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Mental models for building products people love ft. Stewart Butterfield

Mental models for building products people love ft. Stewart Butterfield

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Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams. *We discuss:* 1. Hyper-realistic work-like activities 2. The owner’s delusion 3. Utility curves 4. “Don’t make me think” 5. “We don’t sell saddles here” 6. Tilting your umbrella 7. When to pivot *Brought to you by:* WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Metronome—Monetization infrastructure for modern software companies: https://metronome.com/ Lovable—Build apps by simply chatting with AI: https://lovable.dev/ *Transcript:* https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation *Where to find Stewart Butterfield:* • X: https://x.com/stewart • LinkedIn: https://www.linkedin.com/in/butterfield *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Stewart Butterfield (04:58) Stewart’s current life and reflections (06:44) Understanding utility curves (10:13) The concept of divine discontent (15:11) The importance of taste in product design (19:03) Tilting your umbrella (28:32) Balancing friction and comprehension (45:07) The value of constant dissatisfaction (47:06) Embracing continuous improvement (50:03) The complexity of making things work (54:27) Parkinson’s law and organizational growth (01:03:17) Hyper-realistic work-like activities (01:13:23) Advice on when to pivot (01:18:36) The importance of generosity in leadership (01:26:34) The owner’s delusion *Referenced:* • Slack: https://slack.com • Flickr: https://www.flickr.com • Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal • Blok: https://blok.so • Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b • Magic Link: https://en.wikipedia.org/wiki/Magic_Link • Ticketmaster: https://www.ticketmaster.com • John Collison on X: https://x.com/collision • Patrick Collison on X: https://x.com/patrickc • Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai • Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo • Six Sigma: https://www.6sigma.us • What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system • John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976 • Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law • We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game) • IRC: https://en.wikipedia.org/wiki/IRC • This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke • The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva • Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma • Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little • Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg • Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224 *Recommended books:* • Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021 • Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X • Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996 _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Segments Timeline

1
0:00 - 0:24
0:23 duration99 words

The Humility of Improvement

Stewart Butterfield reflects on the early days of Slack, expressing his belief that a product should always strive for improvement. He emphasizes the importance of recognizing opportunities for enhancement and the embarrassment of presenting a subpar product to the public. This mindset is crucial for anyone involved in product design and development.

"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 ju..."

2
0:24 - 0:51
0:27 duration114 words

Value Creation Over Effort

Butterfield shares a mantra from Slack's company culture: the true measure of success is the value created for customers. He discusses the difference between demonstrating value and actually delivering it, highlighting that effort alone does not equate to success in product development.

"Slack was famous for being one of the early consumerized B2B SAS products >> at more than one company all hands. I made everyone in the company [music] repeat this as a chant. In the long run, the mea..."

3
0:51 - 1:13
0:21 duration105 words

Rethinking Friction in User Experience

Stewart challenges the common assumption that reducing friction in user experience is always beneficial. He argues that comprehension is often the real challenge, and that creating a simple, intuitive experience should be prioritized over merely minimizing clicks or taps.

"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..."

4
1:13 - 1:36
0:22 duration94 words

The Rationality of Pivoting

Butterfield discusses the importance of rational decision-making when considering a pivot in business. He emphasizes the need to create distance from emotional attachments to make informed choices about the future direction of a product or company.

"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..."

5
1:36 - 2:15
0:39 duration141 words

Unlocking Product Wisdom

In this introduction, Stewart Butterfield shares insights from his extensive experience in product development, touching on concepts like utility curves, the owner's delusion, and hyper-realistic work-like activities. He sets the stage for a deeper exploration of product and leadership wisdom.

"Today my guest is Stuart Butterfield, a founder and product legend who rarely does podcasts. Stuart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tec..."

6
2:15 - 2:57
0:41 duration137 words

The Journey of Continuous Improvement

Butterfield reflects on his journey after leaving Slack, focusing on family, philanthropy, and creative projects. He discusses the privilege of spending time with his young daughter and hints at potential future endeavors in software that could help people use technology more mindfully.

