The Ledger

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why aren't all 389 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

Assertion Not checkable as stated
Varanasi: No single large company today is not vertically integrated
“What's ironic to really think about is there is not a single large company in the world today that is not vertically integrated. There's just none.”
Anil Varanasi Dec 10, 2025 ▶ 31:12 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
Prediction Not checkable as stated
Stauch: Product-oriented forward-deployed engineers will reduce PM and SE hiring
“I think the need for a lot of product managers is probably going to go down. If you hire really product oriented for deployed software engineers, then they're going to be increasingly making the decisions on what makes sense to build for the max Some number of…”
Jake Stauch Oct 23, 2025 ▶ 54:34 Go hard early: How lessons from Verkada shaped this AI-native IT platform | Jake Stauch (Serval)
Assertion Not checkable as stated
MacInnis: A top SMB payroll rival lost its edge by adopting Workday
“This company, you know, is pretty well known, and they've got a good SMB payroll business going, but like, at a certain scale, they switched to Workday. When they switched to Workday, they stopped using their own product, and when they stopped using their own …”
Matt MacInnis Apr 25, 2024 ▶ 24:58 How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
Prediction Not checkable as stated
Noronha: AI Agent Organizations Will Still Face Legacy Operational Friction
“I think even an org run by a thousand AI agents would actually hit this friction. It's just that they're all a few months old, and so we haven't seen it yet.”
Jon Noronha Jul 24, 2026 ▶ 50:12 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Prediction Not checkable as stated
Copplestone: AI agents will probably operate self-driving databases in the future
“If agents are building now, then they'll probably be operating in the future. So, at the moment, maybe developers end looking at things, whether the database is healthy or not. But of course, they probably don't want to be doing that, and that's actually where…”
Paul Copplestone Jun 25, 2026 ▶ 34:56 The egoless culture that built Supabase | Paul Copplestone (Co-founder, CEO)
Assertion Not checkable as stated
Moreno: Structured Software Rollouts Far Outperformed Self-Serve Marketplaces at Windsurf
“Because six months in, companies that did structured rollouts were a lot more successful, and we ended up collecting a lot of data on this because it became part of how we sold. Then the companies that said, hey, I've got tool A, tool B, and tool C, we're gonn…”
Graham Moreno May 21, 2026 ▶ 2:56 Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
Assertion Not checkable as stated
Moreno: Top AI sales comp plans require 10x to 30x OTE performance
“In AI right now, the top tier is like. 30 X your OTE. Like I remember in the days where it was like, oh yeah, if you're doing like five X OTE, that's like spectacular. And now quote is like 10 X OTE first accelerator tiers, 20:02 is 30.”
Graham Moreno May 21, 2026 ▶ 52:53 Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
Prediction Not checkable as stated
Hirshberg: Within three years, AI agents will execute most global work
“When we think three years out in the future, we believe that most work will be done by agents. AI will direct the intent, sorry, humans will direct the intent, but AI will execute it. And that would go for probably most, let's say, work in the world, but speci…”
Shachar Hirshberg Apr 21, 2026 ▶ 46:06 Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
Prediction Not checkable as stated
Stauch: AI Software Categories Will Be Dominated by Single Winners
“And I think the same thing is going to happen in AI. And in this case, a lot of times it might be the incumbent that still wins, but there are going to be AI native competitors creating a massive, massive value in these categories. And I don't know That it's g…”
Jake Stauch Oct 23, 2025 ▶ 1:17:28 Go hard early: How lessons from Verkada shaped this AI-native IT platform | Jake Stauch (Serval)
Prediction Not checkable as stated
Stauch: Legacy enterprise software giants will naturally lag in adopting AI
“They have this classic innovators dilemma that it makes it hard to steer the big ship to add these capabilities while still protecting their existing product and revenue not making drastic changes that are not backwards compatible. And so they're just naturall…”
Jake Stauch Oct 23, 2025 ▶ 1:19:39 Go hard early: How lessons from Verkada shaped this AI-native IT platform | Jake Stauch (Serval)
Assertion Not checkable as stated
Major film studios actively seek generative AI video tools from fal
“Something changed this summer and we are getting a ton of interest from basically all the studios in LA or elsewhere. Everyone is really interested to at least do something about it because now they understand this is good enough and they can actually save mon…”
Gorkem Yurtseven Oct 22, 2025 ▶ 25:43 The pivot that paid off: How fal found explosive growth | Gorkem Yurtseven (Co-founder and CTO)
Prediction Not checkable as stated
Model commoditization will drive fragmentation, favoring multi-model platforms like fal
“So it looks like it's going to be really hard for someone to differentiate with the quality of the model. And we believe this is going to lead to even, even more fragmentation. So a company like Fall where you get to access many different models at the same ti…”
Gorkem Yurtseven Oct 22, 2025 ▶ 29:48 The pivot that paid off: How fal found explosive growth | Gorkem Yurtseven (Co-founder and CTO)
Assertion Not checkable as stated
fal employs over 30 engineers with zero dedicated engineering managers
“Yeah, we don't have engineering managers. We have around like. 30 to 34 engineers. We do have leads. Obviously we have leaders in the In the team, but you know, we don't have this engineering manager role. Everyone is always, like, contributing, writing code. …”
Gorkem Yurtseven Oct 22, 2025 ▶ 54:33 The pivot that paid off: How fal found explosive growth | Gorkem Yurtseven (Co-founder and CTO)
Prediction Not checkable as stated
Agrawal: AIs will use the web 1,000x to 1,000,000x more than humans
“We believe that AIs will use the web a thousand X, a million X, more than humans ever have. And as a result, The web will need to transform.”
