BOB, a Miami company that builds an AI finance assistant for small business owners, has raised a $5.5m seed round led by Mischief, which Refresh Miami described as the venture firm founded by Plaid co-founder Zach Perret. The company announced the round in a press release on 23 October 2026; Refresh Miami reported it a day earlier.
Peter Thiel, Codie Sanchez, Zynga founder Mark Pincus and Karman Ventures also invested, along with other investors and operators who were not named. The company did not disclose a valuation or any earlier funding.
“They are running the business, doing the work, and then staying up late trying to make sense of their books. We built BOB to take that work off their plate entirely.”Adam Wininger, CEO, BOB
What BOB does
BOB, whose holding company is BOB AI Holdings Corp., describes its product as an AI finance employee for small businesses. It keeps the books, sends invoices, accepts payments and gives owners a running view of their cash flow. Owners deal with it through channels they already use, including WhatsApp, text messages, Slack, Microsoft Teams and email, as well as BOB's own app.
The service also holds customers' money in a deposit account. The release states that BOB is a financial technology company and not a bank.
Refresh Miami reported that BOB is aimed at Main Street service businesses such as roofing contractors, restaurants and local service firms. The product is free for now and the company is onboarding businesses selectively. BOB launched a private beta in September, and about 500 businesses have signed up, according to Refresh Miami. The company did not disclose revenue or retention figures.
"BOB is really an employee that's joining your company that happens to offer banking services," chief executive Adam Wininger told Refresh Miami.
The founders and the team
BOB was co-founded by Wininger, its chief executive, Jason Brill, its chief technology officer, and Kody Greenbaum, its chief product officer. Wininger previously started a hotel company among other businesses and has lived in Miami for about two years, Refresh Miami reported. The company did not say when it was founded.
Refresh Miami said Wininger met Thiel by chance and approached him directly, and that the two later bonded over chess. Wininger said Thiel quickly began asking about the company's distribution plans and strategy.
BOB has 10 employees, all based in the Miami area, which the company requires. Its office is in Sunset Harbor and is themed after a 1940s Swiss bank, complete with a 1,000-pound vault, according to Refresh Miami.
What the money is for
BOB said it will use the funding to deepen the product's financial capabilities, scale customer onboarding and grow its Miami team, including engineers. It also plans to put its free finance agent in front of more small business owners. Wininger said the company's goal is to be the most useful banking platform in the world.
Dustin Moring, a general partner at Mischief, said in the release that the firm invests in infrastructure that becomes indispensable, and called a financial layer for autonomous agents one of the clearest examples it had seen. He said BOB was entering a large market just as AI moves from advising on transactions to carrying them out.
Company website: joinbob.ai