"Noah Weiss, Chris Cordal, Ally Rail, and Johnny Rogers for suggesting [music] topics and questions for this conversation. This is a really special one and I really hope to have Stuart back to delve ev..."

7
2:57 - 3:40
0:43 duration131 words

The Power of Utility Curves

Stewart introduces the concept of utility curves, explaining how they represent the relationship between effort and value in product development. He illustrates this with examples, emphasizing the importance of understanding where a product stands on this curve to make informed decisions about feature development.

"Here's a puzzle for you. What do OpenAI, Cursor Perplexity Verscell Platt and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, Work OS. If you'..."

8
3:40 - 4:11
0:30 duration100 words

Divine Discontent and Continuous Standards

Butterfield discusses the idea of 'divine discontent,' a term popularized by Jeff Bezos, which refers to the ever-increasing standards users have for software. He explains how this concept drives the need for continuous improvement in product features and user experiences.

"get [music] 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, comp..."

9
4:11 - 4:44
0:33 duration95 words

The Importance of Taste in Product Design

Stewart shares his perspective on taste in product design, arguing that it can be developed and refined over time. He emphasizes that having good taste can create a competitive advantage, as many products lack the attention to detail that delights users.

"Engineers are chasing billing bugs. Finance can't close the books. With Metronome, you hand it all off to the realtime billing infrastructure that just works. Reliable, flexible, and built to grow wit..."

10
4:44 - 5:02
0:18 duration51 words

Crafting Delightful User Experiences

In this segment, Butterfield recounts a personal experience that illustrates the importance of user experience and delight in product design. He emphasizes that creating emotional connections with users can lead to loyalty and advocacy for a product.

"companies in the world like OpenAI and Anthropic run their billing on Metronome. Visit metronome.com to learn more. That's metronome.com. >> Stuart, thank you so much for being here and welcome to the..."

11
14:44 - 15:39
0:54 duration176 words

The Importance of Craft in Product Design

Stewart Butterfield discusses the essential elements of product design, emphasizing the need for continuous improvement in areas often overlooked, such as account creation and sign-up processes. He highlights how Slack's focus on delight and user experience set it apart in the B2B SaaS landscape, showcasing the value of craftsmanship in creating products that resonate with users.

"appreciate or come back to those things often enough. And then there's this category of like really essential parts of the app again like account creation, sign up, forgot password, you know, things l..."

12
15:39 - 16:34
0:55 duration195 words

Developing Taste in Product Design

In this segment, Stewart shares his unique perspective on taste in product design, likening it to culinary skills that can be developed through experience. He argues that while some individuals may have a natural advantage, anyone can improve their taste and create a competitive edge by focusing on quality and detail in their products.

"uh taste. I heard at a talk you gave of a really unique that you gave a talk on taste and you have a really unique perspective on just what taste is what product taste looks like. Can you share that? ..."

13
16:34 - 19:26
2:52 duration545 words

Tilting Your Umbrella: A Metaphor for Empathy

Stewart uses the metaphor of 'tilting your umbrella' to illustrate the importance of empathy in product design. He recounts an experience in Vancouver where he and a colleague observed people's reluctance to adjust their umbrellas for others. This behavior reflects a lack of consideration that can be turned into an opportunity for product creators to enhance user experience and foster emotional connections.

"advantage for yourself, for your product, for your company um by leaning into it because most people don't have good taste and don't invest. And so you're probably familiar with the again Jeff Bezos l..."

14
19:26 - 20:39
1:12 duration235 words

Creating Emotional Connections Through Convenience

Stewart explains how Slack's success was driven by small conveniences that fostered emotional connections among users. He highlights how the product's design led to organic growth as users transitioned between companies, advocating for Slack based on their positive experiences, which were rooted in the product's thoughtful design.

