Khosla Ventures is betting $10M on Ian Crosby, whose first startup, Bench, imploded
Ian Crosby, who led Bench Accounting before its dramatic shutdown in 2024, is stepping into the spotlight again with a new endeavor: Synthetic. Synthetic is focused on building a completely self-operating AI bookkeeper that can produce accrual-based financials with no human involvement. Despite the fact that Synthetic’s technology is still only at the design stage—and Crosby admits full autonomy may not be possible yet—the company has secured $10 million in seed funding from Khosla Ventures, plus participation from Basis Set Ventures and Shopify CEO Tobias Lütke.
Why Khosla Ventures Backed Crosby
While many investors might shy away from a founder facing previous failure and challenging technical goals, Khosla partner Jon Chu embraces controversy. He believes that industry groupthink can obscure reality and points to other comeback stories such as Parker Conrad of Rippling. According to Chu, Crosby’s journey post-Bench—including stints at Shopify and leading the startup Teal (later acquired by Mercury)—demonstrates his capacity for learning and growth.
Crosby’s Perspective on Bench and Beyond
Crosby maintains that he was not to blame for Bench’s collapse, noting he was let go by the board in 2021 after turning down a major acquisition offer and amid disagreements on company direction. Subsequent management failed to turn the company around. After Bench, Crosby stayed in the accounting tech space, and his later ventures convinced Khosla’s team of his focus and resilience.
The Vision for Synthetic
Synthetic targets AI and software companies, aiming to eliminate the need for human accountants. Crosby is adamant about launching only fully autonomous solutions and is realistic about current technology limitations, comparing Synthetic’s progress to a self-driving car that can only navigate a single street. The main challenge lies in expanding the system to reliably handle more diverse and complex scenarios.
With years of funding in hand, Crosby is taking a patient approach, waiting for AI improvements that will make fully autonomous bookkeeping possible. For now, Synthetic is working to perfect its narrow use-case as a step toward broader adoption.
For more details, read the original article by Marina Temkin at TechCrunch.
