After Bench's collapse, Ian Crosby raises $10M for Synthetic, an autonomous AI bookkeeper

Why it matters

Second acts matter in startups, and capital is lining up behind founders with scars if the problem is big enough. If Synthetic can automate accrual bookkeeping end to end, it could compress costs and cycle times for thousands of startups and small businesses. The bet also tests whether contrarian investors can turn founder controversy into outlier outcomes when the technology looks slightly ahead of its time.

Ian Crosby is back. The Bench Accounting founder has raised a $10 million seed round for Synthetic, an AI startup aiming to deliver a fully autonomous bookkeeper that produces accrual-based financials without human intervention, he told TechCrunch.

The round is led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lutke. The product is still in the design phase, and Crosby acknowledged to TechCrunch that the vision may be ahead of what current models can do today.

From Bench to a second act

Crosby is building again less than two years after Bench Accounting shut down in 2024 and was later acquired. He maintains he was not at the helm when Bench hit the wall. In a LinkedIn post, Crosby said the board fired him in 2021, three months after he declined a $250 million offer from Brex, citing strategic disagreements as the company burned cash. Around the same time, his executive team was reportedly frustrated with his direct leadership style, according to Newcomer.

That recent history makes the wager on Synthetic notable. Most investors steer away from controversy or a complex founder backstory. Khosla Ventures partner Jon Chu told TechCrunch the firm sometimes leans into it: "I tend to run towards controversy a little bit." He added, "In controversy, groupthink often shapes the narrative rather than the truth of the story itself," pointing to Parker Conrad's 2016 ouster from Zenefits and his comeback building Rippling, now valued near $17 billion. "I believe people have room for growth," Chu said about backing Crosby.

What Synthetic wants to ship

Crosby's pitch is simple and ambitious: a system that ingests a startup's financial exhaust and continuously produces GAAP-ready, accrual-based statements without a human bookkeeper in the loop. It is a bolder claim than most AI fintech products, which still rely on human review. Even Crosby concedes the technology may not yet exist off the shelf, which is why Synthetic is in design rather than general availability.

If Synthetic can get there, the prize is obvious. Bookkeeping for small businesses has been a tug-of-war between software and services for decades. An agentic system that reliably classifies transactions, reconciles accounts, handles edge cases, and closes the books each month would compress cost and cycle time while reducing errors. For founders, it could mean real-time visibility into burn and runway without the monthly scramble.

The cap table and the bet

Khosla Ventures leading the round signals a willingness to underwrite technical and narrative risk. Basis Set Ventures and Tobias Lutke joining adds operators and early AI investors who have seen ambitious automation attempts before. The firm and Crosby both know they are asking the market to separate the Bench storyline from the new build.

For Crosby, Synthetic is a shot at proving that the hard lessons of Bench can translate into an AI-native product. For Khosla, it is a familiar contrarian posture: back the founder early, when the idea sounds a half-step ahead of the curve, and see if the technology catches up fast enough to make the story true.