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Microsoft Volume II: The Complete History and Strategy of the Ballmer Years (Audio)

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. Chase Center Live Show in SF: Sign up here for the pre-sale list before tickets are available to the public. See you there!! http://acquired.fm/sf Sponsors: Many thanks to our fantastic Season 14 partners: J.P. Morgan Payments https://bit.ly/acquiredJPMP6yt ServiceNow https://bit.ly/acquiredsn Pilot https://bit.ly/acquiredpilot24 Links: Bill Gurley on Android’s “Less Than Free” business model https://abovethecrowd.com/2009/10/29/google-redefines-disruption-the-less-than-free-business-model/ All episode sources https://docs.google.com/document/d/1x77IgRYzQd5G7LZ6yP9Pv0xUXeCb_oU33TWySSDdBIg/edit?usp=sharing Carve Outs: Meta Ray-Bans https://www.meta.com/smart-glasses/shop-all/ Ozlo Sleepbuds https://ozlosleep.com M3 Macbook Air https://www.apple.com/macbook-air/ Model Y https://www.tesla.com/modely More Acquired: Get email updates with hints on next episode and follow-ups from recent episodes https://www.acquired.fm/email Join the Slack http://acquired.fm/slack Subscribe to ACQ2 https://pod.link/acquiredlp Check out the latest swag in the ACQ Merch Store! https://www.acquired.fm/store Note: references to Fortune in ServiceNow sponsor sections are from Fortune ©2023. Used under license. Note: 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. © Copyright ACQ, LLC

Ben GilberthostDavid Rosenthalhost
Jul 22, 20244h 51mWatch on YouTube ↗

CHAPTERS

  1. Setting the stage: Microsoft’s “middle chapter” (1995–2014) and the myth of rise–fall–refresh

    Ben and David frame Volume II as the Ballmer-era story, arguing it’s not simply “Microsoft declined until Satya saved it.” They preview the major arcs—Internet, browsers, antitrust, enterprise domination, consumer stumbles, and the often-misunderstood origins of Azure.

  2. Before the web won: AOL-style walled gardens and the “Information Superhighway” bet

    The hosts revisit early-1990s consumer online services—AOL, CompuServe, Prodigy—and Microsoft’s instinct to compete with them. Microsoft and Wall Street also embrace the ‘interactive TV via cable companies’ vision, spawning ventures like MSN and MSNBC.

  3. Internal awakening: Mosaic, “Cornell is wired,” and Microsoft’s embrace-and-extend Internet strategy

    Two internal memos—Jay Allard’s ‘Windows: The Next Killer App for the Internet!’ and Sinofsky’s ‘Cornell is wired!’—push Gates to treat the internet as an exponential phenomenon. This culminates in Microsoft’s pivot from “superhighway” thinking to internet-first urgency.

  4. Netscape’s birth and the browser becomes the platform threat to Windows

    Jim Clark and Marc Andreessen pivot from set-top box ambitions to Netscape, igniting explosive browser adoption and a new platform narrative. Microsoft recognizes that if the browser owns APIs, Windows could be commoditized into ‘device drivers.’

  5. How Internet Explorer really happened: Spyglass licensing, Windows integration, and the “feature vs app” fault line

    The show unpacks IE’s origin beyond the simplistic ‘Microsoft copied Mosaic’ storyline. IE’s development intertwined with a deeper plan to make Windows itself web-native—an integration choice that later becomes central to antitrust arguments.

  6. Browser Wars outcome: Free IE, distribution power, and Netscape’s rapid collapse

    After Netscape’s blockbuster IPO, Microsoft makes IE free and bundles it with Windows, then secures deals with online services to distribute it. IE’s market share rises to near-total dominance by 2000, demonstrating how platform distribution can decide markets.

  7. Antitrust saga, part 1: FTC-to-DOJ handoff, consent decree, and “is IE a product or a feature?”

    The antitrust story starts earlier than most remember: an FTC investigation (1990) deadlocks, then the DOJ reopens it and negotiates a 1994 consent decree. The IE bundle tests the decree’s boundary between illegal tying and permitted feature integration.

  8. Antitrust saga, part 2: the trial, Gates deposition tapes, breakup order, and ultimate settlement

    The 1998 Sherman Act case escalates dramatically: video depositions (initially barred) become courtroom weapons, Judge Jackson finds Microsoft a monopoly, and orders a breakup. The appeals process removes Jackson for improper reporter contact, leading to a 2001 settlement with relatively modest behavioral remedies.

  9. Ballmer’s early CEO agenda: stabilize morale, make peace legally, and double down on enterprise

    Ballmer’s tenure begins amid existential legal and reputational stress, and interview sources describe him as a crucial emotional anchor. He elevates Brad Smith to pursue settlement and shifts Microsoft’s growth engine toward enterprise systems, where Microsoft can play offense again.

  10. The enterprise flywheel: SQL Server, Exchange/Outlook, Active Directory, and the Enterprise Agreement annuity

    Microsoft builds a powerful client–server enterprise stack and a business model to match it. The Enterprise Agreement (EA) transforms one-time licenses into multi-year renewals, amplifying switching costs and making Microsoft’s suite ‘good enough together’ irresistible for IT buyers.

  11. Consumer/product turbulence: XP peak, Vista/Longhorn collapse, Windows 7 recovery, and Windows 8’s tablet gamble

    Windows XP unifies consumer and enterprise Windows on NT and rides the last great PC growth wave. Vista becomes a costly engineering and coordination failure, Windows 7 restores reliability, and Windows 8 attempts to leap into touch/tablets and a new developer platform—alienating core desktop users and OEMs.

  12. The “missed waves” bundle: search, social, mobile, and the surprising path to Azure

    Microsoft struggles to win search (Yahoo bid, Bing), invests alongside Facebook, and loses mobile economics to Android’s ‘less-than-free’ model. Yet the company quietly accumulates the operational DNA for large-scale services—Hotmail, Xbox Live, and Bing—setting up Azure’s emergence under Ray Ozzie and Ballmer’s sponsorship.

  13. Closing chapter: Nokia, leadership transition, Ballmer-era scorecard, and the narrative gap

    The Nokia acquisition encapsulates late-era tension: defending a doomed mobile strategy while preparing for a leadership reset. The hosts argue Ballmer’s era is widely misread—financially strong, enterprise-defining, and cloud-seeded—yet hampered by poor storytelling and uneven consumer execution.

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