planet / 2026-W09 What’s 🔥 in Enterprise IT/VC #487
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What’s 🔥 in Enterprise IT/VC #487
Fear Is Not a Framework: Rip the Band-Aid, Get Lean, Build Through the Noise
Feb 28, 2026
This week should remind all of us of the power of narratives. I’m still blown away that a substack post which was more science fiction than reality from a little known research shop called Citrini took down the whole market. And it was so powerful that well known Citadel Securities felt like it had to write a response .
No one knows the future but fear around AI is at its peak, and any story that plays into it triggers immediate “sell first, ask questions later” behavior. Claude modernizes COBOL? IBM drops 10%.
The Kobeissi Letter@KobeissiLetterBREAKING: IBM stock, $IBM, falls over -10% after Anthropic announces that Claude can streamline COBOL code. It’s becoming increasingly clear how pivotal the times we are in right now truly are.
Nvidia blows out earnings? Stock drops 5%. Even with Jensen saying the agentic AI inflection point has arrived 🤯.
And this is happening even as agents are diffusing faster than we ever thought.
The Transcript@TheTranscript_$NVDA CEO: "Enterprise adoption of agents is skyrocketing. Our customers are racing to invest in AI compute — the factories powering the AI industrial revolution and their future growth."The Transcript @TheTranscript_Nvidia CEO: "Computing demand is growing exponentially — the agentic AI inflection point has arrived." $NVDA: +3% AH9:49 PM · Feb 25, 2026 · 28.5K Views2 Replies · 6 Reposts · 24 Likes
This FT chart captures it perfectly, three possible futures in one image: tech singularity, human extinction, or just steady trend-line growth with a small AI boost.
Adam Carlson@admcrlsnOne of the greatest charts I have ever seen
My bet? The blue line, but with bigger swings up and down. Short-term reactions to AI diffusion will be violent, but long-term we’ll find equilibrium.
So narratives move markets. The real question is: what do you do about it? Jack Dorsey just showed us. He admitted he overhired during COVID, the dual company structure mistake, the complexity bloat from lending, banking, and BNPL.
jack@jackyes we over-hired during covid because i incorrectly built 2 separate company structures (square & cash app) rather than 1, which we corrected mid 2024. but this misses all the complexity we took on through lending, banking, and BNPL. and that we’re now targeting $2M+ grossWill Slaughter @BamaBondsIn 3 years from December 2019 to December 2022, Block $XYZ more than tripled its headcount from 3,900 to 12,500. Unwinding less than half an insane COVID overhiring binge has much more to do with Jack Dorsey's managerial incompetence than whether AI is going to take your job.7:52 AM · Feb 27, 2026 · 461K Views357 Replies · 195 Reposts · 2.37K Likes
Then he used AI as the catalyst to cut 40% of the company - 4,000 people and in one move. Stock up 20% instantly.
This is unprecedented for a public company. And it gives air cover to every incumbent who wanted to do this but was afraid of the market reaction. Whether you believe the AI narrative or not, the market already voted.
Ed Sim@edsimOnly way to reinvent an incumbent workforce and non-AI native company Hurts and is painful, but rip off the band-aid. Cut deep once to rebuild and grow - better than dying a slow death. While not relevant here - one other thought - the harder part no one talks about: be willingjack @jackwe're making @blocks smaller today. here's my note to the company. #### today we're making one of the hardest decisions in the history of our company: we're reducing our organization by nearly half, from over 10,000 people to just under 6,000. that means over 4,000 of you are10:01 PM · Feb 26, 2026 · 3.06K Views5 Replies · 3 Reposts · 19 Likes
What this shows is the time is now. You can’t wait to rip off the band-aid. Incremental doesn’t cut it any more. The world is moving too fast and in order to grow and build, you have to get lean first.
It’s all hard - hard to let people go, hard to rebuild culture, hard to come cannibalize your existing revenue with agent native products. But the alternative is dying slowly.
Shopify gets this. They’ve been infusing AI culture from the bottom up - hiring people who build with agents and letting the org transform from within (watch below).
Ed Sim@edsimThe hardest part for incumbents isn’t adding AI. It’s changing culture. Hire interns who build with agents. Watch the org transform from the bottom up Learn from @fnthawar @Shopify - it worksTBPN @tbpnThere is a massive advantage to hiring young people, and @Shopify was the first company to figure it out, says Pragmatic Engineer's @GergelyOrosz. "Shopify's Head of Engineering @fnthawar told me that he saw something interesting years back. Shopify was so early to AI. They got1:09 PM · Feb 23, 2026 · 1.85K Views2 Replies · 9 Likes
Here’s the thing everyone gets wrong right now. In the AI era, speed wins so there’s a temptation to just keep shipping until you can’t. But sometimes the better move is to go quiet, think deeply about what’s next, invoke 7 Powers thinking , let the haters wonder what you’re up to, and then just boom 🧨.
