In this exclusive SUCCESS cover story, we dive into what makes this self-made millionaire investor resonate with so many onlookers—and why he’s an open book when it comes to debunking the misconceptions of entrepreneurship.
As the trailblazing founder of the fashion brand FUBU (For Us, By Us) and one of the top dogs on ABC’s multi-Emmy Award-winning business show Shark Tank, Daymond John was the obvious choice to grace the cover of our inaugural entrepreneur-themed issue.
For more than three decades, Daymond has opened doors for budding entrepreneurs and conceptual artists around the globe. In doing so, he has created an enviable life of his own—touting a net worth of $350 million, while changing millions of people’s lives along the way. So, when the opportunity to get a firsthand glimpse at his success playbook crossed my desk, I jumped at the chance to meet with the moneymaker himself.
Just like Daymond, I have made a living investing in others. As a seasoned journalist, I interview the brightest and most strategic minds in business, professional development, entertainment and advocacy. My job is to share pivotal messages on how to build brands that make an impact and why creating a beautiful life is more in-depth than what you have in the bank. People’s stories lead the way to success.
Daymond also empowers people to share their stories. More specifically, he teaches how to make good decisions—and advocates that having open conversations about your shortcomings will get you to the next level. After all, anyone can Google a person’s background and accolades these days; therefore, the key to getting what you want is staying curious and learning from those who have weathered the storms before you.
Living on the edge
Daymond John lives on the 37th floor of a stellar high-rise in Miami. His building hosts a plethora of A-list neighbors, coupled with an incredible view, a pool, personal spa and workout room, as well as an elevator that lifts his cars all the way up to his home in the sky, where he lives with his beautiful wife Heather and 8-year-old daughter Minka.
On the day of the shoot, our creative crew was welcomed with open arms. After a quick tour of their lovely abode, I spoke briefly with Heather, a healthy-lifestyle aficionado and wellness entrepreneur. It turns out the apple doesn’t fall far from the tree in this household. Heather, recognizing the potential behind the global luxury scent brand Aroma360 as it was gaining traction, believed in the product so much that she wanted to help collectively strengthen the brand. Now, it’s the top fragrance brand in its space.
Overflowing with gratitude, it’s easy to see why Daymond is at the top of his game. His impressive portfolio of transformative experiences has led him down a path of self-discovery and resilience. These imperfections in business and in life have made him who he is today—with health, family and the environment at the forefront.
Revered for his no-guff, forward-thinking business acumen, the multimillion-dollar adviser opened up about the importance of second chances. As a devoted father, husband, stage 2 cancer survivor, activist and fashion and art lover, Daymond is a treasure trove of knowledge. As he reflected on his career, I quickly put pen to paper to capture his fascinating journey.
The people’s shark
Over the years, Daymond has invested more than $8 million of his own money to help aspiring business owners build incredible fortunes. Inevitably, he says he looks beyond the person’s pitch and leans into what his gut is telling him. “The other sharks have their own methods, but I get a gut feeling that tells me who will work hard and who wants to prove to the world that they have what it takes to go the distance. I like people with vigor.”
Daymond smiles at the thought of his recent mentees. One startup that he helped catapult to stardom is Bombas, a clothing brand that sells socks, underwear, T-shirts and slippers—and donates a product to those in need for every item purchased. “I look for the long-term impact when investing,” he says. “I want to associate myself with businesses and entrepreneurs who have the guts to put the hard work in like I did in the beginning—even if there are setbacks.” To date, Bombas has donated 120 million clothing items to homeless, at-risk and in-need communities. There’s more to life than dollar bills.
Building empires
Known for helping entrepreneurs build lucrative brand empires, Daymond has a knack for spotting business visionaries a mile away. From startups to CEOs, he prides himself on working with all types and all levels. His ability to spark genuine conversations and get to the root of a person’s abilities is something that comes naturally. He says he learned it at a young age as a form of survival.
“When I was growing up, the rich and famous folk were untouchable. You heard of the Henry Fords of the world, but the reality was that you would never meet them,” he recalls. “It wasn’t until I started to grow in my own entrepreneurial space and got invited into the same rooms as such notables that I realized my idea of entrepreneurship was wrong. I was fascinated by these experts and eager to learn how they got there. Hence, my journey is based in curiosity.”
FUBU Daymond John
In the beginning, Daymond’s vision of an entrepreneur was the guy who hired and fired. So, he created the no-BS tough persona you see on Shark Tank. But, the real FUBU founder is open about his hardships. He even admits that a large part of his career was wasted on things that were insignificant.
“I remember when I was in a room with massively successful people, and yet I wasn’t vulnerable enough to say, ‘Hey, I don’t know this, but can you teach me this?’ Imagine if I had done that in my 20s? Imagine where I would be now. The people in that room were Warren Buffett, Bill Gates and various Hollywood celebrities,” he explains.
