What’s 🔥 in Enterprise IT/VC #500

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What’s 🔥 in Enterprise IT/VC #500

The End of the AI Subsidy Era and the Rise of ROI Per Workflow

May 30, 2026

First, I wanted to thank all of you for embarking on the What’s 🔥 journey with me as we just hit issue #500 🤯!

That’s 500 weeks in a row. So many times I was wiped out, sick, traveling, or just exhausted, but I kept plugging away because writing this newsletter has been invaluable for me personally.

It started simply as notes to myself shared with friends, and over time it evolved into something much more meaningful. I now find it to be a cathartic way to reflect on the week, synthesize my thoughts, connect trends, and think longer term about where the world and technology may be heading.

Thank you all for reading, sharing, and being part of this journey. Here’s to many more issues ahead!

Now back to the regularly scheduled programming…

Ok all, let’s not overreact to every single AI related news announcement. This week it was all about tokenomics and insane costs. As always the reality is more nuanced.

First, here’s what kicked it off…

Ed Zitron@edzitronUber’s COO has said that it’s getting “harder to justify” its AI costs because there was no way to show a link between AI spend and any meaningful increase in useful features. This is the first time I’ve seen a company say this directly. [businessinsider.com/uber-coo-andre…](https://www.businessinsider.com/uber-coo-andrew-macdonald-ai-token-spending-harder-justify-2026-5) 4:01 AM · May 26, 2026 · 2.78M Views357 Replies · 5.04K Reposts · 28.2K Likes

But people tend to overreact to headlines without digging deeply enough into the underlying context, which is why I agree with Simon here 💯.

Simon Willison@simonwI'm suspicious of that that whole story about Uber blowing their AI budget and being disappointed in the results - I dug into it and it appears to have been built on very shaky foundations 3:57 AM · May 29, 2026 · 34.6K Views35 Replies · 36 Reposts · 404 Likes

Sure, there is so much wasted spend especially when you have token leaderboards versus being focused on hard ROI.

Gergely Orosz@GergelyOroszI can now probably say this: Two months ago, inside Anthropic someone suggested building a token leaderboard. A heated internal debate followed and the decision was made to never ever do it… because several people inside Anthropic simply thought ahead of the consequencesTechmeme @TechmemeSources: Amazon has shut down an internal leaderboard that tracked employees' use of AI tools after workers tried to boost their scores with needless tasks (@rafeuddin_ / Financial Times) (Visit Techmeme dot com for the link and full context!)8:25 AM · May 29, 2026 · 92.6K Views30 Replies · 48 Reposts · 927 Likes

Measuring tokens consumed is measuring effort, not output, and it’s the same mistake enterprises made a decade ago measuring lines of code or hours logged. You get what you measure, and if you measure tokens, you’ll get engineers finding creative ways to burn them.

Here’s the real story. We’re entering Phase 2 of enterprise AI.

Phase 1 was the subsidy era, where frontier labs aggressively absorbed costs to drive adoption and enterprises experimented freely because tokens were effectively subsidized.

Phase 2 is the consumption era, where vendors charge real money, CFOs ask harder questions, and procurement re-enters every renewal discussion.

The winners from here will:

Token leaderboards are a Phase 1 artifact.

ROI per workflow is the Phase 2 metric.

Ed Sim@edsimagreed - overblown but... reality is we're entering the next phase where enterprises fully aware of costs as vendors charge more for consumption and subsidy era is over We'll see much more in way of intelligent routing to models, more investment in open source for hybridSimon Willison @simonwI'm suspicious of that that whole story about Uber blowing their AI budget and being disappointed in the results - I dug into it and it appears to have been built on very shaky foundations11:55 AM · May 29, 2026 · 3.58K Views6 Replies · 4 Reposts · 17 Likes

This reminds me a bit of how overblown the “Claude Mythos destroys cybersecurity” narrative became earlier this year. Immediate market reactions tend to overshoot reality as Palo Alto Networks, for example, has already bounced back in stock price!

Gary Marcus shares a few more takes from this tokenomics discussion.

Gary Marcus, MIT PhD and NYU Professor Emeritus@GaryMarcusHot take on what comes next, after the sudden decline of tokenmaxxing: - OpenAI will struggle - with the decline of tokenmaxxing Anthropic will struggle (aside from this quarter) to make a profit - Google will catch up to Anthropic - some Chinese companies might, too - LLMs4:46 AM · May 29, 2026 · 74.2K Views79 Replies · 121 Reposts · 1.1K Likes

The important point many are missing from Gary Marcus’ comments is that he’s not saying agents don’t work. He’s saying enterprises will become more disciplined in how they measure ROI and deploy AI systems. The conversation shifts from token consumption to business outcomes.

And despite all the noise, token consumption itself is still exploding.

The real question is: where does the value accrue?

Regardless of routing strategy, GPU and compute demand still compounds. Look at this chart from Goldman Sachs showing insane token growth in the next few years at 24x!

