Ian Crosbie’s previous startup, Bench Accounting, which famously closed in 2024 before being acquired for scrap, is taking on a new challenge: building a business by automating the arduous task of bookkeeping.
His new startup, Synthetic, aims to build a fully autonomous AI bookkeeper that can generate accrual-based financials without direct human involvement. Although the product is still in the design stage, and Crosby acknowledges that his vision may not be technically feasible yet, 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 fleece a founder facing challenges like the one Mr. Crosby is currently facing, the fallout from the collapse of his previous business and a vision that may exceed the technical feasibility of the current underlying model. But Jon Chu, a partner at Khosla, told TechCrunch that he sometimes does the opposite. “I tend to get a little argumentative.”
“In controversies, groupthink often shapes the narrative rather than the truth of the story itself,” he said, citing Parker Conrad’s 2016 ouster from Zenefits as an example. Although industry opinion was initially critical of Conrad, he went on to found Rippling, a company now valued at nearly $17 billion.
“I believe people have room to grow,” Chu said of the bet on Crosby and synthetics.
Mr. Crosby maintains that he was not directly responsible for pushing Mr. Bench to the brink of bankruptcy. He said he was fired by Bench’s board in 2021, three months after he turned down a $250 million acquisition offer from Brex. The board also disagreed with Mr. Crosby’s strategic direction, especially as the business was cash-strapped and his management team reportedly dissatisfied with Mr. Crosby’s direct leadership style.
“He swung wide and made some mistakes. It didn’t go well,” Chu said.
Bench eventually collapsed as new management proved unable to restore the company to health on its own.
After leaving Bench, Crosby joined Shopify and founded another accounting startup, Teal, which was acquired by Mercury 18 months later.
As part of his due diligence, Chu spoke with several executives who worked with Crosby after he left the bench, and all of them “had great things to say about Ian,” Chu told TechCrunch.
Chu believes the three roles Crosby played after leaving the bench provided the entrepreneur ample opportunity to learn from past mistakes.
Crosby says the company is firmly looking towards creating a fully AI-driven bookkeeping service, rather than relying on human accountants, as most accounting startups such as Xero are currently doing.
“We’re not going to release anything that isn’t fully autonomous,” Crosby told TechCrunch. “It’s either that or bust.”
Synthetic plans to serve only AI and other software startups. But Crosby acknowledged that AI models still make serious bookkeeping mistakes. Synthetic’s prototype works for a limited group of users, but it’s still unclear how it can scale to a broader customer base.
“It’s like a self-driving car that can drive down one street and a self-driving car that can drive down any street. We haven’t driven enough roads to know if we’re going to crash or not,” Crosby said.
Still, the founders say they can afford to be patient until the underlying model improves the reliability of bookkeeping calculations.
“I’ve been raising money for years, so I’m just waiting for it to finish,” Crosby said.
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