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why aren't all 141 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Assertion Supported
Hugging Face Valuation Multiple Far Exceeds Slack's $27B Acquisition
“Slack was bought for twenty seven billion, which is rough and tough twice what Hugging Face apparently is going to get bought of. And we fell out of our chairs and it was the high watermark of that era, right? But it was at a billion in ARR. This one's at a hu…”
Jason Lemkin Sep 3, 2026 ▶ 10:21 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Insight
O'Driscoll: AI agents lurking in Slack capture crucial context to automate work
“Capturing that context is really useful because it allows you, it allows an AI to automate that work. And the truth is a lot of that context exists in Slack. So if you're watching people interact on Slack, and if you watch it autonomously for weeks and months …”
Rory O'Driscoll Jul 2, 2026 ▶ 1:14:38 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Opinion
Petersen: Salesforce's Slack acquisition will prove to be great
“Slack is also going to be a great, turn out to be a great acquisition, because like, that's pretty sticky. Nobody wants to replace, build their own Slack.”
Ryan Petersen Jun 20, 2026 ▶ 48:01 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Disclosure
Foody: Mercor building benchmark to test AI cloning of SaaS apps
“We're building out an eval set that measures how effectively agents can build end-to-end SaaS applications, where twenty-twenty-five was the year of how do you get a model to make a PR and a code base, and twenty-twenty-six is the year of how do you get the mo…”
Brendan Foody Jun 1, 2026 ▶ 36:37 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2026
Lemkin: Slack will achieve Notion-like ARPU growth from AI in 2026
“I suspect as the year goes on, we're gonna see the same thing at Slack, because most folks haven't used it, we're on it. The AI version of Slack for certain use cases is so much better. I don't love that they're not just charging another four bucks a month, bu…”
Jason Lemkin Mar 26, 2026 ▶ 58:33 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
Disclosure
Weinberg clears his Slack inbox every 15 minutes across all channels
“One of the ones I have that I think was a good habit in the beginning of the company is now, and now it's starting to get bad, is I zero out Slack, like, every, like, 15 minutes, and so I'm in, like, almost every single Slack channel, and I read every single t…”
Winston Weinberg Jan 19, 2026 ▶ 4:21 Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings
Assertion Supported
The original SoftBank Vision Fund correctly identified the massive AI opportunity
“They were early to figuring out that there would be a huge opportunity in AI. So, you know, they famously were in NVIDIA in, in that fund you know, and they did some really good investments, like Slack, like Garnet.”
David George Dec 15, 2025 ▶ 36:26 a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings
Assertion Partly supported
Lemkin: Slack and Tableau are growing faster than core Salesforce
“All of their, not all of them, but the light, so many of the acquisitions, Slack, even Tableau, which I think was founded in the fifties. They're actually all growing faster than the core Salesforce. So like, we can say, oh, Slack isn't what it was, which it i…”
Jason Lemkin Jun 19, 2025 ▶ 1:00:30 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Insight
Tennant: Chronological interviews reveal a candidate's true underlying motivations
“Understand the deep history of the individual Over a chronological period of time. I didn't realize that that was a hiring methodology until Bob Fratty taught me that at Slack, which is kind of this who hiring, the who hiring method is what we call a chronolog…”
AJ Tennant Oct 23, 2024 ▶ 36:30 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Assertion Not checkable as stated
AJ Tennant: Slack assigned senior CSMs strictly based on account ARR
“So I think one thing that I learned at Slack is like all Slack did was look at What the ARR was for the specific account, and then tied it, and they would only put a senior CSM on the, you know, whatever, the million dollar contracts.”
AJ Tennant Oct 23, 2024 ▶ 30:28 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Insight
Horizontal products with PMF should move upmarket faster and more aggressively
“It is important when you have, like, such a horizontal product like Slack that has product market fit to move upmarket faster and more aggressively.”
