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
Watch the full episode here: vermilioncliffs.substack.com/p/why-mcp-is...
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…
vermilioncliffs.substack.com
August 26, 2025 at 7:11 PM
Watch the full episode here: vermilioncliffs.substack.com/p/why-mcp-is...
Watch the full episode here -> vermilioncliffs.substack.com/p/open-sourc...
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
July 9, 2025 at 7:25 PM
Watch the full episode here -> vermilioncliffs.substack.com/p/open-sourc...
Watch on Substack ➡️ open.substack.com/pub/vermilio...
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.
open.substack.com
June 26, 2025 at 2:23 PM
Watch on Substack ➡️ open.substack.com/pub/vermilio...
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...
• 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...
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
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...
• 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...
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.
Agent Hack Night felt like 2012 again.
These work because they feel authentic and devs can smell the difference.
May 22, 2025 at 3:04 PM
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.
Agent Hack Night felt like 2012 again.
These work because they feel authentic and devs can smell the difference.
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.
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.
May 22, 2025 at 3:04 PM
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.
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.
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
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
May 22, 2025 at 3:04 PM
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
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
5/ Clear beats clever.
Narrative compounds.
And your message is your moat.
Jump ahead? Full post → vermilioncliffs.substack.com/p/where-tech...
Narrative compounds.
And your message is your moat.
Jump ahead? Full post → 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 21, 2025 at 3:07 PM
5/ Clear beats clever.
Narrative compounds.
And your message is your moat.
Jump ahead? Full post → vermilioncliffs.substack.com/p/where-tech...
Narrative compounds.
And your message is your moat.
Jump ahead? Full post → vermilioncliffs.substack.com/p/where-tech...
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
• Founder-written “Why we built this” posts
• Internal positioning docs shared across GTM + product
• Message consistency across site, docs, and channels
May 21, 2025 at 3:07 PM
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
• Founder-written “Why we built this” posts
• Internal positioning docs shared across GTM + product
• Message consistency across site, docs, and channels
2/ Positioning isn’t fluff.
It’s the starting point for GTM.
Why now? Who’s it for? Why you?
It’s the starting point for GTM.
Why now? Who’s it for? Why you?
May 21, 2025 at 3:07 PM
2/ Positioning isn’t fluff.
It’s the starting point for GTM.
Why now? Who’s it for? Why you?
It’s the starting point for GTM.
Why now? Who’s it for? Why you?
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...
What’s the most important thing in your DevX?
Jump ahead? Full post 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 20, 2025 at 4:59 PM
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...
What’s the most important thing in your DevX?
Jump ahead? Full post vermilioncliffs.substack.com/p/where-tech...