Stewart Butterfield - We Don’t Sell Saddles Here - [Founder’s Field Guide, EP. 43]

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. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Patrick O'Shaughnessy?

  I know firsthand how complex the tech stack is for asset management firms. And seemingly every new tool and data source makes the problem even worse, adding more complexity, more headcount, and more risk. RidgeLine offers a better way forward. One unified platform that automates away the complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more, all at scale. RidgeLine is revolutionizing investment management, helping ambitious firms scale faster, operate smarter, and stay ahead of the curve. See what RidgeLine can unlock for your firm. Schedule a demo at ridgeline.ai. This episode of Founder's Field Guide is brought to you by Dell Technologies. When you run a growing business, no two days are the same. One day you're hiring employees, the next you're launching a website.

• 0:41Patrick O'Shaughnessy?

  Dell Technologies advisors understands your challenges and are here with the right tech solutions so you can evolve your business and stop at nothing for your customers. Call an advisor today at 877-ASKDELL and do more with modern devices and Windows 10 Pro. This episode is brought to you by LinkedIn Jobs. 2021 means new opportunities to grow your business. If part of your strategy is adding new members to your team, LinkedIn Jobs finds the right person quickly. To make things better, your first job post is free. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do all this from your mobile device. That's how LinkedIn Jobs can help you hire the right person faster.

• 1:26Patrick O'Shaughnessy?

  When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now you can post a job for free. Just visit LinkedIn.com/fieldguide. Again, that's LinkedIn.com/fieldguide to post a job for free. Terms and conditions apply. Hello and welcome, everyone. I'm Patrick O'Neal, and this is Founder's Field Guide. Founder's Field Guide is a series of conversations with founders, CEOs, and operators building great businesses. I believe we are all builders in our own way, and this series is dedicated to stories and lessons from builders of all types. Founder's Field Guide is part of the Colossus family of podcasts, and you can access all of our podcasts, including edited transcripts, show notes, and resources to keep learning at joincolossus.com.

• 2:12Speaker 01

  Patrick O'Shaughnessy is the CEO of O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.

• 2:37Patrick O'Shaughnessy?

  Our guest today is Stuart Butterfield, founder and CEO of Slack. Stuart'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 discussed 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 enjoyed this great conversation with Stuart Butterfield. 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 for the Business Breakdowns feed on your preferred podcast player.

• 3:24Patrick O'Shaughnessy?

  I found an interesting place to begin our discussion because of something that happened to me in 2017. So I took over our O'Shaughnessy 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. And there was a couple of 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 Brett Victor. And a third was an essay that you wrote in 2014 called We Don't Sell Saddles Here. And so 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.

• 4:06Speaker 02

  Sure, thank you. I guess that there's two interconnected messages in there, and one of them is to really focus on the kind of impact that we want. And how we convey that to customers. I think we said, and actually we still say today, Slack is the kind of thing that you don't know you want, but once you have it, you can't live without it. And that's great, except that people don't know that they want it. And trying to explain to someone why they might want something that they have no idea that they want is tough. Not just because you have to create that understanding that's a prerequisite for desire, but also because people have a really finite amount of time and they have a set of concerns that are already occupying their mind more or less all the time.

• 4:51Speaker 02

  So we talk about this on the product side of Slack a lot. Someone comes to our website and they come in with, if you imagine like a threshold of intent necessary to do the Google search or to click the link or however it is that they got to the website. They come in with a bare amount to clear that threshold. No one's coming in with an enormous amount of excess intent, the way that they might if they were looking for a ticket for a specific Justin Bieber concert. But if they're looking for a ticket for a specific Justin Bieber concert, it doesn't really matter how bad Ticketmaster's website is. Like it could be slow, it could barf on their credit card detail, it could throw error messages because they know exactly what they want and they really wanted a lot. Whereas when they come to our website, they don't really know what they want exactly.

• 5:33Speaker 02

  They have enough of an idea that they thought this was worth checking out. And the nonspecificity and the bare minimum threshold of intent means that we have to work extra hard and really put things in their terms. I posted this on Twitter many years ago, asking for a name for this phenomenon whereby when you go to a restaurant website, and this is a lot better now because Google Local and all kinds of website service templates and stuff like that. But traditionally, you go to a website for a restaurant and you want the address, the opening hours, the menu or the telephone number. But what you get is like a slow loading Ken Burns effect photo of food and this music, which is really irritating. And then only 30 seconds later, can you get it?

• 6:18Speaker 02

  And when you finally find the phone number, it's an image of the phone number rather than text and you can't tap it. All this stuff. And so I asked like, why is this? And someone came up with a name, owner's delusion, which I thought was perfect because the people who make the restaurant websites and the restaurant tours themselves inevitably have gone to other restaurant websites and been, the situation has been reversed and they know exactly what they want and they're probably frustrated as well. But when it's your own thing, you think it's so important. So significant that everyone is going to see it that way and they don't. So that was a much longer answer than I intended. Curious about the impact it had for you.

• 6:52Patrick O'Shaughnessy?

  The subheader in the essay that says, sell the innovation, not the product. That's sort of the jump off point of why it was so interesting to me. And I think you said something like, the real measure of innovation is some change of human behavior. Maybe you could explain that contrast between innovation and product.

• 7:09Speaker 02

  Innovation is a weird word. It's kind of like collaboration where the meaning is so flexible that it can sometimes be difficult to pick up on what people are saying. And I got this from a extended essay or very short book called, Who Do You Want Your Customers To Become? And that concept of the innovation being in a very literal definitional sense, the change in human behavior was eye opening for me. Because there is no innovation, no great innovation that had the result where people behaved exactly the same before and after. And anytime people change their behavior in a really significant way, it's a result of some innovation. So in the best case, and this is not true of every organization or every individual who tries Slack.

• 7:53Speaker 02

  But in the best case, using Slack is a pretty profound change in how people operate. Because you go from typically a world where the principal means or primary means of communication is email to one that is channel based. And the difference is when you join an organization, you start off with completely empty inbox. Despite the fact that there might have been tens of millions or hundreds of millions or even billions of messages exchanged before you got there. You have no access to that history. And you also have a very partial, incomplete, fragmented view of what's going on across the organization. Maybe if you're lucky, one basis point worth of access to the emails that are flowing through the org. Whereas in Slack, even for an organization that has tens of thousands of people, you could have 10%. So you have three, sometimes four orders of magnitude more access to information.

• 8:37Speaker 02

  And that results in pretty profound changes to behavior.

• 8:40Patrick O'Shaughnessy?

  If you think about the concept of marketing from both ends, this zeros in on why this was so impactful on me. So everyone wants to innovate, right, or create an innovation. But the build it and they will come theory just tends not to work out too well. Like you said, most people don't even know what they're missing. So talk to us about what you've learned about this term, marketing from both ends, what that means and how you've gotten better at it as a business person and leader through your career.

