What’s 🔥 in Enterprise IT/VC #490

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What’s 🔥 in Enterprise IT/VC #490

The Law of Agent Cannibalism - why every company is becoming every company

Mar 21, 2026

On my way to SF for another fun and intense week at RSA. So looking forward to it with our annual Sunday night kick off event with portfolio companies Keycard AI, Surf AI, and Gain Security and also pumped to be a cosponsor for the Piper Event on Monday with Nikesh from Palo Alto Networks as the keynote speaker.

For the Sunday night kickoff event, we have 3 spots open for those interested…click below to get on the list…

Cover Image for RSA 2026 Kickoff Reception with Boldstart, Keycard, Surf AI and GainSecurity

In advance of the week, I wanted to share a couple of big launches from the portfolio with:

Needless to say, these are massive problems CISOs are facing as agents proliferate across their enterprises. I look forward to going deeper on the sights and sounds of RSA in next week’s issue.

But here’s the tension: we simply have way too many cybersecurity companies right now. And it’s about to get worse. Every platform vendor is adding security features. Every security vendor is expanding into adjacent categories. The capital pressure alone forces it - raise at a massive valuation and you must go multiproduct to justify it. And the cost to do so has never been lower.

Zooming out, this isn’t just a cybersecurity problem. When the cost to add a new feature or go multiproduct is near zero, everyone ends up competing with everyone else. Lovable went from app builder to data science, marketing, and decks overnight.

I’m calling it The Law of Agent Cannibalism 👇🏻

Ed Sim@edsimfantastic release! We now have The Law of Agent Cannibalism: Get super successful → raise at a huge valuation → now you must expand into everything. Lovable went from app builder to data science, marketing & decks. Everyone’s eating everyone else’s lunch. When shipping newAnton Osika – eu/acc @antonosikaIntroducing Lovable for more general tasks. Lovable has always been for building apps. Today it also becomes your data scientist, your business analyst, your deck builder, and your marketing assistant. This is a big step toward what Lovable is becoming: a general-purpose5:42 PM · Mar 19, 2026 · 13.1K Views12 Replies · 5 Reposts · 43 Likes

And as every company goes multiproduct, here’s the enterprise consequence: why sign up for a 3-year contract when an adjacent company is creeping into your vendor’s market?

As carrynointerest puts it:

If you look like Rippling, and you have a very talented group of people like their employees, they can attack so many parts of the HR platform space now that they simply couldn't 3 years ago.

That's a lot scarier than vibe coding, than somebody just whipping up [a clone] and going out with a bunch of cold emails. It's the adjacency threats in the market map. Because now, who's Rippling going to go after?

TBPN@tbpn.@carrynointerest says the rumors that enterprise customers are no longer signing up for 3-year contracts — combined with "adjacency in the market map" — is way more of a threat to software private equity than vibe coding: "The entire basis of software PE being one of the best 8:44 PM · Mar 17, 2026 · 22.9K Views6 Replies · 10 Reposts · 109 Likes

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

Scaling Startups

👀 priced to perfection…those were the days

Brian Chesky@bcheskyAfter YC, Airbnb raised $615k at a $3M post-money valuation. We were the highest valuation in our batch.nikhil @uninsightfulthe default yc round this batch (W26) seems like 4m on 40m I remember when I first started in venture exactly three years ago (W23 batch) and most venture ppl were complaining about YC pushing their founders to do 2m on 20m in 3 years the market went from a very begrudging 2 on7:09 PM · Mar 19, 2026 · 191K Views54 Replies · 54 Reposts · 1.41K Likes

how to make an amazing launch video

Lenny Rachitsky@lennysanGreat advice for creating your launch video12:05 AM · Mar 20, 2026 · 297K Views29 Replies · 91 Reposts · 1.57K Likes

💯

Dustin@r0ck3t23Elon Musk just delivered the clearest death sentence for every hybrid company on the planet. Musk: “One laptop with a spreadsheet can outperform a skyscraper of several hundred human computers. Now, if even a few cells in that spreadsheet were done manually, you would not be 9:31 AM · Mar 14, 2026 · 578K Views268 Replies · 657 Reposts · 3.16K Likes

narratives matter - a16z hiring a partner for storytelling to LPs 👀

Katie@katiekirschour @a16z investor relations team is hiring a content marketer right now to make banger content for our LPs. looking for a writer / storyteller who deeply understands the tech market / trends and can distill fast-moving online conversations into thoughtful insights that resonate 3:59 PM · Mar 15, 2026 · 122K Views45 Replies · 39 Reposts · 499 Likes

revisiting theme of last couple weeks

BuccoCapital Bloke@buccocapitalElegant point from @edsim: Velocity is now an org design problem It’s why you’ll see so many layoffs. The AI-native companies are lean. Incumbents are simply too bloated for the AI era. Too many layers. Too many stakeholders. Too many KPIs. Too many overlapping teams. 12:39 PM · Mar 16, 2026 · 32.4K Views26 Replies · 15 Reposts · 356 Likes

