Most great companies are not built the way their founders originally imagine. Stewart Butterfield ‘s career is a rare, almost elegant proof of this truth: twice, he set out to build one thing and ended up creating something far more important. This is the story of how failure, taste, and the discipline of paying attention gave the world Slack – and changed how work itself feels.
Key Takeaways
- Failure often contains better ideas than the original plan.
- The best products come from paying attention to real behavior, not pitches.
- Persistence matters – but adaptation matters more.
- Taste and language are competitive advantages in software.
- Great companies are sometimes discovered, not designed.
The Best Idea Was Hiding in the Wreckage
In 2012, Stewart Butterfield‘s company was dying.
Tiny Speck, the startup behind a whimsical but commercially doomed online game called Glitch, had spent years building a rich, strange digital world – and watching users fail to show up. The team had talent, taste, and engineering prowess. What they did not have was traction.
But inside the wreckage of that failed game lived something else: an internal communication tool the team had built just to survive their own complexity. It was fast, searchable, organized, and – most unusually – pleasant to use. It was not the product. It was the scaffolding.
Butterfield did something that looks obvious only in hindsight: he shut down the game and rebuilt the company around the tool.
That tool became Slack.
Stewart Butterfield: A Career Built on Reinvention
Butterfield’s story is often told as a lucky accident. It is not.
Long before Slack, he had already lived one full cycle of creative destruction. In 2002, Butterfield co-founded a game company – Ludicorp – that also failed – but its photo-sharing feature survived. That feature became Flickr, one of the defining products of the early social web, eventually acquired by Yahoo.
The pattern was already there: ambitious visions, partial failure, and an almost allergic sensitivity to what users actually loved.
Butterfield is not trained as a traditional engineer. He studied philosophy and dabbled in design and photography. That background shows in his work. He is obsessed not just with function, but with how software feels. With language. With the emotional texture of using a product eight hours a day.
When he started Tiny Speck, the goal was not to build enterprise software. It was to build a game. A weird one. A beautiful one. A world.
It didn’t work.
What did work was how the team talked to each other inside it.
Closing Glitch was not just a business decision. It was a psychological one. Most founders cling to the original idea because it feels like identity. Butterfield let go.
Not because he gave up – but because he noticed something better.
The Pivot That Wasn’t a Pivot
Slack did not begin as a grand vision for workplace communication. It began as a practical solution to a team’s own chaos.
Email was slow. Threads were messy. Context disappeared. Decisions got buried.
The internal tool solved that. It made conversation persistent, searchable, and structured without feeling rigid. It made work feel lighter.
Butterfield realized something subtle but profound: most software at work feels like punishment. It is designed for control, compliance, or reporting – not for the humans who actually use it.
Slack would be different.
Even the name reflected this philosophy. “Slack” was not about efficiency theater. It was about breathing room. About reducing cognitive load. About making work a little less heavy.
When Slack launched publicly in 2013, it spread with an unusual pattern: not through executives, but through teams. Engineers invited designers. Designers invited marketers. It moved sideways inside organizations, not top-down.
That wasn’t an accident. It was the product’s personality.
The Nervous System of Modern Work
Within a few years, Slack became the default communication layer for startups, tech companies, and eventually enterprises around the world.
It wasn’t just a chat app. It became:
- The place decisions happened
- The place culture lived
- The place work was narrated in real time
Slack changed not just how teams communicate, but how they think out loud.
In 2021, Salesforce acquired Slack for nearly $28 billion. But by then, Slack had already done something more lasting: it had reshaped the emotional and social architecture of modern work.
Butterfield had not set out to build this.
He had built it by paying attention.
The Founder Psychology: Persistence vs. Adaptation
Startup culture loves the myth of persistence. Never give up. Stay the course. Believe harder.
Butterfield’s story tells a more nuanced truth: the real skill is knowing what to let go of.
He did not abandon ambition. He abandoned the wrong expression of it.
This requires a rare combination of:
- Ego control
- Taste
- Emotional resilience
- Intellectual honesty
Most founders don’t fail because they can’t build. They fail because they can’t change their minds.
Butterfield changed his.
Twice.
Product as Philosophy
Slack’s success cannot be explained by features alone.
It is explained by:
- The obsessive attention to language and microcopy
- The deliberate friendliness of the interface
- The refusal to treat users like resources to be optimized
Butterfield once said that software is where people now live. If that’s true, then designers and founders are building cities, not tools.
Slack feels like a place that respects your time and attention. That is not an accident. That is taste, operationalized.
Takeaway: The Art of Intelligent Reinvention
Stewart Butterfield’s real lesson is not “pivot when things don’t work.”
It is: build things with enough sensitivity that you can hear what is trying to emerge.
Slack was not invented. It was discovered.
Discovered inside failure. Inside use. Inside attention.
The founders who change the world are not always the ones who chase the biggest visions. Sometimes they are the ones who notice the most important byproducts.
FAQs
Who is Stewart Butterfield?
Stewart Butterfield is the co-founder of Slack and Flickr and one of the rare founders to successfully build two category-defining internet products. He is known for his product-driven, human-centered approach to software design and company building.
How did Slack start?
Slack began as an internal communication tool inside a failed game company called Tiny Speck. When the game Glitch was shut down, Butterfield and his team realized the tool they built to communicate was more valuable than the game itself.
Why was Slack different from other workplace tools?
Slack focused on usability, language, and emotional experience rather than just functionality. It made work communication feel lighter, more transparent, and more human than traditional enterprise software.
What happened to Slack after its success?
Slack grew rapidly across startups and enterprises and was eventually acquired by Salesforce in 2021 for nearly $28 billion. It continues to serve as a core communication layer for millions of teams worldwide.
What can founders learn from Stewart Butterfield?
That success often comes not from stubbornly sticking to a plan, but from noticing what’s working and having the courage to rebuild around it. Adaptation, taste, and attention can be more powerful than raw persistence.
Sources:
- https://en.wikipedia.org/wiki/Stewart_Butterfield
- https://www.forbes.com/profile/stewart-butterfield/
- https://buildingslack.com/the-death-of-glitch-the-birth-of-slack/
- https://thehustle.co/news/from-a-failed-game-to-photo-sharing-success
- https://www.cnbc.com/2020/12/01/salesforce-buys-slack-for-27point7-billion-in-cloud-companys-largest-deal.html
