Flickr

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 Metronome—Monetization infrastructure for modern software companies Lovable—Build apps by simply chatting with AI — 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. To hear more, visit www.lennysnewsletter.com

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Stewart Butterfield has been at the forefront of two epochal turning points for tech. First, he was the co-founder of the photo sharing site Flickr, that was one of the defining brands of the so-called Web 2.0 and the world of user-generated content. Several years after that, he co-founded Slack, one of the big winners of the software-as-a-service wars, changing how people work and how companies operate. Now we're at another turning point for the tech industry. Layoffs have occurred across the space and AI is putting traditional business models into doubt. On this episode, we speak with Butterfield about his experiences and what he sees coming next for tech. See omnystudio.com/listener for privacy information.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

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

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Stewart Butterfield is the Founder & CEO @ Slack, the leading channel-based messaging platform, used by millions to align their teams, unify their systems and drive their businesses forward. Prior to their direct listing in June 2019, Stewart raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV and a16z to name a few. Prior to founding Slack, Stewart co-founded Flickr, a company he built into one of the largest web services in the world. Due to his many incredible successes, Stewart has been named to the 100 Most Influential People in the World by Time Magazine, and one of the Top 50 Leaders by BusinessWeek. In Today's Episode You Will Learn: 1.) How Stewart made his way into the world of startups and came to found Flickr? What was his founding moment for the Slack journey? 2.) How does Stewart think about and assess his relationship to money? How has it changed over time? What does Stewart believe are the 3 levels of wealth? How does Stewart think about his identity being tied to the company? Is that a challenge? How does he mitigate it? 3.) How does Stewart describe his management style and philosophy today? How has it changed over time? How does Stewart approach reversible vs irreversible decisions? How does Stewart structure post-mortems? Why does Stewart believe effective entrepreneurship is like parkour? 4.) How does Stewart think about and advise on the debate between direct listing, IPO and SPAC? What has been better/worse and different since making the transition to being a public company? What have been some of the biggest surprises? 5.) Why does Stewart believe that for most companies, comprehension is the reason for the lack of adoption and customer acquisition? How does he look to solve that with Slack? What have been their biggest mistakes on messaging and branding? Item's Mentioned In Today's Episode Stewart's Favourite Book: Leadership and Self-Deception: Getting Out of the Box, Crucial Conversations Tools for Talking When Stakes Are High, The Courage To Be Disliked As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Internet pioneer Caterina Fake knows: Online communities are built one human connection at a time. As the founder, you need to establish guidelines and norms from Day One – because the tone you set is the tone you’re going to keep, even as you go viral. Read a transcript of this episode at https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter at https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Caterina Fake

Co-Founder

FlickrYes VC

These are unique times. In some ways, we can use our playbooks, make adjustments, and in other ways, things are very different. What isn't likely to be very different is that recurring revenue … recurs. This is the bedrock of SaaS. Hear how Slack CEO, Stewart Butterfield, is adapting to change and his advice on how to take care of your team and customers. This podcast is an excerpt from Stewart's session at SaaStr Summit. You can see the full video here: https://youtu.be/5kG3WfUyBJc

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Verge editor-in-chief Nilay Patel talks to Slack CEO Stewart Butterfield about remote working, competition with Microsoft, and the way technology changes how we communicate. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Slack's co-founder Stewart Butterfield wonders what the future of work will look like for his 12 million customers. Springfree Trampoline's co-founder Steve Holmes says the company has seen a 300 percent increase in demand for its products. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders and entrepreneurs about how they're navigating these turbulent times.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Steve Holmes

