Stewart Butterfield
Co-founder & Former CEO, Slack · 1 appearance on the record.
computed by AI from the episodes · how this works → · full disclaimer →
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Stewart Butterfield is the co-founder and former CEO of Slack. He also co-founded the photo-sharing platform Flickr.
24statements → 8claims → 6claims resolved → 83%fully supported → 3.92/5average certainty → 2.21/5average debate potential → ≈4.0/5argument clarity, estimated → 39said about them ↓
5 supported 0 partly supported 1 contradicted 2 not checkable as stated how the 8 claims stand · each chip opens the sources
2 predictions · 6 assertions · 3 opinions · 11 insights · 2 disclosures · every statement was checked. The predictions and assertions are the 8 claims: statements the public record can support or contradict. 6 are resolved, and 2 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.
The record, in short
What the tape says about how Stewart argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.
Their most notable supported claim
Expressed certainty vs assessment result
weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet
How they sound: speaking style how? →
243 words/min while actually speaking · 4.9 um and uh per 1k words
No argument clarity score for Stewart Butterfield: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews. Their coarse estimate from 24 exchanges on the produced feed is ≈4.0/5, shown at half point precision because the sample is small and produced tape scores higher.
Measured by listening to 6,671 words across 1 episode, but every recording we have of Stewart Butterfield is the aired feed, and an editor cleaned that audio before release. Some of the hesitation was cut before we ever heard it, so read these as floors: the true rates are at least this high. These are measurements of speaking style, not scores. How it's measured →
How the interview went all their pushback → series average →
Across 1 rated episode:
host pushback ▾ 1/10
setup questions received 85%
host pushback: the hardest questions Harry asked, tap to play ▶ 13:30“The question to you is, like, when you think about your leadership style, it's like, did you ever have moments of self-doubt and questioning one's ability that one could run in the…” ▶ 9:06“How do you think about your own patience, and do you get frustrated in terms of speed of market adoption and market timing?” ▶ 31:21“Do you worry about the weight of your word within organizations whereby often leaders say, you know, I say things off the cuff, and suddenly a month later it's in action, and I had…”
Everything Stewart Butterfield said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →
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: 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: The ultra-wealthy pursue more money simply to keep score
“And people who have a lot of money want more money, not because they're going to do something with it. Generally, they're going to give it away, but because it's how you keep score.”
Butterfield: Retired tech executives buy sports teams to retain lost prestige
“It is funny that there's like a class of occupation that is professional football team owner, because it's people who have retired from companies where they had a lot of prestige, and they had a lot of power and wealth, and they're not ready to just be that wh…”
Butterfield: Listing Operational Problems Is an Expression of Optimism
“For me, listing all the challenges or the problems or things that aren't going well is Is an expression of optimism, because I believe that we can do something about them, and for certain personality types, I think it's, it feels like the opposite.”
Butterfield: Entrepreneurship is like parkour because stalling causes severe damage
“Being an entrepreneur can be a lot like doing parkour, and obviously not physically, because I'm, I would not be a good parkour participant. But what I mean is, you have to keep moving. You have to keep the momentum, and any kind of stalling or hesitating can …”
Butterfield: Slack Will Become External Collaboration Fabric in Five Years
“So the Slack from five years from now, I think we'll Continue to iterate and improve on the core user experience and the way that we deliver the service and the excellence in support and all that, but I think it will function much more like the lightweight fab…”
Slack reached $100M ARR in less than two years
“Certainly less than two years to get to a hundred million dollars in ARR.”
Butterfield: Product Adoption Speed Depends on Clear Positioning
“The cleaner and more powerful of an answer we have for that or those questions, the faster it'll get adopted.”
Butterfield: Slack Has Passed 2,500 Employees and a $1B Billing Run Rate
“For the scale that we're at now, it's a little over 2500 employees and a billion dollar run rate for billing, so it's, you know, it's a pretty big company”
Butterfield: Deductive reasoning works for functional domains, not leadership
“Because I think you can, to a certain extent, deductively reason yourself to the right answer when it comes to product or marketing, or other functional areas of the business, I guess, finance and sales. You can't do it for leadership.”
Butterfield: Over half of successful software effort goes to technical debt
“Anyone who has been successful with any kind of software project, either in, like, the software industry, meaning enterprise, or consumer apps, or any kind of technology, knows that at some point, more than half of the effort just goes into paying off old tech…”
100% of Slack's $1M+ enterprise customers use custom integrations
“The million dollar plus customers, a hundred percent of them use custom integrations, and the average is in the hundreds that they use.”
Tiny Speck had $5M–$6M remaining when pivoting to Slack
“We had five or six million dollars left when we decided to shut it down and work on Slack”
Slack prepared public company readiness 3 to 4 years before listing
“We started three years or so before, maybe four years before we went public, for what we called public company readiness. In fact, PCR was like an acronym inside the company to refer to that”
Slack Has 700,000 Actively Used Custom Integrations
“There's 700,000 custom integrations that are actively used on Slack today. So 700,000 integrations that customers have set up.”
The other half of the tape: Stewart Butterfield's own voice is left out of every number here. Other people bring the name up 37 times in 25 episodes on 20VC. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Jason Lemkin 8Harry Stebbings 6Noah Weiss 3Merci Victoria Grace 3Emilie Choi 3Sameer Gandhi 1Mamoon Hamid 1Maggie Hott 1
Statements about Stewart Butterfield, by other people (2)
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…”
Every mention by year
tap a year for its mentions
2026 1 mention in 1 episode
2025 2 mentions in 2 episodes 1 per episode
- 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 2 mentions in 2 episodes 1 per episode
2023 11 mentions in 5 episodes 2 per episode
- Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
- 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
- Ariel Cohen: The Death of Salesforce; How OpenAI is Changing the Travel Industry | 20VC #975 · 20VC with Harry Stebbings
- every mention in 2023, scene by scene →
2022 3 mentions in 2 episodes 2 per episode
2021 6 mentions in 4 episodes 2 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
- 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
- 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
- every mention in 2021, scene by scene →
2020 6 mentions in 3 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
- 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?
- every mention in 2020, scene by scene →
2019 2 mentions in 2 episodes 1 per episode
- 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
- 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 →
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 →
Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Level | Nov 16, 2020 | 31m |