Parag Agrawal Aug 14, 2025 ▶ 1:33 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Prediction Not checkable as stated
Agrawal: Recommendation systems, search, and databases are converging into one
“My worldview is currently shaped, shaping into a convergence between recommendation systems and search systems and database systems. I think they're all going to start looking like the same thing.”
Parag Agrawal Aug 14, 2025 ▶ 1:03:47 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Prediction Not checkable as stated
Song: AI agent and human behavior will be indistinguishable in 2-3 years
“Genuinely believe that like within the next two, three years, you won't be able to differentiate human behavior from agentic behavior.”
Rick Song May 8, 2025 ▶ 31:36 From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
Prediction Not checkable as stated
Guild predicts Owner's CAC will match Shopify while LTV will exceed Toast
“Which ends up giving us customer acquisition costs in the future that look more like Squarespace or Shopify with lifetime values that are even greater than toasts over time because the attach rate is so high once you earn the trust on free products.”
Adam Guild Mar 27, 2025 ▶ 1:03:35 Scrappy tactics and a huge post-COVID pivot | Adam Guild (Co-founder and CEO of Owner)
Prediction Not checkable as stated
McCabe: Intercom will be completely done if AI is all hype
“We're certainly betting the entire company on AI. If AI turns out to be all hype, we're done. Completely done.”
Eoghan McCabe Sep 5, 2024 ▶ 31:26 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
Assertion Not checkable as stated
McCabe: Intercom AI bot resolves 48% of tickets vs Zendesk's 29%
“Zendesk Bot has a resolution rate of 29% or high twenties by our benchmark, which is the rate at which it successfully closes the ticket. Ours is currently 48% and that's what a year head start gets you.”
Eoghan McCabe Sep 5, 2024 ▶ 52:13 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
Prediction Not checkable as stated
McCabe: Customer service work done by human seats will be replaced by AI
“AI is about to do the exact same in every category particularly categories of software for people to do work. So customer service, which is the one I focus on and obsess about for a living is about to be fundamentally changed because the work of customer servi…”
Eoghan McCabe Sep 5, 2024 ▶ 57:32 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
Prediction Not checkable as stated
Schillace: AI tooling will expand engineering ambitions rather than shrink team sizes
“Programmers are definitely going to get more effective. We're going to get more agentic programming tools. So you're going to get higher and higher leverage, but I don't think it's going to make the team smaller. I think it's just going to make the ambitions b…”
Sam Schillace Jun 6, 2024 ▶ 31:00 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)
Prediction Not checkable as stated
Schillace: AI will make creating pixels free, radically altering software applications
“I have the suspicion that the nature of applications is going to change radically in the next five to 10 years. And so I think, you know, this idea that just in the same way that the internet made the distribution of information essentially free, AI, generativ…”
Sam Schillace Jun 6, 2024 ▶ 31:52 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)
Assertion Not checkable as stated
Winters: Grubhub data showed resolving bad orders boosted retention over flawless orders
“Early on, we were basically like, look, if there's an issue with the driver, if there's an issue with the order being late, we'll take it on as the marketplace, because we know if we make up for a bad experience by going above and beyond, we'll actually have b…”
Casey Winters May 30, 2024 ▶ 47:51 How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)
Assertion Not checkable as stated
Habib: Writer's largest models match GPT-4 quality at lower hosting cost
“Now we've got 18 models. The biggest ones are GPT-IV level quality, but at a fraction of the cost of hosting. Super, super fast for the enterprise use cases that That our customers run them on.”
