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BOB raises $5.5M to build AI-powered finance employee

October 22, 2026
By
Loren Baker
BOB raises $5.5M to build AI-powered finance employee

BOB, a Miami-based financial technology startup, has raised $5.5 million in seed funding to expand its AI-powered financial assistant for small businesses and grow its team in South Florida.

The funding round was led by Mischief, a venture capital firm founded by Plaid co-founder Zach Perret. Other investors include billionaire Peter Thiel, Zynga founder Mark Pincus, entrepreneur Codie Sanchez, Karman Ventures and several other investors.

BOB was founded by Adam Wininger, Jason Brill and Kody Greenbaum. The company aims to help small business owners manage their finances without using complicated software and multiple dashboards.

Its AI-powered assistant works through platforms such as WhatsApp, text messages, Slack, Microsoft Teams, email and its own app. Business owners can use it to manage financial records, send bills, accept payments and track cash flow in real time.

BOB aims to make financial management easier for local businesses, including roofing contractors, restaurants and service providers that often struggle with traditional financial software.

According to CEO and co-founder Adam Wininger, many small business owners find it difficult to manage their finances and adopt new AI tools. The company wants to help them run their businesses more efficiently, understand their financial position and save time.

The investment comes as investors show growing interest in AI-powered financial technology. Mischief believes BOB has the potential to serve a large market as AI tools move beyond providing advice to completing financial tasks independently.

BOB launched its private beta last month and has already received sign-ups from 500 businesses. The platform is currently free for selected businesses as the company continues to develop its product and onboard customers.

The new funding will help BOB improve its product features, expand customer onboarding and hire more employees in Miami. The company currently has a team of 10 people, all based in the Miami area, and plans to expand its workforce.

Wininger said Miami offers a strong environment for building a startup, with growing investor interest and opportunities to attract talent. He also believes the city’s quality of life and business environment make it an attractive alternative to technology hubs such as San Francisco.

With the latest funding, BOB plans to strengthen its AI financial assistant and help more small businesses manage their day-to-day finances.

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