"advantage and I think that there's many reasons why stock was successful at the moment it was successful and and I think we had a bunch of really wonderful tailwinds and and all of that stuff but it w..."

15
20:39 - 21:47
1:08 duration236 words

Innovating with the Magic Link

In this segment, Stewart discusses the innovative decision to implement a 'magic link' for account creation in Slack's mobile app. By allowing users to authenticate via a link sent to their email, Slack improved the user experience significantly, showcasing the importance of thoughtful design choices in enhancing usability.

"so someone else came up with this idea and I'm I'm trying to remember who it was. um by let's see maybe Andre Torres, maybe Ben Brown, something like that. We was like, "Hey, why did we ask people for..."

16
21:47 - 23:14
1:26 duration306 words

Managing Notifications for User Satisfaction

Stewart shares insights on how Slack approached user notifications, initially opting for a default setting that sent notifications for every message. He explains the rationale behind this decision and how they later refined the notification system to enhance user satisfaction, demonstrating the balance between user expectations and product functionality.

"standard. There is another one which we you know we're really puzzled about in the very early days where people have a long history of using messaging apps from like AOL instant messenger to SMS to um..."

17
23:14 - 24:56
1:42 duration367 words

The Shouty Rooster: Shaping Communication Culture

Stewart introduces the 'shouty rooster' feature, designed to curb the overuse of the 'at everyone' function in Slack. This playful approach not only reduced notification fatigue but also educated users on the impact of their communication choices, illustrating how product design can influence user behavior positively.

"that investment to get people over the hub. A much more uh well, here's I'll give one one more simple one and then one kind of more complex one. people would just like the I can't remember if it's cal..."

18
24:56 - 28:19
3:23 duration635 words

Implementing Do Not Disturb with User Control

In this segment, Stewart discusses the careful rollout of the 'Do Not Disturb' feature in Slack. He explains the complexities involved in balancing user preferences and organizational policies, emphasizing the importance of setting defaults while allowing customization to ensure a smooth user experience.

"difficult for everyone and so try to shape the communication culture inside the organization to take best advantage on it. >> That feature still exists. I see that rooster all it or no I don't see it ..."

19
28:19 - 29:00
0:40 duration150 words

The Role of Friction in Product Experience

Stewart challenges the common notion that friction in user experience is always negative. He argues that in certain contexts, such as when users have low intent, friction can serve as a valuable tool to enhance comprehension and guide users through the product, ultimately leading to better engagement.

"and conflict and and stuff like that. >> Those are amazing examples. I very much appreciate that do not disturb feature when you guys launched that. I still remember that coming out. I'm sure a lot of..."

20
29:00 - 32:50
3:50 duration722 words

Creating Comprehension Over Removing Friction

Stewart elaborates on the importance of comprehension in product design, particularly for new users. He contrasts scenarios where friction is detrimental with those where it can aid understanding, emphasizing that creating a clear path for users is essential for successful product adoption.

"always be trying to remove friction. And uh in in some cases that's true. You know, we would talk about in Slack like it was hard to market. It was hard to explain what it was if you had never used it..."

21
33:10 - 34:00
0:50 duration171 words

Understanding User Needs

In this segment, Stewart discusses the necessity of understanding user needs and behaviors. He uses examples from various applications to illustrate how users often do not know the full capabilities of a product, which can hinder their experience and satisfaction.

"people recognize that. They're like, I want to get people who come to my web page to the sign up form as quickly as possible. But if they don't know what they're signing up for and they don't know wha..."

22
34:00 - 35:01
1:01 duration215 words

The Challenge of Comprehension in Software

Butterfield elaborates on the challenges users face in comprehending software features. He stresses that if users cannot discover or understand the capabilities of a product, they will not utilize them effectively, leading to a suboptimal experience.

"step because like people if they do ever open the preferences tab and look at all the options rarely have an idea. And if you can't teach them, you know, or or make it possible for them to discover wh..."

