The latest Vermilion newsletter is out 🗞️ 🌄 How the AI-native era is expanding the surface area for new companies 🔧 Why the MCP tool layer is becoming essential infrastructure 💰 Keycard raises $38M led by A16z, Boldstart & Acrew 📈 Osmosis announces a $6.3M Seed from CRV & Audacious Link in 🧵

The AI-native era isn’t consolidation, it’s expanding. Infra is maturing. Behavior is shifting. Founders building the connective tissue between humans + AI are early in the best way. 🔗 Read the latest: New Stack, Same Game: Why the AI-native era feels different yet familiar linked in 🧵

At pre-seed/Series A, you don’t need 50 metrics. You need 5. ✅ New users ✅ Activation rate ✅ PQLs ✅ New vs. expansion ARR ✅ (and watch churn quietly) Track something. Every day. The KPIs That Actually Matter at Pre-Seed into Series A 🧵

“One of the biggest surprises is that 12% of the stars on the repo are from organizations of 10,000+ person. That gave us confidence that there's a huge monetization opportunity, even with massive companies.” 🎥 Watch the full interview linked in thread Tori Seidenstein, CEO & Co-founder of Tadata

Vermilion Founder @ashley3.com joined Yaniv Bernstein on The Startup Podcast to discuss everything from why investor playbooks can be dangerous for early-stage founders to why hiring generalists and “specialists in experimentation” is the best early-stage move. Catch the full episode in thread 🧵

“The value to be unlocked over the next 10 years is at the connectivity layer. We immediately recognized MCP was going to be a 100x improvement over what had been out there before.” @ToriSeidenstein, CEO & Co-founder on the Tadata origin story Catch the full episode in the comment below 👇

Catch the Vermilion Cliffs Notes with Tori Seindenstein, CEO & Co-founder of Tadata, on MCP, open source, and how GTM for dev tools is evolving

Search isn’t what it used to be. Developers get answers from ChatGPT and Claude before they ever touch Google. AI Overviews are eating traffic. Your docs, repos, and community threads decide if you show up. Check out this guide from @ashley3.com on AIO, GEO, and AEO 👇

“I didn’t know this world existed until I blogged into it.” @bizza.pizza's startup story didn’t begin with a CS degree, it started with a blog, a few Ruby tags, and a DM. 🎧 Full episode in thread

The best AI teams aren’t just engineering-led anymore. Freeplay helps domain experts take over evals + QA, cutting cycles from weeks to hours. By putting domain experts in the loop, teams are shortening eval cycles and shipping higher-quality AI features. Full Founder Cliffs Notes episode 👇

“We talked to 75 people in the first 90 days. We didn’t want to build for the future, we wanted to solve real problems today” Our first Vermilion Cliffs Notes is live with Ian Cairns CEO and Co-founder of Freeplay. Watch the full interview linked below.

The origin of Freeplay wasn’t a research lab—it was two PMs messing around with DaVinci on weekends. 🎙 Full founder interview up now --> vermilioncliffs.substack.com/p/vermilion-...

Ecosystem and Integration Are the New TOFU Your top-of-funnel isn’t your homepage. It’s where your tool shows up in the developer’s existing flow. 🧵

Developers Are Still Bypassing Search for Signal If you want developers to find your tool, don’t count on Google. Count on the ecosystems they already trust. 🧵

Build in public or be forgotten. Product marketing used to move in months. Now it moves in hours. Launches still matter. But what you do between them is what builds brand, affinity, and momentum. 👇

1/ Technical GTM: A Series Day 2 – The New Influencer: Engineering Founders Are the Face of the Company 🧵

Technical GTM: A Series Today's 🧵 → GEO & AIO: Content Still Matters, but Context Is Everything SEO isn’t dead. But GEO (Generative Engine Optimization) is where the game is headed.

We’re kicking off a series on GTM for technical products in 2025 → follow @ashley3.com to join the conversation.

Valuations are up. Round counts are down. The AI-enabled developer is real, and the best technical founders are building around them. It's not a bubble - It's a major shift. What we’re seeing in the devtools + infra market right now: 👉 open.substack.com/pub/vermilio...

A good LPAC isn’t just a formality — it’s your early fund’s inner circle. Pick people who get your strategy, are responsive, and want to build with you - not just your biggest checks. Loved this take from Screendoor: www.screendoor.co/blog/work-wi...

💡 What makes a strong investment process? Key lessons we loved via Sapphire Ventures: ☑️Consistency > bias ☑️Conviction ≠ consensus (but dissent ≠ automatic) ☑️How you vote matters ☑️Celebrate smart passes, not just wins Process is culture 👇 sapphireventures.com/blog/bridgin...

Today @vermilion.fund is officially launched, learn more about @ashley3.com's story and the principles behind our work. vermilioncliffs.substack.com/p/south-geor...