Ashley Smith

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

12 followers7 following59 posts

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 🥳

Iroh@iroh.computer

We just released the first stable version of iroh, v1.0! Read about it: www.iroh.computer/blog/v1 We're super proud of where we landed with iroh's 1.0. Since version 0.35 it feels like we've entirely replaced the "engine underneath". Are you a fellow key-dialer? Come tell us how you use iroh!

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 🧵

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 🧵

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 🧵

“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.

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 👇

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.comVermilion Cliffs Notes: From MVPs to Agents, How Freeplay Is Helping Teams Ship AI ProductsEval loops and why your best AI workflows might look more like a Slack thread than a sci-fi movie.
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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.

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

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.

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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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

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. 🧵

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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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. 👇 🧵

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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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

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. 🧵

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.

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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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

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. 🧵

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.

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

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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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.

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. 👇

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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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.

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.

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