Ian Crosby raises $10M for Synthetic AI bookkeeper despite Bench Accounting's collapse

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

Ian Crosby, whose previous startup Bench Accounting famously shut down in 2024 before being bought for scraps, is taking another shot at building a business out of automating the arduous work of bookkeeping. His new startup, Synthetic, aims to build a fully autonomous AI bookkeeper that can generate accrual-based financials without direct human involvement. Although the product is still in the design phase -- and Crosby admits his vision may not yet be technologically possible -- the startup has raised $10 million in a Seed funding round led by Khosla Ventures, with participation from Basis Set Ventures and Shopify CEO Tobias Lütke. Most investors would run from a founder facing the kind of challenges Crosby is right now -- the fallout of his previous business collapsing, and a vision that may exceed the technical feasibility of current foundational models. But Khosla partner Jon Chu told TechCrunch he sometimes does just the opposite: "I tend to run towards controversy a little bit." "In controversy, groupthink often shapes the narrative rather than the truth of the story itself," he said, citing Parker Conrad's 2016 ousting from Zenefits as an example. While the industry narrative was initially critical of Conrad, he subsequently founded Rippling, which is now valued at nearly $17 billion. "I believe people have room for growth," Chu said about his bet on Crosby and Synthetic. Crosby maintains he wasn't directly responsible for bringing Bench to the point of insolvency. According to Crosby, he was fired by Bench's board in 2021, three months after he turned down a $250 million acquisition offer from Brex. The board also disagreed with Crosby's strategic direction, especially as the business was bleeding cash, and his executive team was reportedly frustrated with his direct leadership style. "He took a big swing, made a few mistakes. That didn't go well," Chu said. Bench ultimately imploded when its new management proved unable to restore the company to health on its own. After leaving Bench, Crosby joined Shopify and founded Teal, another accounting startup, which was bought by Mercury 18 months later. As part of his due diligence, Chu said he spoke with several executives who worked with Crosby after his departure from Bench, and they all "had fantastic things to say about Ian," Chu told TechCrunch. Chu is convinced that the three roles Crosby held after leaving Bench provided the entrepreneur with ample opportunity to learn from his past mistakes. Crosby says he has his eyes firmly set on creating a fully AI-driven bookkeeping service, rather than relying on human accountants, as most accounting startups such as Xero do now. "We're not going to release anything that's not fully autonomous," Crosby told TechCrunch. "It's that or bust." Synthetic plans to serve only AI and other software startups. But Crosby acknowledges that AI models still make significant bookkeeping mistakes. While Synthetic's prototype works for a narrow group of users, he remains uncertain how it will scale for a broader customer base. Crosby explained with an analogy: "It's like a self-driving car that can drive down one street versus the self-driving car that can drive down any street. We haven't driven down enough streets to know if it's going to crash." Still, the founder says he can afford to be patient and wait for foundational models to become more reliable for bookkeeping calculations. "I've raised years of cash, so we can just wait it out," Crosby said.

Synthetic Raises $10M Seed Led by Khosla Ventures

We're building a bookkeeping service for software startups, run entirely by AI. SAN FRANCISCO--(BUSINESS WIRE)--May 14, 2026-- We've raised $10 million in seed funding, led by Khosla Ventures. Basis Set Ventures also participated, alongside operator-investors Tobi Lütke (CEO, Shopify), Kaz Nejatian (CEO, Opendoor; former COO, Shopify), Zach Abrams (co-founder of Bridge, acquired by Stripe for $1.1 billion), Cosmin Nicolaescu (CEO, Accrual; former CTO, Brex), and Michael Tannenbaum (CEO, Figure; former COO, Brex). Synthetic is a bookkeeping service that employs no human bookkeepers or accountants. It connects to a customer's banks, payroll, billing systems, and inboxes, and comes back with sharp clarifying questions to make sure it understands the context of the business. The output is a clean set of accrual-basis books, ready to hand to a tax preparer. Pricing will start at $49 per month; roughly a quarter of what a human-staffed service costs. Synthetic is available around the clock and doesn't take vacation, hit a backlog, or quit on its customers. Connect the accounts, answer the occasional clarifying question, and your books are done. We have a deliberately narrow focus: only software, SaaS, and AI businesses. We want to build a highly tailored product that works incredibly well for a few businesses, rather than a broad one that serves no one particularly well. We'll be starting with the smallest customers, where the accounting is simplest, until the product is solid enough to start serving larger ones. Our team is currently iterating on a prototype with early design customers. "I'm not sure if it's yet technologically possible to make this work," said Ian Crosby, founder and CEO of Synthetic. "AI is notoriously unreliable, and no one wants to entrust their accounting to a system which might get it wrong. Our focus is on quality control and we're not going to release this until we feel confident that it's more reliable than a human bookkeeper. I'm not sure if that's going to be 6 months or 6 years. But building a truly autonomous AI that helps founders is something worth building, and I'd rather we build something novel and useful than something easy." Our founder, Ian Crosby, previously co-founded Bench Accounting in 2012 and built it into the largest bookkeeping service for small businesses in North America, serving tens of thousands of customers. He started Synthetic with a direct, operational sense of what's actually hard about delivering bookkeeping at scale, and a conviction that the human-staffed model has a structural ceiling on price, speed, and availability that no amount of operational improvement will overcome. "This one's quite simple. You have a large, valuable problem that will inevitably be solved by AI. A founder who's spent multiple decades working on the problem with near perfect founder market fit. And resilience and grit that's been forged through multiple founding experiences and scale ups at companies like Shopify and Mercury," said Jon Chu of Khosla Ventures. "What more can one really ask for here?" Our aspiration goes beyond accounting. We want a founder to be able to press a button and watch a real, running company assemble itself around their idea: the website, incorporation, bank accounts, payments, accounting, and everything else. We want to make starting a software business as easy as starting a code repo. Accounting is our starting point. We're headquartered in San Francisco, where we work in person six days a week. We're hiring engineers and sponsor visas for exceptional candidates worldwide -- open roles at jobs.ashbyhq.com/synthetic. About Synthetic: Synthetic is building autonomous AI bookkeeping for startups. Headquartered in San Francisco and backed by Khosla Ventures. More at synthetic.ai. View source version on businesswire.com: https://www.businesswire.com/news/home/20260514241304/en/