Ian Crosby Bets $10M on Agentic AI Accounting Startup

Ian Crosby is returning to the accounting software world with a bold new startup called Synthetic, a company built around the idea of a fully autonomous AI bookkeeper. Crosby, who previously co-founded Bench Accounting in 2011 and later launched Teal in 2023, is now taking his third major attempt at improving business accounting. This time, his goal is even more ambitious: creating an AI system that can complete bookkeeping and generate accrual-based financial reports without direct human involvement.

Synthetic has raised $10 million USD in seed funding led by Khosla Ventures, with support from Basis Set Ventures, Shopify CEO Tobias Lütke, OpenDoor CEO Kaz Nejatian, multiple former Brex executives, and other notable backers. The investment is notable because Crosby’s last major company, Bench Accounting, collapsed in 2024 before being acquired for its remaining assets. Despite that history, Khosla Ventures partner Jon Chu said he believes controversy can sometimes hide a stronger story. He compared Crosby’s situation to Parker Conrad, who was pushed out of Zenefits before later building Rippling into a company valued at nearly $17 billion.

Crosby says he was not directly responsible for Bench’s collapse. According to him, Bench’s board fired him in 2021, three months after he rejected a $250 million acquisition offer from Brex. The board reportedly disagreed with his strategy while the company was losing money, and some executives were frustrated with his leadership style. Bench later failed under new management. After leaving the company, Crosby joined Shopify and founded Teal, another accounting startup that was acquired by Mercury after about 18 months.

Synthetic’s product is still in development, and Crosby openly admits that the idea may not yet be fully possible with today’s AI models. The company is working on an AI agent that can connect to banking, payroll, billing systems, and inboxes, then ask humans only the clarifying questions needed to complete the books. Crosby described the difference as moving from AI that assists humans to AI that fully takes responsibility for the task, comparing it to the difference between driver assistance and a truly autonomous system like Waymo.

The challenge is that accounting requires extremely high accuracy. Crosby said the system is still in a “crash test phase,” where AI models sometimes pass tests and sometimes fail them. Synthetic’s prototype currently works for a narrow group of users, but Crosby is unsure how well it will scale to a larger customer base. He compared it to a self-driving car that can handle one street but has not yet proven it can drive safely anywhere. Because of this, Synthetic does not plan to release anything unless it is fully autonomous.

Synthetic will focus first on AI and software startups, rather than trying to serve every type of business. Crosby believes he can afford to be patient because the company has raised enough capital to wait for foundation models to become more reliable. He is also building the company in San Francisco instead of Vancouver because he believes the culture there better fits the intense work environment needed for this kind of high-risk, high-reward startup. The five-person team works six days a week, and Crosby plans to hire more employees with a $250,000 USD base salary for exceptional talent willing to work in San Francisco. Looking ahead, Crosby sees Synthetic as more than just an accounting tool, with a long-term vision for AI agents to handle backend business operations such as incorporation, websites, bank accounts, payments, and bookkeeping. For now, Synthetic’s future depends on whether AI can reach the level of accuracy needed for accounting, but Crosby and his investors are betting that within the next 18 to 24 months, the technology may finally be ready.

Works Cited

Riehl, Alex. “Ian Crosby Is Back with a New Accounting Startup for the Agentic AI Era.” BetaKit, 14 May 2026, www.betakit.com/ian-crosby-is-back-with-a-new-accounting-startup-for-the-agentic-ai-era/. 

Temkin, Marina. “Khosla Ventures Is Betting $10M on Ian Crosby, Whose First Startup, Bench, Imploded.” TechCrunch, 14 May 2026, www.techcrunch.com/2026/05/14/khosla-ventures-is-betting-10m-on-ian-crosby-whose-last-startup-bench-imploded/. 

“Ian Crosby Raises $10M to Build an Autonomous AI Accountant despite Bench Bankruptcy.” Mezha, 14 May 2026, www.mezha.net/eng/bukvy/cc129684_ian_crosby_raises/. 

Riehl, Alex. “Ian Crosby Is Back with a New Accounting Startup for the Agentic AI Era.” BetaKit, 14 May 2026, www.betakit.com/ian-crosby-is-back-with-a-new-accounting-startup-for-the-agentic-ai-era/. 

Lewis, Stephanie. “Synthetic’s $10M Gamble on a Fully Autonomous AI Accountant.” Brief Glance, 14 May 2026, www.briefglance.com/articles/synthetics-10m-gamble-on-a-fully-autonomous-ai-accountant.