AJ Tennant Oct 23, 2024 ▶ 11:57 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Insight
Tennant: Enterprise land-and-expand deals require upfront executive alignment on expansion metrics
“I think you need to be very willing to do that. Now, the key thing that we've learned, and I, you know, learned this at Slack as well, but at Glean, You've got to have success criteria. You've got to have, okay, we're going to do, let's say for Fortune, 100 co…”
AJ Tennant Oct 23, 2024 ▶ 18:08 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Disclosure
Hamid shares entry valuations for Slack, Figma, and Rippling
“Probably Slack, I would say, you know, even at the 250 post that's, you know, with all the dilution over time and, If you take the twenty-seven billion or some other number that's a, obviously, a good, great multiple. Figma, you know, the initial investment wa…”
Mamoon Hamid Oct 21, 2024 ▶ 30:24 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
Disclosure
Hamid: Yammer's $1.2B sale freed him to invest in Slack
“There's one particular example that I think ended up working out pretty well. This is when Yammer got acquired by Microsoft it was a 1.2 billion dollar acquisition. At the time it felt like, man, we've got so much ahead of us. Yammer can become the next Slack,…”
Mamoon Hamid Oct 21, 2024 ▶ 28:32 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Hamid: Slack and Figma created entirely new software market categories
“Slack created a market. In some ways, Figma created a market. There wasn't a notion of collaborative design software.”
Mamoon Hamid Oct 21, 2024 ▶ 38:33 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Nejatian: My most frequent Slack phrase to Tobi Lütke was 'I disagree'
“I actually once looked at my Slack history with Toby. And the most common phrase I had told him was, I disagree.”
Kaz Nejatian Aug 14, 2024 ▶ 13:38 Kaz Nejatian: How Shopify Built a $90BN Business to Last 100 Years | E1189 · 20VC with Harry Stebbings
Insight
Adams: Google Wave failed because 2007 browsers and users were unready
“Google wave itself, like the project I work on at Google was really prescient in what it wanted to do in terms of real time communications and collaborations. But it was early for a bunch of reasons, like browsers weren't quite ready. People weren't quite read…”
Cameron Adams Jul 19, 2024 ▶ 4:47 Cameron Adams: How Canva Builds Products: Lessons Learned, What Works? What Flopped? | E1179 · 20VC with Harry Stebbings
Opinion
Grady: Kleiner Perkins partner Mamoon Hamid is an exceptional deal picker
“Somebody who I really admire is Mamoon at Kleiner. I think Mamoon has an exceptional track record of investing in companies that are not at all obvious at the time. And I think about the series B in Figma, which is a round that we looked at and passed on. I th…”
Pat Grady Jul 8, 2024 ▶ 24:59 Pat Grady: Sequoia Partner on Investing Lessons from Doug Leone, Roelof Botha and Alfred Lin | E1174 · 20VC with Harry Stebbings
What-if
Lemkin: Slack Would Be Worth $12B Today Despite Doubling Revenue
“What would Slack be worth today at two billion in revenue? Maybe it would be worth twelve billion, right? At twice the revenue.”
Jason Lemkin May 27, 2024 ▶ 27:51 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
Insight
Arora: Top tech companies achieve product-market fit for unexpected reasons
“Very rarely is it that your first incarnation of your product has perfect product market fit. That's very rare. You really, you know, if you look at the largest companies today, they were all created for a different reason and they ended up getting product mar…”
Nikesh Arora May 20, 2024 ▶ 13:41 Nikesh Arora: Lessons from $102BN Market Cap & How to Create & Sustain Competitive Advantage | E1155 · 20VC with Harry Stebbings
Insight
Brian Halligan warns that managing life via Slack enforces other people's priorities
“There's another thing I would say about prioritizing, Harry, is I think too many people run their life through Slack and through their email, and that's everyone else's priority list imposed on you, and so you're really just spending your whole time working on…”
Brian Halligan Jan 15, 2024 ▶ 46:19 Brian Halligan: Leadership Lessons Scaling Hubspot to $28BN | E1103 · 20VC with Harry Stebbings
Assertion Contradicted
Stebbings: 32% of European corporate enterprises do not know what Slack is
“Like, you know, I think as a stat, 32% of European corporates do not know what Slack is.”