May Habib Feb 29, 2024 ▶ 7:29 Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)
Prediction Not checkable as stated
Habib: AI capabilities will outpace most organizations' capacity to absorb them
“And I do think the capabilities that are possible are gonna outstrip most organizations' capacities to absorb them, for most of their employees to absorb them without a lot of effort.”
May Habib Feb 29, 2024 ▶ 15:20 Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)
Prediction Not checkable as stated
Habib: Writer has the potential to become a 400 percent NRR company
“I think this should be a 400% NRR company.”
May Habib Feb 29, 2024 ▶ 28:51 Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)
Prediction Not checkable as stated
Masad: AI add-ons will become native within a couple years
“GUI was an add-on at some point, and I think this is where we are with AI. But I don't know, I think it's a transitionary period. I think at most couple years where most companies are going to take the approach we're taking.”
Amjad Masad Feb 15, 2024 ▶ 34:38 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
Prediction Not checkable as stated
Masad: AI will bifurcate developers into 'creators' and 'engineers'
“I think that there's going to be a bifurcation of software engineer and software creator. Engineers are not going away. We need engineers in the same way that Instagram did not obviate the need for professional, you know, journalists and photographers and all …”
Amjad Masad Feb 15, 2024 ▶ 36:34 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
Assertion Not checkable as stated
Very few PLG companies outside of DevOps have truly broken out
“There really aren't many successful PLG companies outside of like the DevOps ones like Datadog and Atlassian that have actually really broken out.”
Oliver Jay Jan 4, 2024 ▶ 1:00:11 The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
Prediction Not checkable as stated
Blank: The entire Lean Startup methodology will be enabled by AI
“The entire lean method. Is going to be end to end enabled by AI.”
Steve Blank Dec 21, 2023 ▶ 53:49 Mastering modern entrepreneurship | Steve Blank (Author of The Four Steps to the Epiphany)
Assertion Not checkable as stated
Information retrieval is not the majority use case for Google Bard
“Some people, and it turns out not the majority use case, but some people are going to use it to try to find information.”
Jack Krawczyk Nov 30, 2023 ▶ 23:40 The Bard blueprint | Creating value, shipping fast, and advancing AI | Jack Krawczyk (Google)
Prediction Not checkable as stated
Persistent memory for LLMs will take much longer to solve than expected
“And so I am beyond Fascinated and intrigued by the research that's taking place around memory and being able to reference things from previous conversations, but I think it's going to take way longer than we expect.”
Jack Krawczyk Nov 30, 2023 ▶ 1:13:12 The Bard blueprint | Creating value, shipping fast, and advancing AI | Jack Krawczyk (Google)
Prediction Not checkable as stated
Future websites will be dynamically generated just-in-time for individual users
“The thing that we want to accomplish with the web is that we want to make it truly an AI driven web where when you go to a website, you get a copy of that page that is just for you generated just in time. And it knows it has all this context about what you wan…”
Guillermo Rauch Nov 2, 2023 ▶ 58:57 How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (CEO)
Prediction Not checkable as stated
Adaptive AI systems will eliminate the need for major software re-platforms
“So using AI to continuously modernize, you can think of systems of the future that are self-tuning and adaptive. We no longer have to catch the latest trend or optimization By doing major re-platforms.”
Guillermo Rauch Nov 2, 2023 ▶ 1:00:30 How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (CEO)
Prediction Not checkable as stated
Human software engineers will write very little code in 20 years
“If I had a bet, since you gave me the 20 year out, I would say yes. I think very little code, if any, will be written by engineers.”
Guillermo Rauch Nov 2, 2023 ▶ 1:00:59 How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (CEO)
Prediction Not checkable as stated
Siroker predicts 50% of work will be fundamentally changed within 10 years
“I think a lot of jobs will be gone in 10 years, but they'll likely be replaced with new ones. I think that's probably an obvious Conclusion. I think on the order of probably 50% of work will go away. It would be fundamentally changed.”
