A few months ago I started a sub-newsletter centered around the idea of "what would I invest in if I had a $4m, $60m, or $250m check?". The following investment memos are written under that premise.

Each memo will lead you back to the newsletter where I wrote about the company. Some valuation numbers are best estimates while others I sourced from Pitchbook and other resources.

Antimetal logo

Antimetal

An AI-driven platform that automates and optimizes everything that happens after you deploy your cloud infrastructure.

Current Stage:Series A
Initial Valuation:$200M
Recent Valuation:$200M
Jun 23, 2025
OffDeal logo

OffDeal

The “AI-native” investment bank built to help small and mid-size business owners sell their companies faster and at higher value by automating much of the traditional M&A workflow.

Current Stage:Series A
Initial Valuation:$30M
Recent Valuation:$100M
Jun 16, 2025
Rogo AI logo

Rogo AI

A secure generative-AI platform tailored for elite financial institutions, providing automation, insights and workflow tools for investment banking & finance professionals.

Current Stage:Series B
Initial Valuation:$350M
Recent Valuation:$350M
June 3, 2025
Cursor logo

Cursor

An AI-powered code editor (built on VS Code) that understands your codebase and predicts or assists your next edits to boost developer productivity.

Current Stage:Series C
Initial Valuation:$9.9B
Recent Valuation:Tender - $27B
Jun 9, 2025
Profound logo

Profound

A platform that helps brands monitor and optimize how they appear in AI-powered search and answer engines, not just traditional web search.

Current Stage:Seed
Initial Valuation:$40M
Recent Valuation:$250M
May 26, 2025