Harry Stebbings Dec 20, 2023 ▶ 42:01 Roundtable #7: Spotify, Adobe and Linkedin on How AI Changes The Future of Product & Design | E1097 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lanng: AI startups have largely abandoned Slack for Discord
“Everyone is in Discord, by the way, now. I mean, it's so crazy, like, nobody is on Slack that I know in this environment.”
Christian Lanng Sep 27, 2023 ▶ 1:13:58 Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Late-stage startups spend roughly 3x more per seat on Figma than Slack
“And so how that actually plays out is probably a third of the company from my surveying has paid seats inside of Figma, and they pay about three times as much as they would for something like Slack.”
Miles Grimshaw Sep 18, 2023 ▶ 51:33 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Opinion
Howie Liu: Slack and Dropbox Function as Vertical Products
“Some horizontal products are actually, you know, a vertical of their own, right? When I think about, you know, a Slack or a Dropbox, I think they actually fall into a very well-defined category in my mind. Like, You know what you're going to use Slack for. You…”
Howie Liu Aug 25, 2023 ▶ 4:20 Howie Liu: Decoding Airtable's $11B Valuation; The Impending AI Revolution in Enterprise | E1053 · 20VC with Harry Stebbings
Insight
Sela: Eliminating software tools prevents internal communication fragmentation
“I'm a big fan of like eliminating tools versus introducing more and more tools. Cause then what happens is things become fragmented that no one knows what should I slack versus what should I email, but what should I present via video?”
Ilir Sela Aug 4, 2023 ▶ 26:22 Ilir Sela: How I Founded Slice Pizza & Became One of Macedonia’s Largest Employers | E1044 · 20VC with Harry Stebbings
Assertion Supported
Egan: Slack Reached Tens of Thousands of Organic Users Per Company
“They had, in some cases, tens of thousands of users within single companies that said, Hey, look, we need to come to the table and operate.”
Kevin Egan Jul 12, 2023 ▶ 8:12 Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Egan: Slack Uniquely Combined Enterprise Security With End-User Engagement From Launch
“So Slack from day one had an appetite to work with large teams and large customers yet they had an incredibly engaging platform. So that ability to marry end user love with the enterprise posture right out of the gates, focus on large teams and all the securit…”
Kevin Egan Jul 12, 2023 ▶ 4:03 Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Weiss: Most Slack product and design hires lacked enterprise experience
“The vast majority of people who have worked at Slack on the product and design side had never worked in enterprise software before.”
Noah Weiss Jun 16, 2023 ▶ 25:06 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Assertion Partly supported
Weiss: Slack's original pitch deck targeted teams of 5 to 50
“If you read the initial pitch deck, which they shared when they pivoted the company, It said, Slack is a product for teams of five to 50 people. The initial conception of Slack was, after 50 people, this thing probably won't scale.”
Noah Weiss Jun 16, 2023 ▶ 7:09 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Weiss: Over 85% of Slack enterprise customers originate through self-service
“Over 85% of our enterprise customers, so, you know, customers of over a thousand users, started in self-service. So they didn't call up our sales team didn't call them. They started by signing up on slack.com, like, just like an SMB, sharing it with some co-wo…”
Noah Weiss Jun 16, 2023 ▶ 38:42 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Insight
Weiss: Most product decisions are reversible two-way doors
“The majority of things you're building as a private organization fall into two way door kind of decisions, especially things you can experiment with and then on release.”
Noah Weiss Jun 16, 2023 ▶ 15:07 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Insight
Weiss: Slack prioritizes end-user experience above all enterprise buyer needs
“Our answer is that if we have to choose who we're serving above all else, it's actually the end user who's using the product and living in it for 10 hours a week. Because if we can make something that they love, that they feel like actually makes their working…”
Noah Weiss Jun 16, 2023 ▶ 38:04 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Insight
Weiss: Social features cannot be tested at the individual user level
“Most of the new capabilities that we launch can't be experiments at a user level because there are social features, right? You can't sit in a huddle by yourself. You have to be able to use it with the rest of your organization.”