• 9:04Speaker 02

  I really struggle for the right way to convey this. And lately, this is not very effective so far. But lately, I've been using the yin yang image where one side is market and the other side is product. Because people talk about product market fit. And I think because software is fun for many people to make, or products are fun to think about, or people perhaps have romanticized and incorrect visions of what Steve Jobs does, or something like that, the emphasis really tends to be on product. Whereas marketing, people often reduce to promotion or advertising. But I think you can argue about which side it is. But that boundary between the product and the market, like where the product hits the human attention or the creation of utility is really the important thing.

• 9:49Speaker 02

  And sometimes you can just adjust the product to fit exactly the market or people's mental models or behaviors. But much more often, you have to change those. Changing those is a whole different kind of work. And you have to take advantage of the concepts that people already have, because no one has the time or attention to learn an enormous amount just to figure out what your product is. So going back to the website for a second, I would tell people to imagine someone comes to the website. They're annoyed with their boss because of the conversation they just had, and they have some health concerns, like they're worried they might have ulcerative colitis, and they got in arguing with their spouse that morning, and they're worried their kid is messing up at school. And then they come to the website. It can be really tough to break through that.

• 10:33Speaker 02

  And I think the genius of Steve Jobs was certainly on the product side, but probably even more on the marketing side. Having an intuitive understanding of what people would accept or how people would interpret something. And really trying to focus on where those two meet as opposed to the intrinsic properties of the product, which is where a lot of us get hung up. So you have marketing doing blasts of awareness for your incomprehensible thing, and you end up tweaking and iterating on. Features that people could only possibly understand or get value from once they were already using the product. And then there's just this big yawning gap between the product and the marketer, between what you're making and what people understand they might be buying.

• 11:18Patrick O'Shaughnessy?

  It seems also like one thing to do here or consider is that you want to just create the market in the first place. So if the product is sort of bottom up and it's good and useful, the top down is sell the dream, so to speak. In your essay, again, the idea is sell horseback riding, not saddles. I'm curious how, what you've done in Slack's history or just across your career that you think of as the most successful strategy for that market messaging creation.

• 11:44Speaker 02

  I feel like I, and the team more broadly, have tried hundreds of things. And it's rarely the case that something just works. It's more that each action kind of chips away at the problem. And maybe I'm just especially cynical right now, but I'm having trouble thinking of the ones that actually have been effective.

• 12:03Patrick O'Shaughnessy?

  One way to think about this too, for Slack specifically, is if the idea is changing, so literally the first thing I did when I took over the business after reading the essay was to install Slack. The standard switch, like an email-based culture, a lot of lossiness and lack of context building for even a small firm, we were 40 people or something. By switching, all of a sudden, of course, we get much more context in the way you described, like there was organizational change. And for me, it became clear as it happened and people were skeptical and slowly adopted it, but it was a change to how the business communicated. And another way to think about the question is, the most interesting ways in which you saw companies change as a result of adopting this, that then you could communicate to other companies so that they could participate in that same benefit?

• 12:46Speaker 02

  Thinking about it that way, I think the challenge has often been trying to point out a problem that people don't perceive as a problem, not because it's not a problem, but because they take for granted or are so used to it that they assume that nothing can be done about it. In talking to leaders, it's often, whether they use this term or not, it's a question of alignment. And that just means that everyone on the team has the same understanding of what's happening, where we're at, what the objectives are, what their respective roles are. And when there's a big deviation in people's thinking about this, you end up with a lot of ineffective work in the physics sense being exerted. The difference between the best and the worst performing teams.

• 13:28Speaker 02

  Can be not just like a very large multiple, but often I think the lowest performing teams have a negative impact on the rest of the organization. It's a real challenge. People think about it all the time, but they think about it solely in terms of the kinds of words they can use or what illustrations are in the presentation that they're creating or something like that, as opposed to they have to work against the tools that they're using. So really highlighting the ways in which email has made it difficult for people to achieve the kind of alignment that they want has been one of the most effective ways. But again, it's hard to point out a problem to someone if it's so taken for granted

• 14:08Speaker 02

  or such a deep assumption that this thing can't be changed, that people are unaware that they actually have a challenge.

• 14:15Patrick O'Shaughnessy?

  One of the ideas I really like that I am still in the term from Sarah Tavlet Benchmark is this idea of a core action in software products. So something that you're going to ask the customer to do over and over again, it's kind of obvious what that is in Slack, which is post messages and have conversations in these various channels and sometimes directly with other coworkers. I'm really curious how the concept of design, product design and just design in general has evolved for you, going all the way back maybe to the 5K contest. You could describe what that was and sort of the power of constraint or limitations in design.

• 14:48Speaker 02

  We'll try not to get too deep into a philosophical rabbit hole here, but the

• 14:51Patrick O'Shaughnessy?

  No, let's do it. I like that. I like the rabbit holes.

• 14:54Speaker 02

  Okay. So in 1999, I started a competition called the 5K contest and it was the best website or page that you could create in five kilobytes or less. And that's, you know, from today's perspective, an absurdly small amount of data, but in the world of 1999, where I don't even know, maybe 35% and 40% of US households had internet access of any kind, and it was 95% plus dial up.

• 15:24Speaker 02

  You really had to respect the constraint of bandwidth consumption. And I think because of the excesses of the era and the fact that the competition actually began in early 2000s, when the dot com crash started, there was a real, a much greater degree of enthusiasm for this thing than I would have expected. Because I thought like my community of internet people, some bloggers and stuff like that would enjoy it. But instead, it was like I was interviewed for Playboy and in, so in newspapers and Pravda, like the Russian news service. And it just became a worldwide phenomenon. And part of that has to do just with the depth of the relationship between constraints and creativity.

• 16:07Speaker 02

  You know, some of the people listening here will play music and you think about the key or mode, the time signature, the style of music. In poetry, you have the rhyme scheme and the overall form, the meter. And there's all these conventions in visual art. And the history of the 20th century was often, what happens if we remove constraints? And you get all the way from music that pushes the boundaries with some off notes and dissonance to free jazz and atonal music. And same thing with poetry. You get blank verse and free verse and abstract expressionism in visual arts. But even in, if I have a century, I don't, I don't have one off the top of my head.

• 16:50Speaker 02

  But before the Common Era, there were Latin forms of prose that were just, what is called a lipogram. So what I can write using only this vowel, no words that contain this vowel. There's a great book, it's by Christian Bock, B O K. And it's five chapters. And in each chapter, you're only allowed words that start with one of the vowels. So the E chapter is definitely the best. The U chapter can be very difficult. Anyway, that relationship between constraints and creativity, I think is like an ancient one. It's really so primitive and embedded in creative activity that people fail to notice it.

