Vermilion Cliffs Ventures
@vermilion.fund
Investing in pre-seed and seed stage technical founders building technical products.
vermilion.fund
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 🧵
🌄 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 🧵
November 17, 2025 at 6:03 PM
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 🧵
🌄 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 🧵
🔗 Read the latest: New Stack, Same Game: Why the AI-native era feels different yet familiar linked in 🧵
November 12, 2025 at 6:16 PM
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 🧵
🔗 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 🧵
✅ 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 🧵
September 16, 2025 at 1:30 PM
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 🧵
✅ 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
🎥 Watch the full interview linked in thread Tori Seidenstein, CEO & Co-founder of Tadata
September 11, 2025 at 2:31 PM
“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
🎥 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 🧵
Catch the full episode in thread 🧵
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…
www.youtube.com
September 9, 2025 at 4:07 PM
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 🧵
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 👇
@ToriSeidenstein, CEO & Co-founder on the Tadata origin story
Catch the full episode in the comment below 👇
September 3, 2025 at 3:35 PM
“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 👇
@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
Just dropped a new Vermilion Cliff Notes with Tori Seidenstein, CEO and Co-founder of Tadata.
We talked about why MCP is the 100x connectivity leap, how open source has become the new enterprise wedge, and what modern GTM for dev tools really looks like.
Full interview linked in thread 🧵
We talked about why MCP is the 100x connectivity leap, how open source has become the new enterprise wedge, and what modern GTM for dev tools really looks like.
Full interview linked in thread 🧵
August 27, 2025 at 3:06 PM
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 👇
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 👇
August 21, 2025 at 6:40 PM
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 👇
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
@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
July 10, 2025 at 1:20 PM
“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
@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 👇
By putting domain experts in the loop, teams are shortening eval cycles and shipping higher-quality AI features. Full Founder Cliffs Notes episode 👇
June 18, 2025 at 5:05 PM
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 👇
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.
Our first Vermilion Cliffs Notes is live with Ian Cairns CEO and Co-founder of Freeplay. Watch the full interview linked below.
June 11, 2025 at 3:31 PM
“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.
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-...
🎙 Full founder interview up now --> vermilioncliffs.substack.com/p/vermilion-...
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.
vermilioncliffs.substack.com
June 6, 2025 at 3:12 PM
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-...
🎙 Full founder interview up now --> vermilioncliffs.substack.com/p/vermilion-...
Reposted by Vermilion Cliffs Ventures
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. 🧵
Your top-of-funnel isn’t your homepage.
It’s where your tool shows up in the developer’s existing flow. 🧵
May 19, 2025 at 2:41 PM
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. 🧵
Your top-of-funnel isn’t your homepage.
It’s where your tool shows up in the developer’s existing flow. 🧵
Reposted by Vermilion Cliffs Ventures
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. 🧵
If you want developers to find your tool, don’t count on Google.
Count on the ecosystems they already trust. 🧵
May 16, 2025 at 4:08 PM
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. 🧵
If you want developers to find your tool, don’t count on Google.
Count on the ecosystems they already trust. 🧵
Reposted by Vermilion Cliffs Ventures
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.
👇
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.
👇
May 15, 2025 at 3:17 PM
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.
👇
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.
👇
Reposted by Vermilion Cliffs Ventures
1/ Technical GTM: A Series
Day 2 – The New Influencer: Engineering Founders Are the Face of the Company 🧵
Day 2 – The New Influencer: Engineering Founders Are the Face of the Company 🧵
May 14, 2025 at 3:02 PM
1/ Technical GTM: A Series
Day 2 – The New Influencer: Engineering Founders Are the Face of the Company 🧵
Day 2 – The New Influencer: Engineering Founders Are the Face of the Company 🧵
Reposted by Vermilion Cliffs Ventures
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.
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.
May 13, 2025 at 3:41 PM
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.
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.
Does AI mean the end of devtools? Short answer: No. Long answer: No. Devtools aren’t dying - they’re evolving but GTM playbooks are breaking.
So what’s working and what’s not in 2025 technical GTM?
Lesson 1: We all have the attention span of gnats
vermilioncliffs.substack.com/p/the-golden...
So what’s working and what’s not in 2025 technical GTM?
Lesson 1: We all have the attention span of gnats
vermilioncliffs.substack.com/p/the-golden...
The Golden Age of Devtools Meets the Rise of AI (a series)
Part 1: At the intersection of AI and Devtools sits the AI-enabled engineer
vermilioncliffs.substack.com
May 12, 2025 at 4:12 PM
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...
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...
April 29, 2025 at 7:04 PM
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...
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...
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...
Screendoor Blog | Work with your LPAC, not for your LPAC
www.screendoor.co
April 17, 2025 at 8:29 PM
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...
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...
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...
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.
sapphireventures.com
April 8, 2025 at 5:11 PM
💡 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...
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...
vermilioncliffs.substack.com/p/south-geor...
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
vermilioncliffs.substack.com
February 6, 2025 at 2:39 PM
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...
vermilioncliffs.substack.com/p/south-geor...