In 1999, Microsoft became the most valuable company in the world. And in 2019, Microsoft became the most valuable company in the world, again. But… what happened in the twenty years in between? The answer, as we discovered in our research, is probably not what you think.In this episode we explore and analyze the browser wars and the DOJ case, Windows XP through 8, Surface, Xbox, search, Yahoo!, Bing, the iPhone, Nokia, mobile, social, Facebook… and oh yeah, a little thing called Azure and the enterprise — which ended up becoming so big that no failures mattered. Tune in for Microsoft, Volume II.Sponsors:Anrok: https://bit.ly/anrokacquiredStatsig: https://bit.ly/acquiredstatsig24Anthropic: https://bit.ly/acqclaudeLinks:Bill Gurley on Android’s “Less Than Free” business modelAll episode sourcesCarve Outs:Meta Ray-BansOzlo SleepbudsM3 Macbook AirModel YMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLCNote: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.
Full Episode
I'm a little hoarse today, so hopefully we don't have to do a lot of talking.
Good luck with that.
All right, let's do this.
Okay.
Welcome to Season 14, Episode 6, the season finale of Acquired, the podcast about great companies and the stories and playbooks behind them. I'm Ben Gilbert. I'm David Rosenthal. And we are your hosts. Well, listeners, here we are, Microsoft Volume 2 at long last.
After the ancient history of Volume 1, we now get to the stuff that you grew up with, the internet, Windows XP, Xbox, the browser, search, and mobile. And in this era, Microsoft had a lot of the right ideas. with a lot of the wrong timing and execution on everything from the Zune to Bing.
But despite that, from 1995, where we start our story, to 2014, where we will end this episode, Microsoft grew their annual revenue from $6 billion to $80 billion. They became a phenomenally successful company and really cracked the code on selling enterprise software. I began the research thinking our part one episode would be about the rise and this episode would be about the fall.
Cultural problems, failed consumer products, antitrust, but it's really not that straightforward. And after spending months unpacking it all, I actually don't think that's the right framing anyway. And on Microsoft's 1998 antitrust suit against the Department of Justice, everyone knows of this case, but most people really have no idea what actually happened. Did Microsoft lose?
Well, not really, but the answer is nuanced. Finally, today, we dive into it all. Oh, and listeners, we have just one announcement for you here today. Yes. We told you before that September 10th, we are doing the biggest thing in Acquired's history, and we're doing it in the city of San Francisco.
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