Ian Crosby Raises $10M for AI Bookkeeping Startup Synthetic After Bench Accounting Collapse

Ian Crosby has raised $10 million in a Seed funding round for his new startup Synthetic, which aims to build a fully autonomous AI bookkeeper that generates accrual-based financials without direct human involvement. Khosla Ventures led the round, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke.

The funding comes as Crosby seeks to move past the collapse of his previous company, Bench Accounting.

Bench Accounting shut down in 2024 before being bought for scraps. Ian Crosby was fired by Bench’s board in 2021, three months after he turned down a $250 million acquisition offer from Brex. Bench’s board disagreed with Ian Crosby’s strategic direction as the business was bleeding cash, and his executive team was frustrated with his direct leadership style.

After leaving Bench, Ian Crosby joined Shopify. He then founded Teal, which was bought by Mercury 18 months after it was founded. ” Jon Chu told TechCrunch he sometimes runs toward controversy. “I tend to run towards controversy a little bit,” he said.

“In controversy, groupthink often shapes the narrative rather than the truth of the story itself,” Chu added, citing Parker Conrad’s 2016 ousting from Zenefits as an example. Conrad subsequently founded Rippling, which is now valued at nearly $17 billion. Chu said he believes people have room for growth.

He noted that the three roles Crosby held after leaving Bench provided ample opportunity to learn from past mistakes. “He took a big swing, made a few mistakes. That didn’t go well,” Chu said of the Bench experience.

Synthetic plans to serve only AI and other software startups. Crosby maintains the company will not release any product that is not fully autonomous. “We're not going to release anything that's not fully autonomous.

It’s that or bust,” Ian Crosby told TechCrunch. Crosby acknowledged that AI models still make significant bookkeeping mistakes. The prototype for Synthetic works for a narrow group of users. “It's like a self-driving car that can drive down one street versus the self-driving car that can drive down any street.

We haven't driven down enough streets to know if it's going to crash,” Ian Crosby said. Still, Crosby said he can afford patience as foundational models improve. “I've raised years of cash, so we can just wait it out,” he told TechCrunch.

@techcrunch reported that although the product is still in the design phase and Crosby admits his vision may not yet be technologically possible, Khosla Ventures chose to back the founder despite the controversy surrounding his prior venture. Bench imploded when its new management proved unable to restore the company to health on its own.

Crosby maintains he wasn’t directly responsible for bringing Bench to the point of insolvency.

The new funding round values the bet on Crosby’s ability to apply lessons from both Bench and Teal to the challenge of autonomous bookkeeping.