AI

also referred to as: ais

41 statements across 28 episodes · 14 bullish · 7 bearish · 28 people on the record · first statement Sep 7, 2023 by Ryan Glasgow · across every show →

Everything said about AI, oldest first

Sep 7, 2023 neutral
Prediction Not checkable as stated
AI models will likely never reach total accuracy for subjective feedback categorization
“Cause we will never, it's very unlikely we'll ever get to a hundred percent. And so we'll get, you know, 90, 95, 99. But we'll always make sure that they have the ability to then do that last mile of analysis on their own. And so that's something that we have …”
Ryan Glasgow Sep 7, 2023 ▶ 18:14 A guide to building product in a post-LLM world | Ryan Glasgow and Kevin Mandich from Sprig
Sep 14, 2023 neutral
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)
Oct 26, 2023 positive
Disclosure
Kramer: GitLab positions AI across the entire software delivery lifecycle, not just code completion
“Instead, we stepped back and said, the value of AI on our platform is along every step in the software delivery life cycle. So that will be one piece of it. And customers absolutely need to know we have it and prospects, but we should be telling an end to end …”
Ashley Kramer Oct 26, 2023 ▶ 40:29 The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO)
Nov 2, 2023 bullish
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)
Nov 2, 2023 bullish
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)
Nov 2, 2023 positive
Prediction Not checkable as stated
Software engineering focus will dramatically shift toward product design and UI
“I think a lot of the focus shifts to creativity. Really? The thing that we've been trying to do with the front-end cloud, it accelerates, which is work on your product, work on the user interface, work on the thing that touches another human being and gives th…”
Guillermo Rauch Nov 2, 2023 ▶ 58:02 How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (CEO)
Dec 21, 2023 bullish
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)
Feb 15, 2024
Disclosure
Masad: Replit's seed pitch deck outlined a three-step AI coding plan
“In the first deck that were presented for the seed, random replet, I actually talk about the prospects of AI coming to coding. And so it's like step one, we're going to create this cloud development environment. We're going to make it collaborative. We're goin…”
Amjad Masad Feb 15, 2024 ▶ 12:38 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
Feb 29, 2024 negative
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)
Mar 21, 2024 neutral
Insight
Pilarinos: Products are defined by solved problems, not underlying AI tech
“Even when I think about, like, unblocked and people are like, oh, it's an AI dev tool. And I was like, in the same way it's a Postgres dev tool or a Kotlin dev tool, who cares what technology we're using? It solves a very specific problem for people. It just h…”
Dennis Pilarinos Mar 21, 2024 ▶ 9:44 Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Buddybuild)
Mar 28, 2024 neutral
Assertion Not checkable as stated
Gong initially avoided the term 'AI' because buyers were afraid of it
“It wasn't about AI at the time. I mean, we didn't even use the term AI because people were scared of AI, but it was a lot around more like sense efficiency.”
Eilon Reshef Mar 28, 2024 ▶ 6:56 A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong)
Jun 6, 2024
Insight
Schillace: Incumbents must assume AI blockers get solved and reassess value propositions
“Whatever it is that's in the way of this disrupting your business. Now, like assume that that gets solved. What's your business look like after that gets solved? And then what do you do? What is the thing that your business is about? What value are you deliver…”
Sam Schillace Jun 6, 2024 ▶ 57:21 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)
Jun 6, 2024 neutral
Assertion Supported
Schillace: Physicians paired with AI diagnostic tools perform worse than AI alone
“There's a study I saw a while ago that compared like an AI based system, AI only physician only and AI plus physician An AI plus physician did worse than AI only. The physician kind of dragged the AI down because they didn't trust it.”
Sam Schillace Jun 6, 2024 ▶ 1:02:16 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)
Sep 5, 2024 positive
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
Sep 5, 2024 bullish
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
Dec 5, 2024 neutral
Prediction Not checkable as stated
AI may allow software tools to avoid bloated interfaces by bypassing navigation
“AI bypasses a lot of, like, navigation and complexity. And so we might see kind of like a different set of incentives emerging or kind of tools evolving separately or, you know, tools not feeling the pressure to kind of keep adding to their interfaces and rath…”
Yuhki Yamashita Dec 5, 2024 ▶ 1:02:59 How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO)
Feb 6, 2025 neutral
Opinion
Wang: AI in 2025 is earlier in evolution than early-2010s mobile
“I think there's some interesting parallels, say, to where like AI is today, where I think that AI is probably a few quarters earlier than that, and people still don't know what's, what's going to happen, and there's a lot more change going on, so it's probably…”
Kevin Wang Feb 6, 2025 ▶ 36:49 Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition
Apr 24, 2025 negative
Prediction Not checkable as stated
Enterprise security risks will worsen as personal AI assistants gain broader access
“And that's only going to get worse with AI, because one of the cool things to me about the way we're going with AI is you're going to have your little AI buddy, right, your AI paperclip, for those who remember Clippy, you know, who's going to help you with eve…”
Jeff Shiner Apr 24, 2025 ▶ 45:56 1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)
May 8, 2025 neutral
Prediction Not checkable as stated
Song: In five years, AI's outcome will be viewed as completely obvious
“I've joked with some people right now that regardless of the outcome of AI, it's all going to be completely obvious in five years, right? Like, how can no one tell that, you know, this was all a sham or the greatest thing that we've ever seen, right? And every…”
Rick Song May 8, 2025 ▶ 4:29 From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
May 8, 2025 neutral
Insight
Song: Software engineering is no longer a scarce startup resource
“Engineering used to be a scarce resource. I don't think that's the case anymore. Not to mention, I mean, AI is making everyone be even more capable than ever.”
Rick Song May 8, 2025 ▶ 1:05:15 From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
Jun 19, 2025
Opinion
