The Ledger

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Opinion
Grinberg: Lacking frontier open-source AI models in the US is embarrassing
“I think it's pretty embarrassing that we don't have frontier open models in the United States.”
Matan Grinberg Jun 13, 2026 ▶ 1:10:33 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Believing a good product sells itself is delusional
“There's a very common Silicon Valley fallacy, which is there's like research is like the pinnacle. And then there's engineers who implement the research, you know, they're not quite there, but you know, they're still great. And then there's sales and marketing…”
Matan Grinberg Jun 13, 2026 ▶ 25:13 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Coding speed and syntax memorization no longer matter for engineers
“And the parts of engineering that become less important are funny enough, the things that the Silicon Valley has really bragged about a lot, which is like, Competition winning or like Olympiad type. Are you like as fast as possible at coding? Are you, do you m…”
Matan Grinberg Jun 13, 2026 ▶ 28:36 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Institutional Math Olympiad track records can be an anti-signal in hiring
“Especially there's some high schools that, like, really focus on, like, you must do the math olympic, like, you must do this, the Amy, to then go to the IMO, and, like, this is the path to success, where actually that's kind of anti-signal, because there it's,…”
Matan Grinberg Jun 13, 2026 ▶ 29:56 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Grinberg: Advocating to slow down AI development is harmful and selfish
“And by saying you want to slow down AI, that's saying like, These people who have relationships with loved ones who have dementia, you're like, no, no, no, sorry, you guys, you gotta maintain that relationship for a little bit longer. We're scared. We don't kn…”
Matan Grinberg Jun 13, 2026 ▶ 42:19 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Grinberg: Ivanka Trump provides better hands-on help than traditional VCs
“She is genuinely so kind, so intelligent, and like, people just in, throughout tech, throughout the world, really love her, and for good reason, and she has an incredible network. She's so generous with her time. Like, there is, like, kind of dirty work invest…”
Matan Grinberg Jun 13, 2026 ▶ 1:01:50 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Software requiring forward-deployed engineers to close deals is a bad product
“If we need FDEs to make the product work, we have a shit product. Like, the point of FDEs should be accelerate and get them consuming faster. If you're putting in FDEs, because that's the only way you'll get a deal done, I'm sorry, my friend, you have a shit p…”
Matan Grinberg Jun 13, 2026 ▶ 1:15:15 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Grinberg: AI labor displacement warnings are disingenuous hype designed for mega-fundraising
“I think that has been not only like disingenuine and wrong, but it's like really hurt the psychology of a lot of people, developers, like just people in the world. Does AI a disservice? Does the world a disservice? Because this is again, talking about the use …”
Matan Grinberg Jun 13, 2026 ▶ 1:21:31 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Usage of frontier AI models may contract in the short term
“We might see a short-term contraction of usage of the very frontier models.”
Matan Grinberg Jun 13, 2026 ▶ 17:57 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2029
Grinberg: Kirkland's $500M AI push will ultimately benefit legal AI vendors
“Now, I actually think this is good for Harvey because it's nothing like trying to do something yourself to make you realize, oh, shit, this is actually really difficult. This doesn't actually matter for us to have the in-house ability to build this ourselves. …”
Matan Grinberg Jun 13, 2026 ▶ 7:26 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
Grinberg: AI frontier models will remain roughly equivalent to each other
“The bare case against factory is if one model provider gets significantly better than all of the others. So basically I think a key thing for us is that all the models are going to be roughly as good as each other.”
Matan Grinberg Jun 13, 2026 ▶ 12:05 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Enterprises will realize frontier AI models are unnecessary for most tasks
“A lot of enterprises will realize so many of the tasks that we're doing, we don't need the very frontier to do it. Like, and we can do it much faster, much cheaper with these open models.”
Matan Grinberg Jun 13, 2026 ▶ 14:41 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Enterprises Entering 'AI Hangover' Over High Costs and Unclear ROI
“Phase three is the hangover, where you go and look at the bill, and it's like, oh my god, we are spending so much. I have no idea what the ROI is. Does this, like, is this helping our business? That's where a lot of these companies are at now”
Matan Grinberg Jun 13, 2026 ▶ 17:09 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Assertion Not checkable as stated
Grinberg: Enterprise wasted hundreds of thousands monthly on trivial Opus queries
“One of the CIOs I was speaking with realized we've been spending hundreds of thousands of dollars per month on people asking Opus 4.8 questions like, Hey, how's it going? Like, what should, what are my macros from the food I ate today? Like, what's the weather…”
Matan Grinberg Jun 13, 2026 ▶ 17:28 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Individual AI token spend will range from 0% to tens of thousands % of salary
“I actually think it can be as low as zero percent for some individuals, and it can be as high as like 1010 of thousands of percent for some individuals.”
