Khosla Ventures leads $10 million seed round for Synthetic, an autonomous AI bookkeeping startup by former Bench founder Ian Crosby

Khosla Ventures is leading a $10 million seed funding round for Synthetic, a startup built by Ian Crosby that aims to create a fully autonomous AI bookkeeper for software companies. The round also includes participation from Basis Set Ventures and Shopify CEO Tobias Lütke. Crosby is attempting to rebuild his entrepreneurial reputation after his previous venture, Bench Accounting, collapsed in 2024 following cash burn and strategic disagreements with its board.

Crosby's departure from Bench occurred in 2021 when the board dismissed him three months after he declined a $250 million acquisition offer from Brex. The company subsequently deteriorated under new management before shutting down. Between then and launching Synthetic, Crosby worked at Shopify and founded Teal, another accounting startup, which Mercury acquired roughly 18 months later.

Synthetic's stated vision is ambitious: generate accrual-based financial statements without human intervention, targeting only AI-native startups as initial customers. However, Crosby acknowledged the product exists only in design phase and that current foundational models make material errors in bookkeeping calculations. He described the technical challenge as analogous to autonomous vehicles navigating unfamiliar terrain, stating the company has not yet determined if the approach will scale beyond narrow use cases.

Khosla partner Jon Chu framed his investment as a contrarian bet on founder rehabilitation, citing Parker Conrad's recovery arc—Conrad was ousted from Zenefits in 2016 amid industry criticism, then founded Rippling, now valued at approximately $17 billion. Chu indicated he had spoken with executives who worked with Crosby after Bench and received positive assessments of his performance. Crosby signaled willingness to delay revenue in favor of waiting for AI model improvements, noting the startup had secured multi-year operating capital.