Khosla Ventures is reportedly investing $10 million in a new startup founded by Ian Crosby, the entrepreneur behind accounting startup Bench, which dramatically collapsed in 2024. The new company, called Synthetic, is focused on building a fully autonomous AI-powered bookkeeping platform for startups and businesses.
Ian Crosby previously founded Bench, a venture-backed accounting startup that had raised more than $100 million before shutting down abruptly in late 2024. The company’s collapse left thousands of small business customers scrambling to recover financial records and bookkeeping operations during tax season. Bench was later acquired at a significantly reduced valuation after failing to recover financially under new management.
Despite the failure of Bench, investors at Khosla Ventures appear willing to back Crosby again, largely because of his deep expertise in bookkeeping infrastructure and the belief that generative AI could fundamentally reshape the accounting industry. Synthetic reportedly aims to automate bookkeeping workflows almost entirely through AI systems, reducing the need for large human bookkeeping teams.
After leaving Bench, Crosby briefly joined Shopify and later founded another accounting-focused startup called Teal, which was eventually acquired by Mercury within roughly 18 months. His ability to continue building and exiting startups appears to have helped maintain investor confidence despite Bench’s collapse.
According to reports, Khosla Ventures views the rise of AI as a major technological shift that could create entirely new opportunities in sectors previously considered operationally difficult or labor-intensive. Investors believe that advancements in AI agents and autonomous workflows may now make fully automated bookkeeping commercially viable in ways that were previously impossible.
The investment also highlights a broader trend within venture capital where founders with failed startups are increasingly receiving second chances if they possess strong domain expertise and experience in emerging AI-driven markets. Analysts note that in the current AI boom, investors are often prioritizing technical insight and market understanding over past execution failures, especially in industries undergoing rapid technological disruption.
