Khosla Ventures bets $10M on Ian Crosby, whose last startup, Bench, was

Ian Crosby, whose previous Bench Accounting closed in 2024 before the remainder was bought out, is taking another step towards building a business by doing the hard work of bookkeeping.

His new startup, Synthetic, aims to build an 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 that his idea may not yet be technically 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 of the investors will come from a founder facing the kind of challenges Crosby is currently facing – the collapse of his previous business, and an idea that can exceed the technical capabilities of existing basic models. But Khosla’s colleague Jon Chu told TechCrunch that he sometimes does the opposite: “I tend to shy away from conflict a little bit.”

“In controversies, groupthink often shapes the narrative rather than the truth of the matter itself,” he said, citing Parker Conrad’s firing from Zenefits in 2016 as an example. While industry narratives were initially critical of Conrad, he later founded Rippling, which is now worth about $17 billion.

“I believe people have room to grow,” Chu said of his bets on Crosby and Synthetic.

Crosby says he was not directly responsible for bringing Bench into bankruptcy. According to Crosby, he was fired by the Bench board in 2021, three months after he turned down a $250 million purchase from Brex. The board also disagreed with Crosby’s strategy, especially as the business was hemorrhaging money, and his executive team was said to be fed up with his direct leadership style.

“He took a big swing, made a few mistakes. That didn’t go well,” Chu said.

The bench ended up solid when its new management failed to bring the company back to life.

After leaving Bench, Crosby joined Shopify and founded Teal, another accounting startup, which was bought by Mercury 18 months later.

As part of his due diligence, Chu said he spoke to several executives who worked with Crosby after he left the Bench, and they all “had good things to say about Ian,” Chu told TechCrunch.

Chu is confident that the three roles Crosby has held since leaving the Bench have given the businessman ample opportunity to learn from his past mistakes.

Crosby says his sights are set on creating a fully AI-driven bookkeeping service, rather than relying on human accountants, as most accounting startups like Xero do now.

“We’re not going to release anything that’s fully autonomous,” Crosby told TechCrunch. “It’s like that or it’s over.”

Artificial intelligence systems for AI and other software startups. But Crosby admits that AI models still make significant bookkeeping mistakes. While the Synthetic prototype works for a small group of users, it remains uncertain how it will scale to a wider customer base.

Crosby explained the 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.

However, the founder says he can be patient and wait for the basic models to be more reliable in accounting calculations.

“I’ve saved up for years, so we can just wait,” Crosby said.