Ian Crosby, whose previous startup Bench Accounting famously shut down in 2024 before being bought for scrap, is trying to make a business out of automating the drudgery of bookkeeping.
His new startup, Syntheticaims to create a fully autonomous AI accountant 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 feasible — 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 away from a founder facing the kind of challenges Crosby is facing right now — the fallout from his previous business collapse and a vision that may exceed the technical feasibility of today’s fundamental models. But Khosla’s partner Jon Chu told TechCrunch that sometimes she does just the opposite: “I tend to run toward controversy a little bit.”
“In confrontation, groupthink often shapes the narrative rather than the truth of the story itself,” he said, citing as an example the ouster of Parker Conrad from Zenefits in 2016. While the industry narrative was initially critical of Conrad, he went on to found Rippling, which is now valued at nearly $17 billion.
“I think people have room to grow,” Chu said of his bet on Crosby and Synthetic.
Crosby maintains that he was not directly responsible for driving Benz to the point of insolvency. According to Crosby, it was dismissed by the Bench’s board in 2021, three months after rejecting a $250 million takeover bid from Brex. The board also disagreed with Crosby’s strategic direction, especially as the business was bleeding cash and his executive team reportedly frustrated by his immediate leadership style.
“He took a big swing, made some mistakes. That didn’t go well,” Chu said.
Bench eventually collapsed when its new management proved unable to single-handedly restore the company to health.
After leaving Bench, Crosby joined Shopify and founded Teal, another accounting startup, which was acquired by Mercury 18 months later.
As part of his due diligence, Chu said he talked to several executives who worked with Crosby after he left the Bench, and they all “had fantastic things to say about Ian,” Chu told TechCrunch.
Chu is convinced that Crosby’s three roles since leaving the bench have given the entrepreneur plenty of opportunities to learn from past mistakes.
Crosby says he has his eyes firmly set on creating a bookkeeping service that is fully AI-powered, rather than relying on human accountants, as most accounting startups like Xero now do.
“We’re not going to release anything that isn’t fully autonomous,” Crosby told TechCrunch. “It’s this or bust.”
Synthetic plans to serve only AI and other software startups. But Crosby acknowledges that AI models still make significant accounting errors. While Synthetic’s prototype works for a narrow group of users, it remains uncertain how it will scale to a wider customer base.
Crosby explained with an analogy: “It’s like a self-driving car that can drive on one road versus a self-driving car that can drive on any road. We haven’t driven on enough roads to know if it’s going to crash.”
However, the founder says he can be patient and wait for the underlying models to become more reliable for accounting calculations.
“I’ve been saving years of cash, so we can just wait it out,” Crosby said.
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