Ashley Smith
@ashley3.com
Founding parter at vermilion.fund, a pre-seed & seed stage fund for technical founders creating technical products.
Before: GitHub, GitLab, Twilio, Parse
Before: GitHub, GitLab, Twilio, Parse
In most of my calls with early stage founders we talk about the best metrics to track at the earliest stages. Until there is meaningful ARR, what do you measure from day 0?
The KPIs That Actually Matter at Pre-Seed into Series A - read the full post in 🧵
The KPIs That Actually Matter at Pre-Seed into Series A - read the full post in 🧵
September 16, 2025 at 1:15 PM
In most of my calls with early stage founders we talk about the best metrics to track at the earliest stages. Until there is meaningful ARR, what do you measure from day 0?
The KPIs That Actually Matter at Pre-Seed into Series A - read the full post in 🧵
The KPIs That Actually Matter at Pre-Seed into Series A - read the full post in 🧵
Every week there’s a new GTM acronym trending. PLG, CLG, SLG, ELG. Pick the right one and you win. Pick the wrong one and you’re doomed.
At pre-seed, none of them are “the one.” You’ll do all of them, usually at the same time. That’s the job.
Read the full post in thread 🧵
At pre-seed, none of them are “the one.” You’ll do all of them, usually at the same time. That’s the job.
Read the full post in thread 🧵
Revenge of the Acronyms: Why Founders Have to Do It All
PLG.
vermilioncliffs.substack.com
September 4, 2025 at 4:03 PM
Every week there’s a new GTM acronym trending. PLG, CLG, SLG, ELG. Pick the right one and you win. Pick the wrong one and you’re doomed.
At pre-seed, none of them are “the one.” You’ll do all of them, usually at the same time. That’s the job.
Read the full post in thread 🧵
At pre-seed, none of them are “the one.” You’ll do all of them, usually at the same time. That’s the job.
Read the full post in thread 🧵
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 26, 2025 at 7:11 PM
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 🧵
Open source isn’t about novel code anymore. It’s about execution.
@bizza.pizza shares how one OSS team turned community momentum into a sticky product and a standout fundraise.
🎧 Full episode in thread 🧵
@bizza.pizza shares how one OSS team turned community momentum into a sticky product and a standout fundraise.
🎧 Full episode in thread 🧵
July 15, 2025 at 3:31 PM
Open source isn’t about novel code anymore. It’s about execution.
@bizza.pizza shares how one OSS team turned community momentum into a sticky product and a standout fundraise.
🎧 Full episode in thread 🧵
@bizza.pizza shares how one OSS team turned community momentum into a sticky product and a standout fundraise.
🎧 Full episode in thread 🧵
“You don’t need permission to start.”
On this week’s Vermilion Cliff Notes, I sat down with @bizza.pizza to talk open source, AI agents, and founder momentum.
We cover his path from MBA student to devtools founder and what it takes to stand out in this AI-fueled market.
On this week’s Vermilion Cliff Notes, I sat down with @bizza.pizza to talk open source, AI agents, and founder momentum.
We cover his path from MBA student to devtools founder and what it takes to stand out in this AI-fueled market.
July 9, 2025 at 7:25 PM
“You don’t need permission to start.”
On this week’s Vermilion Cliff Notes, I sat down with @bizza.pizza to talk open source, AI agents, and founder momentum.
We cover his path from MBA student to devtools founder and what it takes to stand out in this AI-fueled market.
On this week’s Vermilion Cliff Notes, I sat down with @bizza.pizza to talk open source, AI agents, and founder momentum.
We cover his path from MBA student to devtools founder and what it takes to stand out in this AI-fueled market.
New episode of Vermilion Cliffs Founder Notes: @austinhay & @patrick__thompson went from early @Branch + @Amplitude to founding @clarify together.
Why they finally made the leap, how they closed their Series A, and the advice they now ignore.
Full episode in first comment 👇
Why they finally made the leap, how they closed their Series A, and the advice they now ignore.
Full episode in first comment 👇
June 26, 2025 at 2:23 PM
New episode of Vermilion Cliffs Founder Notes: @austinhay & @patrick__thompson went from early @Branch + @Amplitude to founding @clarify together.
Why they finally made the leap, how they closed their Series A, and the advice they now ignore.
Full episode in first comment 👇
Why they finally made the leap, how they closed their Series A, and the advice they now ignore.
Full episode in first comment 👇
In our first episode of Vermilion Cliffs Notes, I talk to Ian Cairns, CEO of Freeplay, about agents, eval loops, and why your best AI workflows might look more like a Slack thread than a sci-fi movie.
🎥 Watch the full interview --> vermilioncliffs.substack.com/p/vermilion-...
🎥 Watch the full interview --> 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 3:13 PM
In our first episode of Vermilion Cliffs Notes, I talk to Ian Cairns, CEO of Freeplay, about agents, eval loops, and why your best AI workflows might look more like a Slack thread than a sci-fi movie.
🎥 Watch the full interview --> vermilioncliffs.substack.com/p/vermilion-...
🎥 Watch the full interview --> vermilioncliffs.substack.com/p/vermilion-...
Mary Meeker Returns: What's Shaping the Next Gen of Technical Products, Founders, and the Market
open.substack.com/pub/vermilio...
open.substack.com/pub/vermilio...