That’s exactly what founders like Aravind at Perplexity and Howie at Airtable did — took a bit more time to do something exponential rather than just incremental.
Perplexity@perplexity_aiIntroducing Perplexity Computer. Computer unifies every current AI capability into one system. It can research, design, code, deploy, and manage any project end-to-end. 4:27 PM · Feb 25, 2026 · 1.94M Views562 Replies · 913 Reposts · 8.66K Likes
Perplexity was left for dead by many. Then they dropped Perplexity Computer, 19 models, multiagent orchestration from one prompt, schedules jobs, thinks ahead. OpenClaw-like vibes. Multimodel will win. Must watch.
Aravind Srinivas@AravSrinivashttps://t.co/fkS3HEWF8w5:28 PM · Feb 25, 2026 · 761K Views139 Replies · 311 Reposts · 2.96K Likes
Howie from Airtable also shows what it takes. Founders driving the product, burning billions of tokens alone, then launching Hyperagent.
Howie Liu@howietlI've been personally burning through billions of tokens a week for the past few months as a builder. Today I'm excited to announce Hyperagent, by Airtable. An agents platform where every session gets its own isolated, full computing environment in the cloud — no Mac Mini 10:52 PM · Feb 19, 2026 · 13.8M Views335 Replies · 283 Reposts · 3.95K Likes
Guillermo from Vercel nails it - speed is table stakes now. The new edge is taste, quality, and restraint.
Guillermo Rauch@rauchgIf you thought your company's edge was "how fast you ship", you're in for a rude awakening. Everyone can ship fast now. Obviously, not everyone can ship tastefully, with quality and restraint in mind. That's the new edge.7:53 PM · Feb 26, 2026 · 138K Views201 Replies · 207 Reposts · 2.62K Likes
You can’t do any of this while bloated and burning cash. And you can’t be afraid to burn the boats and kill your existing revenue whether its AI or not.
And if you’re a smaller startup and think this doesn’t apply to you…it does. Lean teams ship faster and win. I wrote about this a year ago, and for new agent-native startups this number should be more like 75% or 100%.
Ed Sim@edsimIf Jack can do it so can your older startup. Every board meeting should have a section on how many agents are doing work setting with code and moving to other areas. The time is now. This was what I posted literally a year ago on this topicEd Sim @edsimEvery single board meeting 👇🏼 - this discussion Sames goes for sales/marketing stack Some of larger startups even have a dedicated person just to test out all of the tools and share best practices If this is not a discussion point, then you will be left behind in future10:13 PM · Feb 26, 2026 · 302 Views1 Reply · 2 Likes
This is the beginning. Narratives are powerful, perception equals reality, and whatever the truth is - every single company needs more efficiency. Now.
Control what you can. Ignore what you can’t.
Ed Sim@edsimFear is not a framework. Nuance matters.1:26 PM · Feb 24, 2026 · 769 Views2 Replies · 13 Likes
As always, 🙏🏼 for reading and please share with your friends and colleagues!
Scaling Startups
🤔
Jonathan Lehr@fendienWild stat from StepStone about emerging managers: In 2021/2022 there were 938 managers who raised a Fund I Since then, only 190 subsequent funds have been raised by this group2:14 PM · Feb 20, 2026 · 124K Views27 Replies · 25 Reposts · 404 Likes
if you want the full version of the StepStone AGM for managers and for founders on how VCs and LPs are thinking, read this:
Ed Sim@edsimTen Companies Beat a Decade of Exits: LP AGM Notes Power law on steroids 💪🏻 Extreme concentration in the top names. Euphoria and anxiety at the same time. Notes from a room with 600 LPs and VCs. Read now - New What's 🔥 #486 [whatshotit.vc/p/whats-in-ent…](https://www.whatshotit.vc/p/whats-in-enterprise-itvc-486)
so many 💎 in here from head of Claude Code - “Anthropic has seen a 200% increase in engineer productivity since adopting Claude Code.”
