Meet Bernard Bentley | Serial Entrepreneur

We had the good fortune of connecting with Bernard Bentley and we’ve shared our conversation below.

Hi Bernard, what was your thought process behind starting your own business?
My thought process behind each business that I’ve ever started has stemmed from 3 aspects. Creativity, helping others and freedom. Along the way I have a passion for everything that I do. The very first business I ever started was a premium streetwear brand called LoveLifeSwagger in which I started at my desk while working at a sweatshop mortgage company in Metro Detroit. Soon after starting the company, I quit my job and moved to Chicago where I studied fashion at the Merchandise Mart Downtown while sleeping on the floor at my uncles house. A whole year went by and I finally had finished my business plan and I moved back to Detroit and opened up a retail store in Downtown Detroit, which took 2 years to start making money but it finally picked up and celebrities from across the country started wearing my clothes, such as Juicy J, Mase, Carl Thomas, Dwele, Anthony Hamilton and many many more. I hired kids from Detroit to work in the retail store and taught them entrepreneurial skills in business and textile.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
What sets me apart from others in business is my ability to connect with people and tell stories through art and whatever I am selling. People don’t really care about what you’re doing until they know you care about them. So with that being said, I make everything I do about “the people”. For example when I remodeled my store, I let the Art Community in Detroit, Chicago & LA place murals all around my store live during store hours so that customers could witness it as well as other art connoisseurs. This created a community art atmosphere which made the LoveLifeSwagger retail store a hub for all things art. Aside from fashion design, I have started to invest in real estate and restaurants. Working with the revitalization of Detroit, I’ve purchased a few properties on the waterfront and I am currently in the market for waterfront property in Miami which I plan to expand under my belt. In business, I’m able to switch gears and explore multiple avenues of interest because of my relationships and honestly good karma. Like I mentioned before, helping people has helped me. I treat people good and help as many people as I can along the way. In return the universe helps me so when I want to switch gears in business, I always have someone there to help me. I believe in karmic energy and somehow the universe always puts me in the right situation and uncovers those that are not right for me. My biggest challenge in the beginning of becoming an entrepreneur was getting rid of the “employee mindset”. I literally had to rewire my brain to think like a business owner. Once I got over that, I then had to envision myself already running a successful business and having my own retail store. Eventually these visions came to life exactly how I had dreamed. But it wasn’t till I changed my mindset and wrote a business plan, then it all started unraveling. The biggest lesson I’ve learned along the way in my entrepreneurship journey is always stay humble and be coachable. Stay accountable to your actions and words and always follow up. I had to learn humbleness the hard way. Right after I opened my 1st retail store, it wasn’t profitable off the back and I became homeless with a retail store. I had to reach out to the local business owners to get help on how to grow my business. At this point I had to be accountable for myself and my own actions. I didn’t have a job to fall back on. So I hopped on the road and started selling my clothes to other retailers in the area and across the country since the sales were down at my store. Those sales across the country fueled my store and eventually gave me enough money to rent a loft after living out of my car for almost a year. One thing I never did was give up. I kept a smile on my face and my eyes on the prize. I’ve never shared this story publicly about being homeless when I opened my store, mainly because it’s so cliche among entrepreneurial stories but it’s real for me and something I had to overcome. I chose to be homeless and not move with any friends or family. I’m glad I made that decision because now I own multiple properties and I can appreciate it coming from someone that had to sleep in a car and on the floor for a year just to save up enough to rent somewhere. I want everyone reading this to know that if there’s something you want to accomplish, never give up and chase your dreams!

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
If my best friend was coming down to Miami and I wanted to show them the best time of their life, I’d make sure we hit every spot that shows off the soul, style, and heat of the city. Miami is more than just beaches – it’s food, culture, nightlife, art, and real energy. Here’s how I’d lay out a full week of vibes, views, and unforgettable moments:

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DAY 1 – Welcome to the 305
• Lunch: We’re starting it off Cuban style—Versailles in Little Havana. Can’t come to Miami and not get a Cubano and cafecito.
• Afternoon: Walk Calle Ocho. Grab fresh fruit, check out street murals, maybe even catch a game of dominoes in Maximo Gomez Park.
• Evening: Sunset at South Pointe Park Pier—sky turns gold over the ocean.
• Dinner: Joe’s Stone Crab if we’re feeling classic Miami. It’s legendary for a reason.
• Nightcap: Drinks at Nikki Beach or The Setai to ease into the nightlife.

