Ian Crosby's last venture imploded spectacularly. Bench Accounting, the startup he co-founded to automate bookkeeping for small businesses, shut down without warning over a three-day period from December 27-29, 2024, leaving thousands of customers scrambling. By early January, the company had filed for bankruptcy in Canada. Eighteen months later, Crosby is back with another bookkeeping play and a $10 million seed round led by Khosla Ventures.
The new company, Synthetic, announced the funding on Tuesday. The pitch is familiar but more ambitious: a fully autonomous AI bookkeeper that handles everything from bank reconciliations to accrual-basis financials without human intervention. Khosla partner Jon Chu is leading the round, joined by Basis Set Ventures and a roster of operator-angels that includes Shopify CEO Tobi Lütke, Opendoor CEO Kaz Nejatian, and Zach Abrams, co-founder of Bridge, which Stripe acquired for about $1.1 billion earlier this year.
"I tend to run towards controversy a little bit," Chu told TechCrunch when asked about backing Crosby so soon after Bench's collapse. "I believe people have room for growth."
The investment is a striking vote of confidence in a founder whose track record is, to put it charitably, mixed. Crosby has said publicly that Bench's board fired him in 2021, three years before the company's eventual demise. He went on to spend time at Shopify, then co-founded another startup called Teal, which Mercury acquired in September of last year. Now he's taking a third swing at a problem he's been chasing for more than a decade.
A Product That Doesn't Exist Yet
Synthetic's ambitions are sweeping. The product is supposed to connect to banks, payroll systems, billing tools, and email inboxes, ask clarifying questions when needed, and produce financials ready for a tax preparer. Pricing is listed at $49 per month, according to a press release issued in May, though the company's website shows only a waitlist and no live product.
At the time of the funding announcement, the product was still in the prototype and design phase, TechCrunch reported. "We're not going to release anything that's not fully autonomous," Crosby told the publication. "It's that or bust." In a separate interview with BetaKit that same month, he was more circumspect: "I don't know if this is possible yet."
That candor is either refreshing or alarming, depending on your appetite for risk. Chu appears to fall into the former camp. In the press release, he framed the bet in almost elemental terms: "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."
The Bench Shadow
Whether you call it resilience or stubbornness, Crosby has certainly been forged by experience. Bench, which he co-founded in 2011, once looked like a success story. The company raised capital, built a sizable customer base, and positioned itself as a simpler, cheaper alternative to traditional bookkeeping. Then it all unraveled.
Bench burned through its capital and shut down over a three-day period ending December 29, 2024, TechCrunch reported. The Canadian bankruptcy filing came on January 7, 2025, followed by U.S. Chapter 15 recognition filings on March 14, 2025. For customers, many of them small-business owners juggling year-end tax prep, the timing was particularly brutal.
Crosby had already left the company by then. After his departure from Bench in 2021, he joined Shopify as a product director for Shopify Balance before launching Teal in 2023. That venture lasted barely a year before Mercury snapped it up.
A Crowded, Lucrative Market
Synthetic is entering a market that's both enormous and fiercely competitive. The global accounting services industry was valued at roughly $685 billion in 2025, according to research from Fortune Business Insights and Grand View Research. The U.S. alone is home to more than 36 million small businesses, per a June 2025 report from the SBA Office of Advocacy, and most of them need some form of bookkeeping help.
Intuit's QuickBooks Live offers human bookkeepers starting at $200 per month for businesses with up to $25,000 in monthly expenses. Pilot, a well-funded startup that provides outsourced bookkeeping and CFO services, tailors pricing by inquiry. H&R Block's Block Advisors service markets itself as delivering "up to 50% savings vs typical accountant," with third-party reviews citing plans ranging from $189 to $309 per month.
Synthetic's stated price of $49 per month would undercut all of them—if the product can deliver on its promise. That's a big if. Autonomous AI systems that handle complex, variable tasks remain aspirational in most domains. Bookkeeping, with its regulatory nuances and need for context-specific judgment calls, is hardly low-hanging fruit.
Hiring for a Six-Day Week
Crosby is targeting an initial cohort of customers in software, SaaS, and AI businesses. Over the summer, he wrote on LinkedIn that the company had assembled a "healthy list of design customers," though he didn't specify numbers. Synthetic declined to disclose a launch date or current customer count.
The startup is based in San Francisco and requires employees to work six days per week in person, according to its LinkedIn page and press materials. That's an unusual policy in an era when even many traditional firms have embraced hybrid work, though it fits a certain strain of Bay Area founder culture that prizes intensity over balance. LinkedIn shows the company with between two and ten employees, and Synthetic is actively hiring engineers.
The company was formally founded in November 2024, according to its LinkedIn profile, which means it raised $10 million on the strength of Crosby's vision and track record rather than a functioning product.
What Comes Next
In the press release, Crosby struck a tone that was equal parts idealistic and defiant. "Building a truly autonomous AI that helps founders is something worth building," he said, "and I'd rather we build something novel and useful than something easy."
Whether Synthetic can deliver where Bench did not is an open question. The collapse of his previous company is recent enough to cast a long shadow, but the capital markets have shown a persistent willingness to back repeat founders with big ideas and hard-earned lessons. Chu's willingness to lean into the controversy suggests he sees something in Crosby that others might overlook.
For now, Synthetic remains a bet on potential rather than proof. The company has funding, a compelling pitch, and a founder who knows the problem intimately, perhaps more intimately than he'd like. What it doesn't yet have is a product that works without humans in the loop. That's the only metric that will ultimately matter.
