Stewart Butterfield
Co-founder & Former CEO, Slack. On 5 shows, 7 appearances. The Shows tab opens the full record on each.
founderexecutiveinvestor
Stewart Butterfield is the co-founder and former CEO of Slack. He also co-founded the photo-sharing platform Flickr.
5shows
7appearances
119statements
20resolved
14supported
4contradicted
70%fully supported
121said about them ↓ Everything Stewart Butterfield said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Butterfield: Founder-CEOs need less leadership skill than hired professional CEOs
“And founders like me, who remain the CEO, I think have a huge advantage. We don't have to be as good as leaders as like a professional CEO would be because we're the founder, because there's like something of the soul of the company that's tied up with us. So …”
Butterfield: Silicon Valley's obsession with A/B testing causes counterproductive incrementalism
“There's a thing that I think has infected Silicon Valley, the kind of corruption of data-driven decision-making. People just haven't really looked at the kind of history and philosophy of science to see how rigorous you have to be to have kind of the scientifi…”
Butterfield: Microsoft Teams competes primarily with Zoom rather than Slack
“Teams, which is the real alternative in some sense, although I think it's much more of a competitor to Zoom or other voice and video calling services than it is a Slack.”
Butterfield: Microsoft Teams is limited to 5,000 users and 200 channels
“It's limited to 5000 people per instance and critically only 200 channels. And if you want to add a 201st channel, you have to hard delete one of them without the whole history.”
Butterfield: Google Calendar's iOS interface is 'bananas how bad it is'
“This is an app that's used by at least hundreds of millions of people, presumably every single Google employee. It's bananas how bad it is.”
Butterfield: Removing friction is the wrong approach when user comprehension is low
“The remove friction kind of orientation is so deep in people. Again, it really makes a difference in, in those cases where people do have an intent and they do know what they're trying to do. It is a poor approach when the challenge is really comprehension.”
Butterfield: Employees instinctively push to hire direct reports to boost status
“The overwhelming majority of people you hire want to hire more people who report to them. And it's not because they're evil and it's not because they're stupid. In fact, they're smart because everyone knows that the number of people who report to you correlate…”
Butterfield: Department heads will never volunteer to freeze or reduce headcount
“Every budget process No head of engineering, no head of sales, no CFO, no GC, is ever going to come back and say like, oh, I actually think like next year we can just hire fewer people, or we're going to keep it flat, or we're going to like shrink through attr…”
Butterfield: Hiring ahead of valuable work creates performative bureaucracy
“If you hire 17 product marketers, you're going to have 17 product marketers worth of demand for work to do. And if you don't have sufficient supply of product marketing work to do, they're just going to do other stuff.”
Butterfield: A CEO's Job Is Crafting a Story People Believe
“Because the job of a CEO is often just to come up with a story that enough people believe that you can make something happen in the world.”
Butterfield: Best software methodology is solving your own aggravating problems egolessly
“This, by the way, I think is the greatest software development methodology that's impossible to replicate, which is, don't think about what you're doing, have no ego, there's no speculation, there's no, I can imagine a user would want to spend the minimum numb…”
Butterfield: The three levels of wealth are debt, restaurants, and vacations
“So I said in some interview, I don't even remember where now it was, but there's kind of three levels of wealth, and one is I don't have to worry about my debts, and the second one is I don't care what anything costs in a restaurant, because I very clearly rem…”
Butterfield: Channel-based messaging will eventually replace all internal corporate email
“At some point, everyone in the world will be using a channel-based messaging platform for internal communication rather than email.”
Butterfield: Slide decks and static mock-ups are product teams' biggest waste
“The biggest waste of time in product organizations is the preparation of slide decks, of static mock-ups of user interfaces, and then people go to the meeting and they all look at the slides and they give their opinion about whether it'll work or not. And to m…”
Butterfield: Direct listings beat IPOs if companies don't need capital
“Pre-SPAC, the real decision, I think, came down to, do you want to raise more money right now? And if you don't, then a direct listing is better than an IPO.”
Butterfield: SaaS adoption fails due to poor comprehension, not price or friction
“The answer is almost never going to be it's too expensive or is lacking some feature I want. The answer is almost always going to be I have no idea what that does, and so the problem is almost always comprehension, but we treat it as if the problem is friction…”
Butterfield: Chamath Palihapitiya was right 90% of the time on Slack's board
“We didn't have Chamath Palihapitiya on the board for that long, but he was always great in that there would be just one or two things that he thought were more important than anything else, and we should be focusing our time on then, and everything else we wer…”
Butterfield: Crises give executives cover to push through difficult organizational restructurings
“The backdrop of global pandemic change is so enormous that you can kind of sneak in anything you want. And we see I see that talking to other CEOs today, not my customers, just like, There's essentially a group therapy SAS CEO round table. And it's like, oh, t…”
Butterfield: Product comprehension and intent matter far more than removing UX friction
“Let's focus on people's comprehension. Let's focus on whether they want to do this thing or not, and less on the friction. You can make it trivially easy and remove every bit of friction from some process, adding an app to a channel in Slack. Let's say, but if…”
Recurring fundamental doubts about a business or employee are almost certainly correct
“There's a saying, if you're thinking about firing someone, a lot
You should just fire them. Meaning that, like, that intuition, if that keeps coming up, it's almost certainly correct, and you wouldn't be thinking that all the time if there was a real shot at m…”
Butterfield: Software that reduces smartphone usage would be a big winner
“I think these things are kind of destroying the world and what we're good at is making software so you can find some way to make software that helped people use Their phones less often, then that would be a big winner, but I haven't come up with anything good.”
