It was Good Friday 1989. Standing on the pavement outside of the Colosseum Mall, on the corner of 165th Street and Jamaica Avenue in Queens, New York, a 20 year-old tried to be discreet as he examined his wad of cash. He thumbed through the crumpled bills, counting them and smoothing them out one-by-one, disbelieving that he was turning a $40 fabric purchase (funded by long hours spent working at fast-food restaurants and busing tables), coupled with days buried in his mother’s basement while curled into a sewing machine, into $800 worth of hat sales. But he knew it meant he was onto something.

Raised by a single mother in the Hollis neighborhood of Queens, and having become the man of his household at only 10 years old, money was an elusive concept. The lack of it loomed over him most of his life, shadowing the trajectory of what his future might hold. College was not on his radar because there were no funds to gain him admittance. Having been diagnosed with Dyslexia, there had never been any silver spoon to feed him, no family member to open the right doors and no privilege spinning in his orbit. But his mother had taught him the value of one thing he knew he had absolute control over: his mind.

And he would use it to visualize and anchor for himself opportunities that were outside of the scope of his present reality. His father’s abandonment had been devastating to them financially, but it had also made an entrepreneur out of him. Just because the right opportunities were not bumping up against him, he thought, didn’t mean they were not in the realm of existence. He’d have to create them.

The 20-year-old was none other than Daymond John, now 49, Founder of the $6 billion company FUBU, Shark Tank favorite and multi-millionaire investor, best-selling author and one of the most Googled entrepreneurs in the world. And this is the story of how he traded in his Red Lobster uniform for $5,000 pinstripe suits.

It was the early days of hip hop, when Public Enemy and N.W.A. rapped about their experiences with police brutality. John’s fellow neighborhood native LL Cool J released a track titled, “Illegal Search.” Though not as highly publicized, prior to the Rodney King beating in 1991, a string of black men and women in Los Angeles fell victim to violence and racism. It created societal quakes that could be felt all the way to the East Coast. Hip hop was on the rise, but the clothing designers weren’t interested in illuminating its culture for the rest of the world.

So John, being a young African-American male and always one to link arms with hustle, decided to freestyle some designs that would not only reflect and contribute to his community, but shine a spotlight over it for the purpose of sharing it with other cultures. On a whim, he made some hats, and then t-shirts with various compelling phrases printed on them, such as, “What happened to poor Rodkey King?’ He sold them on street corners outside of the Apollo Theater and at various events around New York City. Through this, he learned that products with an emotional connection emanated a special kind of selling power. So he coined the mantra, “For Us, By Us,” which was shortened to FUBU. He started sewing the logo onto his apparel. The name stuck, but the money didn’t — at least not in the beginning.

“I opened in 89’ and closed down three times by 92’,” says John. “I’d run out of money and then close it down. Six months later, I’d see somebody and they’d say, ‘Hey man, that shirt you sold me, I’ve been looking for it forever. Everybody loves it.’ So then I’d open it back up. But I’d run out of money again. That whole process of shutting down and starting up again continued until 92’, and I never made any profit.”

John admits that, in those days, his motivation was fueled by the spotlight it shone over him, along with the excuse to gain an all-access pass to hang backstage with the likes of Run DMC. When all of the other kids were being kicked off of the music video sets, he was still standing mere feet from the talent, holding a FUBU shirt. He eventually convinced Brand Nubian to wear the apparel in one of their videos, along with Ol’ Dirty Bastard, Busta Rhymes and LL Cool J.

Photo Courtesy of The Shark Group

“At first, the motivation was feeling like I was part of the hip hop community. Then it became, ‘Wait a minute. I can actually see potential in making money here and I don’t have to depend on somebody else to give me a job. At that time, I wasn’t thinking about millions of dollars or having a global brand. It was more like, ‘Maybe I can make a little money so that I won’t ever have to listen to the manager of Red Lobster or of Church’s Fried Chicken.’”

But soon he would be staring at his accidental business through a different lens — not simply out of sheer force of ambition or desire, but out of urgent necessity.

