Ian Crosby, whose previous startup Bench Accounting collapsed before being bought for scrap, is back with Synthetic—a fully autonomous AI bookkeeper. Despite his vision exceeding current technical capabilities, Khosla Ventures has backed him with $10 million in seed funding.

Khosla partner Jon Chu believes in giving founders room to grow, citing Parker Conrad’s rise from Zenefits controversy to a billion-dollar success story. Crosby argues he wasn’t responsible for Bench’s downfall and hopes Synthetic will revolutionize bookkeeping without human intervention.

While Synthetic plans to serve only AI and software startups initially, Crosby remains cautious about broader scaling due to current AI limitations. Still, with years of funding in his pocket, he's willing to wait for more reliable models.

Crosby’s journey from Bench to Shopify and back to founding new ventures showcases resilience and a willingness to take bold risks. Khosla’s investment could either be a high-stakes gamble or the dawn of a fully automated accounting industry.