John, co-founder and CEO of the successful FUBU hip-hop fashion line and a founding investor-panelist on the Emmy-winning Shark Tank TV show, launched his clothing venture in 1992 with a mere $40 — and has turned that into a $6 billion brand. But if not for support from his mother, who permitted him to convert their living room into a cramped textile factory and who took $100,000 in equity out on the house to fund the startup, John would never have made it, he said.

John would need several more breaks. After cajoling a fellow native of the New York City borough of Queens — rapper LL Cool J — into posing for a photo wearing an FUBU ensemble, and then sneaking himself and a sales team into a Las Vegas trade show to promote the line, he boldly sought funding to help him fulfill orders for companies seeking to sell his edgy wares. No fewer than 27 banks turned him down.

John's mother, who had worked three jobs to support the family, urged him to go out and earn $2,000, so he went back to working long shifts at Red Lobster. Meanwhile, his mother placed an ad in the newspaper: "Millions of dollars in orders needs financing," the ad read, and this drew responses from loan sharks and other unsavories. One response, however, came from Samsung Textiles, offering to provide John the capital. John recalls his mother saying: "Daymond, it takes the same energy to think small as it does to think big, and you must think big."

John, dubbed by President Obama the “Global Ambassador of Entrepreneurship,” is author of three best-selling books, including Rise and Grind, which is about people who have succeeded against tough odds. There will always be disruption, John says. "But real sharks take advantage of that opportunity," he said. "The only thing that is going to stay the same is change." 

FUBU was not John's first business. At age 6, he sold pencils to girls at school with their names colorfully printed on them — before the principal shut him down. He later handed out flyers for a new shopping center then under construction: Colosseum Mall, in the Queens neighborhood of Jamaica. Another break came when John wound up at the same mall working for a group of entrepreneurs who helped him overcome his self-proclaimed "lack of financial intelligence" and taught him a little about business.

John loves his high-profile Shark Tank gig but points out that deals do not flow quite as smoothly as the neatly edited show might imply. "It takes three to nine months to do deals, but the closing rate is 90 percent," he said. John says he can usually tell when a sales pitch is going to work from the presentation and personality of the one pitching the deal. "We don't invest in ideas, we invest in people," he said. 

Not all of John’s struggles have been in the business sphere. He spoke of his battle with thyroid cancer. Having since recovered from that 2016 illness, John recalls that he displayed no symptoms before the diagnosis, as he implored his audience members never to delay health screenings, especially as they grow older.

"We [have a tendency] to take care of others, but we don't take care of ourselves," John said. "The one thing you need in the shark school is to keep on swimming."