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DAY 2 – Beaches + Boujee
• Morning: Brunch at The Local House – rooftop dining, mimosas, and ocean breeze.
• Afternoon: Chill on South Beach. Rent bikes, hit the waves, or just stunt on Ocean Drive.
• Dinner: Baoli – for upscale vibes, great food, and a crowd that came to be seen.
• Night: Hit LIV or Story. Miami clubs hit different. You dress for it.

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DAY 3 – Art, Culture & Good Food
• Brunch: Mandolin Aegean Bistro – perfect courtyard vibes in the Design District.
• Day: Head to Wynwood Walls – grab flicks with murals, then explore galleries and shops. Stop by Zak the Baker for coffee and pastries.
• Dinner: Coyo Taco – and don’t sleep on their secret back bar. It turns up.
• Night: Wynwood’s where we hang—Racket or Gramps for a more local crowd and laid-back turn-up.

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DAY 4 – Island Flow
• Morning: Rent a boat or charter a yacht out of Miami Beach Marina. Pull up to Nixon Sandbar or cruise by Star Island.
• Lunch on the water: Pack some champagne, fruits, and seafood platters. Full boss move.
• Evening: Freshen up, then dinner at Swan Miami (owned by Pharrell – the energy’s luxe).
• Late Night: Lounge vibes at Komodo or Marion – wild dinners turn into nightlife here.

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DAY 5 – Day Trip Energy
• Morning Road Trip: Down to the Florida Keys. Hit Key Largo for snorkeling or Islamorada for chill drinks by the water.
• Lunch: Lazy Days or Morada Bay Beach Café – picture palm trees and seafood towers.
• Back in Miami: Relaxed dinner at Monty’s Raw Bar.
• Night: Keep it chill. Maybe hit Brickell City Centre for dessert and lowkey vibes.

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DAY 6 – Luxury & Little Haiti
• Brunch: Cecconi’s Miami Beach inside Soho House. Beautiful setting, even better food.
• Afternoon: Slide through Little Haiti. Check out Caribbean Marketplace and Clive’s Café if we want authentic Jamaican food.
• Dinner: KYU in Wynwood – hands down one of the best meals in the city.
• Night: Catch live music or hit E11EVEN if we’re back on that late-night madness.

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DAY 7 – Wind Down + Reflect
• Breakfast: Big Pink in South Beach. Classic diner food with a Miami twist.
• Midday: Relax at The Standard Spa – pool, hammam, full recharge mode.
• Dinner: The Wharf Miami by the river for food trucks, drinks, and one last good vibe.
• Final Toast: Sit back, laugh over the week, and say, “Yeah…we did that.”

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BONUS SPOTS / IF WE HAD EXTRA TIME
• Vizcaya Gardens – for the photos, peace, and history.
• Perez Art Museum Miami (PAMM) – cool modern art and Biscayne Bay views.
• The Underline – urban park trails and art under the Metrorail.
• Sunday party at El Patio or a Reggaeton night at La Otra if we’re feeling Latin heat.

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If my best friend left town after this trip and didn’t say it was the best time of their life, they must’ve been sleeping the whole time. Miami’s got that fire, and I’d make sure they felt every ounce of it.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I really have to give homage to a good friend of mines J. Tait that supported me in the early stages of my entrepreneurial career. We met at a Starbucks restaurant and he gave me one of his CD’s and I gave him some LoveLifeSwagger merchandise. He told me that he was the backup singer for one of my favorite music artist, Dwele. I was blown away because I had been following this artist’s whole career from the beginning. He mentioned that he would share my brand, LoveLifeSwagger with him and see how he likes it. Fast Forward a few months and I’m sitting in the library in Chicago and I see a picture online with Dwele wearing my shirt. At that moment, that gave me the confidence and encouragement I needed to keep going because I was thinking about giving up because it was so expensive to open a retail store and make your own brand. Also I had no one to teach me or show me the ropes at the time. To this day, I always go to Dwele concerts and I’ve gotten to know him over the years as a good friend and did some creative work together on some tshirts. Big shout out to J. Tait & Dwele out of Detroit.

Another person I have to pay homage to is my friend Mike which I met while on tour with Juicy J. He was his road manager and he really took me under his wing and helped me to get my brand, LoveLifeSwagger on some stars. This really helped excel the brand and attracted more retailers and other celebrities that wanted to sponsor and or endorse the brand.

Website: https://LoveLifeSwagger.com

Instagram: @bernardbentley @lovelifeswagger