Before her name became linked to legendary football coach Bill Belichick, Jordon Hudson was already drawing up a different sort of game plan, one rooted in entrepreneurship across a few industries.
The 24-year-old former pageant competitor and cheerleader from Maine has quietly assembled a web of 18 limited-liability companies across Massachusetts, carving out a path as a modern small-business owner who treats personal branding like an evolving portfolio.
According to a report by The Defector, this all began right before Hudson and Belichick reportedly started dating and ramped up with the former Patriots coach. Public records show that what began as a few real-estate investments in 2023 has since grown into a cluster of ventures spanning property management, beauty, consulting and media production, with Belichick's image at the forefront.
Hudson’s first filing, TCE Mt. Vernon LLC, came in June 2023, describing a business to “own and manage real estate.” Within months, three more entities followed, which were all tied to rental properties around Boston and Provincetown. Mortgage filings later showed purchases of three multi-family homes in Dorchester and Roxbury Crossing, suggesting a deliberate strategy to separate each property for liability protection, a common but costly safeguard for small real estate investors.
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By that winter, Hudson went another route. She created Roosevelt Beauty LLC and Roosevelt Glam LLC, citing plans for cosmetic product sales and event styling. The filings reflected a natural extension of her pageant experience and selling design and presentation. She later finished as runner-up at the 2024 Miss Maine USA pageant.
The filings kept coming. After Belichick officially parted ways with New England in January 2024, Hudson launched TCE Tech Support, Creative Consulting and management, all focused on digital services and media. Public records listed her as founder and Belichick as agent on one entity, Coach Show LLC, the production company behind his short-lived football analysis series that aired later that year.
An interesting wrinkle to this is that Hudson describes herself as the chief operating officer of Belichick Productions, showing the trust between herself and UNC's coach.
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In early 2025, Hudson added companies such as Chapel Bill LLC, All BB Team LLC and TCE Rights Management. They were moves toward protecting intellectual property, control and merchandising for Belichick, and a notable leap from real estate to content licensing. Another filing, Trouble Cub Enterprises LLC, became the umbrella name she now uses on social media, branding herself as CEO of “Trouble Cub.”
List of Jordon Hudson's LLCs
While the precise operations of each company remain unclear, the pattern suggests an entrepreneur testing ideas with Belichick on board for the ride. Each filing carries a $500 initial fee in Massachusetts, plus annual maintenance costs. Yet Hudson appears to view each entity as a prototype rather than a final product or long-standing business.
Her most recent ventures hint at creative storytelling on the horizon. Spring Street Seafood Co. And Belestrator Bills Version are both tied to multimedia projects involving Belichick’s new coaching life at North Carolina. This might be tied to the recently failed behind-the-scenes UNC docuseries canceled by Hulu.
Real estate (4)
- TCE Mt. Vernon LLC
- TCE Cottage
- TCESFH1
- Gingerbread Apartments
Beauty (2)
- Roosevelt Beauty LLC
- Roosevelt Glam LLC
Bill Belichick related (12)
- TCE Tech Support
- TCE Creative Consulting
- TCE Management
- Coach Show LLC
- Chapel Bill LLC
- All BB Team LLC
- TCE Rights Management
- BBS Version
- Trouble Cub Enterprises LLC
- Trouble Cub
- Spring Street Seafood Co.
- Belestrator Bills
What's next for "Trouble Cub" and "Big Bill"?
Hudson’s rise illustrates how entrepreneurship has evolved for the social-media generation. It's important to note she hasn't filed for any new LLCs during UNC's miserable 2-5 season.
As Belichick’s rough tenure in Chapel Hill plays out publicly, Hudson’s business experiment continues mostly behind closed doors and a growing paper trail of filings. Whatever happens next for Belichick comes with Hudson calling the shots in the background.
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