Enterprise Tech

exactly what I’m hearing from my conversations with F500 tech leaders

Aaron Levie@levieHad meetings and a dinner with 20+ enterprise AI and IT leaders today. Lots of interesting conversations around the state of AI in large enterprises, especially regulated businesses. Here are some of general trends: * Agents are clearly the big thing. Enterprises moving from4:16 AM · Mar 19, 2026 · 77.3K Views83 Replies · 69 Reposts · 584 Likes

been writing about the execution intelligence layer and how context is king - super pumped about port co Surf AI coming out of stealth with $57M of initial funding from Accel who led the Series A and my firm boldstart ventures and Cyberstarts co-leading the Inception round - this is a huge idea - i share some of the “what we saw” from our first meeting and why I’m so excited…watch the product video 👇🏻

Surf AI@trysurfaiHello world. We just raised $57,000,000 raised to operationalize your enterprise security program with AI. Backed by Accel, Cyberstarts, and Boldstart Ventures. 3:15 PM · Mar 17, 2026 · 4.71K Views6 Replies · 1 Repost · 12 Likes

wrote about this last week but enterprises need an easy button for agents and while Anthropic is amazing, open, private, secure and customizable on-prem is also needed - so 🔥 up for this and more importantly how founders can leverage this ecosystem

Alex Volkov@altryne"Every software company in the world, needs to have an @openclaw strategy" - Jensen at @NVIDIAAI GTC Framing OpenClaw as one of the most important open source releases ever, they have announced NemoClaw - a reference platform for enterprise grade secure Openclaw, with OpenShell, 8:33 PM · Mar 16, 2026 · 340K Views88 Replies · 457 Reposts · 3.11K Likes

fake it till you make it until you get called out as fraudulent? turns out when things sound too good to be true, well, they usually are

Ryan@ohryansbeltDelve, a YC-backed compliance startup that raised $32 million, has been accused of systematically faking SOC 2, ISO 27001, HIPAA, and GDPR compliance reports for hundreds of clients. According to a detailed Substack investigation by DeepDelver, a leaked Google spreadsheeterin griffith @eringriffithA detailed and brutal look at the tactics of buzzy AI compliance startup Delve "Delve built a machine designed to make clients complicit without their knowledge, to manufacture plausible deniability while producing exactly the opposite." https://t.co/eiicE64eGr10:03 PM · Mar 19, 2026 · 3.4M Views289 Replies · 514 Reposts · 6.07K Likes

to an extent - question is what’s the ROI from this versus hiring X more number of people, how fast you can ship a new product…going to need some serious monitoring tools to cap token consumption

TFTC@TFTC21Jensen Huang: "If that $500,000 engineer did not consume at least $250,000 worth of tokens, I am going to be deeply alarmed. This is no different than a chip designer who says 'I'm just going to use paper and pencil. I don't think I'm going to need any CAD tools.'" 8:14 PM · Mar 19, 2026 · 1.67M Views359 Replies · 503 Reposts · 6.92K Likes

huge launch out of Keycard in advance of RSA.

turns out focus matters…Anthropic crushing with maniacal focus on coding and business, OpenAI fighting wars on too many fronts

The Wall Street Journal@WSJExclusive: OpenAI’s top executives are finalizing plans for a major strategy shift to refocus the company around coding and business users on.wsj.comExclusive | OpenAI to Cut Back on Side Projects in Push to ‘Nail’ Core Business11:47 PM · Mar 16, 2026 · 627K Views85 Replies · 127 Reposts · 864 Likes

yes more security issues as agents proliferate in the wild

Gary Marcus@GaryMarcusScoop below. Get used to this kind of story. And get used to have your personal data compromised. Amazon last week; Meta this week. Not even the biggest companies can really handle the consequences of AI agents.Jyoti Mann @jyoti_mann1🚨Scoop: A rogue AI agent recently triggered a major security alert at Meta, by taking action without approval that led to the exposure of sensitive company and user data to Meta employees who didn't have authorization to access the data.8:17 PM · Mar 19, 2026 · 17.4K Views22 Replies · 82 Reposts · 255 Likes

