Mental models for building products people love ft. Stewart Butterfield

(instrumental music) 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 the product.

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 our customers. And you can put effort into demonstrating that you have created this value. It's not like that, but there's no substitute for actually having created it.

Something else I heard that you often espouse is friction in a 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 the number one goal, or reducing the number of clicks or taps to 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.

(instrumental music) Today my guest is Stewart Butterfield, a founder and product legend who rarely does podcasts. Stewart 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, Ali Rail, and Johnny Rogers for suggesting topics and questions for this conversation. This is a really special one and I really hope to have Stewart 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, Replit, Bolt, Innit, Linear, Superhuman, Descript, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Cheppi RD, and Mobbin. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Stewart Butterfield after a short word from our sponsors. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercel, Plat, 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. They're essentially Stripe for enterprise features. Visit workos.com to get started. Or just hit up their Slack support where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs and a smooth developer experience. Go to workos.com to make your app enterprise ready today. This episode is brought to you by Metronome. You just launched your new shiny AI product. The new pricing page looks awesome but behind it, last minute glue code, messy spreadsheets and running ad hoc queries to figure out what to bill. Customers get invoices they can't understand, engineers are chasing billing bugs, finance can't close the books. With Metronome you hand it all off to the real time billing infrastructure that just works. Reliable, flexible and built to grow with you. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand and keeps every team in sync in real time. Whether you're launching usage-based pricing, managing enterprise contracts or rolling out new AI services, Metronome does the heavy lifting so that you can focus on your product, not your billing. That's why some of the fastest growing companies in the world like OpenAI and Anthropic run their billing on Metronome. Visit metronome.com to learn more. That's metronome.com. Stewart, thank you so much for being here and welcome to the podcast.