The Brassys - Presented bty Square

Celebrating the boldest businesses in America

The winners have been selected. See who won!
View the winners >
adj. : Shamelessly bold

You have to be bold to start a business. An entrepreneur is “one who undertakes significant financial risk.” So, really, all sellers are brave. You’re all bold. You’re all crazy enough to ignore the odds and tough enough to stick it out.

We at Square hear a lot of these stories, and some stand out. Stories of extraordinary vision and extreme perseverance. Of building your community while you build your business. Of turning an idea into a livelihood into an unstoppable force.

We created the BRASSYs—our first-ever awards program—because we want to recognize these sellers. Five BRASSY winners will receive mentorship from business luminaries at a special one-day Seller Summit, a $10,000 cash prize, Square hardware, and more.

Stories are due by October 9.


Here’s how the BRASSYs work: first the public weighs in, voting on their favorite businesses. Then a judging panel at Square chooses thirty-five finalists from those entries. Popularity counts—that’s where the public vote comes in—but so do things like mission, innovation and originality, community involvement, and customer love. They’ll also consider other factors, like clear and compelling responses, social media presence, and more (think of those like extra credit). See Official Rules for details.

From the thirty-five finalists, the judges will narrow it down to five winners, using the same criteria of mission, innovation and originality, community involvement, and customer love. May the BRASSY-est businesses win.

Thirty-five BRASSY finalists will receive:
  • Custom Square product package
  • Business Power Pack ($2,500 approximate retail value), with prizes from our partners:
    • Avvo
    • Google AdWords
    • Indeed
    • Magisto
    • Twitter
    • Vistaprint
  • Google Chromebook + Chromecast
  • Regional press recognition
  • "BRASSY Finalist" in-store decals
Five National BRASSY winners will receive the Finalist prizes and:
  • $10,000 cash prize
  • One-day mentorship session with the judging panel at the Seller Summit hosted at Square headquarters in San Francisco (all expenses paid)
  • National press recognition
  • "BRASSY winner" in-store decals

BRASSY Timeline

September 13-October 9: Business submissions and public voting period open

mid-October: Square will choose 35 finalists based on contest criteria and public vote

mid-November: Official judging panel will choose five winners from the finalists pool

January 2017: One-day Seller Summit in San Francisco