Sierra recognized this shift early by focusing on outcomes-based pricing rather than token-based pricing.

Sierra@SierraPlatformApplied AI is about jobs to be done, not tokens to be consumed. Token usage may be a reasonable short-term proxy for adoption. But long term, success comes from outcomemaxxing, not tokenmaxxing. It's why we took an early bet on outcomes-based pricing: pay for the value2:14 AM · May 28, 2026 · 105K Views12 Replies · 15 Reposts · 295 Likes

What’s becoming increasingly clear is that the best enterprise AI companies are already building:

Some are even deploying open-weight models on-prem for deep customization and control before selectively invoking frontier models when necessary. Harvey, for example, has used its insane growth to build a powerful proprietary data flywheel and is showing how this gets done.

Harvey@harveyWe're partnering with @trajectorylabs to bring sovereign continual learning to legal AI with NVIDIA Nemotron models. Continual learning allows agents to improve over time from feedback on their work: every redline refines the next draft. Open-weight models offer fullTrajectory @trajectorylabsWelcome to Day 2. Yesterday, we showed the broader work we're doing with the pioneers of continual learning. Today we'd like to deep dive on one: how we post-trained an open model for legal work, in partnership with @Harvey. We've built a platform where production data is the5:19 PM · May 29, 2026 · 40K Views7 Replies · 18 Reposts · 169 Likes

This is exactly where proprietary enterprise context becomes incredibly valuable.

As open-weight models improve, we’ll increasingly see more and more software vendors and enterprises train and customize models directly on private internal data, routing across a mixture of open and frontier systems depending on sensitivity, latency, and economics.

That’s exactly what Larry Ellison has been talking about.

Vivek Sen@Vivek4real_LARRY ELLISON: AI IS RAPIDLY COMMODITIZING BECAUSE MOST MODELS ARE TRAINED ON THE SAME PUBLIC INTERNET DATA. THE REAL COMPETITIVE EDGE ISN’T THE MODEL ANYMORE — IT’S ACCESS TO EXCLUSIVE, PROPRIETARY DATASETS. THAT MAY BE THE ONLY MOAT LEFT. 1:04 AM · May 29, 2026 · 3.08M Views380 Replies · 594 Reposts · 5.47K Likes

LFG - it’s still early!

As always, 🙏🏼 for reading and please share with your friends and colleagues!

Scaling Startups

🎯

Charlie Marsh@charliermarsh“Someone else already tried”, “a lot of people are probably working on it already”, etc., are bad reasons not to do something10:11 PM · May 28, 2026 · 84.3K Views48 Replies · 81 Reposts · 1.32K Likes

founder advice I strongly concur with

Gokul Rajaram@gokulrFounders: don't make the same mistake that many made in 2021-22. Do not sacrifice control at the altar of valuation. In other words, always choose a clean termsheet without structure over a higher valuation with structure (eg: non-standard liquidation preference). As someone11:27 PM · May 26, 2026 · 16.7K Views14 Replies · 10 Reposts · 186 Likes

fun time, lots of parallels between early days of NY and Miami now except timeline is significantly accelerated - listen in or watch

physical AI

Peter Walker@PeterJ_WalkerThere's never been a better time to build a startup based in atoms not bits. Hardware here contains many sub-sectors, but robotics and defense-related hardware are the fastest growing. 5:34 PM · May 24, 2026 · 2.12K Views5 Replies · 6 Reposts · 30 Likes

got to admire the all-in nature of Masa!

MotherCabriniPreys@MotherCabriniNY"SoftBank borrowed against its OpenAI shares to buy more OpenAI shares" Sweet JaysusHedgie @HedgieMarkets🦔New Bloomberg reporting reveals SoftBank has committed roughly $60 billion to OpenAI, and internal advisors who questioned the size of the bet say founder Masayoshi Son shut them down. Former SoftBank insider Habib Imam described the position as "a bet on a worldview about AGI"4:50 PM · May 26, 2026 · 315K Views34 Replies · 246 Reposts · 2.52K Likes

Enterprise Tech

the skeptical view of agents and AI has been all the rage this week…

Sir Escanor (𝘏𝘰𝘱𝘪𝘶𝘮 𝘚𝘭𝘢𝘺𝘦𝘳)@EscanorReloadedCEOs are quietly realizing the AI replacement plan has a problem. Two problems, actually. One: the token costs for running AI agents are now exceeding what they were paying the employees they fired. Two: when the tokens run out, the AI stops. Just stops. No continuity. No2:07 PM · May 27, 2026 · 2.24M Views1.16K Replies · 11.4K Reposts · 44.6K Likes

remember Facebook for Work, its enterprise play - well that didn’t work out but now its back with its own FDEs but who would want theirs?

