Khosla Ventures invests $10M in Ian Crosby, eyeing a comeback after Bench's failure

Khosla Ventures invests $10M in Ian Crosby, eyeing a comeback after Bench's failure

Ian Crosby's new venture, Synthetic, has secured $10 million in seed funding to develop an AI bookkeeper, despite his controversial past with Bench Accounting. What could this mean for the future of bookkeeping?

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Ian Crosby has raised $10 million in seed funding for his new venture, Synthetic, which aims to create a fully autonomous AI bookkeeper. The funding round, led by Khosla Ventures, also saw participation from Basis Set Ventures and Shopify CEO Tobias Lütke. Despite facing challenges stemming from his previous startup, Bench Accounting, which shut down in 2024, Crosby is determined to innovate in the field of bookkeeping.

Although still in the design phase, Crosby's vision for Synthetic involves generating accrual-based financials without human intervention. Khosla partner Jon Chu expressed confidence in Crosby's potential, stating that he prefers to embrace controversy and recognize the capacity for growth in entrepreneurs. Despite Crosby's claims that he was not solely responsible for Bench's insolvency, his previous tenure at the company remains a point of scrutiny.

After being ousted from Bench in 2021, Crosby joined Shopify and later founded Teal, which was acquired by Mercury within 18 months. As part of his assessment, Chu spoke to executives who worked with Crosby post-Bench, receiving positive feedback about his leadership abilities.

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