Khosla Ventures bets $10M on Ian Crosby’s new AI bookkeeping startup after Bench’s collapse

Most venture capitalists would steer clear of a founder whose previous startup imploded, was sold for parts, and whose new product vision may not yet be technically feasible. Khosla Ventures is doing the opposite. The firm has led a $10 million seed round into Synthetic, a new company founded by Ian Crosby, the former CEO of Bench Accounting, which famously shut down in December 2024 before being acquired out of bankruptcy.

A contrarian bet on founder growth

Khosla partner Jon Chu acknowledges the obvious risks. Crosby’s first startup, Bench, collapsed under new management after its board fired him in 2021. At the time, Crosby says he had turned down a $250 million acquisition offer from Brex, a decision the board disagreed with as the company burned through cash. Crosby’s direct leadership style also frustrated his executive team.

But Chu sees the story differently. “I tend to run towards controversy a little bit,” he told Bitcoin World. He points to Parker Conrad, who was ousted from Zenefits in 2016 amid intense criticism, only to later found Rippling, now valued at nearly $17 billion. “In controversy, groupthink often shapes the narrative rather than the truth of the story itself,” Chu said. “I believe people have room for growth.”

As part of his due diligence, Chu spoke with several executives who worked with Crosby after his departure from Bench. “They all had fantastic things to say about Ian,” Chu said. He believes Crosby’s subsequent roles — at Shopify, and as founder of Teal (acquired by Mercury) — gave him the space to learn from past mistakes.

Synthetic: a fully autonomous AI bookkeeper

Crosby’s new vision is ambitious: a fully autonomous AI bookkeeper that generates accrual-based financial statements without any human involvement. Most existing accounting startups, including Xero, rely on human accountants to review and correct AI output. Crosby wants to eliminate that entirely.

“We’re not going to release anything that’s not fully autonomous,” Crosby told Bitcoin World. “It’s that or bust.” Synthetic plans to initially serve only AI and other software startups, a narrow customer base where the product’s prototype currently works. But Crosby is candid about the technical uncertainty. “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,” he said.

Current foundational AI models still make significant bookkeeping errors. Crosby acknowledges that scaling the product for a broader customer base remains an open question. Still, he says the $10 million seed round gives him a long runway. “I’ve raised years of cash, so we can just wait it out,” he said.

Why this matters for fintech and venture capital

The bet on Crosby represents a broader shift in venture capital toward backing founders who have failed — and learned. The narrative around founder failure is evolving, with investors increasingly willing to separate a founder’s past company outcome from their personal capability. If Synthetic succeeds, it could validate a new model for AI-driven accounting that bypasses human labor entirely. If it fails, it will reinforce the view that some problems are harder to automate than others. Either way, the $10 million bet signals that Khosla Ventures believes in Crosby’s growth more than his past.

Conclusion

Ian Crosby’s second act is a high-risk, high-reward wager on both founder redemption and technological possibility. With $10 million from Khosla Ventures, Basis Set Ventures, and Shopify CEO Tobias Lütke, Synthetic aims to build what no accounting startup has yet achieved: a fully autonomous bookkeeper. Whether the technology can catch up to the vision — and whether Crosby has truly learned from Bench’s collapse — will determine if this bet pays off.

FAQs

Q1: What happened to Bench Accounting?
Bench Accounting, founded by Ian Crosby, shut down in December 2024 and was sold out of bankruptcy. Crosby had been fired by the board in 2021 after turning down a $250 million acquisition offer from Brex.

Q2: What is Synthetic building?
Synthetic is developing a fully autonomous AI bookkeeper that generates accrual-based financial statements without human involvement. It is currently in the design phase and works only for a narrow group of AI and software startups.

Q3: Why did Khosla Ventures invest despite Crosby’s past?
Khosla partner Jon Chu believes in founder growth and separates a founder’s past company outcome from their personal capability. He cited Parker Conrad’s journey from Zenefits to Rippling as a parallel example.