Techmeme@TechmemeMemo: Meta plans to embed engineers and product managers within large corporate customers as part of a new Enterprise Solutions unit to help deploy its AI tools (@jyoti_mann1 / The Information) (Visit Techmeme dot com for the link and full context!)3:35 AM · May 28, 2026 · 24.4K Views1 Reply · 2 Reposts · 35 Likes

as I’ve written before - What’s 🔥 #498, larger companies are not only using a constellation of models (SOTA, open source) for token costs but also for creating differentiation - why give my employees brains to a model when I can have my own - this will be a bigger and bigger opportunity over time and also may offset billable hours to outcome based pricing?

Financial Times@FTKirkland & Ellis to spend $500mn building its own AI technology ft.trib.alKirkland & Ellis to spend $500mn building its own AI technology4:38 AM · May 28, 2026 · 33.8K Views8 Replies · 18 Reposts · 76 Likes

seems likes its working…

Cognition@cognition1/ We’ve raised over $1B at a $26B valuation, led by @Lux_Capital, @generalcatalyst, and @8vc. Our enterprise usage has grown >10x since the start of this year, and our run-rate revenue grew to $492 M. We launched Devin two years ago as the first AI software engineer. Since 3:39 PM · May 27, 2026 · 262K Views105 Replies · 129 Reposts · 1.59K Likes

🎯

Aaron Levie@levieCEOs are uniquely prone to AI psychosis because they’re sufficiently distant from the last mile of work that still has to happen to generate most value with AI. So when they play with AI, they see the happy path results, often not considering the next 10 or 20 things that haveMichal Malewicz @michalmalewiczCEOs are the most delusional about AI. Detached from reality.4:14 PM · May 24, 2026 · 164K Views133 Replies · 181 Reposts · 1.77K Likes

🤯 insane growth for inference providers who don’t own their own GPUs - thinner margins but slick software on top to optimize inference, etc - all of them growing 📈

Lin Qiao@lqiaoWe just hit a major milestone — @FireworksAI_HQ passed $800M annualized run rate and reached 4x revenue growth, apart from Cursor, in Q1. We invite curious and courageous minds to join us and define new frontiers of specialized intelligence!5:17 AM · May 27, 2026 · 38.2K Views43 Replies · 15 Reposts · 421 Likes

no surprise Fireworks on this list - great list (congrats Keycard, a boldstart port co) and solid deck in this thread - worth a read

Redpoint@RedpointThe Redpoint InfraRed 100 is now live. These are the companies building the infrastructure that powers everything happening in AI right now, from world models and agent runtimes to the sandboxes, databases, and security tools agents depend on. Congratulations to this year's 1:39 PM · May 27, 2026 · 37.5K Views7 Replies · 35 Reposts · 150 Likes

edge inference coming in a big way - Apple will finally flex its muscles with announcments at its WWDC (The Information)

I spoke about this a couple years ago on this pod!

I feel this every day

Cory House@housecorI run 1-2 agents at once. Rarely more. Why? Because code generation isn’t the bottleneck. Great read.7:49 PM · May 29, 2026 · 31.6K Views7 Replies · 12 Reposts · 148 Likes

why we led the inception round for Generalist AI 2 years ago and investing more in the stack - stay tuned 👀

arian ghashghai@arian_ghashghairobotics is inherently about hardware, however I'm meeting more and more founders who want to find a software (or just non-hardware) business to build for robotics. thoughts: > software is behind hardware (so this realization is correct, but not unique), and "robot brain" is6:02 PM · May 22, 2026 · 108K Views83 Replies · 42 Reposts · 540 Likes

no thank you - but yes, there is no reddit for robotics data

Polymarket@PolymarketNEW: Startup offers free NYC apartment cleanings in exchange for recording the job to generate robotics training data.8:23 PM · May 28, 2026 · 136K Views76 Replies · 63 Reposts · 1.14K Likes

not a surprise but consulting is going to rapidly change

Bearly AI@bearlyaiMcKinsey is “under pressure from clients” to change its business model due to AI. Instead of tying fees to hours worked —AI can do analysis, diagnosis and reports in minutes — clients want “to tie its fees to outcomes achieved” (eg. lower costs, higher revenues, increased 10:04 PM · May 24, 2026 · 198K Views61 Replies · 148 Reposts · 1.03K Likes

🤣

Brandon Carl@brandonjcarlEarnings Before Tokens 6:43 PM · May 28, 2026 · 1.49M Views52 Replies · 731 Reposts · 6.06K Likes

Markets

reminder - software not dead yet - market overreacted to every SaaS co from frontier lab fear but many have bounced back

Jason ✨👾SaaStr.Ai✨ Lemkin@jasonlkOk the SaaSpocolypse is now really, truly over. All the loses, in the aggregate, have been pared. Public software stocks are finally back in the green for the year. After big runs from Snowflake, Twilio, Okta, Datadog, ServiceNow, etc. we're back. Salesforce is up 9% today! 5:45 PM · May 29, 2026 · 3.65K Views1 Repost · 20 Likes

from Jamin Ball - Palo Alto back at 15.9x forward with 29% NTM revenue growth and Datadog at 16.9x with 23% revenue growth