Founder’s Field Guide
Episode 43 We Don’t Sell Saddles Here
Founder’s Field Guide

Episode 43: We Don’t Sell Saddles Here

We Don’t Sell Saddles Here

Stewart is the founder and CEO of Slack. We cover the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models.

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[00:02:51] - [First question] - Discussing his essay We Don’t Sell Saddles Here  

[00:06:19] - Important contrast between innovation and product

[00:08:07] - His thoughts on marketing from both ends and how he’s gotten better at it

[00:10:45] - What across Slack’s history has been the most successful messaging strategy for market creation

[00:13:43] - The 5K contest and how it taught him about the design unlock of limitations

[00:17:44] - How limitations and constraints can power and incentivize innovation 

[00:21:21] - Why both of his attempts to build videogames ended up as consumer software

[00:27:55] - Whether or not there is still white space in digital communication software

[00:30:15] - The dynamic between effective communication and building communication tools

[00:34:02] - A future of digital-first companies and what that might look like

[00:40:15] - Leadership and Self-Deception, plus what self-deception means to him

[00:43:39] - Examples of self-deception he underwent that he was able to learn from

[00:46:59] - Mastery and its importance in the world of business

[00:48:59] - Why hippies and APIs may have a tighter correlation than we think 

[00:54:01] - Whether or not technology is fundamentally amoral 

[00:56:10] - Interesting and open questions about the future that remain unanswered 

[00:58:33] - His current creative outlets that he engages with the most 

[00:59:24] - Yahoo Resignation Letter and why he wrote it the way he did

[01:00:31] - Lessons for investors and builders that he’s learned from building Slack

[01:03:07] - The kindest thing anyone has ever done for him 

[01:04:27] - Why a philosophy primer would be beneficial for virtually everyone

We Don’t Sell Saddles Here

Introduction

Patrick
My guest today is Stewart Butterfield, founder, and CEO of Slack. Stewart's 2014 essay, Why We Don't Sell Saddles Here, had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner's delusion, how to frame the boundaries between product and market, and the challenge of changing people's mental models and behavior when introducing innovative products. I hope you enjoy this great conversation with Stewart Butterfield.

We Don't Sell Saddles Here

Patrick
I found an interesting place to begin our discussion because of something that happened to me in 2017, so I took over our asset management business back then, and probably like any new CEO, I was a little bit floundering trying to figure out what I was going to do, what direction to take the business. There was a couple pieces of content that really influenced my direction. One was Positioning, a book about marketing. Another was this amazing video called Inventing on Principle by a programmer named Bret Victor, and a third was an essay that you wrote in 2014 called, We Don't Sell Saddles Here. I have to begin our discussion with that essay. Could you give us the background of why you wrote it and sort of what the main message was? And I'll have probably several questions about it because it was so influential on me personally.

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