Stitch is really good - been playing around with how to update our website - and as Sheel pointed out, Figma took another hit, down 8% on day of release

Stitch by Google@stitchbygoogleMeet the new Stitch, your vibe design partner. Here are 5 major upgrades to help you create, iterate and collaborate: 🎨 AI-Native Canvas 🧠 Smarter Design Agent 🎙️ Voice ⚡️ Instant Prototypes 📐 Design Systems and DESIGN.md Rolling out now. Details and product walkthrough 6:15 PM · Mar 18, 2026 · 6.1M Views448 Replies · 1.93K Reposts · 19.8K Likes

if skills.md codify how your company operates, then will need this as well - so much scaffolding to build (see last week’s newsletter as well) from package management, collaboration with humans and AI, vuln scans, version control…

🍓🍓🍓@iruletheworldmobookmark this immediately. cognee just solved the biggest problem with ai skills/prompts, they break silently over time and its hard to notice their fix: skills that observe their own failures, inspect what went wrong, and amend themselves automatically. try not to fall behind11:36 PM · Mar 14, 2026 · 247K Views34 Replies · 85 Reposts · 1.38K Likes

how it’s done at Uber from its CTO

Praveen Neppalli@praveenTweetsAgentic software engineering adoption is on fire at @Uber. 1,800 code changes per week are now written entirely by Uber's internal background coding agent, and 95% of our engineers now use AI every month across all the tools we track. This is a real reset moment for engineering;7:31 PM · Mar 16, 2026 · 369K Views149 Replies · 138 Reposts · 1.56K Likes

you can’t change culture with just layoffs, need AI driven leadership as well - 🔑 point

CTO Rajeev Rajan is out (no comment yet), and in his place, they’ve split the role between two CTOs. Atlassian described them as next generation AI talent.

Franziska Hinkelmann, PhD@fhinkelAtlassian just announced they're cutting 1,600 jobs. Roughly 10% of their global workforce. And they aren't just downsizing. This is Atlassian admitting that their existing engineering DNA is a liability in an agentic world. They are decapitating their legacy engineering1:56 AM · Mar 17, 2026 · 18.9K Views43 Replies · 6 Reposts · 88 Likes

💯 2nd derivative of AI generated code…

Logan Kilpatrick@OfficialLoganKThe bottleneck has so quickly moved from code generation to code review that it is actually a bit jarring. None of the current systems / norms are setup for this world yet.1:53 AM · Mar 17, 2026 · 281K Views285 Replies · 133 Reposts · 2.97K Likes

Cursor has own model…well built on top of open source Kimi - if Cursor can raise a new round at $50B with open source at its foundation, then what else can people build? great to see - one point though - they should have given Kimi props from beginning

Kimi.ai@Kimi_MoonshotCongrats to the @cursor_ai team on the launch of Composer 2! We are proud to see Kimi-k2.5 provide the foundation. Seeing our model integrated effectively through Cursor's continued pretraining & high-compute RL training is the open model ecosystem we love to support.7:24 PM · Mar 20, 2026 · 139K Views128 Replies · 240 Reposts · 3.77K Likes

Markets

AI credit bubble?

unusual_whales@unusual_whalesAn "AI bubble” is the biggest concern among credit investors, per Bank of America survey.12:17 PM · Mar 19, 2026 · 97.6K Views152 Replies · 147 Reposts · 1.68K Likes

👀

Tanay Jaipuria@tanayjInteresting datapoint from KKR Co-CEO: “The largest 100 U.S. companies in the United States have seen their margins expand materially in the last 5 years, 14% to 19%. The next 1,400 companies have had their margins flat and are working to stay even.“12:45 AM · Mar 16, 2026 · 114K Views7 Replies · 50 Reposts · 485 Likes

🎯

Jeff Richards@jrichliveA number of “pre GPT” private software cos w/durable moats that went all in on AI 12-18 mos ago + are going to surprise people. Benefiting from AI internally as well, operating at scale w/very low burn to profitable. AI about to become a clear tailwind w/no need to raise $. 🤞10:46 PM · Mar 19, 2026 · 6.22K Views6 Replies · 37 Likes