Matan Grinberg Jun 13, 2026 ▶ 20:23 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2029
Grinberg: Median developer AI token spend will match salary within three years
“I would say order of magnitude will probably be comparable to salary.”
Matan Grinberg Jun 13, 2026 ▶ 22:03 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Assertion Not checkable as stated
Grinberg: Open-source models can execute 80% to 90% of frontier AI tasks
“Probably, like, 80 to 90%. It's typically the planning that really needs the frontier models.”
Matan Grinberg Jun 13, 2026 ▶ 22:19 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: AI startups ignoring sales will fail when market gravity returns
“I think that the reality is it will come to haunt some of these companies one day, because I think right now where there's a gold rush and everyone's like desperate to sign, you know, and get more tokens from these people, it's easy. They're kind of like, in m…”
Matan Grinberg Jun 13, 2026 ▶ 26:36 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Software engineers will build automated factories rather than write code
“The future of software development is where these organizations, instead of having engineers, That build the software. They're going to have engineers that build the factories that build their software.”
Matan Grinberg Jun 13, 2026 ▶ 39:28 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: AI infrastructure is not in a long-term bubble
“Maybe there's like some short term blips, but like long term, absolutely not. Like not even close. I think there might be similar corrections to like this thing at Uber, Where, oh, we were going a little haywire. We weren't allocating it appropriately. And the…”
Matan Grinberg Jun 13, 2026 ▶ 44:37 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Matan Grinberg: Founders should accept valuation discounts for Sequoia Capital
“So generally, yes. I mean, they're the best firm.”
Matan Grinberg Jun 13, 2026 ▶ 58:07 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Major security incidents from AI code will hit within two years
“I think there are probably going to be in the next couple years some pretty big incidents that occur because of,”
Matan Grinberg Jun 13, 2026 ▶ 1:08:27 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
Grinberg predicts at least four AI companies will achieve frontier model parity
“There was a brief period of time where I thought it might be just one or two companies that run away with being kind of the frontier and the best. What seems pretty clear to me is it's probably going to be at least four that are going to probably be approximat…”
Matan Grinberg Jun 13, 2026 ▶ 1:24:01 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Future AI tools will enable anyone to build anything
“The world going forward, there is going to be nothing that no one can build.”
Matan Grinberg Jun 13, 2026 ▶ 8:35 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: The age of the polymath is returning to tech
“The age of the polymath is back.”
Matan Grinberg Jun 13, 2026 ▶ 32:29 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: User ego drives unnecessary reliance on frontier AI models
“There's kind of an ego thing, where, oh no, no, the work that I'm doing, only a frontier model could handle. Oh, this mere open model can't deal with the work that I'm dealing with. And this is like, even admittedly, when I first started switching over, I'd be…”
Matan Grinberg Jun 13, 2026 ▶ 15:15 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Disclosure
Grinberg: Dozens of Factory clients privately capped employee AI spend
“What's happened with Uber publicly has happened privately with a lot of customers of ours.”
Matan Grinberg Jun 13, 2026 ▶ 19:19 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Top AI-era engineers will embrace sales and marketing
“The best engineers are going to be the ones that don't see sales and marketing as dirty work, but as again, an important part of the product, because as an engineer, you're no longer, you know, just your job is ship feature.”
Matan Grinberg Jun 13, 2026 ▶ 27:46 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Developer experience investments yield 10x to 100x impact with AI agents
“These are all things that the best organizations at like developer experience would invest a lot of resources in, but they would do it because it makes it easier for engineers to work, easier for them to onboard. But the impact of doing that well is just like …”
Matan Grinberg Jun 13, 2026 ▶ 37:34 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Matan Grinberg: AI Labor Displacement Is Short-Term; Long-Term Reallocation Is Net Positive
“Short term, yes. Long term, no. Short term, yes, because it's just a shock to the system where, you know, there are all these big layoffs that are happening that are pretty aggressive, and, you know, these are 1010 of thousands of people that had a job that no…”
Matan Grinberg Jun 13, 2026 ▶ 40:29 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
Grinberg: Dementia will eventually be solved using AI and software
“Dementia is kind of a go-to example where everyone understands how big of a deal that is. That is something that can be solved with better AI and better software. Like it's a matter of time. Like we will solve it and we can solve it.”