• 17:33Speaker 02

  Again, until the 20th century, when playing with the constraints themselves became the thing. And I think the Five kilobyte constraint was a really useful one in trying to come up with a very pure concept, but I think the reaction wasn't just about bandwidth consumption, the reaction was about dot com party scenes and accesses and for people who had been online for longer, like I got online in 92, just before the web started to take off, there was definitely the techno utopian hippie ethos of the pioneers of early computing, personal computing technology and the internet and all the commercialism seemed really in conflict with that.

• 18:16Patrick O'Shaughnessy?

  Maybe the second part of the question is how you suggest entrepreneurs think about using constraints or limitations to build better products. You've already pointed out, like limitations create creative output in some interesting way, like by telling people they can do less, they're able to more creatively do more in the strange way. Whether or not you think that can be harnessed in business as well?

• 18:38Speaker 02

  Yeah, I think so. And I'm going to introduce a visual metaphor and no one can see me gesturing with my hands and no one can see the illustration, but probably everyone can imagine two dimensional graph and on the horizontal axis is the effort that you put into some product design creation and on the vertical axis is the value. The curve is almost always very strongly S-shaped. So in other words, it's kind of flat at the beginning and then it has a very steep rise and then it tapers off again. So if you imagine if you're making a software product that has users, early on in the process, you have to design the schema for the users table and then you have to implement it. And then there's a bunch of stuff around authentication and

• 19:19Speaker 02

  salting and hashing passwords and the forgot your password flow. And if you just did all of that, you would be very low on the value scale. You would have exerted some effort and there's no value for anything or anyone because it doesn't do anything yet. And then there's this part that's really steep. And then there's a point beyond which you're expending all this energy and not getting a lot of result. That can be really hard to recognize. I think it takes a lot of experience and practice to understand when you've got to the steep part and understanding the difference between the problem of we're exerting effort and it's because we're past the point of diminishing returns that we're not seeing any value, or we're exerting effort and it's we haven't got to that steep part of the curve yet. Because oftentimes the reaction will be, we added this feature or we made this change

• 20:04Speaker 02

  and we didn't see much of a result, therefore we're not going to pursue it anymore. When they're just shy of the steep part. And the steep part of those utility curves shows up in an inverse way in people's behavior. I lived in San Francisco two different periods and one of them was pre-ride hailing apps and the other one was post-ride hailing apps. And in the pre-ride hailing apps era, you would call a cab and tell them your address. And then mostly they just wouldn't come at all, even though they said they were coming. And other times it would take 45 minutes or even an hour. And the cabs stunk and the drivers were rude. And it was just kind of a terrible system. Now, like most people, I will never call a taxi company on the phone and then tell them

• 20:48Speaker 02

  my location verbally and then wait an indeterminate number of minutes where I have no feedback loop, then get in the cab and then have to pay with cash if I can help it. So if there is a ride hailing service. And from a functional requirements point of view, like specify a location, await arrival, facilitate payment, there's kind of checkmark, checkmark, checkmark. They're in some sense functionally equivalent, but the experience is so different that people's behavior radically changes. And I don't know the number of the increase of hired rides in the US, but I know it's a very large multiple. And I also know that people's preferences, when you cross this threshold of it being easier enough, are such that they will never change their behavior backwards.

• 21:30Speaker 02

  The challenge, I think, is to find those steep parts of the curve. And the constraints are really useful in winnowing down what is more or less an infinite space of possibilities of features to add or things to try or design approaches to something that's a lot more manageable and that helps you determine whether it's worth proceeding down a given path.

• 21:53Patrick O'Shaughnessy?

  Both of the companies for which you're famous Slack and Flickr before it emerged from, don't want to use too harsh a word, but failed attempt at creating video games that would have huge adoption online. Why do you think that was? Why have you continued to kind of go back to that concept? Video games, obviously, an interesting design or constraint challenge in and of themselves. What's behind that happening twice to you? And I doubt that's really happened, except the only other person I can think of is Jason Citron at Discord was also trying to create a game and emerged with a tool, kind of a similar story. Why has this happened twice to you? It's so interesting to me.

• 22:26Speaker 02

  I mentioned that I first got online in 1992. And I should say, I was living in my hometown, Victoria, British Columbia. So it's on an island off the west coast of North America. So it feels very provincial, feels very removed from the rest of society. If it's after 9pm, you can't even get a ferry to go to the mainland. And the web hadn't taken off yet, but the internet was really, had an enormous amount of activity, not relative today, but still hundreds of thousands of people who were connected and they were using Usenet and email and IRC and an old Unix program called Talk, which was like messaging where you could see each letter as it was typed. So it's kind of like a nerve wracking

• 23:09Speaker 02

  and very irritating thing to use. You could see people backspacing to fix their typos. For someone who grew up feeling out of remove to the greater world, the idea that you could transcend geography and you could transcend time and you could find these communities of interest was really just magical. And so from that moment, the idea of the use of computing technology to facilitate human interaction was just the most interesting practical idea in the world. There might be philosophical ideas that are more interesting. The first game was called Game Never Ending and came from the realization that you could make dynamic webpages. And this was 2001, 2002. It was called Remote Scripting. And a friend of mine, Erica Sella, was one of three or four people who were really...

• 23:54Speaker 02

  Invented this, later it became Ajax and then Single Page Apps and now it's just like on my page. But the tech was so cool, we thought, well, we could make a game that's entirely in a browser and make it something that's really dynamic. And I think it failed. I mean, actually, it probably would have failed anyway, because the idea is not especially commercially viable. It was, you know, no combat, absurd surreal, Monty Python meets Dr. Seuss world, has a pretty narrow appeal. But it also failed because it was 2002 when we started it. So it was the dot com crash and then there was WorldCom and Enron accounting scandals. And then there was nine 11. It was just the all time worst market conditions and certainly the worst time to try

• 24:38Speaker 02

  to raise money for something that was online. So when that failed, we created Flickr. The second failure was very different. So we created Flickr, it was acquired by Yahoo. We worked at Yahoo for several years. And then we thought, okay, now it's 2009 versus 2002. And there's all of this amazing open source software that didn't exist before. And we've gone from a world where the Netherlands was the only country to have greater than 50% penetration of internet connections at home to almost every country. You know, there's an order or maybe two orders of magnitude more people online and they had faster connections and they had better computers and hardware was cheaper and we were more experienced. And it's like, it's just all of these 10x factors that led us to believe that, well, we'll never possibly fail this time. And

• 25:21Speaker 02

  we did again, and this is a long story. And maybe the idea wasn't commercially viable, but I think that the real reason was we went all in on Flash as a client technology and kind of a content pipeline management technology at a time when Flash was about to die and people's discretionary computing time shifted from PCs to mobile. And we had been using going way back to 1992, Internet Relay Chatter, IRC, as the backbone of our communications. But because IRC is a 1989 era protocol,