Lenny Rachitsky@lennysanMy biggest takeaways from @bcherny: 1. Coding is now “solved” for most use cases. Boris hasn’t written a single line of code by hand since November, with 100% of his work now authored by Claude Code. At the same time, he remains one of the most productive engineers at Anthropic,Lenny Rachitsky @lennysanClaude Code launched just one year ago. Today it writes 4% of all GitHub commits, and DAU 2x'd last month alone. In my conversation with @bcherny, creator and head of Claude Code, we dig into: 🔸 Why he considers coding "largely solved" 🔸 What tech jobs will be transformed next5:19 PM · Feb 20, 2026 · 332K Views91 Replies · 155 Reposts · 1.29K Likes
more builders coming, time to capitalize
Ed Sim@edsimPost-COVID Miami 🌴 lost some mojo. Just not enough builders. But agents change the game. You don't need 50 engineers. You need 5 killers with agents. Small teams can now build what used to require armies. Let's build off @PalantirTech + others moving here... Miami's builderAI Engineer @aiDotEngineer🏝️ The world’s leading AI Engineering conference is coming to Miami! https://t.co/esPLB2nxOh Join a highly curated room of engineers, founders, and technical leaders building AI systems at @AIEMiami, run by the same world renowned team at @ReactMiamiConf! Learn directly from3:40 PM · Feb 22, 2026 · 13K Views8 Replies · 7 Reposts · 116 Likes
Enterprise Tech
Anthropic wants to be your front door to work. The product is lights out, it has lots of integrations, an ability to build custom enterprise plugins, but just beware.
Ed Sim@edsimThe battle is not to be your software provider. It is to own your work. The real prize is to be the "OS for digital workers" Amazing product 🤯. But remember the more skills you load, the deeper the lock-in and the bigger the token bill. Choose your control plane wisely.Claude @claudeaiIntroducing Cowork and plugin updates that help enterprises customize Claude for better collaboration with every team.5:03 PM · Feb 24, 2026 · 2.41K Views3 Replies · 12 Likes
The vendor-lock in effect can be strong. And even with the ability to use one interface to access and do work across any application, does this just turn these companies eventually into a data repository, the same thing that Satya said last year when he said that every enterprise app is just a front end for a database or CRUD (create, read, update, delete) .
The question that Mark poses is the obvious one - can the traditional SaaS vendors recover from per-seat pricing or find other ways to monetize, pay for agent or data access? Great debate here 👇🏻
Mark Cuban@mcubanIf true and agents work on top of enterprise software, doesn't this eliminate the need for per seat pricing by the software companies ? The coin of the realm for agents and AI in general is tokens. I don't see how enterprise software reconciles this conflict. Particularlyzerohedge @zerohedge"After watching Anthropic's Enterprise Agents briefing event, we have even greater conviction that model providers are unlikely to displace software incumbents and are instead positioning themselves and their agents to be an orchestration layer on top of existing and incumbent4:07 PM · Feb 25, 2026 · 104K Views110 Replies · 9 Reposts · 185 Likes
It’s the customer’s data but seems like the CRUD front-ends will extract their dollars.
Amir Efrati@amir🤖🫰Enterprise apps from Microsoft to HubSpot are plotting to extract fees from the AI agents that access their services.
And Anthropic is not vibe-coding SORs (systems of records) any time soon…
Fiscal.ai@fiscal_aiInvestors: "AI is going to kill Workday" Workday: "We expanded with customers like Anthropic" $WDAY
Akshay from Notion has a super balanced take on this which I 💯 agree with
Akshay Kothari@akothariTo my fellow founders and CEOs, who keep saying “nobody is going to vibe code a CRM or ERP or ,” sharing a few thoughts: 1. You’re right that most companies will not vibe code their system of record. Some startups will experiment (remember Klarna?), but larger2:10 AM · Feb 26, 2026 · 51.4K Views39 Replies · 37 Reposts · 457 Likes
must read - it always starts with early adopters, the developers, but everyday workers should pay attention
“But imo, this is nowhere near “business as usual” time in software.”
Andrej Karpathy@karpathyIt is hard to communicate how much programming has changed due to AI in the last 2 months: not gradually and over time in the "progress as usual" way, but specifically this last December. There are a number of asterisks but imo coding agents basically didn’t work before December6:50 PM · Feb 25, 2026 · 78.8K Views238 Replies · 337 Reposts · 3.1K Likes
case in point
rvivek@rvivekAn engineer at Anthropic wrote a spec, pointed Claude at an Asana board, and went home. Claude broke the spec into tickets, spawned agents for each one, and they started building independently. When the agent is confused it runs git-blame and messages the right engineers in 7:57 PM · Feb 24, 2026 · 991K Views250 Replies · 471 Reposts · 6.37K Likes
massive news - Anthropic as supply chain risk puts it on same footing as Huawei - what are downstream implications?
interesting that Ramp built its own security solutions after having tried Claude’s security product and all of the others from the model providers
Ed Sim@edsimClaude took down the cybersecurity industry on Friday But @tryramp built its own pen test and static analysis solution reminding us the importance of context and having an agent that is customized to your specific environment Agents + context = huge opportunity
Wall Street sold $50B in cybersecurity stocks because Claude launched a security scanner.
