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

"Synthetic aims to build a fully autonomous AI bookkeeper that can generate accrual-based financials without direct human involvement. Although the product is still in the design phase - and Crosby admits his vision may not yet be technologically possible - the startup has raised $10 million in a Seed funding round led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke."

"Most investors would run from a founder facing the kind of challenges Crosby is right now - the fallout of his previous business collapsing, and a vision that may exceed the technical feasibility of current foundational models. But Khosla partner Jon Chu told TechCrunch he sometimes does just the opposite: "I tend to run towards controversy a little bit.""

""In controversy, groupthink often shapes the narrative rather than the truth of the story itself," he said, citing Parker Conrad's 2016 ousting from Zenefits as an example. While the industry narrative was initially critical of Conrad, he subsequently founded Rippling, which is now valued at nearly $17 billion. "I believe people have room for growth," Chu said about his bet on Crosby and Synthetic."

"Crosby maintains he wasn't directly responsible for bringing Bench to the point of insolvency. According to Crosby, he was fired by Bench's board in 2021, three months after he turned down a $250 million acquisition offer from Brex. The board also disagreed with Crosby's strategic direction, especially as the business was bleeding cash, and his executive team was reportedly frustrated with his direct leadership style."

Synthetic is developing a fully autonomous AI bookkeeper intended to produce accrual-based financials without direct human involvement. The product remains in the design phase, and the founder acknowledges the vision may not yet be technologically feasible with current foundational models. The startup has raised $10 million in a Seed round led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke. The founder previously led Bench Accounting, which shut down in 2024 and was acquired for minimal value. Despite concerns about prior failure and technical uncertainty, investors backed the new effort, citing a willingness to pursue controversial bets and allow for founder growth.

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