In Downtown Brooklyn, an informal street vending operation known as "Hoodwill" operates along a public sidewalk near the intersection of Bond and Schermerhorn Streets, directly competing with a nearby Goodwill thrift store. Founded and managed by Tyshawn Kennedy, 35, Hoodwill sells donated goods without a storefront, price tags, or an official license, offering items at significantly lower prices than the nearby registered nonprofit Goodwill Industries of Greater New York and Northern New Jersey.

Hoodwill vendors sell a range of goods, including clothing, electronics, and housewares, often pricing clothing between $2 and $4, and electronics under $10. Kennedy purchases donated bags from individuals arriving to donate to Goodwill and resells the contents directly on the sidewalk, sometimes drawing regular customers looking for affordable or unique items. Kennedy openly acknowledges selling designer and collectible items — such as vintage Chanel scarves or Dior bags — at steep discounts, citing a lack of time and patience to sell online, in contrast to Goodwill’s growing e-commerce operations that auction valuable items at significantly higher prices. For example, Goodwill’s online platform recently listed a diamond ring for $61,999.

Goodwill operates more than 30 retail locations in the region and emphasizes its mission to support people with disabilities and employment barriers, using store proceeds to fund workforce development and other social programs. At the Downtown Brooklyn store, prices for items such as jeans, shoes, and lamps generally range from $8.99 to $29.99. Goodwill has also taken steps to discourage donations to hoodie sellers by posting prominent signs requesting donations only inside, employing security personnel around the store, and working with local authorities to enforce street vending laws.

Tensions between the two operations have occasionally risen, including a confrontation between Kennedy and a Goodwill-hired security guard over intercepted donations. Goodwill’s president and CEO, Katy Gaul-Stigge, said the nonprofit has long sought support from community and government stakeholders, including police and sanitation officials, aiming to address "quality-of-life concerns" caused by unlicensed street vending around its locations.

Local elected officials are involved in managing the issue. City Council member Lincoln Restler, whose District 33 includes Downtown Brooklyn, acknowledged the complexity of the problem, initially sympathetic to the street vendors’ efforts to earn a living but noting increased complaints over aggressive solicitation and litter left behind. Restler described an "element of deception" as some donors may not realize their contributions are diverted from Goodwill to Hoodwill sellers.

Community organizations such as the Downtown Brooklyn Partnership and the Atlantic Avenue Business Improvement District have expressed concerns about the impact of unlicensed vending on neighborhood cleanliness and donor confusion. Meanwhile, some customers and vendors defend Hoodwill’s role in providing affordable goods and economic opportunity. TikTok influencer Jeremy Carr calls for protections for sellers, and reseller Benjamin Rex describes them as "working-class guys" striving to support themselves. Several vendors report difficulty securing permits due to restrictive rules and long waitlists, though recent legislation aims to expand the availability of legal street vending permits in New York City.

Kennedy, who has a criminal record that hinders conventional employment, sees Hoodwill as both a livelihood and a community. He has been operating for more than a decade and hopes to earn $200 to $300 a day to support his family. While acknowledging challenges and a decline from previous years when Hoodwill had a larger presence, Kennedy emphasizes the social aspect of his work, noting instances of charity such as providing shoes to people in need.

Goodwill maintains that its retail operations, despite often losing money, are critical to funding services that helped more than 12,000 people last year. The organization emphasizes that it is committed to inclusive employment and community support, contrasting its regulated operation with Hoodwill’s unlicensed street vending. The ongoing conflict highlights broader tensions in urban thrift economies between formal nonprofits and informal street vendors navigating legal and economic constraints.