Cowboy Ventures

Cowboy Ventures, founded in 2012 by Aileen Lee, is a Palo Alto-based venture capital firm that focuses on seed-stage investments. The firm supports innovative startups aiming to transform large markets through technology. Among Cowboy Ventures' notable investments is Guild, a platform reimagining education and skilling for working adults. Another key investment is Drata, which provides automated compliance for security frameworks, helping businesses ensure they meet necessary standards efficiently. Homebase is another significant investment, a SaaS platform that assists small businesses in managing their teams more effectively. Additionally, Cowboy Ventures has backed Vic.ai, an AI-driven company enhancing accounting and finance processes, and Ironclad, which offers comprehensive contract lifecycle management software. The firm has seen successful exits with companies like Dollar Shave Club, a subscription-based grooming products company; August Home, which develops smart home products; and NuORDER, a wholesale e-commerce platform. Recently, they have invested in CapStack Technologies, a fintech startup focusing on bank-to-bank transactions, and Getaway, which operates in the real estate tech space. Cowboy Ventures emphasizes a hands-on approach, helping portfolio companies with key hires, product development, go-to-market strategies, and preparing for future funding rounds.