Khosla Ventures is betting $10M on Ian Crosby, whose first startup, Bench, was invested.

Ian Crosby, founder of the popular Accounting Bench closed in 2024 before he was buy leftoversthey are also taking a different approach to building a business because of the tedious work of bookkeeping.

His new beginning, Productsthe goal is to create an autonomous AI bookkeeper that can generate accrual-based income without direct human involvement. Although the product is still in the design phase – and Crosby admits that his vision may not be technically feasible – the startup has raised $10 million in seed funding led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke.

Many investors can walk away from a startup that is facing the challenges Crosby is facing right now – the collapse of his previous business and a vision that may exceed the technological capabilities of current startups. But Khosla’s partner Jon Chu told TechCrunch that he sometimes does the opposite: “I like to run into the controversy a little bit.”

“In a debate, groupthink often makes the story rather than the truth about the story,” he said, citing Parker Conrad’s 2016 example at Zenefits. Although corporate news initially criticized Conrad, he later founded Rippling, which is now valued at approximately $17 billion.

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

Crosby is adamant that he was not responsible for bringing Bench to the point of failure. According to him, he was dismissed by the Bench board in 2021, three months after rejecting a $250 million offer from Brex. The organization also disagreed with Crosby’s approach, mainly because the business was losing money, and his main team was told. frustrated by his direct leadership.

“They changed a lot, they made a few mistakes. That didn’t go well,” Chu said.

Bench eventually settled when its new management failed to restore the company’s independence.

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

As part of his due diligence, Chu said he spoke with 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 believes that Crosby’s three stints after leaving the bench gave the businessman ample opportunity to learn from his past mistakes.

Crosby says he has his sights set on creating an AI-powered bookkeeping service, rather than relying on human accountants, as many accounting services such as Xero do now.

“We don’t release anything that isn’t independent,” Crosby told TechCrunch. “It’s that or the explosion.”

Synthetic plans to use only AI and other basic software. But Crosby admits that AI models still make serious storage errors. Although the Synthetic form works for a small group of users, they do not know how to increase the number of customers.

Crosby explained metaphorically: “It’s like a self-driving car that can drive down one road versus a self-driving car that can drive down any road.”

However, the founder says he can afford to be patient and wait for the first samples to be reliable in the calculations.

“I’ve made a lot of money, so we’ll just have to wait,” Crosby said.