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Tilt Your
Umbrella

Stewart Butterfield
Founder of Flickr and Slack · Two failed video games, two successful pivots · Rarely does podcasts
NOV 20 2025
Framework

Utility Curves &
Divine Discontent

YOUR CURVE vs USER EXPECTATION
"Layer on the concept Bezos calls divine discontent. The line moves. Once people are familiar with your feature, their standards go up. The competition is with everyone else's utility."
  • A utility curve maps how much a feature is worth as it improves — convenience, speed, quality, whatever
  • Most features get implemented once, improved periodically if lucky, and never touched again for many
  • Meanwhile everyone else's search, login, forgot-password, checkout keeps improving
  • People obsessed with one small thing keep piling detail on it past the point of noticeable difference
The Mantra

Tilt Your Umbrella

held flattiltedSIDEWALK GAME
"It became a game — will this person tilt their umbrella so we can pass? About one-third would do it."
  • The whole company saying, on swag and everywhere: tilt your umbrella
  • Not "your margin is my opportunity" — more like your failure to be courteous is my opportunity
  • Slack won a lot of moments because it did the small considerate thing that competitors didn't bother with
  • Growth pattern: person leaves startup A for startup B, tells B "we have to try this — it's so good"
Taste is trainableTaste literally comes from tasting food. You can practice it. Some have a natural head start, but most people don't invest in it — which is why leaning in creates a real advantage.
Diagnosis

Hyper-Realistic
Work-Like Activities

  • People book meetings to preview the deck they'll show in the big meeting to get feedback on which slides to improve
  • Superficially identical to work — a projector, a room, a discussion — but actually a fake bit of work
  • Every executive does it. Every board member. Stewart admits he does it too. It's that subtle.
  • The further you are from real context and decision authority, the easier it is to get trapped in it
Known valuable work to do

The antidote. At the very beginning of a company there is enormous known valuable work; a bank account needs opening, and it's obvious. The leadership job is to keep manufacturing that clarity as the company grows.

Parkinson's Law

1956, The Economist: work expands to fill the time available. Stewart says the inverse is also true — give a task to a busy person, it happens. Since he's not that busy, "basic things take a really long time."

On Pivots

The King of Pivots on Pivoting

  • Stewart founded two companies (Flickr, Slack). Both famously pivoted from failed video games
  • If you're six months in, still messing with three co-founders, that's not a pivot — that's still figuring out what you're building
  • A real pivot has weight: with Glitch shutting down, players lost their community, employees lost their jobs, families had already moved cities
  • Create enough distance to make an intellectual, rational decision instead of an emotional one — that's the essential move
Survivorship bias, named out loudStewart is clear: his pivots worked, but that doesn't mean everyone should pivot all the time. The framework is not "pivot when hard," it's "did you make the rational or the emotional decision?"
Contrarian

Stewart's Uncomfortable Takes

✗Optimize the feature you're proud ofINSTEAD →✓ Watch the utility curve. Piling detail on your favorite feature past the point of noticeable difference is a distraction, not craft.
✗Make me decide, I'm the userINSTEAD →✓ Stopping the user for a decision they don't understand costs metabolic glucose and makes them feel stupid. Don't make me think.
✗More meetings ⇒ more alignmentINSTEAD →✓ Most of those meetings are hyper-realistic work-like activities. The leader's job is to supply real, known valuable work in their place.
✗Taste is innate, don't bother teaching itINSTEAD →✓ Chefs are trained. So are product people. Most competitors won't bother developing taste, which is the whole point.
Based on Stewart Butterfield's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTubeFollow @stewart on X
GO DEEPER IN THE EPISODE
04:58 Stewart’s current life and reflections06:44 Understanding utility curves10:13 The concept of divine discontent15:11 The importance of taste in product design19:03 Tilting your umbrella28:32 Balancing friction and comprehension45:07 The value of constant dissatisfaction47:06 Embracing continuous improvement50:03 The complexity of making things work54:27 Parkinson’s law and organizational growth01:03:17 Hyper-realistic work-like activities01:13:23 Advice on when to pivot01:18:36 The importance of generosity in leadership01:26:34 The owner’s delusion
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