23
35:01 - 36:39
1:37 duration325 words

Don't Make Me Think

Stewart Butterfield introduces the mantra 'Don't make me think' as a guiding principle in product design. He explains how unnecessary cognitive load can lead to frustration and disengagement, emphasizing the need for intuitive design that minimizes user effort.

"that are are more important to display. And I could go on and on and on and on and people just don't recognize that. So, like the I want to see if this still true. I'm just going to open my iPhone. Um..."

24
36:39 - 37:30
0:51 duration184 words

Emotional Impact of User Experience

In this segment, Butterfield discusses the emotional impact of user experience. He highlights how software that requires users to think can make them feel inadequate, particularly among less tech-savvy individuals, and stresses the importance of creating a positive emotional association with products.

"have. Um those examples are just to me all over the place. And the the reason I don't use most software where there was an actual choice point or the reason I don't use most features where there was a..."

25
37:30 - 39:03
1:32 duration296 words

Rethinking Click Reduction

Stewart critiques the focus on reducing clicks in product design, arguing that it often leads to poor user experiences. He advocates for a design philosophy that prioritizes simplicity and ease of understanding over mere click reduction.

"like you know cognitive cost of all these things but also there's an emotional aspect which is if you if your software kind of stops me a second and asks me to make a decision and I don't really under..."

26
39:03 - 40:58
1:54 duration350 words

The Complexity of User Actions

Butterfield discusses the complexity of user actions in applications, using Gmail as an example. He points out how poorly organized menus can confuse users and hinder their ability to complete tasks efficiently, emphasizing the need for thoughtful design.

"thousands and thousands of pages, right? And obviously that's terrible. So why do people think that a little bit of that is good? And you know, here's an example. Like you open a menu, there's 14 thin..."

27
40:58 - 42:47
1:49 duration361 words

Simplicity Over Complexity

In this segment, Stewart advocates for simplicity in user interactions. He shares insights from his experiences with various applications, stressing that making actions simple and intuitive is more beneficial than reducing the number of steps.

"really struck me that like, you know, Patrick could have asked for anything. It could have been any talk. It could have been a partnership. It was like it was so irritating to him um that it worked li..."

28
42:47 - 44:49
2:01 duration445 words

Continuous Improvement Mindset

Stewart Butterfield concludes with the importance of a continuous improvement mindset in product development. He shares his philosophy that no product is ever perfect and emphasizes the need for teams to strive for ongoing enhancements to meet user needs.

"really tried to push people to what is the thing that people or what is the two things or what is a maybe three things that people could want to do here and then put everything behind other. And then ..."

29
45:14 - 47:39
2:24 duration480 words

The Drive for Constant Improvement

Stewart Butterfield emphasizes the importance of perpetual dissatisfaction in product development. He shares a personal anecdote from 2014, reflecting on his feelings about Slack's initial product quality and how that mindset fosters a culture of continuous improvement. He argues that product leaders should always seek opportunities to enhance their offerings, rather than settling for mediocrity.

"other products work with your products. And I think that's core like Patrick is a good example of Stripe. I feel like that's a recurring theme with very successful product leaders, just constantly uns..."

30
47:39 - 49:12
1:32 duration303 words

Embracing Direct Criticism

In this segment, Stewart discusses the value of direct criticism within organizations. He draws parallels to Michael Jordan's approach to learning, highlighting how constructive feedback can motivate teams to strive for excellence. Stewart believes that fostering an environment where criticism is welcomed can lead to significant improvements in product quality and team dynamics.

"company or you shouldn't you know um almost nothing you know again you could reduce it down to a tiny feature is anywhere close to to perfect and if a that's acknowledged freely inside the organizatio..."

