
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).
Portfolio
15
Fund Size
—
Top Stage
Seed
Last 12 Mo
1
Team
Alex Ingram
Co-Founder @Zest, Co-Founder @Sunlight Health, Director of Product Management @Flatiron Health
Alexis Lê-Quôc
Co-Founder & CTO @Datadog, Director of Live Operations @Wireless Generation (now Amplify)
Antoine Boulanger
Engineering Leader @Stripe, Co-Founder & CEO @Okay, Senior Director of Engineering @Box, Engineer @Google
Arun Nagarajan
CPO & CTO @Evolve, Co-Founder & CTO @BigSpring, Director Engineering @Uber, VP Engineering @Twenty, Tech Lead, Developer Platform @Google
Ben Birnbaum
Co-Founder, President, and CTO @Inductive Bio, Senior Engineering Director @Flatiron Health, Senior Software Engineer @Google
Chris Crane
Co-Founder & CPO @fiveonefour, Head of Product @Datalogue (acquired by Nike), GM & VP Product @Sysdig, Associate @Bain Capital Ventures
James Boehmer
CTO & Co-Founder @Stealth, Senior Manager of Engineering @Etsy, VP of Engineering @Altana, VP Content Engineering @Disney Media
Liz Maida
Co-Founder & CEO @Fathom, Co-Founder & CEO @Uplevel Security, Senior Director Product Development @Akamai Technologies
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
Portfolio
| Company | Round | Amount | Date |
|---|---|---|---|
| Pre-Seed | $3M | May 2026 | |
| Pre-Seed | $2.3M | Jan 2026 | |
| Pre-Seed | $5.1M | Sep 2025 | |
| Seed | — | Jul 2025 | |
| Seed | $5.5M | Jan 2025 | |
| Seed | $3M | Dec 2024 | |
| Series A | $12.5M | Oct 2024 | |
| Seed | $3M | Jan 2024 | |
| Seed | $3M | Jan 2024 | |
| Seed | $7.5M | Jan 2024 | |
| Seed | $3.9M | Jun 2023 | |
| Seed | $5.5M | Jan 2023 | |
| Seed | $4.7M | Jan 2023 | |
| PPydantic Services Inc. | Seed | $4.7M | Jan 2023 |
| Series B | $25M | Jan 2020 | |
| Seed | — | — | |
| Pre-Seed | $2.8M | — |
Top Co-Investors
Last updated: 20 October 2026