Dan Siroker Sep 14, 2023 ▶ 47:07 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
Prediction Not checkable as stated
Siroker: AGI will eventually perform half the work of human engineering teams
“Eventually, you know, I don't think it will necessarily replace engineers, but it'll certainly augment them. You'll have plenty of, you know, half the work that an engineering team does will be done by AGI, and half will be done by humans, and the human stuff …”
Dan Siroker Sep 14, 2023 ▶ 50:37 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
Assertion Not checkable as stated
Noronha: Presentations are the third most requested enterprise AI use case
“Well, everyone needs just a chat tool for sure. The engineers all need a tool like a cursor or cloud code or whatever. And it turns out the third use case that's bubbling up over and over is presentations. People are wasting all this time just like formatting …”
Jon Noronha Jul 24, 2026 ▶ 6:38 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Assertion Not checkable as stated
Noronha: AI Integration Unlocked Organic Virality and Free Distribution for Gamma
“The inflection point came when we truly solved virality in the product by introducing AI. And at that point, we started getting distribution for free because people would make something great. They would share it with someone else. Those people would try it ou…”
Jon Noronha Jul 24, 2026 ▶ 48:09 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Assertion Not checkable as stated
Gamma surpassed 100,000 daily signups in its first year without paid marketing
“And we were still doing no paid marketing at this time. So the only explanation for this was word of mouth growth, basically, you know, different kinds of word of mouth. But that 10,000 kept climbing upwards, 10,020 1030 thousand, to the point where in our fir…”
Jon Noronha Jul 24, 2026 ▶ 52:42 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Assertion Not checkable as stated
Sager: Fintech competitors that sacrificed precision for speed failed completely
“I think we've had competitors that sacrificed, you know, everything at the altar of speed and it didn't work out and it didn't, and not at all.”
Eric Sager Jul 16, 2026 ▶ 15:01 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Assertion Not checkable as stated
Copplestone: Support outreach boosts Supabase account usage growth to 125% QoQ
“And what we do is we measure those who don't respond, how much did their the usage growth and actually we know like quarter over quarter, it's 25% versus those who have chatted to a success person and that's a 125%. So we can see the incremental uplift from th…”
Paul Copplestone Jun 25, 2026 ▶ 50:36 The egoless culture that built Supabase | Paul Copplestone (Co-founder, CEO)
Prediction Not checkable as stated
Moreno: High-touch enterprise sales principles will persist in AI era
“I think that at any large-scale organization, those foundational principles will continue to exist.”
Graham Moreno May 21, 2026 ▶ 5:38 Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
Prediction Not checkable as stated
Moreno: Basic application sales jobs will be automated by AI
“I think if you're out there selling, like A basic application. It's probably fine. I also think those are the sales jobs that are gonna get AI'd.”
Graham Moreno May 21, 2026 ▶ 40:33 Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
Assertion Not checkable as stated
Xero's AI financial chatbot hits 95% accuracy on scenario and advice queries
“One is like, we're ahead in the market. Nobody else does it. Second, and we're at like, 95% accuracy or something, like in the answers written on.”
Diya Jolly Apr 30, 2026 ▶ 43:40 AI killed the product roadmap | Diya Jolly (CPO & CTO of Xero)
Prediction Not checkable as stated
Compliance demands ensure traditional accounting SaaS workflows will not disappear
“Will SaaS apps completely disappear? I, will the workflows disappear? SaaS is an overload of terms. Probably not, at least in our category, just because it's compliance. You need, like, you need the workflows to prove that you're doing the right thing to submi…”
Diya Jolly Apr 30, 2026 ▶ 46:38 AI killed the product roadmap | Diya Jolly (CPO & CTO of Xero)
Assertion Not checkable as stated
Payne: DoorDash never subsidized expansion by selling dollars for 90 cents
“For a while, there was a narrative like, oh, we're giving away dollars for 90 cents. Absolutely not. You couldn't do that because you would lose money very, very rapidly. Too fast for a company that didn't have a lot of money.”
Christopher Payne Apr 17, 2026 ▶ 1:39 Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
Prediction Not checkable as stated
Degnan predicts the AI sector will face a dot-com-style market reckoning
“AI, same thing. There's gonna be a reckoning. There's going to be, there's a bunch of stupid companies out there or people that aren't operating in the right way.”
Chris Degnan Feb 26, 2026 ▶ 19:18 Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
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