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.

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why aren't all 62 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 5 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 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)
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)
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 Open · timeframe Dec 2026
Degnan predicts Snowflake's enterprise software IPO record will be broken in 2026
“I'm sure someone will break it this year because there's companies that have much more revenue than we did, but the largest IPO software IPO ever and enterprise software IPO ever.”
Chris Degnan Feb 26, 2026 ▶ 13:27 Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
Prediction Open · timeframe Dec 2035
Varanasi: Networking industry will move to square-footage pricing within 5-10 years
“I think now the rest of the industry will move there in the next five, 10 years is some scribbles and notebooks of me and Sunil where we came up with this.”
Anil Varanasi Dec 10, 2025 ▶ 16:34 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
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)
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)
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
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)
Prediction Open · timeframe Mar 2034
Virtual AI representatives will not replace human salespeople within ten years
“So I don't think they're going to go away. I mean, people are like, oh, can a virtual rep call you and sell you something? It's like, I'm not going to pick up the phone for what the next 10 years, but certainly make their work much more efficient.”
Eilon Reshef Mar 28, 2024 ▶ 38:39 A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong)
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)
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)
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 Open · timeframe Sep 2028
Siroker: Thousands of multi-billion-dollar vertical LLM application companies will emerge
“There's whole categories of companies that are going to be cat, you know, Category defining independent successful big public multi-billion dollar companies that are just applications of large language models in a specific domain for a specific user with a gre…”
Dan Siroker Sep 14, 2023 ▶ 42:55 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
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)
Prediction Open · timeframe Jun 2033
Seshan predicts every public company will require carbon accounting in 10 years
“In 10 years, every public company will need to do some level of carbon accounting and have a decarbonization plan to underscore that.”
Tara Seshan Jun 22, 2023 ▶ 31:31 Lessons from Stripe on adding new products | Tara Seshan (Watershed, Stripe)
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)
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)
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)
Prediction Not checkable as stated
Younis: Robotaxi and passenger car autonomy strategies will converge
“There is a ever increasing view that Actually, the strategy of a robotaxi and the strategy of a passenger car autonomy are going to collapse in China. It's showing that more and more.”
Qasar Younis Aug 1, 2025 ▶ 35:52 Inside the ex-YC partner’s $15B self driving car company | Qasar Younis
Prediction Not checkable as stated
Schillace: Durable AI value will accrue to trusted personal data holders
“So that's kind of where that durable value will wind up being, I think, over time. It's kind of the holders of the data and the companies that we can trust to, you know, hold that data and trust to give us the right answers are probably where their value is.”
Sam Schillace Jun 6, 2024 ▶ 35:30 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)
Prediction Not checkable as stated
Winters: GOAT will probably stay sneakers-only, limiting its growth
“It probably always will be a sneaker marketplace, and that will limit ultimately how big that company could get.”
Casey Winters May 30, 2024 ▶ 41:30 How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)
Prediction Not checkable as stated
Habib: Unequal AI access will cause 100x more inequity than language barriers
“Being able to use AI or not, Is likely to create a hundred X more inequity in society than all of us speak in different languages.”
May Habib Feb 29, 2024 ▶ 4:45 Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)
Prediction Not checkable as stated
Masad: Most Replit revenue will come from Teams and Enterprise plans
“We're kicking off a more of a sort of a teams enterprise plan, and we already have early customers there. And so I think that's where the majority of revenue over the next few years will come.”
Amjad Masad Feb 15, 2024 ▶ 32:08 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
Prediction Not checkable as stated
Masad: Software engineers in five years will still manually type code
“Their role, if I, you know, go to the future five years in the future, they're still going to have some kind of code editor, and they're going to still have AI all over the place. They're going to have AI chat GPT, they're going to be talking to different AIs,…”
Amjad Masad Feb 15, 2024 ▶ 38:49 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
Prediction Not checkable as stated
Blank predicts the Tesla Cybertruck will be another Model X-style misstep
“And I think the Cybertruck will be another Model X”
Steve Blank Dec 21, 2023 ▶ 43:58 Mastering modern entrepreneurship | Steve Blank (Author of The Four Steps to the Epiphany)
Prediction Not checkable as stated
Siroker: Highly paid hourly knowledge work like legal tasks will likely disappear
“I do think things like white collar knowledge work that is high paid, lawyers being one of them, is probably a good area. I think anything where today people are paying a lot of money and people are being paid by the hour that a machine could do as better, in …”
Dan Siroker Sep 14, 2023 ▶ 49:41 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
Prediction Not checkable as stated
Elliott-McCrea: Engineering teams could shrink within five years
“I think that over the next 18 months to three years, I actually don't think we'll see substantially different changes, but over the next five years, I could see teams actually getting smaller again.”
Kellan Elliott-McCrea Aug 17, 2023 ▶ 10:35 How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox)
Prediction Not checkable as stated
Elliott-McCrea: The tech industry faces a wave of disappointing internal platforms
“And one of the places where we see this really becoming a problem right now, and I think this is downstream of us all having so much success using Amazon, is that we really see the rise again of internal platforms and teams taking dependencies on, on these int…”
Kellan Elliott-McCrea Aug 17, 2023 ▶ 31:11 How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox)
Prediction Not checkable as stated
Weiss: Next-gen product-led SaaS companies will reach $10B within a decade
“And then I think kind of the next generation of companies like notion air table and so on, you know, these companies are all early on in their life cycle. I think give it another decade. And I think, you know, the companies that are a billion or two billion mi…”
Noah Desai Weiss Jul 13, 2023 ▶ 24:18 Lessons from Slack on decision making, product-led growth, and taking big swings | Noah Desai Weiss
Prediction Not checkable as stated
Payne: AI will make organizations flatter and expand managerial capacity
“And so I think that, that that's gonna have huge implications for how organizations are run and your ability to manage teams of humans and AIs is gonna go through the roof. I do think organizations will likely be flatter in the future.”
Christopher Payne Apr 17, 2026 ▶ 44:36 Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
Prediction Not checkable as stated
Epling: AI enables designers to build front-end experiences without technical depth
“Like now with AI, it's like hopefully going to get like, it's just getting more and more easier for people to do that without all that technical expertise.”
Jeremy Epling Mar 19, 2026 ▶ 1:02:11 The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)
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