Stewart Butterfield
Serial entrepreneur who built two landmark products from failed games
Stewart Butterfield is a Canadian serial entrepreneur who holds a philosophy degree and twice pivoted failed online game projects into era-defining products. In 2004, Flickr emerged from the game Game Neverending, becoming the first social photo platform and acquired by Yahoo in 2005. In 2009 he launched Glitch, which failed again, but from it emerged Slack—launched in 2013, rapidly becoming the standard enterprise collaboration tool, going public in 2019, and acquired by Salesforce for $27.7 billion in 2021. He firmly believes that 'work' itself needs to be redesigned and that great tools can transform workplace culture.
Methodologies
- Failure Pivot Method - At the edge of failure, find the most valuable byproduct the team has inadvertently built
- Bottom-Up Enterprise Penetration - First capture individual user mindshare, then let enterprise decision-makers pay for tools users are already dependent on
Key decisions and timeline
- Founded Ludicorp, developing online games - The failure of the core product doesn't mean all efforts are worthless
- Flickr born from game's ashes - First pivot validated: attention should follow actual user behavior, not founders' vision
- Flickr acquired by Yahoo - Cultural conflict after big company acquisition fundamentally undermines the momentum of innovative products
Beliefs and mental models
- Belief 1 - Butterfield experienced two game project failures, but his mental framework is that failure releases team energy, code, and intellectual capital that can be refocused. Both Flickr and Slack emerged when teams pivoting away from near-shutdown found bigger opportunities in tools they had built for themselves.
- Belief 2 - Butterfield believes email was designed for personal communication and when forced into team collaboration it creates enormous noise and inefficiency. Real collaboration tools should help people focus better and reduce context switching, thus changing the underlying logic of workplace culture.
- Belief 3 - Butterfield studied philosophy at the University of Victoria and Cambridge, believing that the essence of philosophical training is learning to ask 'what is this really?' and 'why do we do this?' This habit of questioning fundamental assumptions allows him to set aside conventions in product design and redefine what users truly need.
- Model 1
- Model 2
- Model 3