31
49:12 - 50:01
0:48 duration164 words

The Complexity of Making Things Work

Stewart reflects on the inherent challenges of getting anything to function properly, drawing from a personal experience about the bureaucratic hurdles involved in simple tasks like installing a stop sign. He critiques the oversimplified narratives often presented in politics and business, emphasizing that the reality is far more complex and requires understanding the multifaceted nature of organizational dynamics.

"Lovable. Not only are they the fastest growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app, but didn't know where to start, L..."

32
50:01 - 51:36
1:35 duration303 words

Parkinson's Law in Organizations

Stewart introduces Parkinson's Law, explaining how work expands to fill the time available for its completion. He discusses its implications in organizational settings, particularly how the number of administrators often grows disproportionately compared to the actual work being done. This insight sheds light on the inefficiencies that can arise in large organizations and the tendency for teams to hire more staff rather than streamline processes.

"This makes me think about a let's call it a rant that you have about how it takes a lot of work to make anything work at all. that just the default state is not working. You just share share what you ..."

33
51:36 - 53:01
1:24 duration243 words

The Illusion of Simplicity

In this segment, Stewart explores the misconception that complex problems have simple solutions. He argues that the complexity of organizational challenges often leads to a search for scapegoats, rather than recognizing the intricate web of factors at play. This discussion highlights the need for a deeper understanding of the multifaceted nature of issues within organizations.

"your jobs or, uh, lazy freeloaders are sucking off the government and causing us all have to pay more taxes or something like that. The reality is like almost nothing works. It's actually another coli..."

34
53:01 - 54:43
1:42 duration301 words

The Cost of Analysis in Product Development

Stewart shares a cautionary tale from Slack's history regarding the introduction of a feature that ultimately proved to be a costly mistake. He emphasizes the importance of evaluating the true value of product changes against the resources required for implementation, warning against the pitfalls of overcomplicating processes without clear benefits.

"biological um it's hard for us to understand the world except by anthropomorphizing it. And so it like if it didn't rain this year, it's because a god is mad and probably because we didn't sacrifice e..."

35
54:43 - 56:22
1:38 duration333 words

Hyper-realistic Work-like Activities

Stewart introduces the concept of hyper-realistic work-like activities, contrasting them with known valuable work. He explains how early-stage startups often focus on tasks that are clearly valuable, but as organizations grow, they can become bogged down in activities that may not yield significant returns. This segment underscores the importance of maintaining clarity on what constitutes valuable work as teams scale.

"little bit subtle. of like um one of the things I found since I don't have a job is there's much less time pressure and and that maximum like uh if you want something done give it to a busy person the..."

36
1:01:21 - 1:02:51
1:29 duration274 words

The Cost of Hyper-Realistic Work

Stewart Butterfield critiques the inefficiencies of hyper-realistic work-like activities in organizations. He explains how extensive analysis and meetings can lead to wasted resources when the potential impact of a feature is minimal. This segment emphasizes the importance of recognizing and eliminating unnecessary work to focus on truly valuable tasks.

"bounds of of certainty that they could have had, but the real thing was, oh my god. So you guys put flags into the product. You AB tested it. You did the instrumentation. You created tables in the in ..."

37
1:02:51 - 1:04:14
1:22 duration268 words

Known Valuable Work

In this segment, Stewart introduces the concept of 'known valuable work' and discusses its significance in startups. He highlights how early-stage companies have clear tasks that are both known and valuable, but as organizations grow, the clarity diminishes, leading to inefficiencies. This insight is crucial for leaders aiming to maintain productivity and focus.

"new versions of the product, to put the instrumentation in, to have it all the API calls, to record every action that people take, to to do all the analytics, to create the dashboard, to put that, you..."

38
1:04:14 - 1:05:38
1:23 duration326 words

The Dangers of Over-Hiring

Stewart discusses the pitfalls of over-hiring in organizations, particularly in product marketing. He explains how an influx of new hires can create a demand for work that exceeds the actual supply of valuable tasks, leading to unproductive meetings and activities. This segment serves as a cautionary tale for leaders about maintaining balance in team growth.