John and his partners ventured to Las Vegas for a trade show, packing a photograph of LL Cool J dressed in FUBU apparel into one their bags. During that show, it caught the attention of potential customers. They were so lured by the magnetic pull of its celebrity endorsement, the friends ended up filling far more orders than they had the funds to satisfy — $300,000 to be exact. With no money to purchase the needed materials and resources, John walked into 27 banks in desperate pursuit of a loan. Every one of them slapped him with a denial. John’s mother, who was present during my entire conversation with him, then offered to take out a second mortgage on her home, which gave him $100,000 to work with. As John unraveled the story for me, she offered up occasional commentary in the background and chuckled as he reflected on the chaotic uncertainty of those early days.

“I think I was around 25 at the time. My mother told me, ‘Look, I’m going to mortgage this house since you keep getting turned down by all these banks. But you’re a grown-ass man, so I’m going to move out and let you figure this out,’” says John.

He moved his friends in, along with eight sewing machines, and turned his mother’s house into a FUBU factory. Every waking hour that was not spent waiting tables at Red Lobster was spent designing, sewing, boxing up orders and venturing to clubs in hopes of getting the apparel into the hands and onto the bodies of more influential people.

“My motivation switched to ‘Holy crap. My mother mortgaged her house. I’ve got a whole lot of people expecting these deliveries to be made. I’ve got to work 10 times harder now in order to make something happen,’” he says.

Most people would have taken the money, popped bottles of champagne with their friends and burned their old Red Lobster uniform. Not John. What I find most fascinating about him is that, even after his designs was being paraded around by iconic rappers in their chart-topping music videos, and new orders were filling up his answering machine every day, he was still tying himself into his server uniform every week. To the metric of the public eye, he had arrived. But he was still serving shrimp and biscuits and counting his tips at the end of every shift, thinking of how he was going to invest it right back into his fledgling empire.

It wasn’t until early 1996, when an ad placed in the New York Times helped him secure an international deal with Samsung, that he clocked out at Red Lobster for the final time, and threw himself into his business completely. And it wasn’t for another year after that that the brand’s popularity would define an era in hip hop history.

LL Cool J was commissioned to rap in a Gap jeans commercial. He wrote a 30-second song, “For Us, By Us,” which was an obvious nod to FUBU’s brand mantra. He was dressed in Gap clothing, but sported a FUBU hat. The commercial reached millions of television viewers and caused the novice brand’s popularity to explode — without having cost them a dime in marketing. It spawned a massive controversy, and became one of the most climactic moments in hip hop history. FUBU rolled in $350,000 million in sales within the year that followed.

Photo Courtesy of The Shark Group

This meant that, as hip hop further dominated television sets and airwaves, nearly every frame was styled by FUBU. John went from hustling his homemade sewn hats on street corners, out of vans and from trade show booths to heading meetings at his office in the Empire State building and dining with then-president Bill Clinton. The apparel wasn’t just for those in urban communities anymore. Boxes of boots, hats and t-shirts were being shipped to wealthy kids in the suburbs. It was a real American rags-to-riches story where he became a hop hop icon in his own right — not by album sales, but by apparel sales.

John admits that his early days of glory were exhilarating, but not met without oppressive racial nuances.

“As an African-American who was distributed by Samsung and who had different partners of different ethnicities behind me, I remember it was like people thought, ‘The black guy can’t possibly own it.’”

He recalls once walking into a room to meet with some men who wanted to collaborate with FUBU. His Jewish partners were preparing for the meeting when one of the potential collaborators turned to them and said, “Hey, so do you want to do this?” John then entered the room wearing a heavy gold chain and dripping with all the bling. One of the men caught his gaze and said, “Wow, they sure pay you well around here.”

John says, “All I could think to say was, ‘Well, guys, I think our meeting is over. You just insulted the CEO.’”

FUBU, which to date has earned a total of $6 billion in global sales, inspired other urban brands like Sean Jean and Roc-a-Wear. By the late 2000s, FUBU’s popularity in the United States had long faded, but John didn’t sweat it. When he was presented with an opportunity to invest in the dreams of others — in front of millions of television viewers on a weekly basis, he said yes.

