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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

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23.11.2024
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Latest posts by Ashley Smith @ashley3.com

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 🧡

16.09.2025 13:15 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Revenge of the Acronyms: Why Founders Have to Do It All PLG.

vermilioncliffs.substack.com/p/revenge-of...

04.09.2025 16:03 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Revenge of the Acronyms: Why Founders Have to Do It All PLG.

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 β€œthe one.” You’ll do all of them, usually at the same time. That’s the job.

Read the full post in thread 🧡

04.09.2025 16:03 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Why MCP Is the 100x Leap for AI Dev Tools: A Conversation with Tadata This week on Vermilion Cliff Notes, I sat down with CEO and Co-founder of Tadata Tori Seindenstein to talk about how the AI dev tools stack is evolving, why MCP represents a step-change in…

Watch the full episode here: vermilioncliffs.substack.com/p/why-mcp-is...

26.08.2025 19:11 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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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 🧡

26.08.2025 19:11 πŸ‘ 4 πŸ” 0 πŸ’¬ 1 πŸ“Œ 1
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Open Source, AI Agents, and the Power of Showing Up: Brian Douglas from Continue This week on Vermilion Cliff Notes, I sat down with Brian Douglas (aka B Dougie) to talk about open source, the new AI-powered dev stack, and what it takes to build a company when the market is…

vermilioncliffs.substack.com/p/open-sourc...

15.07.2025 15:31 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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 🧡

15.07.2025 15:31 πŸ‘ 3 πŸ” 1 πŸ’¬ 1 πŸ“Œ 0
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Open Source, AI Agents, and the Power of Showing Up: Brian Douglas from Continue This week on Vermilion Cliff Notes, I sat down with Brian Douglas (aka B Dougie) to talk about open source, the new AI-powered dev stack, and what it takes to build a company when the market is…

Watch the full episode here -> vermilioncliffs.substack.com/p/open-sourc...

09.07.2025 19:25 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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β€œYou 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.

09.07.2025 19:25 πŸ‘ 1 πŸ” 1 πŸ’¬ 1 πŸ“Œ 0
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Vermilion Cliffs Notes: Why Clarify’s Founders Are Betting Big on the Autonomous CRM Startups, forever founders, and why metrics, not vibes, closed the Series A.

Watch on Substack ➑️ open.substack.com/pub/vermilio...

26.06.2025 14:23 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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 πŸ‘‡

26.06.2025 14:23 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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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.

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.

πŸŽ₯ Watch the full interview --> vermilioncliffs.substack.com/p/vermilion-...

06.06.2025 15:13 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Mary Meeker Returns: What's Shaping the Next Gen of Technical Products, Founders, and the Market Mary Meeker is back!

Mary Meeker Returns: What's Shaping the Next Gen of Technical Products, Founders, and the Market
open.substack.com/pub/vermilio...

02.06.2025 13:42 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

Like every shift from web β†’ mobile β†’ APIs β†’ 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 β†’ vermilioncliffs.substack.com/p/where-tech...

23.05.2025 15:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

And in 2025, event content is evergreen:
β€’ Record it
β€’ Transcribe it
β€’ Turn demos into tutorials

One night can fuel weeks of marketing that doesn’t feel like marketing.
Full post β†’ vermilioncliffs.substack.com/p/where-tech...

22.05.2025 15:04 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

GenAI Collective’s SF demo nights pull 200–300 people monthly.
Agent Hack Night felt like 2012 again.
These work because they feel authentic and devs can smell the difference.

22.05.2025 15:04 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Workshops > booths.
Demos > decks.
The best events feel like extensions of your product.
Partner with tools your ICP already loves.
Debugging tool + agent framework = a joint hack night that converts.

22.05.2025 15:04 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Today’s best events are tighter, founder- or user-led gatherings where real knowledge gets traded.

No fluff. No salesy keynotes.
What’s working:
β€’ 20-person dev dinners
β€’ Hack nights with hands-on builds
β€’ User-led meetups with zero stage, lots of signal

22.05.2025 15:04 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

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. 🧡 πŸ‘‡

22.05.2025 15:04 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

5/ Clear beats clever.
Narrative compounds.
And your message is your moat.

Jump ahead? Full post β†’ vermilioncliffs.substack.com/p/where-tech...

21.05.2025 15:07 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

4/ What’s working:
β€’ Founder-written β€œWhy we built this” posts
β€’ Internal positioning docs shared across GTM + product
β€’ Message consistency across site, docs, and channels

21.05.2025 15:07 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

3/ Great examples:
β€’ Tonic.ai β†’ Owns the narrative on synthetic data
β€’ Astro Web β†’ Defined β€œcontent-first dev” as a category

21.05.2025 15:07 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

2/ Positioning isn’t fluff.
It’s the starting point for GTM.
Why now? Who’s it for? Why you?

21.05.2025 15:07 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

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. 🧡

21.05.2025 15:07 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

5/ Underinvest here and you don’t just lose users, you become invisible.

What’s the most important thing in your DevX?
Jump ahead? Full post vermilioncliffs.substack.com/p/where-tech...

20.05.2025 16:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

4/ Docs, changelogs, and support aren’t just support. They’re GTM surface area.
They’re often the first thing a developer sees.
And they’re indexed by LLMs.

20.05.2025 16:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

3/ Railway and Clerk are good examples.
Their products don’t just work. They feel thoughtful. That matters.

20.05.2025 16:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

2/ Teams are now treating onboarding like a product launch

What that looks like:
β€’ Copy-pasteable examples that just work
β€’ Live playgrounds (CodeSandbox, StackBlitz, custom UIs)
β€’ β€œFirst 5 minutes” metrics that get tracked

20.05.2025 16:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

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. πŸ‘‡ 🧡

20.05.2025 16:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Where Technical Products Should Focus for Effective GTM Part 2 in The Golden Age of Devtools Meets the Rise of AI

4/ TOFU isn’t about awareness anymore. It’s about availability. Be where developers are while being useful in-context before they even land on your site.

Follow alongβ€”sharing one GTM post like this every day this week

Jump ahead? Full post vermilioncliffs.substack.com/p/where-tech...

19.05.2025 14:41 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0