Shishir Mehrotra

Thrilled to announce that Together Fund is investing in Sentra, alongside a16z speedrun! You track results in Jira. Decisions in Notion. Conversations in Slack. But the reasoning, the debates, trade-offs, and context behind why you chose A over B, disappears into what we call "Dark Matter." A decision made in March looks insane by July because no one remembers the constraints that made it smart. I lived this firsthand at Twitter scaling from 800 to 8,000 employees, and at Google while launching AI Overviews to billions at planet scale. The problem isn't process. Process is compensation for something deeper: organizational amnesia. An organization’s "Systems of Record" doesn’t solve this, they encode it. They store what happened, never why. That's why we are investing in Sentra. Sentra is the always-on collective memory that eliminates organizational amnesia by maintaining accurate context for all members and agents, functioning as an operational nervous system. It connects to every channel where work happens, meetings, Slack, email, code commits, docs, calendars, and treats them not as artifacts to search, but as living signals to synthesize. The fleeting and the permanent, unified into a memory that understands. The founding team is built for this: - Jae Gwan Park (CEO): Product-first founder, memory systems research at UofT and MIT - Ashwin Gopinath (CSO): Former MIT professor, created "Reflexion" (NeurIPS 2023), agents that learn from mistakes, 2x founder - Andrey Starenky (CTO): Early Vapi engineer, ex-IBM, built to process enterprise-scale data firehose Together is an operator-led fund. We invest in problems we've lived. This is one of them. Many congrats Jae, Ashwin and Andrey, we are so excited to partner with you! Read the full thesis: https://lnkd.in/gixj9cE4 Book a demo: https://www.sentra.app/ #OrganizationalMemory #AI #Sentra #TogetherFund #a16z #ContextGraphs

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CRV Security: Request for Startups I never know if this actually works for our friends over at YC but figured we'd try. Here's what we want to fund in 2026! 1. Golden Artifacts: Think Chainguard but more broad. Artifact attestation exists for open source. Almost nothing exists for internal software — especially the vibe-coded tooling now running in production. We want the company building cryptographic proof of secure software delivered from secure artifacts: who built it, how, and whether it was reviewed. If more things are being yeeted into the world via Claude Code (myself included), this feels like an issue. 2. MCP & Agentic Security: Agents are getting real credentials and taking real actions. The security posture of most orgs around this is basically zero. That changes fast. You'd never give an employee hardcoded API keys or write access to your email without supervision/trust. Why give it to agents? 3. AI Governance: Boards are asking CISOs to account for AI risk. CISOs have no good answer other than "Palo has a module" 4. Next-Gen Endpoint: CrowdStrike was built for a world of static binaries and human operators. AI workloads, cloud-native infra, and AI-assisted attackers need a new architecture. The category is ready to be reinvented. 5. Networking in the AI Era: Zero trust was designed for humans. What does network security look like when the entity requesting access is an agent? Nobody's really solved this. 6. Email Security + Next-Gen Phishing: LLMs have made spear phishing infinitely scalable. I've never truly understood why Abnormal and KnowBe4 aren't one company. Maybe this time it's different. 7. Frontier Security Lab: We'd back a credible, well-staffed lab focused entirely on red-teaming models and setting the evidentiary standard the industry needs as LLM built apps become the norm. 8. Dependency Security: That Actually Remediates Malicious and vulnerable dependencies are a top attack vector. The tooling is mostly noise — scanners that don't close the loop. The winner here ships fixes, not just alerts. 9. Critical Infrastructure Cyber: Data centers, satellites, power grids, undersea cables. The physical backbone of the internet is increasingly exposed and wildly under-defended. We have data centers in space, for God's sake. Surely we need better cyber for critical infrastructure? 10. PAM for the Modern Era Legacy: PAM was built for static roles, human users, on-prem directories. Cyberark was founded in 1999.....Agents, ephemeral workloads, and cloud-native infra have broken all of those assumptions. Is anyone rebuilding this from scratch? If you're building in any of these areas — or something we haven't thought of — reach out. james@crv.com

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The Headline family is experiencing incredible momentum, and today our portfolio company DeepIP is announcing a $25M Series B, bringing total funding to $40M.  This is the kind of company that doesn’t just add AI to a workflow, but it sets the standard for an entire category. The momentum speaks for itself: 1️⃣ 10x ARR growth in < 18 months 2️⃣ Trusted by 400+ law firms and leading corporate IP teams globally 3️⃣ 2M+ chats on the DeepIP platform We’ve had the chance to back FX (Francois-Xavier) L. and Edouard D., leading their Seed round with Headline. Watching them take on a problem as complex and high-stakes as patent work has been genuinely impressive. And working with them has been an absolute pleasure: these 2 are coupling very high ambition and humility. Tech built in Europe, but opening the US office very early and FX starting a life in NYC with his family with 0 hesitation in order to build a global category leader in the IP industry. What convinced me early is still what stands out today: patent teams don’t need another standalone AI tool. They need something that fits the way the work actually happens: documents, long-running matters, multiple stakeholders, and zero room for sloppy context handoffs. Big congrats to the whole DeepIP team + Korelya Capital, Balderton & Serena Proud that we’re doubling down at Headline and continuing the support for what’s next!

