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    Irregular Expressions

    New York, New York, United StatesFounded 2018

    Irregular Expressions (IrregEx) is an early-stage venture capital firm backed by a group of seasoned software engineering and product leaders. It invests in and advises pre-seed and seed-stage startups focused on infrastructure, data engineering, and machine learning.

    35% of their portfolio is in AI. Deal activity decreased year-over-year (1 deal in the last 12 months vs 4 prior). Their most common stage is seed (65% of deals). Average disclosed round size is $6.1M (across 15 rounds with reported amounts).

    Find people at Irregular Expressions on Goldilocks AI

    Portfolio

    15

    Fund Size

    —

    Top Stage

    Seed

    Last 12 Mo

    1

    Team

    Alex Ingram

    Alex Ingram

    Co-Founder @Zest, Co-Founder @Sunlight Health, Director of Product Management @Flatiron Health

    Alexis Lê-Quôc

    Alexis Lê-Quôc

    Co-Founder & CTO @Datadog, Director of Live Operations @Wireless Generation (now Amplify)

    Antoine Boulanger

    Antoine Boulanger

    Engineering Leader @Stripe, Co-Founder & CEO @Okay, Senior Director of Engineering @Box, Engineer @Google

    Arun Nagarajan

    Arun Nagarajan

    CPO & CTO @Evolve, Co-Founder & CTO @BigSpring, Director Engineering @Uber, VP Engineering @Twenty, Tech Lead, Developer Platform @Google

    Ben Birnbaum

    Ben Birnbaum

    Co-Founder, President, and CTO @Inductive Bio, Senior Engineering Director @Flatiron Health, Senior Software Engineer @Google

    Chris Crane

    Chris Crane

    Co-Founder & CPO @fiveonefour, Head of Product @Datalogue (acquired by Nike), GM & VP Product @Sysdig, Associate @Bain Capital Ventures

    Greg Ratner

    Greg Ratner

    Senior Director of Software Engineering @Slack, Co-Founder & CTO @Troops

    James Boehmer

    James Boehmer

    CTO & Co-Founder @Stealth, Senior Manager of Engineering @Etsy, VP of Engineering @Altana, VP Content Engineering @Disney Media

    Liz Maida

    Liz Maida

    Co-Founder & CEO @Fathom, Co-Founder & CEO @Uplevel Security, Senior Director Product Development @Akamai Technologies

    Marc Brown

    Marc Brown

    CTO @Caire, Director of Engineering @Ro, Co-Founder & CTO @Lever Health

    Renaud Visage

    Renaud Visage

    Founding Partner @Slate Venture Capital, Co-Founder & CTO @Eventbrite, Venture Partner @Point Nine, Venture Partner @Index Ventures

    Steven Kuyan

    Steven Kuyan

    Co-Founder & CEO @Luro Health, Co-Founder & Co-CEO @Culina Health, Director @NYU Center for Responsible AI, Managing Director @NYU Tandon Future Labs

    Portfolio Breakdown

    Stage Distribution

    Sector Distribution

    Investment Activity

    DealsAvg Round Size

    Portfolio

    17 investments
    CompanyRoundAmountDate
    Modiqo logoModiqoPre-Seed$3MMay 2026
    Lemma logoLemmaPre-Seed$2.3MJan 2026
    Alpic logoAlpicPre-Seed$5.1MSep 2025
    TopK logoTopKSeed—Jul 2025
    TopK logoTopKSeed$5.5MJan 2025
    Salt AI logoSalt AISeed$3MDec 2024
    Pydantic logoPydanticSeries A$12.5MOct 2024
    Salt logoSaltSeed$3MJan 2024
    Salt logoSaltSeed$3MJan 2024
    Mermaid logoMermaidSeed$7.5MJan 2024
    Escape logoEscapeSeed$3.9MJun 2023
    Play logoPlaySeed$5.5MJan 2023
    Pydantic logoPydanticSeed$4.7MJan 2023
    PPydantic Services Inc.Seed$4.7MJan 2023
    Shortcut logoShortcutSeries B$25MJan 2020
    Popsink logoPopsinkSeed——
    MecAgent logoMecAgentPre-Seed$2.8M—

    Top Co-Investors

    Last updated: 20 October 2026