• 25:49Speaker 02

  It didn't have really basic things that people associate with messaging services. So it didn't have the ability to store and forward messages. So if you and I, Patrick, weren't online at the same time, I just couldn't send you a message. That's okay, just wouldn't reach you. And so we built a bot to log all the messages that people send. So you could catch up again, you came back online. And just incrementally, over the course of many years, we made these improvements that were based on something being so exasperating that we couldn't stand it anymore, or something being such an obvious opportunity that we couldn't help but take advantage of it. And I say we, I'm 90% Cal Henderson co-founder and CTO. Once we had the messages logged in database, we wanted to be able to search them. And once we realized that everyone's attention was focused or aggregated here, we started doing things like

• 26:34Speaker 02

  database alerts would flow into the channels, or when you uploaded a file to the file server, that would be announced with the URL, so you didn't have to tell people. And the daily stats runs we posted to channels. So you know, a lot of stuff that became precursors to Slack. And then when we decided to shut down the game, we realized we would never work with that system like this again. And so probably other people would like it too. Although when I said other people, at that point, we thought other eight-person software development teams. Here's the thing, all four of those, the two games, Looker and Slack, are, to me, kind of at their essence, the same. It's all the use of computing technology to facilitate human interaction. So you have a massively multiplayer game that didn't work, and massively multiplayer photo sharing that did work. Because that was what separated Looker from other things.

• 27:16Speaker 02

  It was, you could put a photo and make it public, and other people could comment on it. You could tag it, and other people could tag photos, and then they would show up together, and you'd create groups. And then another massively multiplayer game that failed, and then massively multiplayer workplace software. But there is a real deep, common thread, different in the work context than it is in the play context. But there is the establishment of identity and participation or interaction, and the gradual accretion of the residue of those interactions that increases in value over time. So I just like making software that connects people because there's a specific set of challenges there. And the context is less important for me than the fact that that's what it's for.

• 28:00Speaker 02

  And it turns out that that's, excluding Google, I guess, almost all of the value of the consumer internet at this point is different ways of facilitating interaction with other people. And Google obviously takes advantage of those interactions and discreet human actions to build the index and provide search. It's really big and grateful that Slack is the one that was really successful because it's such a deep and interesting problem. A thread that is very common through all of those, even if the veneer is different.

• 28:28Patrick O'Shaughnessy?

  So it's a fascinating idea that most of the value is just finding ways to help people communicate with each other. How much white space do you think is still there? I think even when Slack started, if you had polled an audience like saying, do we need more communication tools? And maybe if you pulled them today, everyone would say, no, like there's 40 different ways that I communicate with other people. In every medium, voice, video, text, Slack, WhatsApp, there's a million places. So it seems like settled ground. Do you think that that's true or that we as people will just continue to find interesting, innovative, new ways to communicate with each other?

• 29:00Speaker 02

  A little bit of both. It's important to understand why I think Slack works or why it's been successful. And it's not because it's a better way to enter text into a box and hit enter to send it or to read other people's texts. Although, you know, obviously we focus on the design. But channel based messaging is just very different than individual messaging. So Slack is a communication platform that puts the team or the organization first as opposed to putting the individual first. So in email, I have a unique inbox that is different from everyone else's, as does everyone else. And the difficulty of that, I mentioned, first day on the job, you have a completely empty inbox despite the fact that there's all these messages that already existed. But the other problem is I just don't see things the same way you do.

• 29:44Speaker 02

  And unless I manually select emails to forward them to you, you'll just forever miss this context. Whereas you can join a channel six months after it started and it didn't matter that you weren't there. The history was being created and indexed and you can catch up on it. So if you end up in a situation where there's a channel for everything that the organization is paying attention to. So for us, that means every customer, every team, every office location, every function within the company, every incident, every event that we're planning, everything. Then everyone knows where to go, at least theoretically, to ask their question or to give their update or to get caught up in something, which is very, very different than email. So I think it's channel based messaging is a new category.

• 30:30Speaker 02

  And there will definitely be continued iteration and competition and other products. But I want to make clearly, it wasn't just. This is better than iMessage because of style of the app or anything like that. It's better than iMessage because you can have channels.

• 30:48Patrick O'Shaughnessy?

  If you think about the future of communication, another angle is how we can get better at it as people, especially within organizations. Because when we talked last time, you made this good point that especially executives, like literally all they do, their entire job is different forms of communication, whether that's message building, message delivery, meetings, planning, talking to other executives, talking to clients, whatever, it's just all communication. We don't ever receive training on this topic in our lives. Like, we're not taught how to communicate well in school. We're really not taught how to communicate well by our organizations, by our jobs. What are your thoughts on the future of this skill? Because if all this value's been created facilitating communication, but there's been nothing invested in like making people better at that,

• 31:32Patrick O'Shaughnessy?

  it seems like a very odd dynamic. What do you make of that?

• 31:36Speaker 02

  It's kind of hard to explain. And I think the only way of really understanding the delta between how much should be invested in helping people become more effective communicators or investigating tools for better communication and the amount that actually is, is that people just, they're so familiar with the problem that they don't see it as a problem. They don't see it as something that can be solved. So people hate email, people hate meetings, people hate Slack, people hate everything that has to do with communication. There's a population for each of these things that hates it because it can be really taxing because you have to overcome different ways of thinking in order to get your idea across. And you have to kind of parse out what people are trying to say.

• 32:17Speaker 02

  And there's subtext and there's power dynamics and there's all these other things at play that make it hard. But yeah, for executives, it's more or less 100% of what they do. For most managers, it's 95%. Where there are real attempts to innovate or to do things differently, they stand out in a pretty profound way. So everyone knows about the six-page Amazon memo. And how many of those things can you count? How many times have people actually taken their frustration with the ineffectiveness of certain communications and said, okay, here's what we're going to try. We're going to write a six-page memo. We're not going to have any presentations. Everyone's going to sit in silence and read it all together from the beginning of the meeting. So I really understand we're in the same place and then we're going to discuss this.

• 32:59Speaker 02

  And that format forces people to come up with a lot more clarity in how they're communicating and all the rationale that goes along with it. That's one. Another one I've heard, and I don't know if this is apocryphal or not, but Sheryl Sandberg saying no more PowerPoint presentations, but she meant in meetings with her. And the sales team, thousands and thousands of people took that as no more PowerPoint presentations, period. And then they had an all hands and there was a big complaint from the salespeople saying, it's really hard to sell to people without giving them presentations. It's slightly worse than that because most of that communication is just about really basic acts of coordination and communicating state.

• 33:41Speaker 02

  Or, I guess if you include changes in objectives as state, then it's more or less all communicating state. And that's the daily stand up and the quarterly business review and all the approval meetings and the catch ups. I would say 50% plus of the communication that's happening, or 50% often of the effort of knowledge workers, is just that basic communication and coordination. It's not the interesting, creative, strategic parts, although obviously those are really important. And when you look at it that way, you have a company with 10,000 employees and let's say a billion dollars in payroll costs and 50% of the effort, 50% of the time is going into this basic communication coordination. There's $500 million. Maybe zero effort towards trying to improve the efficacy of that. If you were able to make any difference at all, it's disproportionate to more or less

• 34:25Speaker 02

  any change you could make across the company. And that is the biggest difference between the best performing teams and the worst performing ones, and also the best performing organizations.

