The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
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
O'Driscoll: Enterprise API lockdowns signal a decaying software empire
“I just think it's a sign of a decaying empire. It's a sign that you can compete on the merits, and it's, I, it's a little bit of a dangerous sign.”
Expecting Ordinary Enterprises to Build Custom Vertical AI Tools Is Moronic
“Majority of Enterprises, especially in Europe, do not know what Slack is, let alone what Notion is. So the fact that they're going to create their own verticalized AI tools is absolutely fucking moronic.”
Hamid: Invested in Slack at a $250M valuation on $500k ARR
“It was 500 K of ARR at the time... Two hundred fifty million post.”
Cohen: Navan is seeking Slack alternatives due to declining product quality
“The team right now is looking for alternatives. Not because you know, we love Slack. But you can see that over time, the search works a little bit, you know, worse. The buttons are moving to the wrong places. I care a lot about product and design. And I think …”
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 …”
Lovinsky: Slack no longer improves my effectiveness as a Chief Product Officer
“But I have to say in my role now, I'm not sure that slack actually makes me better at what I do and makes my day better and more effective.”
Jason James: Tezi won't hire full-time PMs until reaching 50 employees
“Like for us, my theory was we didn't need PMs until call it 50 people or so. We actually do have some gaps. And so we have PM That's like former senior director at Slack that contributes about 15 hours a week, and it really helps fill the gaps on his enterpris…”
Graves: AI sellers remain far from replacing enterprise sales reps
“I will say, I believe it would work if it's a very transactional product. Like, if you're like, hey, we're a conference, and we are selling conference booths, this is the price. I think, like, an AI Seller can actually probably sell that quite well, but when y…”
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…”
Slack lost to Microsoft by over-relying on product-led growth
“We lost the distribution war at Slack. I think part of why we lost that war was, yes, like, monopolistic behavior by Microsoft, but Because we didn't lean into other effective fast distribution strategies other than PLG.”
Slack was acquired for $27B but is worth $2B today
“Slack was worth twenty seven billion when Salesforce bought it and probably worth two billion today.”
Farquhar: Atlassian built a better product than Slack in many cases
“In, in many cases, I think against Slack, we had a better product.”
Egan: Startups Must Master PLG Before Layering On Enterprise Sales
“I think you can, but I think it's extremely difficult. I think Slack was able to do it. I think they nailed PLG first, and then enterprise, but they always had an eye towards enterprise. The reason why I say it's extremely difficult is to capture the end user'…”
Weiss: Small-scale product acquisitions do not accelerate time to market
“When they were trying to actually buy a product, I think you're right. I think often the thing we've learned is that it doesn't actually decrease time to market. You might bring in expertise and that's a good reason to do it, but that's at least what we've lea…”
Weiss: Launching Slack Connect earlier would have driven massive network adoption
“And I think frankly, especially given the competitive backdrop there, I think if we had not rushed it, but expedited into market back before there were more products that, you know, people were starting to use or get for free as defaults. And back when I think…”
Overly Generous Self-Serve Tiers Cannibalize Future Enterprise Sales Revenue
“Is they have their, essentially their self-serve or their lower end product cannibalize what could be their future enterprise product. We ran into that at Slack. We run into it at Webflow all the time where there has to be a huge product differentiation outsid…”
Slack Delayed Building an Outbound Sales Motion Too Long During Hypergrowth
“I actually helped to build out our very first ever outbound motion at Slack, was the very first person to ever do it and ever do our first, which we called Proactive outreach. Cause outbound was, you know, of course a dirty word back then, but it is so importa…”
Pearl: Every major PLG company must add direct sales
“Every iconic PLG company, whether it's Slack or Dropbox or Asana or Zoom, you know, at some point they have to add on that sort of direct selling motion to complement the PLG business.”
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: 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: 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…”
Palihapitiya: D&O insurance in direct listings is nearly impossible to get
“On top of that, the ability for directors to get D&O insurance via direct listing is next to impossible, and I went through this at Slack, so I can tell you firsthand.”
