Khosla Ventures is betting $10M on Ian Crosby, whose last startup, Bench, imploded
techcrunch.com May 14, 2026

Khosla Ventures is betting $10M on Ian Crosby, whose last startup, Bench, imploded

AI-summarised brief · reviewed before publication

Ian Crosby, founder of the failed startup Bench Accounting, has raised $10 million in Seed funding for his new startup, Synthetic, which aims to build a fully autonomous AI bookkeeper. The funding round was led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke. Synthetic's product is still in the design phase, and Crosby acknowledges that his vision may not yet be technologically possible. Despite the challenges, Khosla partner Jon Chu is betting on Crosby, citing his potential for growth and learning from past mistakes. Crosby's new startup plans to serve AI and software startups with a fully AI-driven bookkeeping service.

💡 Why It Matters

  • · Khosla's investment in Synthetic highlights the firm's willingness to take risks on founders with controversial pasts, potentially uncovering hidden gems like Parker Conrad, who went on to found Rippling after being ousted from Zenefits.
  • · Crosby's experience and newfound patience to wait for foundational models to improve could lead to a breakthrough in autonomous bookkeeping.