Mary Meeker Returns: What's Shaping the Next Gen of Technical Products, Founders, and the Market
Mary Meeker is back!
open.substack.com
June 2, 2025 at 1:42 PM
Mary Meeker Returns: What's Shaping the Next Gen of Technical Products, Founders, and the Market
open.substack.com/pub/vermilio...
open.substack.com/pub/vermilio...
Like every shift from web → mobile → APIs → big data, today’s GTM playbooks are evolving fast. Over the past two weeks, I shared daily snapshots of the shifts every technical founder should know.
Get the full deep dive → vermilioncliffs.substack.com/p/where-tech...
Get the full deep dive → vermilioncliffs.substack.com/p/where-tech...
Where Technical Products Should Focus for Effective GTM
Part 2 in The Golden Age of Devtools Meets the Rise of AI
vermilioncliffs.substack.com
May 23, 2025 at 3:59 PM
Like every shift from web → mobile → APIs → big data, today’s GTM playbooks are evolving fast. Over the past two weeks, I shared daily snapshots of the shifts every technical founder should know.
Get the full deep dive → vermilioncliffs.substack.com/p/where-tech...
Get the full deep dive → vermilioncliffs.substack.com/p/where-tech...
Events Work. Especially Now.
In a world of async everything, in-person time is more valuable than ever.
We’re seeing a resurgence in technical events but not the vendor-heavy expos of the 2010s. 🧵 👇
In a world of async everything, in-person time is more valuable than ever.
We’re seeing a resurgence in technical events but not the vendor-heavy expos of the 2010s. 🧵 👇
Where Technical Products Should Focus for Effective GTM
Part 2 in The Golden Age of Devtools Meets the Rise of AI
vermilioncliffs.substack.com
May 22, 2025 at 3:04 PM
Events Work. Especially Now.
In a world of async everything, in-person time is more valuable than ever.
We’re seeing a resurgence in technical events but not the vendor-heavy expos of the 2010s. 🧵 👇
In a world of async everything, in-person time is more valuable than ever.
We’re seeing a resurgence in technical events but not the vendor-heavy expos of the 2010s. 🧵 👇
Your message matters more than your metrics
In a crowded market, clarity is the killer feature.
If you can’t explain why your product exists in one sentence, your AI-generated competitor will outrank you. 🧵
In a crowded market, clarity is the killer feature.
If you can’t explain why your product exists in one sentence, your AI-generated competitor will outrank you. 🧵
May 21, 2025 at 3:07 PM
Your message matters more than your metrics
In a crowded market, clarity is the killer feature.
If you can’t explain why your product exists in one sentence, your AI-generated competitor will outrank you. 🧵
In a crowded market, clarity is the killer feature.
If you can’t explain why your product exists in one sentence, your AI-generated competitor will outrank you. 🧵
A Developer Tool Is a Developer Experience
The line between product and marketing is gone.
If onboarding is bad, growth slows.
If docs are confusing, retention tanks. 👇 🧵
The line between product and marketing is gone.
If onboarding is bad, growth slows.
If docs are confusing, retention tanks. 👇 🧵
May 20, 2025 at 4:59 PM
A Developer Tool Is a Developer Experience
The line between product and marketing is gone.
If onboarding is bad, growth slows.
If docs are confusing, retention tanks. 👇 🧵
The line between product and marketing is gone.
If onboarding is bad, growth slows.
If docs are confusing, retention tanks. 👇 🧵
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. 🧵
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. 🧵
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.
👇
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 🧵
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.
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 4:05 PM
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...
Is this an AI bubble? Maybe.
But we’re still seeing real traction—especially from technical founders building for the AI-enabled developer.
Some notes on valuations, GTM shifts, and why seed pricing is higher than ever
👉 open.substack.com/pub/vermilio...
But we’re still seeing real traction—especially from technical founders building for the AI-enabled developer.
Some notes on valuations, GTM shifts, and why seed pricing is higher than ever
👉 open.substack.com/pub/vermilio...
April 29, 2025 at 7:08 PM
Is this an AI bubble? Maybe.
But we’re still seeing real traction—especially from technical founders building for the AI-enabled developer.
Some notes on valuations, GTM shifts, and why seed pricing is higher than ever
👉 open.substack.com/pub/vermilio...
But we’re still seeing real traction—especially from technical founders building for the AI-enabled developer.
Some notes on valuations, GTM shifts, and why seed pricing is higher than ever
👉 open.substack.com/pub/vermilio...
Thank you Allie Garfinkle of @fortune.com for learning about my journey into VC and highlighting the launch of @vermilion.fund 🤠
Vermillion Cliffs Ventures launches with $13 million debut fund
Ashley Smith, previously of GitLab and GitHub, has launched Vermillion Cliffs Ventures with a debut $13 million fund, Fortune can exclusively report.
fortune.com
February 6, 2025 at 2:43 PM
Thank you Allie Garfinkle of @fortune.com for learning about my journey into VC and highlighting the launch of @vermilion.fund 🤠
I look great with bangs and my wardrobe hasn't really changed.
Excited to launch my debut $13m early stage fund @vermilion.fund
Excited to launch my debut $13m early stage fund @vermilion.fund
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 2:40 PM
I look great with bangs and my wardrobe hasn't really changed.
Excited to launch my debut $13m early stage fund @vermilion.fund
Excited to launch my debut $13m early stage fund @vermilion.fund