Cramer: Ignoring AI, most internet and software problems are already solved
“Like that era for me is like when the internet was like very creative, like most problems were not solved. Right. Whereas today ignoring the AI kind of shift. A lot of problems are already kind of solved and there's like, I don't know, it's different.”
David Cramer Jun 19, 2025 ▶ 3:49 How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder)
Aug 6, 2025
Insight
Akhund: Startup iteration cannot succeed without societal-level macro tailwinds
“If you start in an idea with like, You know, if there isn't like a societal level trend that's pushing your kind of space forward, which, you know, I think was true in FinTech in 2017, or it's true in AI now, like it's very hard to iterate around it.”
Imad Akhund Aug 6, 2025 ▶ 14:35 Ignoring Silicon Valley advice to build a $3B fintech unicorn (Mercury)
Aug 14, 2025 bullish
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)
Aug 14, 2025 bullish
Disclosure
Agrawal: Parallel aims to ensure AI agents have permissionless web access
“I think that's the same ethos we're taking at parallel, which is like, I think we want the web to be open, and we want it to be permissionless, and we want it to be a free market, and we want everyone to have access to everything, including AIs. We want AIs to…”
Parag Agrawal Aug 14, 2025 ▶ 15:30 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Aug 14, 2025 neutral
Insight
Agrawal: Building AI products shifts focus from user needs to stochastic feasibility
“People need everything with AI. So that's almost obvious. And now all you really have to zoom into what works and what can work. And where is it going? And you have to look sort of a step ahead and build towards that. And it's a very different art. Like, every…”
Parag Agrawal Aug 14, 2025 ▶ 5:30 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Aug 14, 2025 neutral
Insight
Agrawal: Vibe coding without understanding creates bugs and cleanup work for teams
“I think it's a learned skill to be productive with AI in a real production system. And I've personally, I know my team sees this like vibe coded stuff without deep, full understanding of what I was doing. And my team has had to clean up behind me.”
Parag Agrawal Aug 14, 2025 ▶ 45:23 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Aug 14, 2025
Insight
Agrawal: AI improves at repetitive tasks while human team performance declines
“And then we realized that AI performance, when you have repetitive, well-specified work, Improves. Human performance, when you have to train 50 people to do repetitive work, declines.”
Parag Agrawal Aug 14, 2025 ▶ 23:00 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Oct 23, 2025 bullish
Insight
Stauch: AI lets startups combine product simplicity with enterprise configurability
“AI gives them a chance to compete both on simplicity and user experience and also configurability because you're using AI to set these configurations or maybe achieve value propositions that these other platforms just can't touch.”
Jake Stauch Oct 23, 2025 ▶ 1:19:18 Go hard early: How lessons from Verkada shaped this AI-native IT platform | Jake Stauch (Serval)
Nov 19, 2025 neutral
Insight
Building a best-of-breed enterprise product from scratch takes at least two years
“To build a world-class best of breed product in each of these, it takes time. It takes about two years. Like by the time you say, okay, let's build this thing and you mature it enough that you can sell to our enterprise customer base. It's normally a two year …”
Jyoti Bansal Nov 19, 2025 ▶ 58:27 How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
Feb 26, 2026 bearish
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)
Mar 19, 2026 bullish
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)
Apr 17, 2026 bullish
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)
Apr 21, 2026
Insight
Shiebler: Prior AI experience fails to predict workplace AI tool adoption
“I think that the, where somebody stands in terms of their prior experience at this point right now, given how long of a time that these tools have been around is, is not necessarily a great predictor of how much they'll lean into it and really adopt it.”
Dan Shiebler Apr 21, 2026 ▶ 18:13 Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
May 21, 2026 neutral
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)
May 21, 2026 negative
Opinion
Moreno: AI startup culture unnecessarily glorifies misery and overwork
“I think right now in AI, especially there is this like glorification of misery where people are like, we work 11 hours a day, 500 days a week. And you're like that. Okay. And I didn't read the part of the book that said that you can't have fun.”
Graham Moreno May 21, 2026 ▶ 39:32 Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
May 21, 2026 bearish
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)
Jun 4, 2026 negative
Opinion
Tech companies do not yet know how to market AI effectively
“Frankly right now, people don't yet know how to talk about AI generally. If you drive down one-on-one, everyone's just putting AI on a billboard. They're not even really explaining what you get for it.”
Sheila Joglekar Vashee Jun 4, 2026 ▶ 29:38 Playing it safe with marketing is the riskiest thing you can do | Sheila Joglekar Vashee (Figma CMO)
Jul 24, 2026 bearish
Opinion
Noronha: AI is an anti-incumbent force questioning every software moat
“And AI is such a sea change that I do think it is just this anti-incumbent technology across the board. It is, I mean, this is why we have a SaaSpocalypse now, is it's kind of questioning every software company's moat.”
Jon Noronha Jul 24, 2026 ▶ 25:37 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Jul 24, 2026 bullish
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)
Jul 24, 2026
Insight
Noronha: Early LLM guardrails actively hold back modern AI models
“Now what we're finding, actually, is that all those guardrails we put in place are holding these much more intelligent AIs back. And so we're now in a mode not of even adding functionality, but trying to throw things out, loosen the requirements, and let AI do…”
Jon Noronha Jul 24, 2026 ▶ 16:01 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Aug 27, 2026 positive
Insight
AI makes code an output and dramatically shortens software development lifecycles
“Writing code is not the long pole in the tent anymore, and code is an output now. It's not an input, and the half-life of the, as I will talk about, the typical software development life cycle or the product Development life cycle. The half-life of that is dra…”
Jay Parikh Aug 27, 2026 ▶ 38:45 The most expensive mistake in outsourcing your tech stack | Jay Parikh (EVP CoreAI, Microsoft)
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