Schalit: Pure SaaS margins beat tech-enabled physical businesses on profitability
“When you think about some of the very large public or non-public companies like, you know, ride sharing and office space sharing, these are tech-enabled companies for which technology is somewhat important, but that structurally have very low gross margins bec…”
Lemkin predicts Slack will surpass HipChat within six months
“Slack is going to be bigger than HipChat or its entire competitive landscape in six months.”
Cliff Weitzman: Most long Slack messages should be phone calls
“Most long Slack messages should have been a phone call.”
Randle: Market is the least important investment factor because it is fungible
“The way you said it, honestly, people, product and market. I think the people, Define everything else. They are the upstream engine that makes everything go. They're the most important piece. Two, I think the product that the people build tell you a lot about,…”
Slack deliberately avoided sales outreach to community workspaces despite high user counts
“And so at Slack, we saw that our biggest workspaces were actually communities. They were professional networks that were using Slack to trade best practices. There were student groups that were using Slack to work on projects. And the sales team was tempted to…”
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.”
Stebbings: 62% of large European enterprises do not know what Slack is
“In Europe, 62% of large enterprises still don't know what Slack is.”
AJ Tennant: Sales skills are entirely learnable, not innate personality traits
“I fundamentally believe they can be learned. You know, I think a lot of people would say it's innate, you know, you, you're born with it, it's that your personality, someone that's outgoing, but my philosophy is that pretty much humans can learn anything if th…”
Stebbings: Enterprise clients lack the technical sophistication to build in-house AI solutions
“I think we drastically overestimate the technology sophistication of these companies. To be able to build with AI their own vertical solutions. Are you kidding me? They struggle to onboard Slack.”
Gonto: Early growth at Slack and LinkedIn was not driven by growth loop frameworks
“When you go to the leaders in Slack and LinkedIn at those times, they will tell you they will not, they were not implementing growth loops. They didn't know what a growth loop was. They were trying to find creative ways to get other users and other people to c…”
Weiss: Slack uses manual spreadsheets to track executive quarterly priorities
“We wind up solving this like most people do at the end of the day, you use spreadsheets. So we have a Monday meeting, PD Monday meeting, as we call it, where like literally we just review in a spreadsheet, super manual process, but the top priorities for the q…”
Weiss: In-product trials were Slack's top driver for paid conversion
“And so we want to building a really robust in product trial program, many ways to flow into it, a guided experience. How can you make sure you're getting the value out of it? And that was probably, I mean, honestly, the single biggest thing we did on top of th…”
Weiss: Slack succeeds at talent integration but struggles with product integration
“I think we're good at talent integration. I think we struggle at product and technical integration.”
Weiss: Slack product innovation slowed from 2018-2020 due to enterprise focus
“I mean, I think where internet was most true was 2018 to 2020. And I think I would, I think we would fess up to it entirely because back then, you know, this is again, I don't know if we could have done it differently. You're a small company. You can't do ever…”
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…”
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: 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…”
Venture funding must rely less on exclusive operator networks
“I hope that venture funding becomes less of a closed circle, and actually that these networks become less important, and that access to this life-changing financial tool is democratized for many more people who didn't have the incredible luck That Jana and I h…”
Cannon: Slack Is Synchronous Flow, Notion Is Asynchronous Stock
“If Slack was the flow of information, Notion was the stock, or if Slack was kind of synchronous communication, then Notion was the place for asynchronous communication.”
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.…”
Young tech workers should join mid-stage growth startups like Stripe or Slack
“I think there's merits to all of them, but I would now lean more toward go to that medium-sized growth company. You know, if you can get in today at a company like Stripe or Slack, for example, I think you get incredible growth opportunities, and if you know, …”
Volpi: Slack's enterprise viral growth velocity is unprecedented
“Slack, which is spreading virally at a, you know, velocity that's, I don't think I've seen before in the enterprise environment.”
Fushman: Slack will become workplace productivity's primary operating system
“Slack is one of the fastest growing companies, I think, that's been around, and it's poised to transform how people work and communicate, and build a true operating system and platform for productivity going forward.”
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…”