Irregular Expressions
Irregular Expressions, IrregEx for short, is a group of seasoned software engineering and product leaders investing in and advising early stage technology startups. We’ve spent many cumulative decades bringing high-growth consumer and enterprise products to market, and are driven to help founders scale their own teams, products and businesses faster, by leveraging both our know-how and our network. Having co-founded, built and scaled hundreds of companies, primarily in the San Francisco, New York, and now remote-first ecosystems, we love working closely with the founders and teams we back, and think through thorny challenges on the product, engineering, and business fronts alike. Per Crunchbase, Irregular Expressions has made 73 investments across 70 portfolio companies, with 13 exits.
Investing activity
Irregular Expressions has made 73 investments according to Crunchbase across 70 portfolio companies, and has seen 13 exits.
Irregular Expressions appears in 2 AI deals tracked by the Lounge deals desk. The rounds are mostly Pre-seed, with a median round size of $3M. The most recent are Lemma (Pre-seed, $2.3M, Aug 2026) and Modiqo (Pre-seed, $3M, May 2026).
Irregular Expressions most often invests alongside Comma Capital, Position Ventures, Cervin Ventures and Liquid 2 Ventures, and the companies it backs on Lounge are mostly in AI.
Deals
Frequently asked questions about Irregular Expressions
What AI companies has Irregular Expressions invested in?
Irregular Expressions's AI investments include Lemma and Modiqo. The 2 rounds on Lounge are listed on this page with amounts, dates and co-investors.
Where is Irregular Expressions based?
Irregular Expressions is based in New York, New York, United States.
What stage does Irregular Expressions invest at?
In the rounds tracked on Lounge, Irregular Expressions has invested at Pre-seed, with a median round of $3M.
Who does Irregular Expressions co-invest with?
Irregular Expressions's most frequent co-investors on Lounge are Comma Capital (1 deal), Position Ventures (1 deal), Cervin Ventures (1 deal), Liquid 2 Ventures (1 deal) and Matrix Partners (1 deal).
How can founders reach Irregular Expressions?
Founders on Lounge can see Irregular Expressions's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with the firm under Warm Paths, and add Irregular Expressions to their Investor Pipeline to track the conversation.