• 34:35Patrick O'Shaughnessy?

  Do you think that means that we might start seeing really fast acceleration and productivity at firms that start placing more emphasis on this? I like Dustin Moskowitz's phrase work about work and how much of our time is, like you just said, spent on just coordinating stuff. Now that we have a glimpse into what a purely digital organization might look like, thanks to COVID, what do you think that means? Like, what is digital first? What does that mean for you as you think about your company? What do you think it unlocks potentially? Does it start to address this more structured, well-thought-out communication problem for companies to move faster in the future?

• 35:11Speaker 02

  There's an enormous opportunity in front of us now, and my hope is that we'll collectively really take advantage of it. I'm a little bit pessimistic about it, though, because that's not where the conversation is at. The conversation is at how many days per week do people come into the office? I think that the term hybrid, while it may be useful right now. In 10 or 20 years, it's going to feel like paperless office does now. It's kind of a quaint and in some sense bizarre way to think about it because the amount of paper in an office is no kind of indication of how effective it is or even the methods that it employs to operate because paper is useful in many ways and people getting together physically is useful. But we obviously have the technology today to do what was so exciting for me and others in

• 35:56Speaker 02

  the 90s, which is transcend geography and transcend to a large degree time. And the degree to which we take advantage of that, I think we'll have real productivity impact. And then maybe there's a footnote there that whether that shows up in the econometric sense of productivity, we'll see because the solo wrote the productivity paradox, maybe in 1980s. We've been struggling with why isn't there the kind of impact from information technology that we all know that there must be. But yeah, right now, I think there's just this real opportunity to think about how we change the way that we work and never waste

• 36:36Speaker 02

  a crisis. We've been knocked so far off of equilibrium that people will accept changes that might have been more difficult to implement previously. And I think Dustin and I are very aligned in how we think about this stuff with maybe one exception and maybe work about work is just more kind of marketing speak. But while I can list all these reviews and update meetings and catch-ups and stuff like that in a way that the tone of voice indicates, I don't think they're important. I actually think they're critically important. Without the context of the objectives and current state and rules, you just are adrift and people end up working on the wrong things. And I think the most fundamental lament of

• 37:20Speaker 02

  CEOs that I've talked to, and we have a great weekly SaaS CEO call and obviously spend a lot of time talking to the people and there's all this support and commiseration and stuff like that. But at heart, most of it is. Trying to figure out why someone ended up doing something when, from your perspective, that's obviously the wrong thing, but they're not dumb. So something's wrong somewhere in the system. We really should, we again collectively, use this as an opportunity to get creative and to explore, and I don't have all the answers here, obviously, but to kind of explore and iterate and experiment on new ways of communication that give us the best of both worlds. Because the other thing about digital first, work from home, hybrid, all of this stuff, this came from

• 38:03Speaker 02

  a comment that in a very heated staff meeting, my team at Slack, our head of people, Nadya Rollinson, pointed out, like, when we're talking about what's different, are you talking about what's different from February 2020? Are you talking about what's different from today? Because it's easier to imagine February 2020. So everything's the same, except we only come into the office two days a week. But obviously, we move into the future from the present moment. That's quite different. It's not reducing our time in the office to two days a week. It's increasing our time in the office to two days a week. The other thing about thinking about starting from today is, none of this work remotely stuff had to be in people's houses, except that there was a deadly pandemic that forced us all to be effectively quarantined inside of our houses. But you could just as easily go work in a coffee shop or a coworking

• 38:48Speaker 02

  space. That's not your office, because you live in a place where your company doesn't have any physical offices. And, you know, there's huge advantage to companies to be able to hire in a greater variety of places. There's a huge amount of optionality and value for employees to have the choice about how much time they spend in the office. So everything kind of worked out. And if you think about what's different from today, life will be better for everyone, because we'll be able to eat at restaurants and go to the theater and grandparents can visit their grandkids and all that kind of stuff that we were prevented from doing during the pandemic. So everything is, has worked, and life gets better for people at an individual level. And then we'll also get back the office and in-person collaboration as another tool for creating that kind of alignment, which is necessary for the organization to achieve stuff.

• 39:33Speaker 02

  There's, I think, where the struggle is in most conversations because the purpose of an office is manifold, right? We have, and San Francisco is our headquarters, probably, I think about half of our employees are based there, although many have moved during the pandemic. We have a 10-story glass tower and it has our logo on the side of it and it's this projection of power into the world and it's a place to bring recruits and impress them. It's a cultural touchstone for existing employees. It's a place to host customers. It's a place for these all-hands and events and training people and inspired collaborative conversations. And then it's like factory farm, battery chicken housing for people to sit and use their laptops all by themselves with no interaction. That's the least valuable, but takes up the most square footage.

• 40:16Speaker 02

  I've said almost that exact same thing verbatim for like nine months, maybe 12 months now, yet there are zero new plans for how Slack intends to lay out their offices. So I want to point out the potential hypocrisy in how hard it is to affect these changes because I don't want to go back to an office. That's the greatest amount of square footage. And I do want to think about all of those other uses of the office and all sorts of purposes and how we can get the most value out of that investment, but also just have the greatest impact in how well people work together.

• 40:48Patrick O'Shaughnessy?

  One of the things that sits next to this issue is how leadership changes in a digital-first organization. I think in some ways it's easier, there's maybe more leverage like Slack provides. In some ways, it's a lot harder to no substitute for sitting in a room with people and having them see you and communicate with them. You've said elsewhere that there's this book called Leadership and Self-Deception, which has, I think, informed some of your thinking on leadership. And I'm really interested in this idea of self-deception. And maybe you could describe what that means to you in the context of leadership and then we can talk about how that might apply to becoming a better leader in a digital-first world.

• 41:23Speaker 02

  So Leadership and Self-Deception is a book that was given to me by a Slack employee. And if you ever read it, or maybe when this conversation is done, you'll think that if anyone ever recommends this book to you, then they think you're an asshole. So I swear, it's a very intriguing title. And so this employee gave it to me and it was on the, literally on the coffee table and the stack of other books for like a year. And then I finally brought it upstairs to the bedroom and put it on the bedside table where it sat for another year. And then I finally read it. There's a lot in it, but I think that there's a pretty easy way to synopsize it. That's using one of its stories where it's a man who's in bed and it's two in the morning and his wife is there and the baby starts crying and the man wakes up and then he starts thinking,

• 42:05Speaker 02

  "Oh, that's so annoying. I'm so tired. I hope my wife wakes up. I have a really important meeting tomorrow. I just really need to get some sleep. God, why isn't she waking up? What's the matter with her? She's so lazy." And you can do this with a lot more nuance and color than what I just did. But the point of the book is when one violates their own sense of what's right, the immediate response is to create a narrative where someone else is wrong. So he's being lazy. He should have been at bed and taking care of the baby when he heard the baby crying. And despite the fact that he's already awake and not going to take care of the baby, there's an instinctual response to come up with an narrative for why his wife is at fault. And leadership and self-deception is mostly about how that shows up in the workplace.

