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There are two stories from this time I would like to tell. The first is about the political dimension of the anti-trust trial. A prominent politician of the day, Orrin Hatch, said on the record that if Microsoft would have been giving its political contributions that it would have been protected and not had any anti-trust issues. He of course used veiled language, but the message was clear. This started a journey for me participating in the Microsoft Political Action Committee (PAC) and gaining a front row seat to the accelerating money corruption of the US political system. I've dedicated myself to political reform since I left Microsoft.

As part of my political reform work, I have come to know Lawrence Lessig, who was the "special master" assigned to help the court with the anti-trust trial. No matter what one thought of the findings of fact regarding the Windows monopoly and Microsoft's abuse of it, clearly the remedy of breaking up the company made no sense at all. Literally it would have left the teams that created all of the accused behavior intact. (Internet Explorer was part of the Systems Division.) I had an interesting conversation with Lessig about this. He said the thought was not so much to prevent IE from remaining a problem, but the hope that Office being separate would unchain it from "having" to rely on Windows and allow for a Linux version. It was an interesting inversion of incentives and to this day the breakup remedy makes absolutely no sense to me.

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I remember how frustrated you were. We took different paths on the PAC. I used that era as a time to double down on the idea that the wrong way to participate is with money. The key strategy to push back on the likes of Hatch was to compel us to donate to the PAC which I always felt too ironic to me (as I often shared as feedback to the email reminders).

It was totally insane that the remedy was basically just a restrcutring penalty that had nothing to do with the case. Amazing. We're seeing the same thing today when it comes to Google and FB (how would removing YT from Google solve abuse other than for YT to have fewer resources?)

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I was trying to raise money for a startup focused on mobile in this time period. I loved (love) productivity software so every investor meeting started with “how are you going to compete against Microsoft?” (They mostly ended that way, too, actually.)

I was scared to death of the decree to break up Microsoft. I figured it was more dangerous to have two Microsoft’s than one, but most everyone in the mobile space didn’t see it that way.

It is amazing to me how much the tech and software space changed in just the next few years after that. SaaS became dominant, iOS and Android became bigger than Windows, and Google became the bigger threat to most Internet businesses, even though they didn’t know it yet.

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Great story. It was always incredible to learn about the kind of shadow Microsoft cast while we were so inherently afraid of the whole thing just collapsing. Such a challenging difference in perspectives.

Only the paranoid survive.

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Missed a few of these over the past two months and just catching up! Thanks for writing this one. I remember having to sit through hours and hours of legal review for one API that I was adding to Win7 because it somehow triggered aspects of the consent decree. I could have spent those hours writing code to add value for our customers instead. I didn't really understand at the time that other companies were were able to move faster simply because they were not under such conditions. And yes, the recent climate for Google feels very similar. It's striking how so many of the stories from the 1990s that you have told have poignant lessons for tech in the 2020s.

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What API?

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Gosh I barely remember now. Something In the networking stack for making peer to peer connections resilient to sockets closing iirc

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