The Ledger

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why aren't all 25 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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

Prediction Held up
O'Driscoll: Slack restricting customer data access will fail over the medium term
“I don't know if you can get away forever in a horizontal app like Salesforce with a channel like Slack denying access, the denying the customer access to their own content over the medium term. I don't think it stands.”
Rory O'Driscoll Jun 26, 2025 ▶ 1:04:10 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Assertion Supported
Early Slack Sales Reps Received Flat Salaries Without Commissions or Quotas
“As I mentioned, when I came into Slack, there had been absolutely no reach outs ever to anything proactive. Everything that we were doing, our single biggest goal, our single biggest charter was talk to the customers, was understand what is it That the custome…”
Maggie Hott Dec 15, 2022 ▶ 12:17 Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960 · 20VC with Harry Stebbings
Assertion Supported
Hsu: Slack and Carta didn't build dedicated data teams until Series C
“I just want to think back to Slack and Carter, two companies that we've worked with, you know, in the last couple of years, you know, both of them didn't really start investing in this Full bore, you know, well into about the series C, if I remember correctly.…”
Jonathan Hsu Jun 17, 2019 ▶ 16:34 20VC: Why Historical Loss Ratios Are Simply Too High, Why Data Is The #1 Most Important Piece When Evaluating Effective Reserve Allocation & Why Nothing Is Truly Defensible Today with Jonathan Hsu, Co-Founder and General Partner @ Tribe Capital
Prediction Held up
Shah: Late-stage SaaS companies face an inevitable valuation course correction
“There are a lot of companies that have raised a lot of money at very high valuation, and I don't think that's going to work, and that's very clear in SaaS. Not all, not every company has the growth rate of slack. But many companies have the valuations that are…”
Hiten Shah Mar 4, 2016 ▶ 19:20 20VC FF: Hiten Shah on VC Funded vs Bootstrapped Businesses and How He Decides Which Startups To Advise
Assertion Supported
Lemkin: Slack hit $24M run rate one year after monetizing
“Slack just hit a twenty-four million run rate, basically one year after monetizing.”
Jason Lemkin Jul 1, 2015 ▶ 9:03 20 VC 050: Starting, Building and Selling in SaaS with the King of SaaS, Jason Lemkin, Managing Director @ Storm Ventures
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
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 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 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
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
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
Assertion Supported
Wilkinson: MetaLab designed Slack and worked with Shopify, Coinbase, and Pinterest
“Also worked with a lot of startups really early on, Shopify, Tumblr, Coinbase, Pinterest. We designed Slack.”
Andrew Wilkinson Jun 22, 2020 ▶ 5:33 20VC: Andrew Wilkinson on Building The Berkshire Hathway of Tech, Sustainable vs Unsustainable Growth and The Relationship Between Money and Freedom
Assertion Supported
Merci Victoria Grace grew Slack from 500K to 6M daily active users
“There I became the head of product and I started and ran the growth team in the effort to drive our daily active users from 500,000 to over six million in about three years.”
Merci Victoria Grace Jun 8, 2020 ▶ 3:56 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
Prediction Held up
Kadavy: AI bots will exist everywhere across existing platforms, not standalone
“My hypothesis is that at least at the beginning for sure, and I think going forward, they will live everywhere. One bot, I should think of a bot like I think of a contact person. It should be in my contact list. It should be in my Facebook messenger. Maybe it'…”
Annie Kadavy Jun 22, 2016 ▶ 22:17 20VC: Why Bots Are The New Black, Conversational Interface Is The Next of For Consumerisation and The Determinants Of A Successful Marketplace with Annie Kadavy, General Partner @ CRV
Prediction Held up
Tunguz predicts a massive ecosystem will be built on top of Slack
“You know, I think there will be a couple of, I think there will be an ecosystem built on top of Slack. And then I think there will be a handful of companies that that take that UI metaphor and become really successful outside of Slack.”
Tomasz Tunguz Mar 7, 2016 ▶ 22:04 20VC: Tom Tunguz on Why Now Is The Best Time To Be Investing and The Effect of Late Stage Valuations on Startups
Assertion Supported
Lipman: Two-year-old Slack valued at $2.8B compared to Etsy's $3.5B IPO
“And when you look at, like, the recent IPO this week of Etsy you know, they're a ten-year-old company, and Slack, You know, is a, you know, two-year-old company, and they, Slack is valued at a two-point-eight billion dollar valuation, where Etsy is, you know, …”
Brandon Lipman Apr 20, 2015 ▶ 14:35 20 VC 029: The Potential Upside To A Technology Bubble with TechCrunch's Brandon Lipman
Assertion Supported
Lemkin: Slack achieved 140% NRR without raising prices
“Slack never raised prices and still grew at 140% NRR.”
Jason Lemkin Jan 29, 2026 ▶ 1:17:32 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Assertion Supported
Seibert: Twitter, Slack, and YouTube originated as completely different products
“Twitter was a podcasting startup. Slack was a game. YouTube was a dating website.”
Jeff Seibert Nov 22, 2023 ▶ 14:00 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Assertion Supported
Atlassian had 200 employees on Stride before selling to Slack
“And so in the end, like, you know, deciding to shut down that product, we had a couple hundred people working on it. It was hard because a lot of people had poured their light, you know, heart and soul into it. We sold it to Slack”
Scott Farquhar Oct 9, 2023 ▶ 34:23 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Stuart Butterfield offered to return remaining capital when gaming startup failed
“Stuart Butterfield, when it didn't make it, his second gaming company, he offered to give all the money back. He offered to give what was left.”
Jason Lemkin Aug 9, 2023 ▶ 35:02 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Assertion Supported
Weiss: Slack has around 1,200 employees in product, design, and engineering
“Slack has probably around 1200 people across product design and engineering.”
Noah Weiss Jun 16, 2023 ▶ 16:29 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Assertion Supported
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.”
Stewart Butterfield Nov 16, 2020 ▶ 40:53 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
Slack Raised Over $1.3 Billion Prior to Its Direct Listing
“Prior to their direct listing in June, 2019, Stewart raised over 1.3 billion dollars from the likes of Excel, Thrive, SoftBank, Kleiner, IVP, T-Road, GV, and Andreessen, to name a few incredible investors.”
Harry Stebbings Nov 16, 2020 ▶ 0:25 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
Butterfield: Slack Emerged from Failed Gaming Startup TinySpec
“Most of that original Flickr team got back together to start another company called TinySpec to build a web-based massively multiplayer game that didn't work, and then we ended up with Slack.”
Stewart Butterfield Nov 16, 2020 ▶ 3:44 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
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