iiinova — where your digital self keeps evolving

Ashley Smith @ashley3.com · 15/06/2026

v1 launch from @b5.bsky.social & the @iroh.computer team! With Iroh your device is addressable anywhere in the world. 200M+ endpoints created on their public relays in the last 30 days alone. Rust, Python, Node.js, Swift, and Kotlin all speaking the same stable wire protocol. Dial keys, not IPs 🥳

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Ashley Smith @ashley3.com · 16/09/2025

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 🧵

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Ashley Smith @ashley3.com · 04/09/2025

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 🧵

vermilioncliffs.substack.com

Revenge of the Acronyms: Why Founders Have to Do It All

PLG.

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Ashley Smith @ashley3.com · 26/08/2025

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 🧵

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Ashley Smith @ashley3.com · 15/07/2025

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 🧵

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Ashley Smith @ashley3.com · 09/07/2025

“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.

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Ashley Smith @ashley3.com · 26/06/2025

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 👇

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Ashley Smith @ashley3.com · 06/06/2025

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-...

vermilioncliffs.substack.com

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.

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Ashley Smith @ashley3.com · 02/06/2025

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

open.substack.com

Mary Meeker Returns: What's Shaping the Next Gen of Technical Products, Founders, and the Market

Mary Meeker is back!

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Ashley Smith @ashley3.com · 23/05/2025

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...

vermilioncliffs.substack.com

Where Technical Products Should Focus for Effective GTM

Part 2 in The Golden Age of Devtools Meets the Rise of AI

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Ashley Smith @ashley3.com · 22/05/2025

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. 🧵 👇

vermilioncliffs.substack.com

Where Technical Products Should Focus for Effective GTM

Part 2 in The Golden Age of Devtools Meets the Rise of AI

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Ashley Smith @ashley3.com · 21/05/2025

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. 🧵

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Ashley Smith @ashley3.com · 20/05/2025

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. 👇 🧵

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Ashley Smith @ashley3.com · 19/05/2025

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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Ashley Smith @ashley3.com · 16/05/2025

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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Ashley Smith @ashley3.com · 15/05/2025

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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Ashley Smith @ashley3.com · 14/05/2025

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

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Ashley Smith @ashley3.com · 13/05/2025

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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Ashley Smith @ashley3.com · 12/05/2025

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...

vermilioncliffs.substack.com

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

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Ashley Smith @ashley3.com · 29/04/2025

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...

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Ashley Smith @ashley3.com · 06/02/2025

I look great with bangs and my wardrobe hasn't really changed. Excited to launch my debut $13m early stage fund @vermilion.fund

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