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a friend just texted me: "Hearing there are 'senior devs' who are very skeptical of AI generated code (aka not using any AI tools) at a startup I’m interviewing with… interesting that they are still employed in a startup against this backdrop [see image]" my response: seems like there are just different games being played those who embrace AI as a medium for expressing ideas are playing the right game — they're not just treating it as a "better tool" if you've been in industry awhile, you may need an intellectual reboot to see it last night i went to a VentureBeat event; mostly enterprise folks… several people (from IBM, Walgreens, etc) asked about “change mgmt” and how to convince their teammates to adopt AI tools… someone raised the question of brown-field vs green-field opportunity w/r/t AI… is it worth it to upskill existing workers or better to just start fresh…? Great question! for people entrenched in a job fiefdom, e.g. where the power players and how to execute reliably, the perceived risks of novelty are infinite. they're not wrong, they're just not interested in changing the game they've mastered. aaand also, developers are the self-disclosed laziest people in the world. but they're incredibly productive because they'll happily spend a week automating some repetitive task so they never have think about it again. this is why generative AI and coding go so well together: the existing developer culture despises inefficiency, and is always looking for ways to cut corners in favor of a more elegant, efficient route. this is because developers are incredibly sensitive to the tiniest impediment to achieving persistent flow states. it's like noticing a typo in that green-on-black matrix screensaver and instead of ignoring it as a minor irritant, they'd prefer to rewrite the screensaver from scratch to fix it. but for non-developery roles, this gameplay is totally foreign. maintaining those impediments ensures job security. since they know how to navigate around known obstacles, their tacit knowledge is an insurance policy against obsolescence — for now. so it makes that sense that some senior devs, whose sunk costs could represent hundreds of thousands or millions of $$$ into existing, _stable_ systems might resist the quasi-non-deterministic output of AI coding tools. except (as they say) there is more than one way to skin a cat. here's a new game to invite resistants to play: have the skeptical senior devs review several blind PRs, all submitted by “new,” unfamiliar contributors (a mix of humans and AIs), and see if they prefer the human or AI-generated code. if the AI code really is as good as many of us believe, the experience might snap them out of their sunk-cost fallacies. because until you surprise yourself with what these tools can actually accomplish—in a blind taste test—you’ll never really see what winning this new game looks like, even if it's happening right in front of your eyes.

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Martin Eberhard played a key role early at Tesla and even brought in Elon Musk. Then he was pushed out of the company for pennies. Founders get most of the attention in Silicon Valley, but the ecosystem is built on the people who take a chance and join early stage ventures. Unfortunately, those same people are often the easiest to cut out. Founders can dilute early employees, change vesting terms, and restructure equity with little effort and zero consequences (you can literally do it in Carta in 5 minutes). Daniel Kottke was a close friend of Steve Jobs and helped build the Apple I and II computers. He got no equity (Steve Wozniak eventually gave him a few of his own shares). Brian Acton co-founded WhatsApp and stayed through the Facebook acquisition. When he left Facebook over privacy concerns, he had to walk away from $850 million in unvested stock. There’s more awareness now around how vesting works, what happens during a liquidity event, and how to think about re-ups and dilution. That’s good. But the truth is, if someone really wants to screw you, they can. It still comes down to one thing: trust the people you work with. Or don’t work with them at all.

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Reading Metronome’s Monetization Operating Model, I kept coming back to one idea: pricing has become product. Software now delivers outcomes, not access. Yet most companies still charge as if they’re selling seats or licenses. That disconnect creates friction: for customers, unpredictability; for companies, stalled growth. The paper’s argument is simple but sharp—monetization isn’t a late-stage decision. It’s strategic infrastructure. Pricing needs the same ownership and iteration as any feature. Treat it like a surface that customers touch, not a spreadsheet buried in finance. If value is continuous and dynamic, pricing must be as well. That means product, GTM, finance, and engineering working from one system of truth. How many of us still treat pricing as an afterthought—when it should be a growth engine? https://lnkd.in/gnH7WzYf #Monetization #ProductStrategy #AI

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