Photo Courtesy of The Shark Group

“I remember when FUBU was slowing down,” says John. “I was already thinking about what else I was going to do. I didn’t just get upset because it wasn’t becoming Louis Vuitton or Nike. Even the most successful fashion brands are often only hot for five to 10 years. You know, my mother and I were just talking a minute ago and she was saying that no matter whatever happens in her life, she’s going to work it out no matter what. It’s always been the same with me. So I had the drive to keep going and thinking of new things to involve myself with.”

At the center of those “new things” was an opportunity to star on ABC’s Shark Tank as a business executive — a gig that began in 2009 and continues still. John became an instant fan favorite. Through his investments made on the show, he has raked in more than $7 million.

But he says his success can’t be reduced to the expensive cars, flashy suits or the notoriety, because money and fame offer no escape from problems. “When I was first starting out,” he says, “ I used to think, If I could only be rich. But now success means something entirely different.”

John relates with those who subscribe to the concept that money and success exist only in parallels, though he wants people to expand their perceptions of what a fulfilling life entails. “If you’ve never had any money, it’s easy to assume that most of your problems would be solved by having it,” he says. “If you’re standing at a bus stop with snow or rain all over you and you see somebody pass by in a Benz, it’s easy to view money as a cure. But the truth is, once you attain the money, different problems will always arise.”

He pauses for a moment, seeming thoughtful, before moving into a story about a conversation he once had with a paparazzi.

“One day I was coming out of a restaurant and a paparazzi stopped me. He asked, ‘How do you feel being rich and successful?’ I said to him, ‘Well, I kind of feel the same.’ He was taken aback and so I said,’ Well, money just drives everybody to new problems in a brand new Bugatti.’ Then, he said, ‘Well, I’d love to drive into any of my problems in a brand new Bugatti,’ and I said, ‘Well, if it were stage 4 cancer, how great is that ride going to be?’ Then he put the camera down.”

John With Shark Tank Cast | Photo by S. Bukley

John says the real luxury about being on a show every Sunday night and doling out half a million dollars is that he is void of the inclination to shout, “Look at me! Listen to me, I’m rich!” It’s obvious to the world that he is established, and this commands that people pay attention to what he says. But what this means for him is that he is in a position to reach the masses with more enlightening and consequential modes of thought, and he is committed to total transparency with every television appearance, book, post and Tweet — including his own diagnosis and treatment of stage 2 thyroid cancer a couple of years ago.

“With what happened to Kate Spade and Anthony Bourdain, I think it’s important that I talk to people about this pressure to keep up the whole Instagram image of being a boss. We tell everybody to go balls to the wall, to go hard or go home. I’ve been guilty of that, too, but I think entrepreneurs often think of committing suicide because they have to live this life of fronting,” says John. “There is this pressure to take care of so many people. They may be listening to all of their staff members’ problems, but in reality they don’t really have anybody to talk to. This whole mentality of, ‘Look at me, look at my accomplishments, look at my Benz, I’m a boss,’ has put so much pressure on people that it’s dangerous.”

I’ve come to believe the mark of a truly successful person is that they possess a certain nature of resilience in their attitude, but also an insatiable hunger to contribute to the world indefinitely. They desire to be a participant, to engage and create through progressive modes of thought, or business, or art or literature or opportunity. There is no desire to simply reach a specific destination per se — to anchor recognition and exaltation and then just exit the scene once a monetary or popularity goal has been reached. They wish to be alive and active within their quest, to toss the ball back and forth in tandem, and to birth something of value. It’s not solely about the glory; it’s about contribution. As their wealth grows, their heart grows. I get the feeling that John demonstrates the epitome of this concept.

A couple of years ago, despite having amassed an estimated net worth of $250 million from his appearances, investments and string of companies, including the establishment of a brand consulting and management firm called The Shark Group, he thought of yet another offering of contribution. After having published four successful books, one of which, “The Power of Broke,” held strong on the New York Times bestseller list for weeks, John had a flash of inspiration to write another.

“I was texting ‘Rise and Grind’ to people every morning, and posting it to my social media,” says John. “Then I thought, OK, I’m going into my eighth year of Shark Tank. I have 16 companies. I have a brand new daughter and two that are grown. I’m almost 50. How can I be more efficient with my day? Daymond John at 25 worked 18-hour days, but at 49 I can’t do that. So I went out to talk to all of these highly successful people and asked them, ‘Can you give me some tips about how you execute your days?’ I began to notice that all successful people have pretty similar habits the first 90 minutes of every day. I then realized I had a book.”