Matan Grinberg Jun 13, 2026 ▶ 42:08 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: AI models must be decoupled from applications for optimal incentives
“So I think what is necessary for the best outcome for the consumers Is going to be models that are separate from the applications. You, as a consumer, do not want to use applications that are provided for you by the same people that are giving you the model, b…”
Matan Grinberg Jun 13, 2026 ▶ 1:03:02 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Assertion Not checkable as stated
Grinberg: Every Enterprise CIO Demands Model-Agnostic AI to Avoid Lock-In
“Every CIO I speak to is really keenly aware of, we cannot, you know, throw our lot in with just one model provider. We're gonna need to be agnostic.”
Matan Grinberg Jun 13, 2026 ▶ 1:05:04 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Enterprise AI Coding Governance Will Be Controlled by Engineers, Not Non-Technical Staff
“I think it would be ill-advised if they were to try and go to the niche of non-technical people writing code for code sake, because I think that is going to be run by, like, if you're going to need enterprise controls over who has access to what databases and …”
Matan Grinberg Jun 13, 2026 ▶ 1:07:30 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Matan Grinberg: Europe is unlikely to catch up on frontier AI labs
“Probably on the, like, frontier model lab side.”
Matan Grinberg Jun 13, 2026 ▶ 1:10:47 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
What-if
Grinberg: Nuclear power would have given Europe an AI energy advantage
“In Europe, I mean, it's a, it's tough. I think that there were some, there was some good positioning that Europe had, you know, a few years ago, a few decades ago with nuclear that I think hasn't been, you know, delivered on as much as of late, but that would …”
Matan Grinberg Jun 13, 2026 ▶ 1:12:38 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Mandating extreme hours or office beds signals poor hiring
“I think you are doing a bad job on hiring if you need to, like, mandate certain crazy hours or you need a bed in the office.”
Matan Grinberg Jun 13, 2026 ▶ 1:16:37 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Grinberg: Anthropic is a safer IPO investment than OpenAI due to volatility
“In my mind, the answer here is, I think they're approximately equivalent. Like, to me, it doesn't really matter. The biggest reason that affects like the EV is like volatility of the company. That's the only, like, cause I think from the business perspective, …”
Matan Grinberg Jun 13, 2026 ▶ 1:20:46 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Top companies will manage teams like Seal Team Six
“We will see the best companies treat teams more and more like seal team six or like professional athletes.”
Matan Grinberg Jun 13, 2026 ▶ 0:48 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Token, dollar, and headcount allocation will dominate C-suites within 24 months
“This resource allocation problem of token, it's not just tokens, it's like dollars, it's tokens, it's people. This is, I think, going to be the thing that over the next 24 months, every C-suite is going to be thinking about.”
Matan Grinberg Jun 13, 2026 ▶ 5:08 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Corporate bloat was caused by evaluating teams on intermediate metrics
“I think part of the reason why so many organizations got so bloated is because we were in a period of time where everyone was focusing on intermediate metrics.”
Matan Grinberg Jun 13, 2026 ▶ 6:11 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Value Accrual in AI Is Dynamic, Not Static
“The reality is value accrual is a time dependent phenomenon. So like, it's not like there is one person who steady state gets all of the value. That's not how it works.”
Matan Grinberg Jun 13, 2026 ▶ 10:40 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
Grinberg: Discrete AI model releases will be replaced by continuous updates
“I think eventually we'll stop seeing them as model releases, and they'll feel more continuous.”
Matan Grinberg Jun 13, 2026 ▶ 13:10 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Standardizing AI token spend targets across all engineers is a mistake
“In fact, I would argue that if your org has a standard number where it's like, we want every engineer to be at this percent of their salary and token use, you're probably painting with way too wide a brush.”
Matan Grinberg Jun 13, 2026 ▶ 21:45 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Not checkable as stated
Grinberg: Software engineers will increasingly transition into full business outcome GM roles
“I think, so it's starting to exist more and more, but I think it's kind of this like GM or general manager Like role for someone who used to be an engineer, where basically you own end to end an outcome that is not just a shipped feature, but like a business o…”
Matan Grinberg Jun 13, 2026 ▶ 31:11 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
Grinberg: Engineers won't manually write documentation or release notes in five years
“Five years from now, it's going to be like, oh my God, I cannot imagine, cannot believe that these people that get paid so much money spent hours of their time doing this. I think that's something that, you know, we definitely won't do.”
Matan Grinberg Jun 13, 2026 ▶ 35:58 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Grinberg: AI documentation equalizes software docs and reduces Stripe's documentation edge
“Yes. But I think Stripe has plenty of places that they can differentiate. And I think it's a better world where everyone has documentation as good as Stripe's.”
Matan Grinberg Jun 13, 2026 ▶ 36:12 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Human behavior change is the top bottleneck for enterprise AI
“I think the biggest bottleneck by far working with all these organizations is the human side of it. It's just like behavior change.”
Matan Grinberg Jun 13, 2026 ▶ 44:58 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
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