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Justin Calabrese

Entrepreneur, Author, Business Consultant, & Digital Music Artist

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Justin Calabrese Begins Doctor of Business Administration at South College

Posted on January 24, 2026June 1, 2026 by Justin Calabrese

Justin Calabrese has officially begun his Doctor of Business Administration (DBA) studies at South College, an accredited institution based in Knoxville, Tennessee. South College is accredited by the Southern Association of Colleges and Schools Commission on Colleges (SACSCOC) to award associate, baccalaureate, master’s, and doctoral degrees. Calabrese enters the doctoral program with a strong foundation…

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The Most Expensive Message I’ve Ever Paid For In New York City — And Why It Was Worth It

Posted on January 5, 2026June 1, 2026 by Justin Calabrese

Standing on a big digital billboard in New York City is one of those moments that doesn’t feel real at first. You grow up seeing those screens in movies, watching brands fight for attention in the brightest, loudest, most crowded advertising space in the world. They’re symbols of arrival. Of success. Of money. Of influence….

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Stepping Into 2026: Creating What Matters, On My Terms

Posted on January 3, 2026June 1, 2026 by Justin Calabrese

2026 feels different to me. Not in the loud, fireworks-and-noise way, but in a quieter, more intentional way. It feels like a year where I stop rushing to prove things and start choosing what genuinely brings me joy, clarity, and meaning. I’m not chasing chaos this year. I’m planning with purpose. For me, 2026 isn’t…

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What Running Multiple Businesses Taught Me About Focus, Burnout, and Momentum

Posted on December 31, 2025June 1, 2026 by Justin Calabrese

Running multiple businesses at once sounds impressive on the surface. And sometimes, it is. But it also comes with a cost that isn’t always visible from the outside. In the early days, I equated doing more with being more capable. More projects meant more ambition. More ideas meant more potential. What I didn’t realize was…

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The Hard Truth About Entrepreneurship No One Told Me Until I Lived It

Posted on December 31, 2025June 1, 2026 by Justin Calabrese

Entrepreneurship is often sold as freedom: flexible schedules, independence, control over your future. What rarely gets mentioned is the weight that comes with it. The responsibility. The isolation. The quiet pressure of knowing that every decision—good or bad—rests on your shoulders. No one told me how lonely it can feel to be the one making…

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Why I Stopped Chasing Revenue and Started Building Real Value

Posted on December 31, 2025June 1, 2026 by Justin Calabrese

For a long time, I measured success almost entirely by revenue. If the numbers were going up, I felt like I was winning. If they dipped, I questioned everything. Revenue became the scoreboard for my worth as an entrepreneur. But somewhere along the way, I realized something uncomfortable: revenue alone doesn’t mean stability, sustainability, or…

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What I Learned About Business Growth After Failing More Times Than I Can Count

Posted on December 31, 2025June 1, 2026 by Justin Calabrese

Failure is an uncomfortable teacher, but it’s also the most honest one I’ve ever had. When I first started building businesses, I believed growth meant constant forward motion—more clients, more revenue, more recognition. I thought success was linear. It turns out, growth rarely is. I’ve failed more times than I can comfortably admit. I’ve launched…

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An Evening Above the Noise: What I Learned at Kitt Peak

Posted on December 22, 2025June 1, 2026 by Justin Calabrese

Standing atop Kitt Peak in southern Arizona, I felt something I don’t experience very often anymore: perspective. The kind that quiets your thoughts instead of amplifying them. Visiting the Kitt Peak National Observatory wasn’t just about telescopes and stars—it was about learning how small we are, how patient science must be, and how much clarity comes when…

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Sharing My Business Knowledge Through Daily Social Media Reels

Posted on December 8, 2025June 1, 2026 by Justin Calabrese

If there’s one thing I’ve learned after nearly two decades in entrepreneurship, it’s that business never sleeps. The economy moves fast, consumer psychology shifts overnight, and entrepreneurs everywhere are constantly trying to keep up. That’s exactly why I’ve made it a personal mission to show up every day and share what I know in a…

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What 150+ Businesses Taught Me About Entrepreneurship, Ego, and the Power of Being Teachable

Posted on November 22, 2025June 1, 2026 by Justin Calabrese

I still remember the moment I realized people were finally starting to take me seriously. I was young, ambitious, and building what many would have called a “small business,” yet my vision was anything but small. When NPR featured me for launching a company at such a young age, it felt surreal — not because…

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justincalabrese

Entrepreneur, Author, Tech Business Consultant, Digital Musical Artist, Human Rights Advocate, and Former @HuffPost Contributor.

Over the water in #Cayman Over the water in #Cayman
Tonight’s dinner view from #tukkarestaurant in #Ca Tonight’s dinner view from #tukkarestaurant in #CaymanIslands #vacation #dinner
Dinner with this guy ☝️ @tukka_east_end Dinner with this guy ☝️ @tukka_east_end
This is one salad I can endorse. Highly recommende This is one salad I can endorse. Highly recommended #AsianSalad from @sunshinegrillcayman345 #GrandCayman #restaurant #lunch #salad
Sitting on the #beach in #GrandCayman Sitting on the #beach in #GrandCayman
After a day of rain… #rainbow #islands #dinnerdate After a day of rain… #rainbow #islands #dinnerdate #love #vacation
Athens never disappoints. #Athens #Partheon #Greec Athens never disappoints. #Athens #Partheon #Greece #Family #Travel
6 years ago. #loveislove 6 years ago. #loveislove
#NeverForget #NeverForget
#September is suicide awareness month. Remember to #September is suicide awareness month. Remember to take time for yourself. #suicide #selflove❤️ #suicidepreventionmonth #health
#Caldor is still trucking. #Caldor is still trucking.
It’s a #Saturday state of mind. #happiness #weeken It’s a #Saturday state of mind. #happiness #weekend #travel
No explanation needed. #rolex #watch #rolexdatejus No explanation needed. #rolex #watch #rolexdatejust #collection #heaven
Wishing my husband a happy 37th birthday! We had a Wishing my husband a happy 37th birthday! We had a blast celebrating at Jacob’s & Co.  #happybirthday #jacobandco #watch #love
Remember to take time for yourself. #MentalHealth Remember to take time for yourself.  #MentalHealthAwareness #MentalWellness #AnxietySupport #DepressionAwareness #ChooseHope
Home away from home. Sun, sand, family, health, me Home away from home. Sun, sand, family, health, memories - so much to be grateful for. See you soon! #Cayman #beach
On our way to the Vet as Obee watches me drive. On our way to the Vet as Obee watches me drive.
Letting the Tesla drive itself while I’m not in th Letting the Tesla drive itself while I’m not in the car.
No trip to NYC is complete without watch shopping. No trip to NYC is complete without watch shopping.  My favorite brand. Every now and then I fall apart and I need @jacobandco tonight and I need you more than ever. 😆
I ❤️ NY I ❤️ NY
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