Slack founder: Mental models for building products people love ft. Stewart Butterfield
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this rare podcast appearance, Stewart Butterfield, co-founder of Slack and Flickr, shares the product frameworks and leadership principles that contributed to his extraordinary success. Currently focusing on family and philanthropy after selling Slack to Salesforce, Butterfield dives deep into concepts like "utility curves," "hyper-realistic work-like activities," and "the owner's delusion" – frameworks that apply to anyone building products or leading teams. (04:58)
- Core themes: Product craft and taste, user comprehension over friction reduction, organizational efficiency, generous leadership, and creating genuine customer value through thoughtful design decisions.
Speakers
Stewart Butterfield
Stewart Butterfield is the co-founder of two of the most influential products in internet history: Flickr and Slack. After successfully selling Slack to Salesforce in one of tech's biggest acquisitions, he stepped away from the CEO role and now focuses on family time, philanthropic work, and creative projects. Known for his deep product intuition and generous leadership style, Butterfield has become a legendary figure in the product development world.
Lenny Rachitsky
Lenny Rachitsky is the host of this podcast and author of Lenny's Newsletter, one of the most popular publications for product managers and startup operators. He brings extensive experience from his time at Airbnb and has built a reputation for conducting in-depth interviews with top product leaders and entrepreneurs.
Key Takeaways
Master the Utility Curve Framework
Butterfield introduces the concept of utility curves - an S-curve where initial effort produces little value, then there's a steep rise where massive value is created, followed by diminishing returns. (06:44) This framework helps teams understand whether they're in the "junk" phase where more investment is needed, or if they've hit the point of diminishing returns. The key insight is that most features fail not because they're bad ideas, but because teams don't invest enough to get up the steep part of the curve where real value is created.
Focus on Comprehension Over Friction Reduction
Rather than obsessing over reducing clicks or friction, focus on reducing the amount of thinking users need to do. (28:48) Butterfield argues that when users have low intent and don't understand what your product does, the challenge isn't friction - it's comprehension. Users need to understand what your product is and what they should do next. This reframes product design from "how do we make this faster?" to "how do we make this immediately understandable?"
Embrace "Divine Discontent" and Never Stop Improving
Butterfield famously called Slack "a giant piece of shit" even after its successful launch, exemplifying his philosophy of "divine discontent." (47:02) Great product leaders should always see limitless opportunities for improvement. This isn't about being negative - it's about maintaining the drive to continuously make your product better. If you can't see obvious ways to improve your product, you probably shouldn't be in charge of it.
Recognize and Eliminate "Hyper-Realistic Work-Like Activities"
As organizations grow, people start doing work that looks like valuable work but actually isn't. (63:17) Examples include meetings to preview meetings, over-analyzing minor feature changes, or extensive research on trivial decisions. The solution is ensuring there's always sufficient "known valuable work to do" - tasks that are both clearly defined and obviously valuable. Leaders must actively identify and eliminate these activities while providing clear priorities.
Practice Generous Leadership for Long-Term Success
Butterfield's approach to leadership emphasizes extreme generosity - from paying 100% of employee health insurance to creating employee-friendly acquisition terms. (78:31) This isn't just ethics; it's strategy. Generous leadership demonstrates cooperation in what he calls the "iterated prisoner's dilemma" of business relationships. When you consistently show you'll cooperate and prioritize others' success, they reciprocate, creating competitive advantages through trust and loyalty.
Statistics & Facts
- Butterfield and Cal Henderson have worked together for 23 years, spanning both Flickr and Slack, demonstrating the value of long-term product partnerships. (06:09)
- By 2017 when Slack implemented do-not-disturb, they had tens of thousands of paying customers, hundreds of thousands of organizations, and millions of users - showing the massive scale considerations for feature rollouts. (25:51)
- When Slack had their biggest outage after going public, their generous SLA policy of 100x money back resulted in approximately $8 million in credits, forcing them to revise their terms. (84:48)
