Khosla Ventures is investing $10 million in Ian Crosby's new startup Synthetic, aiming to develop an AI bookkeeper capable of generating accrual-based financials independently.
Massive Investment Despite Past Challenges
Crosby previously founded Bench Accounting, which shut down in 2024 and was acquired in a distressed sale. Despite this, Khosla Ventures, along with Basis Set Ventures and Shopify CEO Tobias Lütke, are backing his new venture.
Synthetic, still in the design phase, seeks to offer a fully autonomous AI bookkeeping service. Crosby acknowledges that his vision may not be currently feasible but remains committed to the concept.
Investor Confidence in Controversial Founders
Jon Chu, a partner at Khosla Ventures, is not deterred by controversy. “I tend to run towards controversy a little bit,” he told TechCrunch, citing Parker Conrad’s story as a precedent for successful comebacks.
Chu believes that Crosby has the potential for growth, despite not directly causing Bench’s collapse. Crosby claims he was fired by Bench’s board in 2021 after rejecting a $250 million acquisition offer from Brex.
Crosby's Journey Post-Bench
After Bench, Crosby joined Shopify and founded another accounting startup, Teal, which was sold to Mercury. This track record has convinced Chu that Crosby has learned from past mistakes.
Chu reported that executives who worked with Crosby post-Bench had positive feedback about him.
AI-Driven Vision for Synthetic
Crosby is determined to create a bookkeeping service that relies solely on AI, contrasting with competitors like Xero that still use human accountants. “We’re not going to release anything that’s not fully autonomous,” he stated.
Synthetic is initially targeting AI and software startups. However, Crosby admits that current AI models still make significant errors, and the scalability of the service remains uncertain.
Drawing an analogy to self-driving cars, Crosby explained, “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.”
Despite these challenges, Crosby is prepared for a long journey. “I’ve raised years of cash, so we can just wait it out,” he said.
Source: https://techcrunch.com/2026/05/14/khosla-ventures-is-betting-10m-on-ian-crosby-whose-last-startup-bench-imploded/
