Vermilion Cliffs Ventures
@vermilion.fund
📤 13
📥 23
📝 27
Investing in pre-seed and seed stage technical founders building technical products. vermilion.fund
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 🧵
about 1 month ago
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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 🧵
about 1 month ago
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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 🧵
3 months ago
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“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
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3 months ago
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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 🧵
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Growing a Pre-Seed Startup? This Is The Core Knowledge You Need
Pre-seed founders want explosive growth early on, but are you following the wrong playbook too soon? These days strategies, acronyms, and well-intended advice are everywhere, but today's guest argues…
https://www.youtube.com/watch?v=QA6f4Y8c6GM
4 months ago
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“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 👇
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4 months ago
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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
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4 months ago
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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 👇
4 months ago
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“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
6 months ago
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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 👇
6 months ago
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“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.
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7 months ago
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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-...
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Vermilion Cliffs Notes: From MVPs to Agents, How Freeplay Is Helping Teams Ship AI Products
Eval loops and why your best AI workflows might look more like a Slack thread than a sci-fi movie.
https://vermilioncliffs.substack.com/p/vermilion-cliffs-notes-from-mvps
7 months ago
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reposted by
Vermilion Cliffs Ventures
Ashley Smith
7 months ago
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. 🧵
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reposted by
Vermilion Cliffs Ventures
Ashley Smith
7 months ago
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. 🧵
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reposted by
Vermilion Cliffs Ventures
Ashley Smith
7 months ago
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. 👇
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reposted by
Vermilion Cliffs Ventures
Ashley Smith
7 months ago
1/ Technical GTM: A Series Day 2 – The New Influencer: Engineering Founders Are the Face of the Company 🧵
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reposted by
Vermilion Cliffs Ventures
Ashley Smith
7 months ago
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.
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We’re kicking off a series on GTM for technical products in 2025 → follow
@ashley3.com
to join the conversation.
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8 months ago
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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...
8 months ago
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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...
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Screendoor Blog | Work with your LPAC, not for your LPAC
https://www.screendoor.co/blog/work-with-your-lpac-not-for-your-lpac
8 months ago
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💡 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...
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Bridging Perspectives: Investment Process Lessons for Both Managers and LPs
Investment processes are critical for both managers and LPs. Sapphire Partners shares explore key lessons from Sapphire Partners on decision-making frameworks, healthy dissent, voting procedures, and recognizing the value of passes—all essential for building a thoughtful and effective investment strategy.
https://sapphireventures.com/blog/bridging-perspectives-investment-process-lessons-for-both-managers-and-lps/
9 months ago
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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...
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South Georgia, the internet, and startup-land (and also I launched an early-stage venture fund)
What VC has to do with my dog, my grandpa, and a national monument
https://vermilioncliffs.substack.com/p/south-georgia-the-internet-and-startup
11 months ago
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