“At that time, I was in the middle of the hip-hop scene and just launched my apparel company FUBU, which broke the mold for urban culture. I had a bodyguard with me because the East Coast/West Coast battle was going on. I didn’t care about all that nonsense—I was just trying to dress everybody and get my brand out there. I never spoke to Gates or Buffett at that event, but I often think what might have happened if I did. Mark Cuban would be scraping the gum off my shoes today,” he laughs.
The moral of the story: Don’t waste opportunities to connect with the movers and shakers—especially when they’re right in front of you. Be bold.
Your health is your wealth
Daymond grew up in a poor family and learned the value of a dollar out of necessity. He prides himself on getting out of a bad situation through a diligent work ethic and perseverance. “It was either work and figure it out on my own or I wouldn’t survive,” he explains. But with every action, there is an equal and opposite reaction, and Daymond soon learned that wealth can also lead you down a destructive path. “Instead of turning to my family for help, I turned to alcohol to soothe my anxiety—something I’m not proud of.”
Fortunately, his wife Heather opened his eyes to self-care and leading a healthy lifestyle. So, with some serious convincing and a lot of love from his better half, he decided to take a step back from the pressures of success and implement wellness practices into his daily routine. “It sounds ironic, but this has changed my definition of wealth. After a few close calls, I came to realize that wealth is just the reciprocal of your health. In other words, the healthier you are, the more abundance you receive in your life,” Daymond adds. And he’s right: If you want to live a long and abundant life, and be there for your family, you have to make tough choices and hang around people who have the same values.
Keeping a positive mental attitude
While Daymond attributes a large part of his rags-to-riches story to old-fashioned hard work and taking calculated risks, he has adopted the notion that a positive mindset is imminent to obtain and maintain monumental success. After a recent cancer scare, he realizes the first pillar to success is your health. In other words, if you’re not healthy in your mind, body and spirit, then you’re not going to have clarity to be productive.
“My wife is my healthy-living advocate. If she didn’t get me to go to the doctor a few years back, I may not be here today. She helped me through some of the worst days in my life, and I am thankful for a second chance. This is the definition of prosperity to me,” he says. “She pushes me to watch what I eat and put into my body. I’m so fortunate to have her in my life because that’s what a partner does. When you respect each other and value your partner’s opinions, you know they’re looking out for you unconditionally—and that’s all you can ask for.”
Today, Daymond understands that health is wealth—especially when raising a young child who deserves all his attention. He is also grateful for losing the weight that was holding him down literally and figuratively. “It might sound cliché, but my mindset has evolved just as I have evolved in business. These are my youngest daughter’s developmental years, and I want to be around to walk all of my girls down the aisle one day.”
Learning to let go
Living a healthy lifestyle has not only changed Daymond’s outlook, but it’s also proven to be a positive influence on his overall success. Eight years ago, he started to incorporate an intense physical and mental health practice into his daily routine. He also began an annual emotional deep dive, which equates to eliminating toxicity out of his life.
“Every New Year’s Eve, I decide who I am going to cut out of my life. I literally write down people’s names on a piece of paper if they are toxic or create havoc and let them go,” he says. “For instance, if we’re not good friends or they’re not good for my business, there’s no reason to stay in touch. This doesn’t mean that I’m a cruel person—I have just learned through trial and error that people who judge you, diminish your efforts or turn their back on you in times of need are not worth your time.”
Walking away from toxic work environments
Daymond tells his mentees that cutting people out of your life can be difficult, but it is often necessary. “Tough conversations in the workplace are a critical part of personal and professional growth. A lot of people don’t understand that we die by paper—and paper cuts—often,” he adds. “When you walk away from toxic work environments, business partners or social circles, it opens up opportunities to bring more positive energy into your life. When you cut low-energy people out of your life, you make room for the people who deserve your love and attention. Doing this has changed my life tenfold. It becomes a way of life.”
Not surprisingly, self-love has played a critical role in Daymond’s decision to turn away from the bottle and manage stress in a more meaningful way. “When you start to see the negative impact that toxicity has on your life, you realize the only one who can pivot is you. I started to really listen and take note of how I could grow and move forward in a more positive way, which has brought so much peace to my life.”
Connecting winners
Another important entrepreneurial pillar is the act of service. Daymond’s ability to mentor those coming up the ranks, coupled with the gravity in which he inspires C-suites, has become evident everywhere he goes. Over the years, he has guided thousands if not millions of emerging entrepreneurs to success status. Today, he also works with executives who want to know where to go next.
Daymond’s exciting new business venture is CEO Access. A few times a year, he brings top-tier businesspeople, experts and entertainers together to make quality connections. “It’s like getting a sneak peek at my Rolodex,” he says. “There’s no agenda; it’s just come and meet other smart, like-minded people—and maybe get a contact or two—and leave whenever you want. It’s something new I’m trying because I believe success is about getting access to the people you want to collaborate with. I’m basically putting a bunch of powerful people in the same room and watching the magic happen. It’s organic, and it works!”
