Wool ski hats with their tops tied off with fishing line were popular, and John noticed them being sold for $20, which he considered overpriced. He went home and sewed around 90 hats with his next-door neighbor. They sold their homemade hats for $10 each on the corner of Jamaica Avenue and made $800 in a single day in 1992. After the hats, they began selling screen-printed T-shirts. To break into the market, they sold on consignment and at large events around the Northeast. To make ends meet, John held a full-time job at Red Lobster, working on the FUBU business in between shifts.

In 1992, or 1994, John received $300,000 in orders and also an offer for participating in Macy’s (M) at a Las Vegas fashion trade show, MAGIC. They had to take out a second mortgage of his mother’s house in order to fulfill the orders. After being turned down by 27 banks for a loan, his mother used the last of their money to take out an advertisement in the NY Times. As a result of the ad, FUBU made a deal with Samsung Textiles, allowing them to complete their orders.

Sensing potential, John and his mother mortgaged their house for $100,000 to generate start-up capital. In addition to Brown, he recruited longtime friends J. Alexander Martin and Keith Perrin into the business, and began sewing the FUBU logo onto hockey jerseys, sweatshirts, and T-shirts. They loaned about 10 of the hockey jerseys out to rappers for their music videos for 2 years and got product placements in about 30 videos. They were perceived as a large clothing brand, despite being a relatively small company and stores started requesting their brand. In 1993, he convinced LL Cool J, an old neighborhood friend, to wear a FUBU T-shirt for a promotional campaign. Later, while filming a 30-second advertising spot for The Gap, LL Cool J wore a FUBU hat in the commercial and incorporated the line “for us, by us” in his rapping.

In 2009, John received a call from Mark Burnett asking him to join the cast of ABC’s new reality business show Shark Tank, which gives entrepreneurs the opportunity to pitch their businesses to investors, or “Sharks” in the hopes of receiving an investment. The show is now in its 11th season. John has invested $8,567,000 of his own money in Shark Tank companies as of May 12, 2017. His favorite investments on record by 2015 were Al “Bubba” Baker’s boneless ribs and Bombas socks. In 2016, Shark Tank won an Emmy Award, and won Outstanding Reality Program from 2012-2014.

In 2015, John co-founded Daymond John’s Success Formula, a program designed to teach business owners and entrepreneurs how to start and grow their business.

In 2015, President Obama appointed John as an ambassador to promote underserved entrepreneurs.

John invested in Bubba’s-Q Boneless Ribs on Season 5 of Shark Tank and has helped grow the company from $154,000 in sales to $16 million in 3 years. In 2017, Bubba’s-Q Boneless Ribs partnered up with Carl’s Jr. to create the limited-edition Baby Back Rib Burger.

In April 2017, John was diagnosed with stage II thyroid cancer. John successfully underwent surgery to remove the cancerous nodule.

In 2018 John married Heather Taras, his second wife, with whom he has a daughter named Minka Jagger. He has two daughters from his first marriage, named Destiny and Yasmeen.

In September 2019, Daymond John’s Success Formula rebranded to Next Level Success.