"Taste is mostly developable through practice — some people have a natural edge, but you can absolutely get better, and because most people don't invest in taste, leaning into it becomes a structural advantage."
"The decision is about whether you've exhausted the possibilities — be coldly rational, not emotional"
Evidence from the Archive
Slack / Flickr
Tiny Speck / Slack: Butterfield's game Glitch had 45 employees and $17.2M in venture capital but would never scale...
Create emotional distance and apply cold rationality -- the decision is whether you have exhausted the possibilities, not whether you have tried hard enough.
Stewart Butterfield is arguably the most successful serial pivoter in tech history -- he pivoted a failing game into Flickr (acquired by Yahoo for $35M), then pivoted another failing game into Slack (sold to Salesforce for $27.7B), making him uniquely credentialed on when to change course. Their core argument: Create emotional distance and apply cold rationality -- the decision is whether you have exhausted the possibilities, not whether you have tried hard enough.
The evidence is specific: Tiny Speck / Slack: Butterfield's game Glitch had 45 employees and $17.2M in venture capital but would never scale to justify the investment. The team's internal communication tool was generating more evident value than the game itself, making the rational case for pivoting clear even though the emotional cost was enormous.. Furthermore, game Neverending / Flickr: Butterfield's first game company also failed, but the photo-sharing feature within the game showed organic pull. The pivot to Flickr was driven by the same 'exhausted possibilities' logic..
In Stewart Butterfield's own words: "The decision is about have you exhausted the possibilities? Creating the distance so that you can make an intellectual rational decision about it rather than an emotional decision is essential." (Lenny asks Butterfield about his framework for deciding to pivot, given that he famously pivoted two companies.)
Slack
Slack made a Vancouver umbrella observation — that only a third of people tilt their umbrella for others — into a new-hire welcome ritual
Stewart Butterfield argues taste is literally trainable (the word comes from food) and most people don't invest, so leaning into it is a structural advantage
Butterfield threads the needle on the innate-vs-teachable debate. He starts from etymology: the word 'taste' literally comes from putting food in your mouth and forming discernments over time. Chefs measurably improve with training, so people can develop product taste through deliberate exposure and practice. He concedes some have a natural advantage, but refuses to let that collapse into fatalism.
The economic argument is sharper: most people don't have good taste and don't invest in developing it, so any team that bothers gains a defensible advantage. He invokes Bezos's 'your margin is my opportunity' to frame taste as a commercial moat. The umbrella story became a Slack new-hire ritual — observing that only about one-third of people in Vancouver would move their umbrella out of the way for a stranger, and making that discipline of attention a core cultural metaphor for what product taste actually is.
In Stewart's own words: "So one is can you learn to develop it? I think so because the word literally comes from experiencing food and putting stuff in your mouth. And can people become better chefs with training? Yes, absolutely. Undoubtedly, some people have a natural advantage... But you can definitely practice and you can definitely get better." (Answering directly whether taste can be learned.)