Stewart Butterfield
13 statements across 2 episodes · 3 bullish · 2 bearish · 3 people on the record · first statement Nov 16, 2020 by Stewart Butterfield · said 37 times in 25 episodes since 2016 · across every show →
On the record as a speaker too: Stewart Butterfield's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Jason Lemkin (8), Harry Stebbings (6), Noah Weiss (3), Merci Victoria Grace (3), Emilie Choi (3), Sameer Gandhi (1), Mamoon Hamid (1), Maggie Hott (1)
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 →
Everything said about Stewart Butterfield, oldest first
Nov 16, 2020 neutral
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.”
Nov 16, 2020 negative
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…”
Nov 16, 2020 positive
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 …”
Nov 16, 2020 positive
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.”
Nov 16, 2020
Nov 16, 2020
Nov 16, 2020
Nov 16, 2020
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…”
Nov 16, 2020
Nov 16, 2020 neutral
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…”
Nov 16, 2020 positive
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 …”
Nov 16, 2020 negative
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…”
Jun 19, 2025 neutral
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…”