Noah Weiss Jun 16, 2023 ▶ 42:47 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Insight
Startups with network effects should hire growth talent earlier to engineer loops
“If your product has a social collaboration, network effect, that kind of thing, think about Slack, LinkedIn, right, or anything like, or Airtable, Figma, hiring for growth early on, a little bit earlier, will allow you to engineering those growth loops into th…”
Hila Qu Jan 18, 2023 ▶ 19:16 Hila Qu: The Ultimate Guide to Product Growth at Your Startup | 20VC #967 · 20VC with Harry Stebbings
Disclosure
Hott Mistakenly Authorized a $200,000 Customer Discount as a New Slack Manager
“So I gave the authority to approve a 200,000 dollar credit to a customer at Slack that my team was selling into.”
Maggie Hott Dec 15, 2022 ▶ 52:08 Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960 · 20VC with Harry Stebbings
Assertion Supported
Slack Did Not Build an SDR Team Until 2017
“At Slack is we didn't even start building an SDR team until 2017. So we had been around for almost three years at that point before we've really ever started dialing up this outbound motion.”
Maggie Hott Dec 15, 2022 ▶ 20:49 Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960 · 20VC with Harry Stebbings
Prediction Held up
Liaw: Salesforce will pause major M&A while digesting Slack
“Now, I think Salesforce is probably going to be quiet for a little bit as they digest Slack.”
Eric Liaw Apr 8, 2022 ▶ 12:27 20VC: What Happens To Growth Rounds in this New Environment? Where is the Funding Crunch? How Does This Impact M&A and Going Public? How do Crossover Funds Respond? What Does it Mean For Early Stage and more with Eric Liaw, General Partner @ IVP
Opinion
Rachitsky: No community platform compares to how well thought through Slack is
“I've tried so many other types of community platforms, and none of them compare to how well thought through Slack is.”
Lenny Rachitsky Mar 16, 2022 ▶ 35:29 20 Product: Lenny Rachitsky on The 3 Key Roles of the Product Manager, 5 Skills All The Best PMs Have, When To Hire Your First PM, How to Structure the Hiring Process for PMs & What Leaders Can Do to Make Their PMs Successful
Assertion Not checkable as stated
Herzberg: Slack initially harbored internal cynicism toward sales
“To be honest, there was a bit of cynicism around sales in the beginning at Slack, and I totally got that.”
Dannie Herzberg Feb 2, 2022 ▶ 10:16 20 Sales: How To Build Sales Teams with a Product-Led-Growth GTM, What is a Sales Hiring Scorecard and How To Construct Yours & How To Structure the Onboarding Process for all New Sales Hires with Dannie Herzberg, Partner @ Sequoia Capital
Insight
Elena Verna: Premortems are far more effective than postmortems for growth teams
“I learned from Fareed, who was director of growth at Slack, that premortems are far more effective than postmortems.”
Elena Verna Oct 28, 2021 ▶ 29:04 20 Growth: The 3 Levers to Successful Growth Models, The 3 Types of Growth Hires Startups Need To Know, The 3 Stages All Successful Growth Teams Need To Go Through with Elena Verna, Advisor @ MongoDB and HP
Assertion Supported
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”
Stewart Butterfield Nov 16, 2020 ▶ 10:40 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour
Insight
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.”
Stewart Butterfield Nov 16, 2020 ▶ 13:59 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour
Assertion Contradicted
Slack reached $100M ARR in less than two years
“Certainly less than two years to get to a hundred million dollars in ARR.”
Stewart Butterfield Nov 16, 2020 ▶ 7:47 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour
Assertion Supported
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.”
Stewart Butterfield Nov 16, 2020 ▶ 41:03 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour
Insight
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.”
Stewart Butterfield Nov 16, 2020 ▶ 9:32 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour
Insight
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…”
Stewart Butterfield Nov 16, 2020 ▶ 21:34 20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour
Disclosure
Levine: Accel's Slack, Sentry, and Cloudera investments originated as seed deals
“Even at Excel, our first investment in Slack was a seed. Our investment in Sentry started as a seed. Our investment in Cloudera was an EIR.”
Daniel Levine Nov 12, 2020 ▶ 29:35 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?
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