• 42:50Speaker 02

  It shows up a lot. Maybe there are opportunities in a digital first era to help people move beyond those, but the least effective relationships between managers, employees, executives, the rest of the company, or CEOs and everyone else, I think, arise out of this disconnect. Because the buck stops here. It's our responsibility as leaders to figure out what needs to happen to create the kind of work and the culture and the results that you want. Instead of being a CEO of a company with a bunch of people, you were the physicist doing basic research and trying to develop a new material for something. You might get frustrated and hurl something against the wall or something like that, but you don't blame physics for

• 43:34Speaker 02

  the difficulty that you're having for accomplishing this thing. Leaders blame people all the time. And sometimes people are in the wrong role, but if they're in the wrong role, who put them there? There's a lot of thinking or falling back on the idea that these people are too stupid, or they have some other defect or problem that prevents them doing the thing that your genius mind has envisioned them doing. That's never the case, though. It's on you to figure out, just like the physicists or the material scientists struggling to create some new material, what it is that's causing the results that you don't want, and how to uncover that dynamic and repair it.

• 44:12Patrick O'Shaughnessy?

  So it could sort of be summarized as the classic, it's not you, it's me problem that we always fall in over and over. Is there a particular example from your own history of, I just think it's a really powerful concept, of some sort of self deception that you underwent and ultimately fixed or recognized that you think could nail home the point?

• 44:31Speaker 02

  I was gonna say it's everything I ever do. It's very deeply ingrained. And there's no one single dramatic story, but it is my instinctual reaction when something doesn't kind of unfold the way that I hope or expected is to blame people, to blame other people. And one time out of a hundred, or maybe even less than that, there is some one person who did the wrong thing and therefore like a blame worthy action. But it's almost in every case, a failure on my part, sometimes other leaders, to recognize the incentives that have been created that lead people to do the thing that you don't want them to do. And to make that a little bit more concrete, I have put enormous effort over the course

• 45:16Speaker 02

  of many years with limited success into getting product managers and designers to understand that it's fine to be wrong. Being wrong is just the process of getting to the right answer. And if you imagine you're sitting down to write something, you have an important message, you write the first sentence, and then you write the second sentence, and then you start the third sentence, but you realize, oh, the first two sentences are way too grammatically complicated, and I can simplify that. And you change it, and you're editing, you make typos, you go back and forth, back and forth, and it's this real iterative process. And you don't at every stage berate yourself or chastise yourself for making some mistake. That's just how you get to a good piece of writing in the end. That's the only way to make good software in exactly the same way is to take a best guess and make your attempt and then realize what's wrong with it.

• 46:01Speaker 02

  There are a number of things that lead up to this position where people feel like their job is to be right on the first try. And being right on the first try is more or less impossible unless you do something that really doesn't matter. And so people end up in this position where you're rather than thinking about the food that you're cooking at the end, they're thinking about the recipe and before they ever try cooking it, they're arguing about the recipe and preparing slide presentations that have static images of the recipe and then debate about whether it's a good recipe or not. Static images of user interfaces, for example, that haven't ever built anything. If you're really cooking something, you taste it along the way and you adjust as necessary and you thicken it

• 46:42Speaker 02

  or reduce it or you add more water or make these adjustments in response to what's happening. But if you feel like you can't proceed until there's a high degree of certainty, both in yourself and critically in others, then you use up all of the time that was available on sitting in conference rooms, looking at photos of recipes and then asking people if they think it's okay. Because if enough people say they think it's a good idea, then if it doesn't work, there's a diffusion of responsibility. My job, if I don't think that's what should happen, my job is to figure out what incentives to put in place, what to communicate, what techniques, what kind of training you need, how I need to articulate the goals so that that doesn't happen. But the self deception is the fault is external to me.

• 47:25Speaker 02

  An error that these people are making and these people are causing all the problems. When you're the CEO, you're the CEO.

• 47:31Patrick O'Shaughnessy?

  Does it follow then that the highest calling of a leader would be to create the conditions for others to experience or achieve mastery in what they do? What do you think about that concept of mastery and its importance in business?

• 47:47Speaker 02

  People like exercising their talent and improving and learning. I try to take a lot of inspiration on the software product development side from the way video games work, because you think about, first, you can move, and then you can move and jump, and then you can move and jump and shoot. Each level kind of unfolds, introducing a new dynamic for you to master until, basically, the game ends, because the game is essentially one very long tutorial, and once you figure it out how to play the game, it's over. I think that's a good approach to making any kind of software, but the satisfaction that people get from that learning is something that feels universal, and it cuts across different forms of creativity, and different hobbies, and different everything.

• 48:32Speaker 02

  And there's nothing more frustrating than having that thwarted. And people end up very unhappy at organizations where nothing can get done. That's probably, this is kind of a separate topic, but I was having a long discussion with a CIO of one of the big banks, and we were talking about how to measure software developer productivity, and she had been around for a long time, too, and all of the, there's kind of all these famous failures, like count the number of lines of code that people write, and then people just change their coding style, or count the number of bugs that are fixed, and people, before they make any change, will file a bug and then close it afterwards, introducing all this overhead, which obviously slows things down. Maybe the best way to measure productivity is employee engagement or happiness, because

• 49:17Speaker 02

  people can be unhappy for different reasons, but they can't be happy without being effective. It's a necessary condition. So if the engagement scores are low, if your software engineers are unhappy, then they're definitely not effective.

• 49:32Patrick O'Shaughnessy?

  For context for these conversations, I write down like these weird little notes to myself, and one of the ones that I wrote for this one is hippies and APIs. I think you've talked before about how the hippie mentality may shed some light on this software concept of APIs and how powerful they are. Can you explore why those two things might belong in the same sentence?

• 49:50Speaker 02

  The idea of open source software, open protocols, and APIs that are available to everyone, I think, is one that's ingrained in the approaches and kind of the antecedents of where we ended up today. Often, there's a humanitarian approach that has real value for the people who engage in it. Basically, every open source software company has followed that same pattern of make this freely available when there's still an opportunity to profit off it rather than keep it a black box and proprietary. But I will say that in the early days of Flickr, one of the things that made it successful was we had APIs for everything. I mean, you could just do anything you wanted, and that excited people and they experimented. And

• 50:32Speaker 02

  a handful of apps that people created out of the APIs, I think, had genuine popularity and were useful, but mostly just created a community of enthusiasts. In the case of Slack, it created 2,000 apps in the app directory and something like 900,000 custom integrations that are actively used by customers. So these are integrations that customers created themselves. That's like a mind-boggling number. Had we not done that, had we kept it a lockbox, I think there would have been a lot less utility.

