A Miami fintech startup just landed $5.5 million in seed funding from a roster of heavy hitters, including Peter Thiel, to build what its founder calls “an employee that joins your company.” BOB, founded by CEO Adam Wininger, develops an AI-powered financial assistant that handles bookkeeping, bill payments, and cash flow tracking for small businesses through text, WhatsApp, Slack, email, and its own app.
Small business owners typically juggle a mess of financial tools, yet BOB automates these chores through conversational interfaces people already use daily. The company targets Main Street service providers: roofing contractors, restaurants, local firms that mainstream software often overlooks. Wininger knows the pain firsthand. He previously launched a hotel company and other ventures, watching finances spiral into chaos for operators who lack time or expertise to set up complex systems.
The seed round was led by Mischief, the venture firm co-founded by Plaid’s Zach Perret. Other backers include Thiel, entrepreneur Codie Sanchez, Zynga founder Mark Pincus, and Karman Ventures. Wininger met Thiel through a cold approach during a chance encounter. They connected over chess. Thiel grilled him on distribution strategy immediately. “He’s as good as it gets,” Wininger said.
Mischief General Partner Dustin Moring framed the investment around infrastructure. “A financial layer for autonomous agents is one of the clearest examples we’ve seen,” he said. BOB attacks a massive market at the exact moment AI shifts from advising to executing transactions.
The capital will fund product expansion, customer onboarding, and Miami hiring. BOB launched a private beta last month, attracting 500 businesses. Currently free, the company selectively chooses which companies receive the service.
Wininger co-founded BOB with CTO John Henry and CPO Kody Greenbaum. The 10-person team works from a Sunset Harbor office designed like a 1940s Swiss bank, complete with a 1,000-pound vault bought on Facebook Marketplace. Wininger demands in-person work and equity-sharing employees. “The 100X is the new 10X,” he said.
He chose Miami over San Francisco deliberately. Lower salaries, less poaching, less groupthink. “I’ve never felt optimism like I do in Miami,” Wininger added. As more investors relocate south, BOB positions itself at the intersection of fintech, AI, and a city betting on its tech future.
