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

And in 2025, event content is evergreen: • Record it • Transcribe it • Turn demos into tutorials One night can fuel weeks of marketing that doesn’t feel like marketing. Full post → 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

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.

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

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.

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

Today’s best events are tighter, founder- or user-led gatherings where real knowledge gets traded. No fluff. No salesy keynotes. What’s working: • 20-person dev dinners • Hack nights with hands-on builds • User-led meetups with zero stage, lots of signal

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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

5/ Clear beats clever. Narrative compounds. And your message is your moat. Jump ahead? Full post → 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 · 21/05/2025

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

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

3/ Great examples: • Tonic.ai → Owns the narrative on synthetic data • Astro Web → Defined “content-first dev” as a category

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

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

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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

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...

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 · 20/05/2025

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.

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 · 20/05/2025

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

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

2/ Teams are now treating onboarding like a product launch What that looks like: • Copy-pasteable examples that just work • Live playgrounds (CodeSandbox, StackBlitz, custom UIs) • “First 5 minutes” metrics that get tracked

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 · 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

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 along—sharing one GTM post like this every day this week Jump ahead? Full post 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 · 19/05/2025

3/ What’s working: • Starter kits tailored to frameworks • Community integrations that remove setup friction (e.g. Replit, VSCode) • Lightweight plugins that don’t need deep vendor deals

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

2/ A well-placed plugin or integration can outperform 10 blog posts. If your product can integrate with Vercel or Replit - do it. If your SDK can plug into a Bun starter or Next.js demo, build it and distribute it where those devs hang out.

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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

5/ Want to reach developers? Skip the SEO checklist. Go where they already hang out. Contribute something useful. Sharing one GTM post like this every day next week Jump ahead? Full post → 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 · 16/05/2025

4/ What’s working right now: • Sponsoring niche, ICP-specific dev newsletters • Founders showing up on Reddit with real answers • OSS-adjacent content that delivers value before a signup

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

3/ These aren’t just distribution channels. They’re validation mechanisms. A mention in a trusted Discord or repo can drive more traffic than a blog post

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

2/ That increasingly means: • Newsletters like Console.dev, Pragmatic Engineer, or Bens Bites • GitHub lists, “Show HN,” and high-signal Twitter/Bluesky • Discord servers for LangChain, Supabase, Bun, etc.

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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

5/ This kind of content lasts. LLMs train on it. Changelogs scrape it. Search indexes reward it. In a world of AI summaries, these artifacts are gold. The best marketing is progress, out loud. 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 · 15/05/2025

4/ Sid Sijbrandij at GitLab was way ahead of the curve. Launched every month on the 22nd, like clockwork. Bugs, weekends, didn’t matter. That consistency built real trust and real momentum.

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

3/ @zed.dev nails this. @supabase.com does it so often they created “launch weeks” They’re not massive companies. But they feel present. And that presence compounds.

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

2/ We’re seeing more founders adopt a “no feature left behind” mindset. If it ships, it gets shared. That doesn’t mean every update needs a blog post but if it’s meaningful, show it. Explain it. Ask for feedback.

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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

5/ Yes, it’s awkward at first. Yes, someone might critique your writing. Do it anyway. Silence is worse. I'm sharing one GTM post like this every day for the next 2 weeks. Jump ahead here → 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 · 14/05/2025

4/ In a world where every dev tool is “AI-powered,” specificity wins. Founder content cuts through because it’s honest: tradeoffs, failures, bugs, and breakthroughs.

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

3/ Think: • @charity.wtf (Honeycomb) • Michael Grinich (WorkOS) • Christina Cacioppo (Vanta) They’re not “doing marketing.” They’re building in public and sharing product decisions in real time

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

2/ The best GTM channel is still trust. And trust spreads fastest through founder-led content—especially in devtools. Developers follow people, not brands. Founders who show their face and share what they’re learning build gravity fast.

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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

6/ GTM for devtools is changing fast—and content is still the foundation. But now the audience is an AI system before it’s a human. Follow along—sharing one post like this every day for the next 2 weeks. Jump ahead? Here’s the full post → 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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