From waiting tables at Red Lobster to a $300 million fortune: the rags-to-riches story of Daymond John

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"Shark Tank" investor and entrepreneur Daymond John, 47, wanted to run his own business as long as he can remember.

"I never knew anything other than wanting to be an entrepreneur," the New York native told Business Insider.

Before he made a fortune launching the clothing line FUBU ("For Us By Us"), his entrepreneurialism started in grade school. He would scrape the paint off pencils and customize them with the customer's name for a fee — and his market was exclusively the prettiest girls in his first grade class.

At age 10, his parents divorced, and from that point on, he was raised by his mom alone.

"We went from middle class to poor," John told Business Insider. "I became the man of the house and started working at that age." He handed out flyers in his neighborhood of Hollis, Queens, for $2 an hour.

After scraping by in high school — John spent years struggling with reading and writing, only to be diagnosed with dyslexia much later in his adult life — he waited tables at Red Lobster in the early 1990s.

One day, his mom said to him, "Listen, you're going to have to figure out what you're doing the rest of your life, one way or another." He told her that he wanted to start an apparel company for young men, so she taught him how to sew wool caps.

He immediately bought cheap fabric, sewed 80 of them, and sold them for $10 a pop, which earned him $800, John explained on a podcast with James Altucher.

"Did you go back the next day and sew more?" Altucher asked.

John responded: "No. I went back the next hour and sewed more."

After seeing her son's passion and scrappy attitude, John's mom decided to mortgage her home to raise $100,000 to fund his business, which officially launched in 1992. He set up camp in her house, splitting his time between FUBU and Red Lobster.

His brand started to take off after he got big names to wear his product in music videos, but he continued waiting tables.

"Even though I had placed our product in the hottest music videos out there, I was still working full-time at Red Lobster," John told Tim Ferriss. "To the public, FUBU was a huge company. Little did they know that I was still serving them shrimp and biscuits!

"At the point where I had enough money to quit, I decided that I had to give the business all of my attention and effort. So I quit Red Lobster around '95 or '96, and went completely full-time with FUBU."

John quickly realized he could dream even bigger. "When I made my first million, I realized how poor I really was," he told Business Insider. "It takes about a million to get you out of debt."

John's hustle helped him turn a small operation based out of his mom's home into a booming business, bringing in $350 million in revenue within six years. Today, FUBU has earned over $6 billion in global sales.

While his brand's popularity faded in the early 2000s, John did not.

He jumped on the opportunity to reinvent himself by taking a risk on a new reality show: "Shark Tank," which allows budding entrepreneurs to pitch their ideas to five investors, called "sharks," including John.

Although the first season cost him about $750,000 of his own money, he says he's a more savvy investor because of it, and his small businesses now make millions of dollars in annual profit.

Today, his estimated net worth is $300 million, according to Wealth-X, but John strives to get back to that feeling of being broke that he became so familiar with in his early days. Rather than abandon the "broke mindset" as he continues to thrive, he leverages it, which he details in his new book, "The Power of Broke."

"When your back is up against the wall and you have no other way to advance or create relationships and you can't buy anybody — you can't buy things to help you — you start to become creative," John told Business Insider. "When you become creative, that's when you think outside the box — and that's utilizing the power of broke."

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RELATED: Mark Cuban's best business quotes

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From waiting tables at Red Lobster to a $300 million fortune: the rags-to-riches story of Daymond John

#1: "I still work hard to know my business. I'm continuously looking for ways to improve all my companies, and I'm always selling. Always."

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#2: "When you've got 10,000 people trying to do the same thing, why would you want to be number 10,001?"

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#3: "Because if you're prepared and you know what it takes, it's not a risk. You just have to figure out how to get there. There is always a way to get there."

Credit: Getty

#4: "Go out there and get rich. Get so obnoxiously rich that when that tax bill comes, your first thought will be to choke on how big a check you have to write."

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#5: "​In the past, people used to tell me to shut up a bit. But what I believe is to put out your opinion and let everyone else react. If I'm wrong, I'm wrong."

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#6: "I've learned that it doesn't matter how many times you failed. You only have to be right once. I tried to sell powdered milk. I was an idiot lots of times, and I learned from them all."

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#7: "Work like there is someone working 24 hours a day to take it all away from you."

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#8: "Forget about finding your passion. Instead, focus on finding big problems."

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#9: "It's not about money or connections -- it's the willingness to outwork and outlearn everyone when it comes to your business. And if it fails, you learn from what happened and do a better job next time."

Credit: Getty

#10: "What I've learned is that if you really want to be successful at something, you'll find that you put the time in. You won't just ask somebody if it's a good idea, you'll go figure out if it's a good idea."

Credit: Getty

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