bomber was so adamant, we gotta make a Surface, we gotta show the OEMs.
  • ▶ 3:08:08 David Rosenthal It's the same thing as the Microsoft Surface strategy, why Bomber was so adamant, we gotta make a Surface, we gotta show the OEMs.
  • ▶ 3:13:31 Ben Gilbert And Microsoft did miss it.
  • ▶ 3:14:20 Ben Gilbert You know, we've jumped over some failures, but it's been hit after hit after hit in a lot of these areas that really matter, just like we talked about on the Microsoft episodes.
  • ▶ 3:21:47 Ben Gilbert The whole Chrome and Bing thing was defense against Microsoft, Android was defense against Apple and Microsoft, and Google Plus is now defense against Facebook.
  • ▶ 3:21:47 Ben Gilbert The whole Chrome and Bing thing was defense against Microsoft, Android was defense against Apple and Microsoft, and Google Plus is now defense against Facebook.
  • ▶ 3:28:19 David Rosenthal In our Microsoft saga, we talked about how Vista slash Longhorn was the most damaging thing to the company because of the distraction and the siphoning of resources and the best talent away from working on what really mattered.
  • ▶ 3:28:40 David Rosenthal So like with Microsoft, it was clear.
  • ▶ 3:28:45 David Rosenthal Like, the whole reason Microsoft let Google fester from their perspective for all these years and didn't kneecap them was they were tied up with all the distraction from Vista.
  • ▶ 3:30:30 David Rosenthal And Google had the wrong strategy in cloud for many years, and as a result, that's why their cloud business is way behind Amazon and Microsoft.
  • ▶ 3:40:39 David Rosenthal Mustafa runs AI at Microsoft today.
  • ▶ 3:45:19 Ben Gilbert For example, in this episode, talking about Android, they massively counterpositioned against Microsoft.
  • ▶ 3:51:07 Ben Gilbert Microsoft, pure play platform company.
  • ▶ 3:55:21 David Rosenthal It is the Google version of Azure from our Microsoft series.
  • ▶ 3:55:21 David Rosenthal It is the Google version of Azure from our Microsoft series.
  • ▶ 3:57:55 David Rosenthal Microsoft has two.
  • ▶ 3:57:57 David Rosenthal Windows and LinkedIn.
  • ▶ 4:10:14 Ben Gilbert Most of you have probably listened, but if you have not, go check out our first episode on the origin of Google and the creation of the search engine and the search business, and of course, our Microsoft series part one, part two, and an…

Google Part I: Origins of Search. How the Best Business in Human History Happened (Audio) · Acquired Jun 30, 2025 · 25 mentions

  • ▶ 2:10 Ben Gilbert More than Apple, Microsoft, Exxon Mobil, JPMorgan Chase, Berkshire Hathaway.
  • ▶ 3:21 David Rosenthal Well, you know, uh, Microsoft may take a little issue with that with Bing, but, but only a little issue.
  • ▶ 6:47 David Rosenthal Like right at the same time as the PC era is coming online and Microsoft, to just have that be
  • ▶ 7:34 David Rosenthal And then when he graduates, he goes out to the west coast, actually to the Pacific Northwest, and he works fairly early at Microsoft and then, uh, Mentor Graphics down in Oregon.
  • ▶ 49:46 David Rosenthal But DEC, I mean, the company we talked all about in our Microsoft series, where Dave Cutler came from, wrote Windows NT, you know, legendary, legendary company.
  • ▶ 2:01:40 Ben Gilbert There's a little bit of a bidding war back and forth with Microsoft, but that's the final price.
  • ▶ 2:39:57 David Rosenthal Which, by the way, Microsoft owns the browser right now.
  • ▶ 2:40:05 David Rosenthal It's Microsoft.
  • ▶ 2:40:06 Ben Gilbert And Microsoft definitely did figure out this secret.
  • ▶ 2:40:22 Ben Gilbert Which almost no one except Microsoft has.
  • ▶ 2:40:32 David Rosenthal Microsoft.
  • ▶ 2:40:34 Ben Gilbert Okay, so Microsoft's got Internet Explorer.
  • ▶ 2:41:31 Ben Gilbert Google's paranoid about Microsoft entering and using Internet Explorer as a weapon.
  • ▶ 2:41:35 Ben Gilbert If Microsoft owns the browser, they can direct the traffic wherever they want.
  • ▶ 2:45:10 Ben Gilbert They even did a deal with Dell directly to make sure that when new PCs shipped with Windows, they shipped with Google toolbar pre-installed
  • ▶ 3:01:12 David Rosenthal So I don't think other than Microsoft there had ever been another company like this where there was no good reason for Google to go public.
  • ▶ 3:01:40 David Rosenthal And actually, even more so than Microsoft, Google had a really, really good reason not to go public, which was Microsoft.
  • ▶ 3:01:47 David Rosenthal As we alluded to, there was desperate paranoia in the company of, we can't let Microsoft, they are the actual front door to the internet for
  • ▶ 3:02:02 Ben Gilbert And they have no idea what a good business this is.
  • ▶ 3:02:05 David Rosenthal Yes, we can't let them know how good this is.
  • ▶ 3:03:20 David Rosenthal Just like Bill and Paul and Microsoft, it was extremely rare that because Google never needed to raise VC money after the Series A, Larry and Sergey, together with the employees in the option pool, you know, controlled the majority of the…
  • ▶ 3:03:35 Ben Gilbert Google, Microsoft, there's something correlated between founder control and incredibly good capital efficiency in a business.
  • ▶ 3:12:04 David Rosenthal Amazon's PE is 35, Microsoft is 37, Nvidia is 46, Apple is 30, and Meta is 27, and Google Alphabet is down at 20.
  • ▶ 3:31:13 David Rosenthal The company that shows up once in a very long while, the Google of yesterday, the Microsoft of long ago,
  • ▶ 3:31:40 David Rosenthal Microsoft was the first that company.

