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Irregular Expressions is a venture capital firm that invests in and advises pre-seed and seed-stage startups focused on infrastructure, data engineering, AI, DevOps, security, observability, and developer productivity. The firm leverages the expertise and network of its backers, who are seasoned software engineering and product leaders, to help founders scale teams and businesses. Founded by Jean Sini, a former CTO at Mint, Cadre, Fountain, and One Kings Lane, the firm draws on Sini's prior angel investments in Canva and Treasure Data. Its network includes Hiro Yoshikawa, Founder and CEO of Treasure Data. The firm's portfolio features companies with founders such as Cliff Obrecht of Canva, John Honchariw of Companion, and Basel Fakhoury of User Interviews. Its business model centers on invests in early-stage startups, backed by a group of engineering leaders.