Steven Sinofsky on Apple at 50, Microsoft, and the Future of Computing

June 3, 2026

1:06

Steven Sinofsky on Apple at 50, Microsoft, and the Future of Computing

Here’s something that might surprise you — Sinofsky points out that the biggest shift in tech isn’t just about new gadgets, but how product design and hardware-software integration have become the real game changers. According to Steven Sinofsky, speaking with Theo Jaffee from a16z, Apple’s focus on seamless user experience and hardware-optimized software has kept it ahead for 50 years. Meanwhile, Microsoft’s journey with Windows and Surface shows how competing visions and product cycles often repeat themselves — like the recurring battles between Apple and Microsoft. Sinofsky highlights that understanding these patterns helps us see what’s coming next. As he explains, the future of computing isn’t just about faster chips or cooler gadgets, but about designing systems that adapt — and that’s where the real value lies, especially with things like Apple’s Vision Pro. So, if you want to stay ahead in tech, it’s less about chasing the latest shiny object and more about understanding these deep, repeating cycles — something Sinofsky hints will shape the next decade.

Theo Jaffee speaks with Steven Sinofsky about Apple’s 50th anniversary and the evolution of personal computing over the last four decades.

Drawing on his experience helping lead Microsoft through the Windows era, Sinofsky reflects on the cultural differences between Apple and Microsoft, the rise of the Mac, the history of Windows, and how product design, hardware integration, and software platforms shaped the modern technology industry.

They also discuss the Apple Vision Pro, the new MacBook Neo, gaming, operating systems, and why some technology cycles seem to repeat themselves. Along the way, Sinofsky shares lessons from Windows, Surface, and Microsoft’s battles with Apple, offering a firsthand perspective on some of the most consequential product decisions in computing history.

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Find Steven on X: https://x.com/stevesi

Find Theo on X: https://x.com/theojaffee

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Audio Transcript