The Steve Ballmer Interview · Acquired Jun 2, 2025 · 35 mentions

  • ▶ 1:09 Ben Gilbert In 2014, when Steve left Microsoft, his net worth was twenty billion dollars.
  • ▶ 1:15 Ben Gilbert Almost entirely comprised of Microsoft stock.
  • ▶ 1:25 Ben Gilbert It is incredibly rare to reach this stratospheric level when you are A, not the founder of the company, and B, no longer CEO or even employed by the company.
  • ▶ 1:40 Ben Gilbert Just keep holding substantially all of his Microsoft stock.
  • ▶ 1:49 Ben Gilbert Now, as most of you know, we did a big two-part Microsoft series last year on the history of the company up through when Steve transitioned the CEO role to Satya Nadella.
  • ▶ 2:06 Ben Gilbert You know, things like what made Microsoft so fabulously successful, what his missteps were as CEO.
  • ▶ 4:25 Ben Gilbert Listeners should know, we didn't ask for this in any way, but at 10 p.m. last night, you sent us a PowerPoint deck and said, I, I made you some slides.
  • ▶ 4:48 Steve Ballmer And I kind of think of this as a time to reflect on things I've learned, primarily at Microsoft, but also the Clippers about business.
  • ▶ 4:58 Steve Ballmer And their PowerPoint.
  • ▶ 5:07 David Rosenthal I think the word cheerleader is actually in the PowerPoint deck, though.
  • ▶ 5:14 David Rosenthal Microsoft is the most valuable company in the world.
  • ▶ 5:22 David Rosenthal And I think everybody would agree it's an enterprise company.
  • ▶ 5:30 Ben Gilbert It is reasonable to call you the founder of Microsoft's enterprise business.
  • ▶ 5:55 Steve Ballmer Of course, there are many fathers to the enterprise business at Microsoft, and I feel both good and bad about it because the truth is Microsoft started out as a consumer company and we built a very important consumer business.
  • ▶ 6:17 Steve Ballmer And one of my regrets is we lost the consumer muscle along the way, because I think the ability to be ultra ultra, I mean, we're a great company, Microsoft's great company, but to have both of those muscles totally firing, if I'd been able…
  • ▶ 7:01 Steve Ballmer And the truth of the matter is Microsoft office slash M three 65, whatever exactly it's called today is super important.
  • ▶ 7:01 Steve Ballmer And the truth of the matter is Microsoft office slash M three 65, whatever exactly it's called today is super important.
  • ▶ 7:56 Ben Gilbert Well, to contextualize all this, we want to go back almost all the way to the beginning, right around the time you joined Microsoft, and talk about Microsoft's relationship with IBM.
  • ▶ 8:26 Steve Ballmer Uh, when I, when I get here and the company started obviously in 1975 and there were IBM computers.
  • ▶ 9:24 Steve Ballmer And all the initial Microsoft software was developed actually on deck computers, digital equipment equals deck.
  • ▶ 12:10 Ben Gilbert Well, I just think you look three and a half trillion dollars later at Microsoft's market cap.
  • ▶ 12:24 Steve Ballmer And we met with the founder who later came to work in Microsoft, a guy named Tim Patterson, and we offered him, I think we paid 4005 or 49,000 for this operating system.
  • ▶ 13:48 Steve Ballmer If you got a new version, we charged another time and we did the same thing for basic and everything else because
  • ▶ 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.
  • ▶ 16:53 Ben Gilbert Oh, we've got some protection from Microsoft kind of disintermediating us from all the developers and all the potential customers, because targeting our BIOS is going to be important and unreplicatable.
  • ▶ 18:04 Ben Gilbert By allowing someone to distribute a wide operating system that ends up being the target that everyone standardizes on, which eventually, you know, created all of modern Microsoft.
  • ▶ 18:24 Steve Ballmer One of the things my little PowerPoint here says is luck is important in the creation of great companies.
  • ▶ 21:36 Ben Gilbert And maybe walk us through a little bit the OS two windows world.
  • ▶ 23:26 Steve Ballmer And it was convoluted, and we did then keep, for, for speed of action, we kept going on Windows, which we had started.
  • ▶ 23:43 David Rosenthal And Windows was like your plan B.
  • ▶ 23:46 Steve Ballmer No, Windows was our plan, and then they wanted, they, they wanted to do this new operating system, and we convinced them, you got to have a graphical user interface.
  • ▶ 23:56 Steve Ballmer And we tried to sell them Windows, and they were resisting.
  • ▶ 24:07 Ben Gilbert We really think the future is Windows.
  • ▶ 24:19 Steve Ballmer So I had windows, I had shipped when I'd been the development manager for windows one.
  • ▶ 24:53 Steve Ballmer And so Bill's pushing windows hard, but we still suspected OS two could be the winner because it came from IBM, but we couldn't just like stop for three or four years.
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