Ian Crosby, whose accounting startup Bench collapsed in 2024, has raised $10 million for his new venture Synthetic. The seed round was led by Khosla Ventures with participation from Basis Set Ventures and Shopify CEO Tobias Lütke. Synthetic aims to create a fully autonomous AI bookkeeper that generates accrual-based financials without human intervention.

Khosla partner Jon Chu sees opportunity where others see risk. Despite Bench's dramatic failure—Crosby was fired by his board in 2021 after rejecting a $250 million acquisition offer from Brex—Chu believes founders deserve second chances. He points to Parker Conrad's post-Zenefits success with Rippling, now valued at nearly $17 billion, as precedent.

Synthetic targets AI and software startups specifically, avoiding the human-accountant model used by companies like Xero. However, Crosby acknowledges current AI models still make significant bookkeeping errors. His prototype works for narrow use cases, but scaling remains uncertain.

Crosby compares the challenge to self-driving cars: "We haven't driven down enough streets to know if it's going to crash." With years of runway secured, Synthetic can afford to wait for foundational models to improve before launching broadly.