Daymond John, from Shark Tank to CEO Access
In a world where deals are often made via cyberspace, these modern mixers are transforming the way people interact. How it works: Every 15 to 20 minutes, Daymond will address the crowd and ask one person a question. Then, he lets someone ask him a question. “It’s a win-win for everyone because it’s not scripted and the energy always seems to flow. This nonthreatening vibe gives entrepreneurs the opportunity to lend their ideas to fate rather than experiencing pressure to bring someone into your circle who may not be the right fit.”
The shark is a master connector and says being vulnerable is something entrepreneurs don’t do enough. “The goal of CEO Access is to make authentic connections that might lead to business alignments or personal growth. Even TMZ picked up the one in Los Angeles,” he says. “It’s a new way to look at business relations in our cutthroat world. CEO Access has been so successful to date that I am constantly getting calls from people asking when the next one is.”
Entrepreneurship and vulnerability
When asked about misconceptions in entrepreneurship, Daymond says that success should not be defined by wealth. He also believes that the challenges faced by individuals in business are due to a lack of curiosity and willingness to start over.
As a result, Daymond’s ability to be vulnerable has become integral in his life. “I would tell my staff where I’m weak and when I didn’t have the answers. And when I started having authentic conversations, people started to really communicate with me. As a result, I found way more value in speaking to entrepreneurs and founders, and I got smarter by osmosis. And boom, I’m on Shark Tank wanting to know more stories.
“The most successful entrepreneurs I know are the ones who have started over many, many times. They are the ones who ask questions, take risks, do their homework, manage their time and who are intentional about prioritizing personal relationships,” he adds. “You also have to realize that, although entrepreneurship can provide flexibility and financial gains, people shouldn’t be misguided into thinking that entrepreneurs aren’t the ones up earlier than everyone else and up later at night. It’s a hard-core lifestyle.”
Turning over a new leaf
When it comes to business, Daymond reiterates that leaning into your failures is critical. Never give up. During his 20s, he stressed about making ends meet. Just as any parent who lives paycheck to paycheck would, Daymond did everything he could to ensure there was food on the table for his young family. However, the stress was building and impacting his mental health. “During my first marriage, I thought making fast money was the only way I could protect my first two daughters. I had the best of intentions but didn’t always make the best choices. Now, I realize that it’s not only your net worth that leaves a lasting impression; it’s how you act and show love to your family.”
With a passion for startups, middle-tier entrepreneurs and CEOs, Daymond is determined to pass along his knowledge to help others achieve their dreams. If he can do it, anyone can. “I’m told that everyone can see a little bit of themselves in me, no matter what race, color, creed or gender background,” he says. “My story is similar to the American dream, where hard work and tenacity are at the core of longevity and survival.”
Daymond is the first to admit that he’s not the most educated or sophisticated person on the planet (although he confessed that he only repeated seventh grade because he enjoyed it so much). “Everyone has a story to tell and a life lesson to pass along. Just make sure you stay on track, and if you have to take a step back, that’s all right. Take it from me, your external world can (and will) trickle into your entrepreneurial spirit if you’re not careful. Negative energy is always detrimental to your success, so remember to make wise decisions and align yourself with people who have the same values at home as they do in their business.”
Daymond John bestselling author
With five bestselling books under his belt, Daymond is also a fan of the arts community. “I want to continue to bring attention to talented artists because they bring us joy in the world. I also think it’s imperative to educate children on how to manage money and become financially independent, so they don’t have to depend on anyone when they get older. Our kids will be the ones to take innovation and creativity to the next level, so we have to give them the tools when they are young.”
Lastly, Daymond is a big supporter of female entrepreneurs. (As mentioned previously, his wife Heather saved his life.) He spoke highly about stay-at-home moms and the challenges they face, stating that they are often undervalued and don’t have a blueprint for raising their children. “Women are the ones leading the charge in the most important areas of life,” he says. “Growing up in a single-parent home, I quickly learned that the next generation will be filling our shoes, and our mothers should be praised for that.”
Alignment in business and in life
Suffice it to say, Daymond continues to lead successfully by pushing the boundaries and inspiring people to embrace the ever-changing business landscape. From identifying smart market opportunities to taking chances on people who are “all-in,” his insights serve as a beacon of inspiration for aspiring entrepreneurs and seasoned owners alike.
Trust me, there’s way more to the people’s shark than you see on TV. Let’s just say, I will be forever enlightened by his pearls of entrepreneurial wisdom—and inspired by his love and devotion in building supportive relationships.
Perhaps that’s because his success story aligns with his soul purpose. His personal values include financial security for his family and empowering others, but more importantly, he cherishes good energy and a healthy lifestyle so he can live long enough to see his youngest grow up. His ability to spread awareness about environmental issues through unique art projects also fills his cup.
“You can make all the money you want and work your a– off, but you can’t take anything with you. That’s why creating a world we can be proud of and where our children are safe, happy and healthy is the true definition of wealth.”
This article originally appeared in the September/October 2024 issue of SUCCESS magazine. Photo by Bianca Pierre
