Caffeinated Capital, a San Francisco-based venture firm led by Raymond Tonsing, is aiming to raise $400 million for its fifth fund, as revealed in a recent regulatory filing. So far, the firm has secured $160 million towards this goal. If successful, this would mark the largest capital raise in the firm’s 15-year history. Caffeinated has notable past investments, including Airtable and Saronic. Varun Gupta, who joined Tonsing as a general partner in 2020, adds experience from his role at Affirm, a platform Tonsing also backed early on.