Miami’s BOB raises $5.5 million for an AI finance assistant
· Funding announced October 23, 2026; product in private beta
BOB is a Miami startup building an AI assistant that handles the money side of small businesses: bookkeeping, invoices, payments and cash flow, all by text or WhatsApp. It has just raised $5.5 million from investors to build it.
The headline
Finance work, in a conversation
Miami-based BOB announced on October 23, 2026 a $5.5 million seed round led by Mischief, the venture firm founded by Plaid co-founder Zach Perret. Other investors include Peter Thiel, Codie Sanchez, Mark Pincus and Karman Ventures, Refresh Miami reported.
BOB is building an AI assistant that keeps a business’s books, sends bills, takes payments and shows cash flow in real time, working through everyday tools like WhatsApp, text, Slack, Teams and email, as well as its own app. It targets service businesses such as contractors, restaurants and local firms.
The company says the money will fund product development, onboarding customers and growing its Miami team. Its private beta launched in September.
- Funding
- $5.5 million seed round, announced October 23, 2026
- Lead investor
- Mischief
- Other investors
- Peter Thiel, Codie Sanchez, Mark Pincus, Karman Ventures and others, per Refresh Miami
- Product
- AI finance assistant for small businesses: bookkeeping, invoicing, payments, cash flow
- Founders
- Adam Wininger (CEO), Jason Brill (CTO), Kody Greenbaum (CPO)
- Team
- 10 people in the Miami area, per Refresh Miami
- Status
- Private beta since September 2026; not yet broadly available
Why it matters · Our view
Paperwork is one of the biggest daily headaches for local business owners, from restaurants to contractors. This is a concrete bet on Miami building practical AI for them. Funding alone does not prove the product works; customer results will tell.
Still to be confirmed
Public availability and pricing; results with customers; which financial partners provide the banking services.
Sources
- BOB announcement, October 23, 2026 (opens in a new tab) (funding, lead investor, use of funds)
- Refresh Miami, October 22, 2026 (opens in a new tab) (investors, founders, team, customers)
- BOB — official site (opens in a new tab)
Want to know more?
Ask Cathy Mai Phung, founder and editor-in-chief of Miami Reimagined and Miami real estate advisor.