Cowboy Ventures

Portfolio Companies 2026 for Cowboy Ventures: investors, rounds, and co-investor patterns from StartupFundraising.com research, updated for 2026.

Cowboy Ventures accounts for 8 tracked companies with verified cap-table data, 8 of which disclose round sizes totalling $1.4B. The median disclosed raise is $100M, and the largest is Guild Education at $554M, ahead of Drata ($328M) and Homebase ($169M).

The names that recur most often on these portfolio cap tables are Cowboy Ventures (8 companies), Harrison Metal (2 companies), Emergence Capital (2 companies), Wellington Management (1 company), Citi Impact Fund (1 company), Citigroup (1 company). By latest disclosed round, the market skews Series D (2), Series A (2), Growth (1), Series C (1).

Best funded Cowboy Ventures companies

  1. Guild Education — $554M (latest: Growth)
  2. Drata — $328M (latest: Series C)
  3. Homebase — $169M (latest: Series D)
  4. Vic.ai — $100M (latest: Series A)
  5. Crunchbase — $100M (latest: Series D)
  6. Hone — $50M (latest: Seed)
  7. Textio — $43M (latest: Series B)
  8. Stockly — $18M (latest: Series A)

Cowboy Ventures — related firms and companies (51)

Cowboy Ventures alternatives · All research reports