Butterfield: Slack wouldn't have grown without emotional product conveniences
“It wouldn't have grown the way it did without those little conveniences which caused people to form an emotional connection because a lot of our growth came from, you know, startup A uses Slack, and then someone leaves startup A for startup B, and startup B do…”
Butterfield: Designers should reduce cognitive burden instead of click count
“And if we, if people could get over the idea of reducing friction as a number of goal or reducing the number of clicks or taps, do something, and instead focus on how can I make this simple? How, how do I prevent people from having to think in order to use my …”
The other half of the tape: Stewart Butterfield's own voice is left out of every number here. Other people bring the name up 113 times in 57 episodes across the shows. 8 statements on the record name them. every mention, with the transcript →
Who brings them up most Jason Lemkin 22Guy Raz 18Lenny Rachitsky 12Alan Yen 8Kenneth Berger 6Harry Stebbings 6Maggie Hott 5Kevin Egan 5
Statements about Stewart Butterfield, by other people (8)
Lemkin: Slack faced an existential ceiling by refusing to become multi-product
“My view, Stuart is a generational founder, right? Did it multiple times. Did the kind of CEO we'd all love to work for, right? But I think deep down in his heart, he didn't want to do multi-product or they would have been multi-product. Like it had an existent…”
Yehoshua: Stewart Butterfield is Silicon Valley's best product thinker
“I think he is the best product thinker in the valley, or he's not working in product right now. He's taking time off, but he's got this combination of long-term thinking in, in the details.”
Stewart Butterfield's 2014 Slack master plan already included AI
“So in 2014, he wrote a master plan for Slack, which was build a product people love. Build a network that Slack connect, build a platform that makes all of your other SaaS products more valuable, the Slack platform, and then do some magic AI stuff.”
Lemkin: Eric Yuan and Stewart Butterfield learned SaaS from SaaStr
“It's where Eric Wan learned SAST, and Stuart Butterfield learned SAST, and so many, that's why we get so many great speakers, because they were part of SASTR so early on.”
Grace: Video games act as continuous onboarding experiences until they end
“Games are basically onboarding experiences forever until the game is over, because you're always learning something new.”
Fain: Slack created unstructured feedback sessions after Stewart Butterfield rejected designs
“We implemented something at Slack with Stuart because we realized we were coming to him with, like, done designs, and he was like, what the fuck is this? This is completely different than how I had this in my mind. So Allie Rail, early Slack employee, implemen…”
Hoffman: Glitch Raised $17.5M and Employed 45 People Over Four Years
“Four years of development, 45 employees, tens of thousands of players, 17 and a half million dollars raised.”
Every mention by year
tap a year for its mentions
20VC 37
the Official SaaStr Podcast 37
Lenny's Podcast 21
How I Built This 18
2026 2 mentions in 2 episodes 1 per episode
2025 10 mentions in 7 episodes 1 per episode
- How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
- Why I’m Scared to Buy New SaaS Apps Now with SaaStr CEO and Founder Jason Lemkin
- Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
- The new AI growth playbook for 2026 | How Lovable hit $200M ARR in one year
- What’s Working Now: AI’s Real Impact on Sales with SaaStr's CEO and Co-Founder, and SVP & GM
- 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves
- Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
- every mention in 2025, scene by scene →
2024 18 mentions in 4 episodes 5 per episode
- Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua
- Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)
- AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
- Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
- every mention in 2024, scene by scene →
2023 23 mentions in 9 episodes 3 per episode
- Etsy: Rob Kalin
- Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
- The 10 traits of great PMs, AI, and Slack’s approach to product | Noah Weiss (Slack, Google)
- Why You're Unfundable Today: The Cold, Hard Truths About SaaS Part 2 with SaaStr CEO Jason Lemkin
- Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
- Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
- Nikhil Basu Trivedi: Why 99% of AI Investments Will Go Bust | E1057 · 20VC with Harry Stebbings
- SaaStr APAC AMA with Jason Lemkin, SaaStr CEO
- 1 more episode that year, every mention in 2023 →
2022 5 mentions in 4 episodes 1 per episode
- Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
- Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960 · 20VC with Harry Stebbings
- SaaStr CRO Confidential: How to Raise in Late 2022 with Jason Lemkin and Sam Blond of Founders Fund
- VC State of the Market with SaaStr CEO Jason Lemkin and Cowboy Ventures Founder & MP Aileen Lee
- every mention in 2022, scene by scene →
2021 12 mentions in 9 episodes 1 per episode
- 20VC: Coinbase President & COO Emilie Choi on Building Coinbase Ventures into One of the Best Performing Funds with 0 Employees, How Coinbase Thinks Through Internal Resource Allocation and Prioritisation & Why, When and How To Hire Your COO and Head of C
- Ask Me Anything About Customer Success with SaaStr CEO Jason Lemkin and ChurnZero CEO You Mon Tsang
- 20 Sales: When To Hire Your Head of Sales/ First Reps, What To Look for in 10x Sales Candidates, How To Structure The Hiring Process, How To Onboard New Reps Efficiently, How To Set First Quotas and more with Kyle Parrish, Figma's VP Sales
- 20VC: The Crowdstrike Memo: Accel's Sameer Gandhi on Leading Multiple Internal Rounds for Crowdstrike, Telling George Kurtz to Go Shop His Term Sheet, How To Think Through Market Sizing & The Importance of Speed of Execution and Knowing When To Go Slow To
- Live From The HIBT Summit: Adam Grant
- How to Build a Unicorn in 8 Simple Charts with SafeGraph
- The Twists and Turns Along the Way to Building a Unicorn with Salesloft's CEO Kyle Porter
- 20VC: Why "Founder Insight" is Overrated, Why Big and Bold Product Visions Can Be Dangerous & Why Getting To Product Market Fit by Accident Can Lead to Danger with Hubert Palan, Founder & CEO @ ProductBoard
- 1 more episode that year, every mention in 2021 →
2020 12 mentions in 8 episodes 2 per episode
- 20VC: Lightspeed Partner, Merci Victoria Grace on The Future of Collaboration Tools, Bundling vs Unbundling, Synchronous vs Asynchronous & What It Means To Productise The S*** Out of Venture
- 20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset
- How I Built Resilience: Live with Tobias Lütke and Jon Stein
- Kodiak Cakes: Joel Clark
- 20VC: Accel's Dan Levine on The Current State of Seed & Series A, The Rise of Pre-Emptive Rounds, Solo Capitalists and Multi-Stage Funds Entering Seed & Market, People and Product; What To Prioritise?
- How I Built Resilience: Live with Tony Xu and Marcia Kilgore
- Fitbit: James Park
- How I Built Resilience: Live with Simon Sinek
- every mention in 2020, scene by scene →
2019 13 mentions in 8 episodes 2 per episode
- From Freemium to Enterprise with Slack
- Live From The HIBT Summit: Tariq Farid Of Edible Arrangements
- Live From The HIBT Summit: Sara Blakely Of Spanx
- 20VC: Worklife Ventures' Brianne Kimmel on Why More Operators Should Start Their Own Fund, How To Structure Your Round for the Highest Signal Round & What The Multi-Stage Funds Playing At Seed Means For The Rest of The Asset Class
- Dave's Killer Bread: Dave Dahl
- Stacy's Pita Chips: Stacy Madison
- Zappos: Tony Hsieh (2017)
- 20VC: Carta Founder Henry Ward on Why The Best Companies Are Not Product Led But Distribution Led, 3 Requirements Needed For A New Market/Investment To Be Exciting and Why Small Markets Are So Attractive
- every mention in 2019, scene by scene →
2018 14 mentions in 2 episodes 7 per episode
2016 4 mentions in 4 episodes 1 per episode
- 20VC: Why There Is A Revolution In VC, Why Boards Are Inherently Inefficient & Why Data Will Be Central To VC In The Future with Chris Farmer, General Partner @ SignalFire
- 20VC: Index's Ilya Fushman on The Key Lessons From Scaling Dropbox To 400m Users, Is Excessive Amounts Of Capital Driving Valuations Too High In The Valley & Why Venture Is Like Being On A Swim Team Not A Soccer Team
- Immediately's Branko Cerny on The Rise Of Bottoms Up Sales and The Importance of Branding For Enterprise SaaS Companies
- 20VC FF: Hiten Shah on VC Funded vs Bootstrapped Businesses and How He Decides Which Startups To Advise
- every mention in 2016, scene by scene →
One line per show, most statements first. The link opens Stewart's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| HOW I BUILT THISLEDGER | Co-founder & Former CEO, Slack | 3 | 47 | 64% 7/11 | full record on How I Built This → |
| 20VCLEDGER | Co-founder & Former CEO, Slack | 1 | 24 | 83% 5/6 | full record on 20VC → |
| LENNY'S PODCASTLEDGER | Co-founder & Former CEO, Slack | 1 | 22 | — | full record on Lenny's Podcast → |
 MASTERS OF SCALELEDGER | Co-founder & Former CEO, Slack | 1 | 13 | 100% 1/1 | full record on Masters of Scale → |
| SAASTRLEDGER | Co-founder & Former CEO, Slack | 1 | 13 | 50% 1/2 | full record on the Official SaaStr Podcast → |