Khosla Ventures Bets $10M on Ian Crosby, Founder of Imploded Bench.

Ian Crosby, whose previous venture Bench Accounting famously ceased operations in 2024 before its assets were acquired, is embarking on a new entrepreneurial journey focused on automating the complex task of bookkeeping.

His latest startup, Synthetic, aims to develop a fully autonomous AI bookkeeper capable of generating accrual-based financial statements without any direct human input. Despite the product still being in its initial design phase—and Crosby acknowledging that his ambitious vision might currently exceed technological capabilities—Synthetic has successfully secured $10 million in Seed funding. This round was spearheaded by Khosla Ventures, with additional contributions from Basis Set Ventures and Shopify CEO Tobias Lütke.

While most investors might shy away from a founder facing Crosby's specific challenges—the collapse of a prior business and a vision potentially outstripping current foundational AI models—Khosla partner Jon Chu revealed to TechCrunch that he often takes an contrarian stance: “I tend to run towards controversy a little bit.”

Chu elaborated on his philosophy, stating, “In controversy, groupthink often shapes the narrative rather than the truth of the story itself.” He drew a parallel to Parker Conrad’s 2016 removal from Zenefits; despite initial industry criticism, Conrad went on to found Rippling, now valued at nearly $17 billion, demonstrating a founder's ability to rebound from adversity.

Regarding his investment in Crosby and Synthetic, Chu affirmed, “I believe people have room for growth.”

Crosby, for his part, asserts that he was not directly responsible for Bench's eventual insolvency. He claims he was fired by Bench’s board in 2021, just three months after declining a $250 million acquisition offer from Brex. The board reportedly also disagreed with Crosby's strategic direction, particularly as the company was experiencing significant cash burn, and his executive team allegedly expressed frustration with his direct leadership style.

Chu offered a concise summary of Crosby's previous endeavor: “He took a big swing, made a few mistakes. That didn’t go well.”

Bench ultimately failed when its subsequent management proved unable to independently restore the company's financial health.

Following his departure from Bench, Crosby joined Shopify and subsequently founded Teal, another accounting startup, which was acquired by Mercury a mere 18 months later.

As part of his comprehensive due diligence, Chu informed TechCrunch that he interviewed several executives who had worked with Crosby after his time at Bench. He noted that they all “had fantastic things to say about Ian.”

Chu is confident that the three professional roles Crosby undertook after leaving Bench provided him with substantial opportunities to learn from his past missteps.

Crosby maintains an unwavering focus on developing a purely AI-driven bookkeeping service, distinguishing Synthetic from most current accounting startups like Xero, which still integrate human accountants.

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

Synthetic intends to exclusively serve AI and other software startups. However, Crosby openly acknowledges that current AI models still commit notable bookkeeping errors. While Synthetic's prototype demonstrates functionality for a limited user group, he remains uncertain about its scalability for a broader customer base.

Crosby illustrated this challenge with an analogy: “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.”

Nevertheless, the founder states he is in a position to exercise patience and await the necessary advancements in foundational AI models to ensure greater reliability for complex bookkeeping calculations.

“I've raised years of cash, so we can just wait it out,” Crosby concluded.