It's been a long time since Daymond John stood on a street corner in Queens, New York, with a few dozen hats in hand and little more than the moral support of some childhood friends.
Yet, sitting in his spacious 10th floor office in Manhattan's garment district, the American entrepreneur and investor speaks fondly of those early years spent peddling his handmade creations in his childhood neighbourhood, saying that's where he originally found "real proof of concept".
Today, John is the founder, CEO and president of FUBU, or "For Us, By Us," the urban clothing company he started in 1992 - now a $US6 billion brand.
But it took John some unconventional moves to get there.
When he first started he was an ambitious 20-year-old with $40 in his pocket and a loving mother who taught him how to sew and took out a mortgage on her home to help him along his way.
And it all started with one hat. A tie-top hat he had seen on a rap group in a video that was being sold for $20 but wasn't widely available. John went home, sewed around 90 knock-off hats with his next-door neighbour, and began selling them on the street for $10 apiece. He recalls making $800 in a single day.
Sensing potential, hats progressed into jerseys, sweatshirts, jeans, shoes and T-shirts and he and his mates began sewing the FUBU logo onto whatever they could get their hands on. A big break finally came when John convinced then upcoming rapper LL Cool J, who had grown up on his street in Queens, to pose for a photograph wearing a FUBU shirt.
From here, the FUBU name grew, and the young businessman soon saw himself running a factory, showroom and office from his home. By 1998, he was reportedly worth an astonishing $250 million.
"Growing up in New York and being able to stand in Queens, or Harlem and trying to sell a hat, that's when we get what you call real proof of concept," the entrepreneur extraordinaire told news.com.au. "Because people in New York aren't shy, so when I was selling those hats, they would tell me what they thought about them and my mother at the same time!
"They weren't shy about it so it makes you go back to the shop and fix what you already have," he added.
John's pathway to super success is one of the most inspiring rags-to-riches stories of modern times. An only child of a single parent who struggled through school, he refused to let his difficulty with dyslexia or his lack of finances hold him back.
"Most people would think that these things are challenges or hurdles," he said. "The fact that I got held back in school, my father left when I was 10, I didn't have any money, I didn't have an education in the field I wanted to go into.
"The field that I wanted to go into was predominantly run and operated by a different culture, they didn't allow me in," he added. "I didn't own any retail stores myself, I didn't have any financial intelligence so I initially didn't know how to go out and seek funding. Then, after I did acquire any kind of money I blew it all. Not blowing it on frivolous things but not understanding how to utilise the tool of money and then when I did acquire wealth I almost lost it all again due to not understanding the tool of money."
These days, the 47-year-old billionaire is possibly best known as one of the five savvy business executives, or "sharks" on America's reality show, Shark Tank, alongside Dallas Mavericks owner Mark Cuban.
He's also a New York Times best-selling author and motivational speaker and is heading to Australia next month as one of the key motivators at the National Achievers Congress held in Sydney and Melbourne. It's here that John says he intends to share his somewhat controversial wisdom - that being broke is a great business advantage.
John, who ran out of money three times and then relaunched FUBU, credits his success with starting out broke, which he says forced him to think more creatively, use resources more efficiently, connect with customers more authentically, and market his ideas more imaginatively.
"I always say that it's so hard to make money but it's so hard to keep it," he said. "Then being in the business of fashion is very fickle. A true fashion brand will last five years ... so after [FUBU] went down and everybody said to me, 'you got struck by lightening, you only had one bite of the apple,' how did I go to convert into doing other brands, how did I convert my personal brand into somebody that you now see on television?
"Even at this stage in my life, if you're a true entrepreneur, you still think about making payroll, moving ahead, how are you going to make sure your staff is happy and content, how do you stay ahead of the curb but not too ahead of the curb where you are too new, where nobody supports you."
John often talks openly about his failures, both personally and professionally, during his keynote speeches - something that he believes is essential to long-term success.
"So many people out there in the world compare their blooper reel to everybody else's sizzle reel and they don't think that everyone went through challenging or even more challenging times," he said.
"I failed at a marriage, got divorced, lost my family, how did I rebound from that? Many of my friends are dead or in jail. So there are so many ways that I have failed and even when everything was going well and it wasn't dramatic failures, here were other brands that I launched that have failed too."
The Shark Tank star proposed to his longtime girlfriend, Heather Taras on the set of the US show in September. The couple have a 10-month-old daughter together.
On his ventures that have flunked over the years, John says it always comes back to the same thing. "I wasn't enamoured enough with it or I wasn't fascinated enough by it.
"If you're not making enough mistakes, you're not making enough moves," he adds. "So it's the process. For most entrepreneurs, the key to what they do is they act, they learn and they repeat."
So, what's the secret to success that he tells all budding entrepreneurs who seek out his advice?
"Firstly, do something that you are absolutely obsessed with and would do for free.
"Secondly, you have to do your homework and you have to research it because there's nothing you can create that's new in this world, it's just going to be a new form of delivery.
"Every big thing has started off with a movement. Mark Zuckerburg started off with one friend, now he has 1.5 billion of them. I started off with one hat."