Founder

Springfree Trampoline

Slack CEO Stewart Butterfield talks with Recode's Kara Swisher about how coronavirus changed everything for Slack and its customers, the sudden transition to "work from home" across the country, and how the company is handling a surge in usage at the same time that other plans and resources are being constrained. Butterfield also discusses Slack's recent redesign, how communication inside organizations has evolved over the years, and the state of innovation in Silicon Valley and the US as a whole. Plus: What would he do if he weren't running Slack? Featuring: Stewart Butterfield (@stewart), CEO, Slack Host: Kara Swisher (@karaswisher), Recode co-founder and editor-at-large More to explore: On Reset, Arielle Duhaime-Ross explores why — and how — tech is changing everything. On Recode Media, Peter Kafka interviews business titans, journalists, comedians and podcasters about the collision of tech and media. On Pivot, Kara Swisher and Scott Galloway talk about the big tech news stories of the week, who's winning, who's failing, and what comes next. And on Land of the Giants, Jason Del Rey chronicled the rise of Amazon. Season 2 will focus on Netflix and is coming soon! About Recode by Vox: Recode by Vox helps you understand how tech is changing the world — and changing us. Follow Us: Newsletter: Recode Daily Twitter: @Recode and @voxdotcom Learn more about your ad choices. Visit podcastchoices.com/adchoices

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Our sixth episode from the 2019 How I Built This Summit features Stewart Butterfield, the co-founder of Flickr and Slack. Both companies emerged out of failure. In this live conversation with Guy, Stewart describes how he pivoted from two unsuccessful video games into two multi-million dollar brands. We'll be releasing a few more episodes from the HIBT Summit over the next few weeks, so keep checking your podcast feed.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

In your company’s darkest moment, remember: You CAN pivot from failure to success. But only if you slash and burn everything that isn’t working. Slack’s co-founder and CEO, Stewart Butterfield, has twice navigated this kind of Big Pivot. He launched two different game companies, which both (surprise!) turned into game-changing communications platforms: Flickr and Slack. Hear the thinking behind making a hard left turn —and bringing your team along with you. Read a transcript of this interview at: https://mastersofscale.com/stewart-butterfield-the-big-pivot/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

with Marc Andreessen (@pmarca), Ben Horowitz (@bhorowitz), and Stewart Butterfield (@stewart) A lot in technology -- and venture -- happens in decades. New cycles of technology come and go, including some secular shifts; a new generation of founders matures; and so much more changes. So when Andreessen Horowitz (dubbed with the numeronym "a16z") was founded a decade ago as of this month, the tech landscape looked very different between then and now: Not only had the global economy just seen a recession, but trends like mobile and cloud and even social were just taking off. Now, 10 years later, what's changed -- not just in tech, but in profiles of entrepreneurs? And what's changed in the firm itself, given that Marc and Ben -- the Andreessen and the Horowitz -- were yet again entrepreneurs in founding the firm too? As another repeat entrepreneur from then to now, guest host Stewart Butterfield, CEO of Slack, interviews the a16z co-founders in this special episode of the a16z Podcast to commemorate our 10th anniversary. The views expressed here are those of the individual AH Capital Management, L.L.C. (“a16z”) personnel quoted and are not the views of a16z or its affiliates. Certain information contained in here has been obtained from third-party sources, including from portfolio companies of funds managed by a16z. While taken from sources believed to be reliable, a16z has not independently verified such information and makes no representations about the enduring accuracy of the information or its appropriateness for a given situation. This content is provided for informational purposes only, and should not be relied upon as legal, business, investment, or tax advice. You should consult your own advisers as to those matters. References to any securities or digital assets are for illustrative purposes only, and do not constitute an investment recommendation or offer to provide investment advisory services. Furthermore, this content is not directed at nor intended for use by any investors or prospective investors, and may not under any circumstances be relied upon when making a decision to invest in any fund managed by a16z. (An offering to invest in an a16z fund will be made only by the private placement memorandum, subscription agreement, and other relevant documentation of any such fund and should be read in their entirety.) Any investments or portfolio companies mentioned, referred to, or described are not representative of all investments in vehicles managed by a16z, and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. A list of investments made by funds managed by Andreessen Horowitz (excluding investments for which the issuer has not provided permission for a16z to disclose publicly as well as unannounced investments in publicly traded digital assets) is available at https://a16z.com/investments/. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see https://a16z.com/disclosures for additional important information. Stay Updated: Find a16z on YouTube: YouTube Find a16z on X Find a16z on LinkedIn Listen to the a16z Show on Spotify Listen to the a16z Show on Apple Podcasts Follow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

