Matt Cynamon, an AI project lead at Union Square Ventures, discusses the innovative AI operating system he's building for the firm. He highlights tools like 'The Librarian,' a chatbot trained on vast blog content, and 'Portfolio Tracker,' which analyzes investments. Their new meeting notes tool enhances discussions by extracting actionable insights. Matt also shares his excitement about 'The Dream Machine,' a unique project transforming words into art, and emphasizes how AI is revolutionizing both venture capital and creative processes.
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Becoming USV's AI Lead
Matt Cynamon became USV's "AI guy" by following his curiosity.
He sent weekly emails about talent, but included AI-generated movie trailers he made for fun.
volunteer_activism ADVICE
Embrace Tinkering
Follow your curiosities and experiment with new technologies.
Don't be afraid to share your side projects, even if they seem unrelated to your main work.
insights INSIGHT
AI Empowering Generalists
AI empowers generalists to become creators by lowering the barrier to entry for creative expression.
It allows experimentation and skill development alongside the creative process, unlike traditional methods.
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Moby-Dick is a novel that tells the story of Captain Ahab's maniacal quest for revenge against Moby Dick, the giant white sperm whale that bit off his leg. Narrated by Ishmael, the story follows the crew of the whaling ship Pequod as they embark on a journey that explores themes of obsession, man vs. nature, and the existential questions of good and evil. The novel is rich in detailed descriptions of whale hunting and life aboard a culturally diverse crew, and it has become a cornerstone of American and world literature[2][3][5].
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 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. We even try out an art project at USV’s office called The Dream Machine, which generates art from conversations. 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.
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