Investors include Mischief, Peter Thiel, Codie Sanchez, Mark Pincus and Karman Ventures
By Maria Derchi Russo and Nancy Dahlberg
BOB, a financial technology startup based in Miami, has just raised $5.5 million in seed funding as it looks to expand its AI-powered financial assistant for small business owners and grow its South Florida team.
That’s today’s news. But how this company and funding round of prominent investors came together is where this startup story gets really interesting.
The seed round was led by Mischief, the venture firm founded by Plaid co-founder Zach Perret, and included backing from billionaire investor Peter Thiel, whom BOB’s CEO and co-founder Adam Wininger cold approached him during a chance encounter and they later bonded over a mutual interest in chess. Thiel “was super cool and we connected,” said Wininger, in an interview with Refresh Miami. “He’s as good as it gets. He immediately started asking us about distribution plans and different strategies.”
Other participants in the round were investor and entrepreneur Codie Sanchez, Zynga founder Mark Pincus, Karman Ventures and additional investors and operators.
What is BOB? Rather than requiring business operators to log into complex software dashboards, BOB autonomously performs tasks directly through conversational interactions many entrepreneurs already use, including through WhatsApp, text messaging, Slack, Microsoft Teams, email and the company’s own app. BOB’s capabilities include automatically maintaining accurate financial records, sending bills and accepting payments seamlessly and providing business owners with 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.”
BOB is also laser-focused on Main Street service businesses such as roofing contractors, restaurants, and local services firms that have traditionally been underserved by mainstream software tools.
“I’ve had a few small businesses before. I started a hotel company. I’ve started a few businesses and I know that these finances are a mess for so many businesses,” said Wininger. “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.”
The funding also comes amid growing investor interest in AI-powered financial technology tools. “We invest in infrastructure that becomes indispensable, and a financial layer for autonomous agents is one of the clearest examples we’ve seen,” said Dustin Moring, General Partner at Mischief. “BOB is attacking an immense market at the exact moment AI is moving from advising on transactions to executing them.”
The new capital will be used to expand its product capabilities, scale customer co-onboarding and hire talent in Miami following Bob’s launch of its private beta last month.
Already, 500 businesses have signed up and BOB is currently free for them to use, said Wininger, who founded the company with CTO John Henry and CPO Kody Greenbaum. “We’re pretty selectively taking on businesses right now that we want to do that free work for. People are loving it.”
BOB’s office in Sunset Harbor is set up like a 1940s Swiss Bank, complete with a 1,000-pound vault purchased on Facebook Marketplace for a few hundred bucks, Wininger said. BOB is a team of 10 people right now – all in the Miami area, a requirement – and it’s hiring.
“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,” said Wininger, who has lived here about two years.
Why Miami? “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 said.
Miami’s also the place where so many investors are moving to and of course the best quality of life in the country is a bonus, he added.
“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,” Wininger said. “It’s stupidly obvious that Miami’s the best city to build a company in.”
Pictured above: BOB Co-Founders (left to right) John Henry (CTO); Adam Wininger, (CEO); Kody Greenbaum (CPO).
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I am a writer and editor with extensive media experience and a passion for journalism and serving the community. Most of my career has been spent with the Miami Herald in business news, and my expertise is writing about tech and entrepreneurs. I love hosting this blog for Refresh Miami and we aim to be the go-to site for South Florida startup and tech news, features and views. Have news? Contact me at [email protected]. Thanks for reading!
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