Khosla Ventures Backs Bench Founder’s New AI Startup

Venture capital firm Khosla Ventures is making a bold new bet on entrepreneur Ian Crosby, despite the dramatic collapse of his previous startup, Bench Accounting, in 2024.

Crosby’s new company, Synthetic, has raised $10 million in Seed funding to build what he describes as a fully autonomous AI-powered bookkeeping platform. The funding round was led by Khosla Ventures, with participation from Basis Set Ventures and Tobias Lütke.

Synthetic’s goal is ambitious: creating an AI system capable of handling accrual-based bookkeeping entirely without human accountants. While many fintech startups currently use AI to assist human bookkeepers, Crosby wants to remove manual involvement altogether.

The idea comes with significant risk. Crosby openly admits the technology may not yet be fully capable of achieving his vision. The product is still in the design stage, and even the company’s prototype currently works only for a narrow set of users.

Still, Khosla Ventures partner Jon Chu believes controversial founders can sometimes become the biggest success stories.

“I tend to run towards controversy a little bit,” Chu told TechCrunch, explaining that public narratives often fail to tell the full story behind failed startups.

Chu compared Crosby’s situation to that of Parker Conrad, who faced heavy criticism after leaving Zenefits in 2016 before later building Rippling into a company valued at nearly $17 billion.

According to Crosby, he was not directly responsible for Bench’s eventual collapse. He said the company’s board removed him as CEO in 2021 after disagreements over strategy and spending. Crosby also revealed he had previously rejected a $250 million acquisition offer from Brex shortly before his departure.

Bench later struggled under new leadership and ultimately shut down in 2024 before being acquired at a significantly reduced value.

Following his exit from Bench, Crosby joined Shopify and later launched another accounting startup called Teal, which was acquired by Mercury about 18 months later.

Chu said he spoke with several executives who worked with Crosby after the Bench era and received highly positive feedback about his leadership and growth since then.

Despite the confidence from investors, Crosby acknowledges that current AI models still make major bookkeeping mistakes. He compared the challenge to self-driving technology, saying an AI system that works in one environment may still fail when exposed to more complicated situations.

“It’s like a self-driving car that can drive down one street versus the self-driving car that can drive down any street,” Crosby explained.

For now, Synthetic plans to focus mainly on AI startups and software companies while the technology matures. Crosby also said the company has enough funding to wait patiently for foundational AI models to improve before launching a broader product.

“We’re not going to release anything that’s not fully autonomous,” Crosby said. “It’s that or bust.”

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