Khosla Ventures is betting $10M on Ian Crosby, whose last startup, Bench, imploded

Khosla Ventures has led a $10 million seed funding round for Ian Crosby’s new startup, Synthetic, which aims to build a fully autonomous AI-driven bookkeeping service. This marks Crosby’s return to startup funding after his previous company, Bench, collapsed in 2024, an event that drew significant industry attention.

Ian Crosby, founder of the now-defunct accounting startup Bench, has secured $10 million in seed funding for his new venture, Synthetic. The round was led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke. Synthetic’s goal is to create an AI system capable of generating accrual-based financials without human input, a challenge that remains technologically complex.

Crosby emphasizes that Synthetic will target only AI and software startups, aiming for full automation. He admits that current AI models still make significant bookkeeping errors and that scaling the technology remains uncertain. Despite these challenges, Crosby states he has secured sufficient funding to wait for foundational AI models to improve, comparing the current stage to a self-driving car that can only operate on certain streets.

While Crosby’s previous startup, Bench, failed after leadership disagreements and financial difficulties, he maintains that his subsequent roles at Shopify and Teal provided valuable experience. Khosla partner Jon Chu expressed confidence in Crosby’s growth potential, citing his willingness to pursue controversial or risky ventures as a reason for backing him.

Why It Matters

This investment highlights a willingness among some venture capitalists to back founders with troubled histories, betting on their capacity to learn and innovate. It also underscores ongoing interest in automating accounting processes using AI, despite current technological limitations. The funding could influence the future of AI-driven financial services, especially for startups seeking fully autonomous solutions.

Express Schedule Free Employee Scheduling Software [PC/Mac Download]

• User-friendly drag & drop interface: Simple shift planning
• Manage time-off and leave: Add sick leave, breaks, holidays
• Email schedules to employees: Direct email scheduling

View Latest Price

As an affiliate, we earn on qualifying purchases.

As an affiliate, we earn on qualifying purchases.

Background

Ian Crosby’s previous startup, Bench, was a prominent online accounting platform that imploded in 2024 after leadership disputes and financial struggles. Crosby was ousted from Bench in 2021 following disagreements over strategic direction. After leaving, he joined Shopify and founded Teal, which was acquired by Mercury in 2025. Despite the failure of Bench, Crosby’s subsequent roles have been viewed as learning experiences that inform his current ambitions with Synthetic.

“I tend to run towards controversy a little bit. In controversy, groupthink often shapes the narrative rather than the truth of the story itself.”

— Jon Chu, Khosla Ventures partner

“We’re not going to release anything that’s not fully autonomous. It’s that or bust.”

— Ian Crosby, founder of Synthetic

Express Schedule Free Employee Scheduling Software [PC/Mac Download]

• User-friendly drag & drop interface: Simple shift planning
• Manage time-off and leave: Add sick leave, breaks, holidays
• Email schedules to employees: Direct email scheduling

View Latest Price

As an affiliate, we earn on qualifying purchases.

As an affiliate, we earn on qualifying purchases.

What Remains Unclear

It remains unclear whether Synthetic’s AI system will be able to reliably handle bookkeeping at scale, given current technological limitations. The startup’s prototype works for a narrow user base, but broader adoption and accuracy are still unproven. Additionally, the timeline for achieving fully autonomous AI bookkeeping remains uncertain.

What’s Next

Next steps include further development and testing of Synthetic’s AI prototype, with plans to expand user testing and demonstrate scalability. The company may also seek additional funding to accelerate AI model improvements and address technical challenges. Industry observers will watch closely to see if the technology can meet its ambitious goals.

Heveboik Income & Expense Log Book – A4 Income and Expense Tracker for Small Business, Accounting Bookkeeping Tracking for Woman and Man, 8" x 10.5", Green

• Easy Daily Management: Track income and expenses daily
• Year-Long Tracking: Undated for a full year use
• Comprehensive Layout: Includes weekly spreads and summaries

View Latest Price

As an affiliate, we earn on qualifying purchases.

As an affiliate, we earn on qualifying purchases.

Key Questions

Why did Khosla Ventures invest in Ian Crosby’s startup despite his previous failure?

Khosla partner Jon Chu stated that he believes in Crosby’s growth potential and is willing to back founders with controversial or risky histories, especially when they have learned from past mistakes.

What exactly does Synthetic aim to do?

Synthetic plans to develop a fully autonomous AI system capable of performing bookkeeping tasks, including generating accrual-based financial statements, without human intervention.

What are the main challenges Synthetic faces?

The primary challenge is ensuring AI accuracy and reliability at scale, as current models still make significant bookkeeping mistakes. The company is also uncertain about how quickly the technology can be made broadly operational.

What is Crosby’s track record with startups?

His previous startup, Bench, failed in 2024 after leadership disputes and financial difficulties. He subsequently worked at Shopify and founded Teal, which was acquired by Mercury in 2025.

What happens next for Synthetic?

The company will focus on further developing its prototype, expanding testing, and seeking additional funding to improve AI accuracy and scalability. Industry watchers will monitor progress toward full automation.