The Trump administration's Small Business Administration is bringing Nicki Minaj, Dean Cain and prominent business figures to Washington on Sept. 18 for a live pitch competition in which five small businesses will divide $1 million in privately funded prize money.
Minaj will judge the finalists alongside entrepreneur and private-equity fund manager Grant Cardone and Airbnb co-founder Joe Gebbia, whom President Donald Trump appointed as the first U.S. Chief Design Officer in 2025. Cain, best known for portraying Superman in "Lois & Clark: The New Adventures of Superman," will host the event.
The competition is part of the SBA's Freedom 250 initiative celebrating 250 years of American free enterprise. The agency launched the program in May under the name Patriot Pitch Competition and is calling the Washington finale the Million-Dollar Pitch Competition.
Five companies were selected from 1,182 submissions:
- Compotech, Inc. of Brewer, Maine
- Winton Machine of Suwanee, Georgia
- Plas-Tech Tooling of Garner, Iowa
- Red River of Gillette, Wyoming
- VetPowered LLC of San Diego, California
Every finalist will receive prize money. The winner will collect $400,000, while second place will receive $250,000, third place $150,000, fourth place $125,000 and fifth place $75,000.
The $1 million pool is being funded by Clover Network, Inc., rather than taxpayers, according to the SBA. Clover operates financial-technology products including point-of-sale and business-management systems used by merchants.
That funding structure gives the event an unusual public-private character. A federal agency is organizing and promoting the competition, while a private company is supplying the cash awards that the SBA describes as growth capital.
The agency said applicants were assessed on competitiveness, innovation, economic impact, job creation and underlying business fundamentals. The finalists also had to be businesses that had used qualifying SBA capital products.
The SBA said the competition is intended to showcase companies that used government-backed financing to expand operations, develop products and create economic opportunities. The Sept. 18 finale will be held alongside the Freedom 250 Supplier Matchmaking Expo at the Ronald Reagan Building and International Trade Center.
The format gives a traditionally bureaucratic small-business program some of the trappings of reality television. Entrepreneurs will make live presentations before a judging panel that combines entertainment, investment and technology figures, inviting comparisons with "Shark Tank."
The structure also carries echoes of Trump's own television career. Trump hosted "The Apprentice" and "Celebrity Apprentice" for 14 seasons from 2004 through 2015, with contestants competing in business challenges before facing elimination.
The SBA contest differs in a central respect. The five finalists aren't seeking employment with Trump or an investment from the judges; they are competing for predetermined cash awards administered through the federal program and financed by Clover.
Minaj gives the event its highest-profile entertainment name, while Cardone brings experience in private equity, real estate and entrepreneurship. Gebbia adds a technology background from co-founding Airbnb as well as his current role inside the Trump administration.
Cain will serve as host rather than participate in judging. His presence, along with Minaj's, gives the event a substantially different public profile from a conventional SBA financing or supplier program.
