Ian Crosby is back with a new accounting startup for the agentic AI era | BetaKit

Ian Crosby is back with a new accounting startup for the agentic AI era | BetaKit


Three-time Canadian founder raises $10 million USD for San Francisco-based Synthetic.

Ian Crosby is on his third accounting startup, and he’s not even sure if this one is possible.

After co-founding Vancouver-based business bookkeeping software Bench Accounting in 2011, and then the “Stripe for accounting” with Teal in 2023, Crosby is back with Synthetic and a big bet: that he can make the future of bookkeeping autonomous.

“I don’t know if this is possible yet.”

Ian Crosby, Synthetic

The elevator pitch is that Synthetic can provide software businesses with an AI agent that automatically completes their books by connecting to banking, payroll, billing systems, and inboxes, before asking its human bosses the necessary clarifying questions to fill in any blank spots. 

“It doesn’t have to get everything right on its own, as long as it knows what things it should ask about,” Crosby told BetaKit in an interview last month. 

Synthetic is “the next level up” in AI software, Crosby said, because instead of an assistive AI tool being the responsibility of the human, it’s entirely on the system. 

“It’s like a drive assist tool [where] if you crash the car, it’s still on you; you’re supposed to have your hands on the wheel,” Crosby said, comparing Synthetic to “a truly autonomous system, like Waymo, where …  no one’s touching the steering wheel, and if it crashes, it’s Waymo’s fault.”

Of course, Crosby is dealing in theoreticals. He’s been working on Synthetic with his five-person team since last year, and the system is still making mistakes in the “crash test phase,” as AI does. While every new AI model release improves performance, there are still some tests that the bookkeeping agents sometimes ace and sometimes fail.

The Synthetic team. Image courtesy Synthetic.

Accounting is a space where customers need 100-percent accuracy, Crosby explained, and while it’s “perfectly common to hire a terrible bookkeeper,” businesses need better than that to trust an AI agent with the books. 

“I don’t know if this is possible yet,” Crosby said. “We don’t know what sort of hang-ups we’re going to come across, [but] it’s high risk, high reward, right?”

Even so, investors seem to trust Crosby to get the job done. Synthetic has raised $10 million USD ($13.7 million CAD) in seed funding, led by Khosla Ventures and with backing from notable angels like Shopify CEO Tobi Lütke, OpenDoor CEO Kaz Nejatian, multiple former Brex executives, and Basis Set Ventures (where Crosby is also a venture partner). 

RELATED: US-based business banking startup Mercury acquires accounting platform Teal for an undisclosed amount

In a statement, Khosla partner Jon Chu said that Crosby has “resilience and grit” forged from his multiple accounting startups and stints at Shopify and Mercury. 

“This one’s quite simple. You have a large, valuable problem [and a] founder who’s spent multiple decades working on the problem with near-perfect founder market fit,” Chu said. “What more can one really ask for here?”

The value of setting a culture

While Crosby earned trust from his time at Bench and Teal, the experience taught him the value of setting a culture. That’s why he’s building Synthetic in San Francisco instead of Vancouver. 

Crosby explained that the business environment and culture in Canada simply isn’t conducive to what he’s trying to build this time around. The Synthetic team works six days a week, and though it’s not the back-breaking 996 schedule, people in Vancouver would still think that’s “weird and intense.”

“Here, we’re kind of middle of the pack for working hours,” Crosby said. “In Vancouver, we would be the hardest-working team … The culture is different.” 

“Here, we’re kind of middle of the pack … In Vancouver, we would be the hardest-working team.”

Crobsy added he’s a Canadian who loves working with Canadians (one of Synehtic’s founding engineers is Canadian), but a Vancouver office is not in the cards at the moment. Instead, he’s looking to hire five more people, and wherever they are, they’ll have to come to San Francisco for the $250,000 USD base salary. 

“We will pay to get people who are exceptional, and want to put them in the absolute most exceptional environment to create a potentially exceptional upside,” Crosby said. “It’s about creating the best conditions for a serendipitous success to occur.” 

Crosby envisions Synthetic eventually consolidating more backend business operations into a simple push of a button. Want to start a business? Enter your name, and let the agent incorporate your business and build your website, bank account, payments, and accounting systems. He just has to get that last point working first. 

“It’s just a bet that sometime in the [next] 18 to 24 months this becomes possible, and that we’re in the right place at the right time,” Crosby said. 

Feature image courtesy Synthetic.



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