Miami fintech BOB raises $5.5M seed led by Mischief, with Peter Thiel on board

Miami-based fintech startup BOB has raised $5.5 million in seed funding to expand its AI-powered financial assistant for small business owners and grow its South Florida team. The round was led by Mischief, the venture firm founded by Plaid co-founder Zach Perret, and included billionaire investor Peter Thiel, investor and entrepreneur Codie Sanchez, Zynga founder Mark Pincus, and Karman Ventures, along with additional investors and operators.

How Thiel came into the round is the part practitioners will appreciate. BOB's CEO and co-founder Adam Wininger cold approached him during a chance encounter, and the two later bonded over a mutual interest in chess. Thiel "was super cool and we connected," Wininger told Refresh Miami. "He's as good as it gets. He immediately started asking us about distribution plans and different strategies."

What is BOB actually selling?

BOB doesn't ask business owners to log into complex software dashboards. Instead, it autonomously performs tasks through conversational channels entrepreneurs already use: WhatsApp, text messaging, Slack, Microsoft Teams, email, and its own app. Its capabilities include automatically maintaining accurate financial records, sending bills, accepting payments, and giving owners real-time cash flow visibility.

"We're trying to build the most useful banking product in the world, and we think that'll feel much more like an employee in your company rather than a dashboard to log into," said Wininger. "BOB is really an employee that's joining your company that happens to offer banking services."

The company targets Main Street service businesses — roofing contractors, restaurants, and local services firms — a segment that mainstream software tools have traditionally underserved. Wininger speaks from experience: he previously started a hotel company and several other small businesses.

"I know that these finances are a mess for so many businesses," he said. "And a lot of these business owners don't know how to get all this stuff set up with AI – it's scary. So we're really trying to help them run their business better, have better visibility into what's going on, and just give them a lot of their time back."

Why investors are writing the check now

The round lands amid growing investor appetite for AI-powered financial technology. Dustin Moring, General Partner at Mischief, framed the thesis in one sentence: "We invest in infrastructure that becomes indispensable, and a financial layer for autonomous agents is one of the clearest examples we've seen." He added: "BOB is attacking an immense market at the exact moment AI is moving from advising on transactions to executing them."

That last line matters for anyone tracking where fintech AI is heading. The shift from advisory tools to autonomous execution is precisely what separates the current wave from earlier chatbot-style finance products — and Mischief is explicitly pricing that transition into the deal.

What does the new capital change?

The funding will expand product capabilities, scale customer co-onboarding, and fund hiring in Miami, following BOB's private beta launch last month. The traction is early but concrete: 500 businesses have already signed up, and the product is currently free for them.

"We're pretty selectively taking on businesses right now that we want to do that free work for," said Wininger, who founded the company with CTO Jason Brill and CPO Kody Greenbaum. "People are loving it."

The team stands at 10 people, all based in the Miami area — a hard requirement, not a preference. The company is actively hiring, and Wininger has a specific bar: "We're always hiring 100X engineers. The 100X is the new 10X. If you want to be an employee and have equity in the company, you've got to be here, be a part of the team, and be part of our energy." Wininger has lived in Miami for about two years.

The office itself signals the brand: it's set up in Sunset Harbor like a 1940s Swiss bank, complete with a 1,000-pound vault Wininger bought on Facebook Marketplace for a few hundred dollars.

The Miami bet

Wininger's argument against San Francisco is cost and churn: "You start a company in San Francisco, your salaries are way higher. Your employees are getting poached left and right by these big tech companies. And I just think there's a lot of boring group think." He added that Miami's investor influx and quality of life make it the obvious choice.

"I've never felt optimism like I do in Miami. Everyone's moving here. Everyone's excited for the future… I think in 10 years, people will be like, 'Oh, good call doing Miami 10 years ago,'" he said. "It's stupidly obvious that Miami's the best city to build a company in."

For small business owners, the near-term test is whether BOB can convert a free beta with 500 signups into a paid, autonomous finance product — before larger banking and software players make the same move from dashboards to AI employees.