"And so that's like everyone's going to work in the morning. like right on and like I have 10 things to do and every single one of them is like something I know how to do and it's like definitely going..."

39
1:05:38 - 1:07:13
1:35 duration325 words

Recognizing Fake Work

Stewart elaborates on the concept of hyper-realistic work-like activities that mimic real work but lack substance. He emphasizes the need for leaders to identify and eliminate these activities to ensure that teams focus on meaningful contributions. This segment is a call to action for managers to foster clarity and purpose in their teams.

"don't have sufficient supply of product marketing work to do, they're just going to do other stuff. Again, very important. Not because they're stupid, not because they're evil, but because they're lik..."

40
1:07:13 - 1:08:31
1:18 duration252 words

Leadership Responsibility in Work Clarity

In this segment, Stewart stresses the responsibility of leaders to ensure their teams are engaged in known valuable work. He discusses the importance of providing clarity and alignment on priorities to prevent teams from getting lost in unproductive tasks. This insight is vital for effective leadership and team management.

"valuable work to do um and there almost always is but you know it's creating the clarity around that creating the alignment making sure everyone understands that that's what they're supposed to be doi..."

41
1:08:31 - 1:09:36
1:05 duration244 words

The 'We Don't Sell Saddles Here' Memo

Stewart reflects on his famous internal memo, 'We Don't Sell Saddles Here,' which emphasizes the importance of communicating the value of a product beyond its features. He shares the backstory of the memo and its role in aligning the Slack team around a shared vision. This segment highlights the significance of effective communication in product development.

"it might appear. >> Okay. Uh before we run out of time I want to touch on two other topics. One is when people think of Stuart Butterfield I think a lot of people think of we don't sell saddles here. ..."

42
1:09:36 - 1:11:54
2:17 duration462 words

Creating Markets, Not Just Products

Stewart discusses the necessity of not only building great products but also creating markets for them. He emphasizes the importance of articulating the value proposition to potential users and how this aligns with historical marketing strategies. This segment is essential for understanding the broader context of product positioning.

"I did not change a word of what I said inside the company. What I think we were still eight people maybe, you know, at most 10, but I think it was eight people. >> It was before Slack launched even. >..."

43
1:11:54 - 1:13:05
1:11 duration287 words

The Importance of Selling Experiences

In this segment, Stewart explains the concept of selling experiences rather than just products. He uses analogies from various industries to illustrate how effective marketing focuses on the benefits and experiences that products provide. This insight is crucial for anyone involved in product marketing and branding.

"They're really kind of one and the same. The reason I wanted to touch on it is I think still people continue to not listen to this advice and can continue to overinvest in more features, more more pro..."

44
1:13:05 - 1:14:44
1:38 duration315 words

Advice on Pivoting

Stewart shares his insights on when to pivot a business, drawing from his experiences with Glitch and Slack. He emphasizes the importance of exhausting all viable options before making the decision to pivot and the emotional challenges that come with it. This segment provides valuable guidance for entrepreneurs facing tough decisions.

">> Yeah, the nail. Anyway, >> yeah. What is that one? [laughter] There's the Well, there's the one I think about is instead of trying to convince men to build a ship, instill a yearning for the sea. >..."

45
1:14:44 - 1:16:43
1:59 duration382 words

The Emotional Weight of Pivots

In this segment, Stewart discusses the emotional toll of pivoting a business, including the impact on team members and the community built around a product. He highlights the importance of making rational decisions rather than emotional ones when considering a pivot. This insight is vital for leaders navigating the complexities of business changes.

"commercially successful. Um and so decided to um to abandon it. But you know the default advice for anyone in anything is persevere is like you know a kitten hanging off the branch and a poster says h..."

