Dev War Stories, with Steven Sinofsky (a16z, ex-Microsoft) - S04E01

In this episode, we speak with Steven Sinofsky, currently a board partner at Andreessen Horowitz and previously of Microsoft. We discuss what it was like shipping code at Microsoft in the early days, what he learned from Bill Gates, how it applies to software development today, what the big Windows 8 rewrite was like, and why the Copilot AI naysayers are completely wrong. Although the software landscape has changed dramatically since Steven’s early days at Microsoft in the 80s, he shares some of the lessons he learned along the way which are still as relevant today as they were back then. 

Hosted by David Mytton (Console) and Jean Yang (Akita Software).

Things mentioned:

• Microsoft
• Windows 8
• Copilot 
• Cornell University
• IBM
• Halt and Catch Fire
• Apple
• Jon DeVaan
• Webflow
• Mythical Man-Month, The: Essays on Software Engineering
• Bill Gates
• “A Hard Line on Software” (Video)
• Jensen Harris
• Hardcore Software
• ChatGPT
• Bing
• ChatGPT on 60 Minutes
• M2 Mac Mini
• MacBook Air
• One Strategy: Organization, Planning, and Decision Making
• Substack

ABOUT STEVEN SINOFSKY

Steven Sinofsky is an investor, a board partner at Andreessen Horowitz, a general advisor, and a self-described “person-about-town” in Silicon Valley. Shortly after he graduated from Cornell University, he became a software design engineer at Microsoft back in 1989. In his time at the company, he oversaw six major releases of the full range of Office apps and servers in his role as a senior executive. He also worked on Windows 7 and the Windows 8 rewrite as the president of the Windows division. He is a co-author of the book One Strategy: Organization, Planning, and Decision Making, as well as the writer of Hardcore Software, a Substack newsletter about the rise and fall of the PC revolution.

Highlights:

Steven Sinofsky: Bill was super interesting. He was, in a sense, this very interesting combination of business strategy, product strategy, and technology strategy. And whenever he would really push it, he was most comfortable trying to be a technology strategist. And to him, that was all about architecture. And so architecture, if you read a book like Fred Brooks, Mythical Man-Month, architecture is everything. Architecture in software is like this Nirvana.

— [0:22:37 - 0:23:08]

Steven Sinofsky: And the beauty of how Apple managed their operating system was they just didn't add a lot of features. But we had a team five times as big, adding features every release, and it was just not getting— My measure of success is not “Did we get the release done?” but “Was it making people do new things with the product?” And Windows had long stopped doing that. The ecosystem of software and hardware had probably died around 2000. And so when it came time to do Windows 8 — and obviously Hardcore Software has the whole timeline and all this stuff — but the thing we really wanted to do was take the product and build on it and all the things that were great about it, but bring it into a new era of computing from top to bottom or what we said was “from the chipset to the experience".

— [0:28:43 - 0:29:34]

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