Dan Shipper is the CEO and cofounder of Every. Every week he explores the frontiers of AI in his column, Chain of Thought, and on his podcast, ‘AI & I.’
How Union Square Ventures Built an AI Brain for Venture Capital
Inside Matt Cynamon’s suite of custom AI tools for the tier-A firm
Oct 30, 2024 · 9 min readUpdated May 15, 2026
TL;DR: Today we’re releasing a new episode of our podcast AI & I. I go in depth with Matt Cynamon, who runs experiments with AI at Union Square Ventures. We get into how AI enables generalists to build and conduct live demos of the suite of AI tools he’s building for USV. Watch on X or YouTube, or listen on Spotify or Apple Podcasts.
Union Square Ventures is building an AI operating system to support their investment team.
But it’s not what you think: It’s a constellation of AI tools that captures and synthesizes the firm's collective wisdom. It’s evolving every day, and Matt Cynamon is the mad scientist in charge.
Matt calls himself a “regular” at USV. In practice that means he’s responsible for running experiments with AI for the firm. As an inherently curious person with the professional obligation to tinker, he’s built a suite of tools for the firm, including:
- The Librarian, a chatbot trained on around 15,000 articles from USV’s blog
- Portfolio Tracker, a GPT that analyzes the investments made by the firm
- Meeting Notes, a tool that makes it possible for team members to interact with meetings
I sat down with Matt to talk about how AI is enabling him to bring his ideas to life as a generalist, get demos of the tools listed above, and exchange notes on all the other projects he has in the works at USV. We try out an art project at USV’s office called The Dream Machine, which generates art from conversations. And we edit actionable insights extracted by an AI from meetings at USV and prepare them to be posted on the firm’s X handle live on the show. Here’s a link to the episode transcript.
This is a must-watch for anyone interested in riding the AI wave by learning how to ship useful products quickly.
Watch on X or YouTube, or listen on Spotify or Apple Podcasts.
Sponsored by: Every
Tools for a new generation of builders
When you write a lot about AI like we do, it’s hard not to see opportunities. We build tools for our team to become faster and better. When they work well, we bring them to our readers, too. We have a hunch: If you like reading Every, you’ll like what we’ve made.
Go deeper with Matt
Every paid subscribers can read the top takeaways from this episode, such as:
- Why generalists will thrive in the age of AI
- Demos of four custom AI tools that USV uses in-house
- The projects that Matt has in the pipeline at USV
Want to get all of this and more? Subscribe to Every below.
Subscribe to read the full articleThe Only Subscription
You Need to
Stay at the
Edge of AI
The essential toolkit for those shaping the future
"This might be the best value you
can get from an AI subscription."
- Jay S.
Every Content
AI&I Podcast
Dan Shipper
