TAG

# Pivot

2026-11-04

Global PM Ranking #50 Stewart Butterfield: Twice Bankrupted Making Video Games, Twice Salvaged the Internal Tool for $27.7 Billion

【The 100 PMs Who Changed the World · #50】No founder in Silicon Valley history has lived a wilder Groundhog Day loop than Stewart Butterfield (87 OVR). Armed with a Cambridge philosophy degree, he tried twice to build an online multiplayer game (Game Neverending in 2002 and Glitch in 2009). Both games failed—and both times, he pulled the internal tool his team built from the ashes, creating Flickr and the $27.7 billion enterprise juggernaut Slack.

2026-10-29

Instagram: How a 1:1 Square Frame and One-Tap Filters Dropped the Cost of a Beautiful Photo to Zero — and Set the Visual Taste of the Smartphone Era

Ranked #34 on the 100 Products That Changed the World: Instagram (2010), OVR 88.60 (Scale 91, Impact 90, Experience 90, Durability 89, Business 87, Originality 85). In the summer of 2010, Kevin Systrom and Mike Krieger looked at their struggling location check-in app Burbn and made one of the boldest cuts in Silicon Valley history: they threw away 90% of their code to keep only photo sharing. Inspired by a comment on a Mexican beach, Systrom coded the X-Pro II filter, Krieger engineered background pre-uploading, and 13 employees sold the company for $1 billion before growing it past 2 billion monthly users.