• 51:02Patrick O'Shaughnessy?

  So it's almost like if you adopt this open mindset to give tools away, it's a long-term advantage, even if it comes at maybe a perceived short-term cost. Like, if you just kept everything proprietary, maybe you capture more value in the near term. But it sounds like your experience is in the long term, kind of a hippie idea, that open source or just letting people have access is a net benefit to companies, even if it might not seem like that in the short term. Does that kind of sum up the idea?

• 51:28Speaker 02

  Yeah, and I think people talk about abundance mindset or growth mindset. And if there's one part of this interview that is most interesting or relevant to people who are more on the investor side, it might be this. Software is still far from zero-sum as an industry. There might be a handful of software categories that are more or less saturated. In other words, every large organization has chosen an email platform. So to get your new platform adopted, you're going to have to take a customer from someone else. But the whole thing is growing at a mind-boggling rate. And I haven't done it, but someone could easily look back over the software companies that have gone public in the last 24 or 30 months and sum up their market cap or sum up their revenue today. And all of that is stuff that didn't exist five years or seven years prior.

• 52:12Speaker 02

  You think about the number of software vendors that any given company has and Slack, a company of twenty seven or twenty eight hundred people, has buy software from four hundred and fifty different vendors. Netsco claims the average for large enterprises is a thousand different cloud services in use. That number has just gone up monotonically for decades and will continue to go up decades. Where you look at the number of dollars per employee per year that any company spends on software and that just goes up. The number of minutes per day that people spend using software goes up inexorably as well. And all of these things are going up. So I think you're much better off in the world of software to have that abundance mindset or that growth mindset and not think about zero sum dynamics.

• 52:55Speaker 02

  Because we're really, I think, I picture today, maybe not quite this bad, but like things that are going to disappear or ways of working are going to disappear because of what computers did right before they were disrupted in that way. So I'm old enough that I had a college job that was a file clerk. That was like correspondence comes into the office and you make a photocopy of it and then put it in a file. And that's like the database of correspondence of the company and same thing with stuff that was outgoing. And I don't, maybe there's people who still do that at the margin, but there's definitely not very many of those people left. But the weirder ones for me to imagine are like, if you went to a bank in nineteen thirty two, how did they know how much money you have?

• 53:37Speaker 02

  Like, is there an index card that says Patrick Pashanov and they just like flip through the O's until they find it and then they pull it out and says you have three hundred dollars? I mean, genuinely, I have no idea. Computing completely revolutionized the stuff that was easy. In other words, like doing arithmetic perfectly at scale and remembering things perfectly forever. And, you know, a bunch of other stuff that computers do much better than people. But we're getting into finer and finer territory and automating all the things that are automatable, which, you know, almost definitely more tractable problems for software to approach. But that means that the work that's left over for humans to do is going to be more demanding of their intelligence and creativity, because that's the hardest stuff to automate.

• 54:18Speaker 02

  This comes from that openness, APIs and taking a generous approach. And I think that has worked really well. For many, many companies. And I think it gives you a better and more accurate picture of the future that you're working towards.

• 54:34Patrick O'Shaughnessy?

  Can you talk about this idea of the backhoe and the shovel? And whether or not, you just talked about how much leverage software technology is giving us, whether or not you think technology is fundamentally amoral. And I know that's kind of a weird philosophy question, but you're a philosophy guy like me, so I figure, why not? What do you think about maybe the downsides or the amorality of technology?

• 54:54Speaker 02

  I mean, I think it is largely amoral. And there's a bunch of famous examples of that. But the research that went towards both fertilizers that allowed the green revolution and Nazi death chambers, stuff like that, not to be too grim. But the shovel and the backhoe is something that I use to explain the value of slack, but also some of the challenges that come along with it. And I apologize, it becomes a grim analogy. We want to do for organizations what backhoes do for people whose job it is to dig ditches, because digging a ditch with a backhoe is a lot easier than digging it with a shovel, a hundred times easier or something like that. And you can dig a lot more ditches. You also can accidentally do damage with a backhoe if not wielded properly that you couldn't possibly accidentally do with a shovel.

• 55:39Speaker 02

  You could kill someone with a backhoe, but accidentally. But you can't accidentally kill someone with a shovel. You have to really be determined to do it. And I think a lot of technology ends up in that way, where it's simultaneously much more powerful, but introduces new dangers or new risks, or at least a greater requirement for mastery or understanding in how you wield that technology so that you have the positive impacts without the negative ones. And if you look back at mid 19th century, the Thames and the Charles River in Boston would catch on fire. Clearly, and eventually we learned how to have the benefits of the industrial revolution without as many people dying of black lung and dangerous factory conditions and all that. I don't think workplace software.

• 56:25Speaker 02

  Has the same danger profile as like the first coal-fired plants and stuff like that. But I do think there's a similar phenomenon where it takes us a while to figure out how to incorporate this new power into our existing habits and practices in a way that gives us the benefit without some of the side effects.

• 56:43Patrick O'Shaughnessy?

  What do you think are the most interesting, open questions about the future?

• 56:48Speaker 02

  So one of the big ones, I think, is how much more effective we're able to get in materials and energy. I listened to the podcast with Mark Andreessen. I don't know if it's new or if it-

• 56:59Patrick O'Shaughnessy?

  Yeah, like a police go ahead.

• 57:00Speaker 02

  The first half hour was like just, it was a remarkable summary, both of the power of software, but also the kind of the long arc of technology. At an intuitive level, I feel like everything will work out. But looking at the world in a more practical way, with my often naive understanding, it can be hard to figure how it's going to work out. Okay, given climate change and the impact of bringing the other several billion people up to the standard of life that is enjoyed by the people in the richest countries. That's a big one. The maybe less existential, but really interesting to me is, do we ever get to the 15-hour work week? Does that ever happen? The jobs that

• 57:44Speaker 02

  disappear, as Mark points out, are almost, well, they're usually the worst jobs, either the most dangerous or the most mind-numbing and repetitive. And humans are amazing at inventing new needs because there's just a lot more life coaches and massage therapists and aromatherapy people than there were 100 years ago. But John Adams has this quote, I'm going to brutally mumble the paraphrasing, but it's something like, "I must study politics and war so that my sons may study commerce and navigation," very important, "net naval architecture, so that their sons may study porcelain and tapestry and painting." So the idea is, this brutal period we're going through right now is just laying the groundwork

• 58:27Speaker 02

  for productive capacity and economic interactions and growth and prosperity. But the reason that you do that is so that people can express themselves creatively, which is certainly something that I relate to. I mean, there's no right or wrong to this, but my feeling is that the purpose of life, to some degree, is that creative expression, whether that comes out in- Sculpture, or management, or technical innovation, or whatever it is, do we ever get there? Or do we invent new work challenges that reduce our capacity for creative activity?