When people see their bosses or mentors breeze into the workplace, ready to roll, or they spot an influential person on television, social media or Youtube whom they admire, they are only observing them after they have pulled themselves together. John says he was most interested in the question: “What do all of these people who are so admired and successful — what do they do to get ready? That’s what I wanted to find out,” he says. “I knew other people would benefit from hearing from these people as well.”

The book, which became an instant New York Times bestseller, is sort of an infinite number of books contained within a single bound. It transcends age, industry, interest, religion, and personality. The goal of its creation was for the tools within it to be applied to a multitude of frames within the trajectory of a person’s life. It can be picked up over and over again throughout a single journey, but it will never be the same book for them as it was the time before.

“When it was coming together, I realized that I wanted it to be everlasting. I want somebody to read it at 30 years old and say, ‘I want to work like this guy or that guy. I like what they are doing.’ But then I want them to be able to come back to the book at 50 and say, ‘You know, I connect with the way Joel Osteen works.’ It’s for the working single mother who wants to be more efficient in her day. It’s for the new entrepreneur and the seasoned ones,” says John.

As for his own personal tips for taking reign over his days — anchoring the power of the “Rise and Grind”?

“First of all, never answer any emails within the first hour, because all of those emails are somebody else telling you their problems. You don’t need to start your day thinking about the rest of the world’s problems. Also, don’t go on social media either — even if it’s my social media,’” he says, laughing. “Everybody on social media is sexier and skinnier, and happier — except they’re not. The truth is they are all screwed up just like everybody else.”

John’s philosophy seems to be simple yet earth-shattering: If you enter into consciousness already focusing on how high everyone else seems to be climbing, how fabulous everybody but you is looking and how rich your competition is becoming, you’ve already lost yourself by breakfast.

Photo Courtesy of The Shark Group

“If you wake up in the morning taking on the burn of everybody else’s problems, and feeling depressed watching everybody else’s success, then you’ve already started your day off bad,” he says. “But if you wake up and meditate, set goals, pray, work out, or whatever else that is going to feed you and serve you, you are setting yourself up to be better equipped and in total control of your day. That system of routine spent focusing on themselves is what every single successful person in that book has in common.”

John means serious business, but he has a sense of humor, too. When asked to examine his whole life and all of its multitude of stops and starts, highs and lows, straight lines and jagged angles, while honing in on the one thing he is sure to have executed absolutely right, he says, half-joking, “I’m thankful that I haven’t publicly embarrassed myself as much as I could have.”

His answers are refreshingly authentic, fair and even modest at times, but never in a self-deprecating, nor syrupy way.

“Look, we can get mad at these Justin Biebers all day long, but I wouldn’t want you to have had 1,000 cell phones on me when I was 16 years-old. Do you know how stupid I was at 16? Or at 25 even? Thank God the world doesn’t know how stupid I am — or was,” he says with a laugh.

But then his tone turns a bit more contemplative. “I’m proud of everything I’ve done, but there is nothing in my life I can look at and think I did it completely right and never messed up. I’ve had failures, but all failures have made room for something else,” he says. “I’m extremely proud that I’ve been able to employ a lot of people. I’ve taken friends of mine out of the neighborhood or out of Red Lobster and given them opportunities. I was able to know that they weren’t going to be let go of a job because of their gender, or religion or the color of their skin. They were either going to prosper or they were going to fail, but it would be according to their work ethic and nothing else. I’ve been able to see those people raise their kids and, in some cases, grandkids. So I gave them opportunities that they will then pass on in their families.”

Before I have a chance to respond, he is prompt to add, “I have never made anybody successful, though. I’ve given them opportunities, but I didn’t make anybody successful. I guess that’s what I want people to get most of all: People can only ever make themselves successful. Nobody else but you is ever going to be able to do it for you. That’s just the way it is.”

This exclusive travel feature was published in The Connect’s Summer 2018 issue. You may purchase the full issue here, or download the digital version here.