46
1:16:43 - 1:18:07
1:23 duration311 words

Perseverance vs. Rational Decision-Making

Stewart contrasts the common advice of perseverance with the need for rational decision-making in business. He discusses the importance of recognizing when to let go of an idea and the challenges that come with that decision. This segment encourages entrepreneurs to balance passion with practicality.

"It's like it's wrenching. It has a bad impact. You know, like there's when we shut down Glitch, there's a lot of people who loved it and would spend all of their free time and couldn't wait to get hom..."

47
1:18:07 - 1:19:00
0:52 duration196 words

The Power of Generosity in Leadership

Stewart reflects on the theme of generosity in leadership, sharing anecdotes from colleagues about his supportive actions. He emphasizes the importance of generosity in building strong teams and fostering a positive work environment. This segment highlights the human side of leadership and its impact on organizational culture.

"podcast. Uh they went through a hundred investors rejected her before somebody finally decided to invest and she just kept pushing. >> Yeah. But I think that's a slightly different example, right? Bec..."

48
1:19:28 - 1:21:03
1:35 duration356 words

The Prisoner's Dilemma and Cooperation

Stewart introduces the concept of the Prisoner's Dilemma to explain the importance of cooperation in business. He discusses how acts of generosity can lead to mutual benefits and a more ethical approach to leadership. This segment underscores the significance of creating value for customers and employees alike.

"do. Someone else shared that you paid 100% of employees health insurance to give them just fewer things to think about. uh when you went public you did a you basically created the best possible situat..."

49
1:21:03 - 1:22:59
1:56 duration362 words

Creating Value for Customers

In this segment, Stewart emphasizes that the measure of a company's success lies in the value it creates for its customers. He discusses the ethical implications of business decisions and how prioritizing customer satisfaction leads to a better workplace and overall success. This highlights the importance of integrity in business practices.

"the prisoners dilemma. Um the you know acts of generosity to me are a way of demonstrating that I am going to cooperate as we iterate in this game. >> Um and if you do that then people will also coope..."

50
1:22:59 - 1:24:32
1:32 duration310 words

Lessons from Generosity Policies

Stewart shares a cautionary tale about a generous service policy that backfired during a major outage. He reflects on the importance of balancing generosity with practical business considerations, illustrating how policies can impact a company's financial health. This segment provides insights into the complexities of customer service and operational strategy.

"You have to actually make their lives better. Um, and you can put effort into like pointing it out to them and and demonstrating that you have created this value and stuff like that, but there's no su..."

51
1:24:32 - 1:25:17
0:45 duration177 words

Automatic Customer Compensation

Stewart discusses the implementation of automatic compensation for customers during service outages, highlighting the proactive approach taken by his company. This segment illustrates the importance of customer-centric policies and the impact of transparency in building trust with users.

"Um and so uh we we definitely changed the terms of service after that because being a public company is a little bit different but you know in every other respect I think you know there were all reall..."

52
1:25:17 - 1:26:06
0:49 duration197 words

The Owner's Delusion

Stewart introduces the concept of the 'owner's delusion,' explaining how business owners often overlook the needs of their customers. He emphasizes the importance of empathy and understanding user experience in product design. This segment serves as a reminder for entrepreneurs to remain grounded in their customers' perspectives.

">> Yeah. What was that mantra again that you uh had the company chant? I think this is a really nice way to end it. >> In the long run, the measure of our success will be the amount of value we create..."

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1:26:06 - 1:30:05
3:59 duration858 words

Final Thoughts on Leadership and Generosity

In the closing segment, Stewart reflects on his journey and the values that have shaped his leadership style. He reiterates the importance of generosity, empathy, and creating value for customers. This segment encapsulates the key themes of the discussion, leaving listeners with a powerful message about ethical leadership.

"in in a movie, a novel, TV show, whatever, there's only the loser Stewart and the [ __ ] Stewart. It's it's like it's obviously in the collective consciousness a terrible name and I shouldn't have cho..."