Vermilion Cliffs Ventures Fund II has closed at $25 million, with solo GP Ashley Smith targeting AI infrastructure, security, and developer tools through cheques of $500,000 to $1 million per company. The Delaware-registered vehicle, filed with the SEC, is the follow-on to a $13 million debut fund that punched above its weight before anyone was paying close attention.
Smith told TechCrunch she raised the new fund in around four months, with the bulk of capital coming from existing investors. Make of that what you will: re-ups from LPs who already know your portfolio is usually the most honest signal a manager can offer.
What Vermilion Cliffs Ventures Fund II Is Actually Backing
The thesis is tight. Technical founders building in AI infrastructure, security, and dev tools, with Smith deploying from Fund II into at least 25 companies over the next two and a half years. Six portfolio companies are already in.
The firm’s value-add pitch rests on go-to-market rather than another generic ‘we help founders fundraise’ line. Smith spent time in marketing roles at Twilio, Facebook, GitHub, and GitLab, and the argument is that selling to developers and security teams is genuinely different from selling to enterprise buyers. ‘Selling to developers and security teams is its own discipline, and most founders learn it the expensive way with time,’ she told TechCrunch. ‘I try to help them skip mistakes I’ve made or seen other founders make.’
That’s a narrower and more credible positioning than most seed managers offer. Whether it scales past 25 bets is the question Fund III will eventually answer.
How Fund I’s Portfolio Has Performed
The Fund I Delaware entity backed 35 companies on that $13 million base, making the average cheque somewhere south of $400,000. Two names from that cohort have since broken into the open.
Keycard, a cybersecurity startup founded by former Snyk and Okta senior leadership, emerged from stealth with $38 million in total funding: an $8 million seed followed by a $30 million Series A, according to SecurityWeek. That is a tidy result for a Fund I that wrote sub-$400,000 cheques.
CopilotKit, the AI infrastructure company co-founded by brothers Atai and Uli Barkai, has raised $27 million in total: $6.5 million in seed funding co-led by Glilot Capital Partners, NFX, and SignalFire, and a $20.5 million Series A, per Ctech. Its AG-UI open standard has since been adopted by Google, Microsoft, Amazon, and Oracle, and the company claims more than half of the Fortune 500 use its tools, according to GeekWire. Whether you treat that Fortune 500 claim at face value probably depends on how carefully you read the fine print about open-source usage versus paying enterprise customers.
Two strong-looking logos out of 35 is not a verdict yet. But for a $13 million fund run by one person with no back-office, it is a reasonable foundation for asking LPs to write another cheque.
Solo GPs, Sector Focus, and Why Both Matter Here
Smith operates in a part of the market where genuine differentiation is scarce. Most seed funds will tell you they back technical founders, help with distribution, and move fast. The solo GP structure at least removes the partnership dynamics that slow larger firms down, and the sector concentration in AI infrastructure, security, and dev tools is specific enough to mean something.
The developer-go-to-market angle is worth watching. The companies most likely to struggle in this cohort will be the ones with strong product and weak sales motion, and that is precisely the gap Smith says she fills. If CopilotKit’s enterprise traction is any guide, the thesis has at least one live proof point behind it.
The 25-company target over two and a half years implies roughly 10 investments per year at $500,000 to $1 million a pop. For a $25 million fund, the maths works out comfortably. The harder question is whether the portfolio companies generating real revenue can pull the rest of the fund’s returns. The answer to that one comes with Fund III.
