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

Ian Crosby, whose previous startup Bench Accounting famously shut down in 2024 before being bought for scraps , is taking another shot at building a business out of automating the arduous work of bookkeeping. His new startup, 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. …