Invest Like the Best with Patrick O’Shaughnessy
Business:Investing
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 my conversation with Stewart.
Before we transition to the episode, I also wanted to highlight our newest series Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. For more information go to joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.
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Show Notes
[00:02:51] - [First question] - Discussing his essay We Don’t Sell Saddles Here
[00:06:19] - Important contrast between innovation and the product
[00:06:46] - Who Do You Want Your Customers to Become?
[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 market messaging creation strategy
[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 and 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 that anyone has ever done for him
[01:04:27] - Why a philosophy primer would be beneficial for virtually everyone
Adam Sandow - The Power of Print Media - [Invest Like the Best, EP.376]
Howie Liu - Building Airtable - [Invest Like the Best, EP.375]
Mark Groden - The Future of Flying - [Invest Like the Best, EP.374]
Dev Ittycheria - The Database Evolution - [Invest Like the Best, EP.373]
Nico Wittenborn - Finding the Adjacent Possible - [Invest Like the Best, EP.372]
Mitch Rales: The Art of Compounding - [Art of Investing, Forever Episode]
Marc Lasry - Making Bucks in Credit and Sports - [Invest Like the Best, EP.371]
Bill Gurley & Michael Mauboussin - Putting Theory into Practice - [Invest Like the Best, EP.370]
Tim Ferriss - Curating Curiosities - [Invest Like the Best, EP.369]
Ken Langone - The American Dream - [Invest Like the Best, EP.368]
Robin Dunbar - Optimizing Human Connection (Dunbar's Number) - [Invest Like the Best, EP.367]
Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, EP.366]
Dave Fontenot - The Monastery of Code - [Invest Like the Best, EP.365]
Anne-Marie Peterson - The Capital System - [Invest Like the Best, EP.364]
Aravind Srinivas - Building An Answer Engine - [Invest Like the Best, EP.363]
Ali Hamed - Building an Investment Firm - [Invest Like the Best, EP.362]
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, EP.361]
Danny Meyer - The Power of Hospitality - [Invest Like the Best, REPLAY]
Chuck Akre - The Three Legged Stool - [Invest Like the Best, REPLAY]
Alex Telford - Unlocking Innovation in Pharma - [Invest Like the Best, EP.360]
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