"I really am a big believer in people's creativity flourishing when they come at things from a different direction and see things in a different way." — Caterina Fake Caterina Fake (@caterina) is a long-time Silicon Valley pioneer. She is the Cofounder of Yes VC, a pre-seed and seed stage fund investing in ideas that elevate our collective humanity. Previously, she worked at Founder Collective as a Founder Partner, served as Chair of Etsy, and was the co-founder of Flickr. At Flickr, Caterina and her team introduced many of the innovations — newsfeeds, hashtags, "followers," "likes" — that have become commonplace online. Caterina went on to found several more startups (Findery, Hunch) and became an active investor, advisor and board member, helping to build companies like Etsy and Kickstarter from their beginnings. (Other investments include Stack Overflow, Cloudera, and Blue Bottle Coffee.) Caterina is an early creator of online communities and a long time advocate of the responsibility of entrepreneurs for the outcomes of their technologies. Caterina sits on the board of Public Goods, the Sundance Institute, and McSweeney's. She was given the Silicon Valley Visionaries award in 2018 and has received honorary doctorates from both the New School and the Rhode Island School of Design (RISD). Caterina is also the host of the new podcast Should This Exist?, which asks the question, "What is technology doing to our humanity?" Should This Exist? can be listened to on Apple Podcasts, at shouldthisexist.com or anywhere podcasts are found. Please enjoy! Click here for the show notes for this episode. This podcast is brought to you by Athletic Greens. I get asked all the time, “If you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. As a listener of The Tim Ferriss Show, you’ll get a free 20-count travel pack (valued at $79) with your first order at athleticgreens.com/tim. This podcast is also brought to you by Uber. Uber makes getting around town easier than ever before, and now Uber is introducing Uber Rewards, a new rewards program that helps keep modern life going. With Uber Rewards, you can earn points on Rides and Uber Eats and unlock rewards such as Uber Cash for your next Uber ride or your next Uber Eats order. You can unlock new benefits at every membership level, such as flexible cancellations with Gold, price protection with Platinum, complimentary surprise upgrades with Diamond, and more. For terms and to learn more about all the ways you can earn Uber Rewards, go to Uber.com/Rewards. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews! For show notes and past guests, please visit tim.blog/podcast. Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Interested in sponsoring the podcast? Please fill out the form at tim.blog/sponsor. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss Facebook: facebook.com/timferriss YouTube: youtube.com/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Caterina Fake

Co-Founder

FlickrYes VC

In the early 2000s, Stewart Butterfield tried to build a weird, massively multiplayer online game, but the venture failed. Instead, he and his co-founders used the technology they developed to create the photo-sharing site Flickr. After Flickr was acquired by Yahoo in 2005, Butterfield went back to the online game idea, only to fail again. But the office messaging platform Slack rose from the ashes of that second failure — a company which, today, is valued at over $5 billion. PLUS, for our postscript "How You Built That," how a peanut butter obsession turned teenager Abby Kircher into a CEO before she was old enough to drive. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Whatever you are when you're small gets amplified when you grow. So if you're starting any kind of online community (social media, ecommerce, crowdfunding), be careful what you cultivate. Caterina Fake has founded or invested in companies with interesting and influential communities — Flickr, Etsy, Kickstarter, Stack Overflow, even Blue Bottle Coffee. Her wise words for every founder: You have a responsibility to shape the community from day one -- because the tone you set is the tone you’re going to keep, even as you go viral. Hear Caterina's own brilliant podcast, Should This Exist? https://shouldthisexist.com/ Read a transcript of this interview at: https://mastersofscale.com/caterina-fake-build-a-more-human-internet/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Caterina Fake

Co-Founder

FlickrYes VC

In your company’s darkest moment, remember: You CAN pivot from failure to success. But only if you slash and burn everything that isn’t working. Slack’s co-founder and CEO, Stewart Butterfield, has twice navigated this kind of Big Pivot. He launched two different game companies, which both (surprise!) turned into game-changing communications platforms: Flickr and Slack. Hear the thinking behind making a hard left turn —and bringing your team along with you. Read a transcript of this interview at: https://mastersofscale.com/stewart-butterfield-the-big-pivot/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Stewart Butterfield

Co-Founder and CEO

SlackFlickr

Kara Swisher interviews Slack CEO Stewart Butterfield, Lauren Goode talks about Apple Music and more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Stewart Butterfield

Co-Founder and CEO

SlackFlickr