Bull Theory@BullTheoryioMASSIVE CRASH IN CYBERSECURITY STOCKS SINCE ANTHROPIC LAUNCHED CLAUDE CODE SECURITY. Over $52.6 billion wiped out in just 2 days. CrowdStrike is down 20%, wiping out $19.6 billion. Palo Alto Networks is down 8.9%, wiping out $11.7 billion. Cloudflare is down 18.5%, wiping out
Meanwhile, Claude is out here helping hackers breach entire governments because someone said ‘bug bounty.’
Maybe we still need those cybersecurity companies after all 🤔
NIK@ns123abc🚨 BREAKING: Hackers Used Anthropic’s Claude to Steal 150GB of Mexican Government Data > tell claude you’re doing a bug bounty > claude initially refused >“that violates AI safety guidelines” > hacker just kept asking > claude: “ok I’ll help” > hack the entire mexican government
🎯 little bit to a torrent
DEGEN NEWS@DegenerateNewsNEW: STRIPE CO-FOUNDER @collision PREDICTS A TORRENT OF AGENTIC COMMERCE IN THE FUTURE, AND THAT AGENTS WILL TRANSACT WITH STABLECOINS ON “REALLY HIGH-THROUGHPUT BLOCKCHAINS” 10:51 PM · Feb 24, 2026 · 76K Views88 Replies · 64 Reposts · 701 Likes
this is percentage of total calls to Anthropic API which means that mostly devs are using now and that the other industries are still lagging - will be interesting to see how fast this makeup changes over time?
Anthropic@AnthropicAISoftware engineering makes up ~50% of agentic tool calls on our API, but we see emerging use in other industries. As the frontier of risk and autonomy expands, post-deployment monitoring becomes essential. We encourage other model developers to extend this research.
agree or disagree?
Tenobrus@tenobrusgigafucked: - grammarly - calendly - miro - retool - webflow - langchain - writer - harvey - glean - expedia - monday fucked: - accenture - intuit - notion - jasper - canva - alphasense - postman - airtable - talkdesk - sierra - zapier - replit - solace probably fucked: -7:05 PM · Feb 22, 2026 · 453K Views299 Replies · 119 Reposts · 3.48K Likes
advantage data, Google - sees 3.2x more of web to train vs. OpenAI - who wins in long run?
TBPN@tbpnCloudflare CEO Matthew Prince says Googlebot sees 3.2x more of the web than OpenAI, and 4.8x more than Microsoft. And he worries this advantage will allow Google to run away with the AI race, with no one else being able to catch them. "For every one page that OpenAI sees, 5:30 PM · Feb 21, 2026 · 39.3K Views22 Replies · 39 Reposts · 387 Likes
Nikesh speaking his own book at Palo Alto Networks but still lots of truth to this…
The Transcript@TheTranscript_$PANW CEO on the impact of AI on cybersecurity: "The LLMs are a net positive and additive to our capability to deliver security.. I'm still confused why the market is treating AI as a threat to at least cybersecurity. I can't speak for all the software because one thing we're3:13 PM · Feb 22, 2026 · 8.16K Views8 Replies · 8 Reposts · 72 Likes
every website and application should also be built for agents first so they can easily discover, understand and use said product/service
Kurt Elster@kurtincStraight from @Shopify's latest partner briefing: - AI agents are pulling the first ~6,000 characters of your product descriptions as their source of truth. - Meta descriptions, SEO titles, theme presentation logic, none of it gets touched. - If your product data isn't7:40 PM · Feb 24, 2026 · 54.4K Views21 Replies · 23 Reposts · 392 Likes
Markets
just be aware - this talk is rising more and more in political circles
Andrew Yang🧢⬆️🇺🇸@AndrewYangMillions of office jobs will evaporate in the next 12 - 24 months. This will be an epic disaster for millions of workers and families. blog.andrewyang.comThe End of the Office2:32 PM · Feb 16, 2026 · 611K Views440 Replies · 349 Reposts · 1.92K Likes
👀 glad the markets bounced back a little…
Shay Boloor@StockSavvyShayTHE SAASPOCALYPSE 2026 SCORECARD SaaS in 2026 is getting repriced from growth engine to plumbing layer in an Agentic AI stack and the YTD damage has been brutal: • $DDOG −15% • $CRWD −17% • $MDB −18% • $ZETA −20% • $SNOW −21% • $SHOP −22% • $PLTR −24% • $ADBE
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nik koblov @koblovinamericawe’ve built an AI pentest agent that’s is continuously and autonomously making @tryramp more secure: https://t.co/CDztiq2D0r12:43 PM · Feb 23, 2026 · 55 Views2 Likes
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