• 59:05Patrick O'Shaughnessy?

  What is your creative outlet? What is the creative output that gets your juices flowing the most that you can do repetitively?

• 59:13Speaker 02

  In the work context, it's writing, and I don't think I take enough time to leverage that. Because if I really work hard and think about something carefully and get to that degree of clarity, the impact of something I've written has been certainly disproportionate to the the impact of the time I spend in meetings, hour by hour basis. Outside of that, though, I recently started playing jazz guitar again. Basically, when I was in high school, I played in the jazz band, mostly bass and also a little trumpet. And it's really, I'm less good than I would like to be. So there's like a whole element of mastery, but it's also just like a whole fascinating theoretical component that interacts with the creative component in a really interesting way.

• 59:57Patrick O'Shaughnessy?

  You wrote this fabulous resignation memo, leaving Yahoo, I think of it as the tin resignation memo. What was so interesting about it to me was just like an obvious mental clarity that you had reached about the state of things for you personally in your career. Can you just describe why you wrote, and we'll link to it so people can read it, this highly unusual and entertaining and unique memo?

• 1:00:19Speaker 02

  The proximate cause of that is pretty prosaic. I told my then boss that I'm quitting, and he said, okay, that's fine. Can you please send it to me in an email so I can forward it to HR? And people have parsed it for all of this meaning, because Yahoo was in a really weird state at that point in 2008. When I started there, it had significantly more revenue than Google. By the time I left, Google was, I don't know, probably 5X or 8X Yahoo's revenue. But I was just ripping off the style of Thomas Muzwebel, the fictional publisher of The Onion, in the paper versions of The Onion. I don't know, maybe they do it online too, but he had a column that was written from this like crotchety 19th century titan of business perspective. And so that's how that came to be.

• 1:01:04Patrick O'Shaughnessy?

  If we go back to where we started this concept of we don't sell saddles here. And obviously, a lot of people out there are either investors looking into businesses that they want to be exceptional, or people that want to start businesses. What closing advice would you have for that batch of people through the context of what you've learned building Slack? What is deserving of someone's care and attention and creativity and potential mastery?

• 1:01:28Speaker 02

  Anything that is worth doing. I mean, anything that's worth doing is worth doing well. Gosh, I mean, I'm trying to think of like, which part of this is more important? Because it's called we don't sell saddles here. And there's this whole history that I wasn't aware of when I wrote it. But I use the examples of Lululemon selling athletic wear and trying to juice the market for yoga by hosting free yoga classes to kind of grow that. Or I can't remember enough. I mentioned Harley Davidson are up and they sell motorcycles, but they also sell like independence and freedom and stuff like that. But there's another part to this as well, which is just the degree of craft that you put in because of the owner's illusion. It is far too easy to assume that people care or understand something in a way that's

• 1:02:12Speaker 02

  similar to the way that you care or understand the product that you're making when they are coming at it from a totally different angle. Remember, I've got six months ago or something like that. I won't say what brand of television interrupted the show to say that in an upcoming software update, some app that I'd never heard of for news would be unavailable. There's definitely a disconnect between the degree of importance that had in the minds of the people who caused that notification to appear and the end users like me. That's why the degree of consideration really matters, the degree of effort, the attempt to get into the shoes of the people who are going to be using the product and making it good. And I worry that I'm not conveying that well because it just sounds like do a good job and everyone who presumably everyone wants to do a good job.

• 1:02:57Speaker 02

  But there is this concept of the steep part of the utility curve on the one hand, or the point at which something is easier enough or more convenient enough that people won't go back. I think that any product, any service that ends up massively successful, found that, found something that it makes so much easier than the alternatives that everyone changes their behavior in a pretty profound way. And that would even include. Older generations of enterprise software that people love to hate and complain about, that was easier enough than the alternatives of the paper files or trying to build the software yourself or whatever, that people adopted it en masse and continue to use it today.

• 1:03:40Patrick O'Shaughnessy?

  I think that's such a cool closing point. Your idea of innovation being the sum of behavior change, like the aspiration to make something so good that people change how they live their lives is cool closing motivation. I think you might know my closing question for everybody, which is to ask, what is the kindest thing that anyone's ever done for you?

• 1:03:55Speaker 02

  You know what's funny, Patrick, is I don't know how many episodes I've listened to, but many. I always thought, if I was ever on that podcast, I'd have to think of a really good answer for that question. And I actually completely forgot if we got to this point. It's hard to know the kindest, but I think something that came from a place of great kindness and had a really positive impact on my life was actually one of my undergraduate professors. I still wanted to go into grad school for a long season. Didn't work exactly, but telling me, you don't want to do this. If you love it, you can subscribe to the journals, you can go to the conferences and you're good at it. But I wish that I wasn't a professor and I started in the 60s and have graduated hundreds or even thousands of PhDs and they're all looking for jobs.

• 1:04:38Speaker 02

  In 98, I made the choice to give up on the PhD program and go work on the internet, which was like new and exciting and paid twice as much as any philosophy related job you could get. But I think if he hadn't done that, I very likely just would have ended up in academic, which is not a horrible life, but I'm very grateful for the life that I ended up with.

• 1:05:00Patrick O'Shaughnessy?

  If you had to assign one philosophy book for everyone in the world to read, what would it be?

• 1:05:05Speaker 02

  It depends how much support they had, because I think like Spinoza's Tractatus would be a great thing for everyone to read. But it's

• 1:05:12Patrick O'Shaughnessy?

  Advanced material.

• 1:05:13Speaker 02

  Yeah. I bet it would actually just be a philosophy 101 primer, like to give an overview of it. People will say, and I definitely believe that the most profound question is why is there something instead of nothing? By profound, it might just be the most unanswerable. But the reason, maybe this ties it all up, that we don't put the effort into helping people become more effective communicators that they know that they should is because you can't go through life questioning everything unless you are a professional philosopher, because it's just exhausting and paralyzing. And yet, the effort that humans have put into digging deep into fundamental assumptions.

• 1:05:52Speaker 02

  Has created most of the progress, the most political and economic theories that have led us to this state in the world, for better or worse, I guess, but all good, all advancement, all travel down the upward arc comes from questioning things that we have assumed answers to and don't question enough.

• 1:06:13Patrick O'Shaughnessy?

  Well, Stuart, I'm so appreciative of your time and for your writing, and I hope you continue to do more of it as someone that was directly affected by that essay and some of the other things you put out there in particular. It's a pleasure to get to connect with you in this format today. Thank you so much.

• 1:06:26Speaker 02

  Yeah, thank you.

• 1:06:28Patrick O'Shaughnessy?

  This episode of Founder's Field Guide was brought to you by Dell Technologies. When you call a Dell Technologies advisor, they're focused on you, ready to give advice on everything from laptops to cloud to keep your small business ready for what's next. Call an advisor today at 877-ASK-DL and do more with modern devices and Windows 10 Pro. If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning. You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.