Slack founder: Mental models for building products people love ft. Stewart Butterfield
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What is Stewart Butterfield doing now and why does he focus on family and philanthropy?
This is 2014. That was the year that Slack actually launched. I was interviewed by MIT Technology Review and asked if we were working to improve Slack. I said, I feel like what we have right now is just a giant piece of shit. It's just terrible and we should be humiliated that we offer this to the public. To me, that was like you should be embarrassed. If you can't see almost limitless opportunities to improve, then you shouldn't be designing it.
Slack was famous for being one of the early consumerized B2B SaaS products.
At more than one company, all hands, I made everyone in the company repeat this as a chant. In the long run, the measure of our success will be the amount of value that we create for customers. And you can put effort into demonstrating that you have created this value and stuff like that, but there's no substitute for actually having created.
created it. Something else I heard that you often espouse is friction in the product experience is actually often a good thing.
It it became an assumption that you should always be trying to remove friction when the challenge is really comprehension. If your software kind of stops me and asks me to make a decision and I don't really understand it, you make me feel stupid. If people could get over the idea of reducing friction as a number of goal or reducing the number of clips or taps or do something, and instead focus on how can I make this simple? How do I prevent people from having to think in order to use my software?
You started two companies, both famously pivoted. I imagine many people come to you for advice on pivoting.
The decision is about like 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. And the reason I say you have to be coldly rational about it is because it's fucking humiliating.
Today, my guest is Stuart Butterfield, a founder and product legend who rarely does podcasts. Stuart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tech history at the time. There is so much product and leadership wisdom locked away in his head. I feel like our conversation just scratched the surface. We chat about utility curves, something he calls the owner's delusion, a hilarious pattern he sees at companies, he calls hyper. Realistic work-like activities, what he's learned about product and craft and taste and Parkinson's Law, why you need to obsess with not making your users think, the backstory on his legendary We Don't Sell Saddles here memo, and so much more, a huge thank you to Noah Weiss, Chris Cordle, Ally Rale, and Johnny Rogers for suggesting topics and questions for this conversation.
This is a really special one, and I really hope to have stored back to. Delve even deeper. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get 17 incredible products for free for an entire year, including Devin, Lovable, Repli, Bolt, Inid, and Linear Superhuman, D Script, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Japy RD, and Mobbin. Head on over to Lenny's Newsletter.com and click product. pass. With that, I bring you Stuart Butterfield after a short word from our sponsors. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercell, Platt, and hundreds of other winning companies have in common?
The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, skim, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs. With a modern developer platform built specifically for B2B SaaS. Whether you're a seed stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unlocking growth.
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Chapters
7 chapters
1
What is Stewart Butterfield doing now and why does he focus on family and philanthropy?
0:00–15:15
2
How does Stewart define and use utility curves to decide where to invest product effort?
15:15–29:04
3
What is “divine discontent” and how does it influence product strategy?
29:04–41:21
4
Why does Stewart say product “taste” matters more than features?
41:21–56:13
5
What is the “tilt your umbrella” mental model and how does it create a competitive advantage?
56:13–1:10:18
6
Why does Stewart argue that reducing friction is less important than reducing user thinking?
1:10:18–1:24:13
7
How does Parkinson’s Law affect team size and productivity at Slack?
1:24:13–1:30:31
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