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Justin Calabrese

Entrepreneur, Author, Business Consultant, & Digital Music Artist

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Month: November 2025

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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The Holidays, Through My Eyes: Why Family, Kindness, and Connection Matter Most

Posted on November 22, 2025May 31, 2026 by Justin Calabrese

The holiday season has always meant more to me than twinkling lights, perfectly wrapped gifts, or a table overflowing with food (though let’s be honest — I will never say no to a second helping). For me, the holidays are about something far deeper: connection. They are about slowing down in a world that constantly…

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Still Here: A Journey Through Healing and Self-Discovery

Posted on November 22, 2025May 31, 2026 by Justin Calabrese

Twelve years have passed since I walked out of the darkest season of my life, and my understanding of mental health has transformed into something far more layered, intentional, and sacred. Back then, mental health meant survival. Today, it means awareness, gentleness, boundaries, and the courage to keep choosing myself even when memories echo louder…

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Exploring the White House: A Personal Journey Through America’s Most Iconic Home

Posted on November 14, 2025May 31, 2026 by Justin Calabrese

Exploring Washington, D.C. always brings out the inner history buff in me. There’s something powerful about walking through a city where every corner, every statue, and every monument tells a story that shaped the country we all call home. But no matter how many times I visit, there’s one experience that always rises above the…

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Weekend in London: The Time We Chased Umbrellas at Stonehenge

Posted on November 12, 2025May 31, 2026 by Justin Calabrese

Sometimes spontaneity leads to the best adventures—and that’s exactly what happened when we decided, on a whim, to fly to London for the weekend. Time permitted, and with no children, we figured… why not? (Let’s be honest—one of the perks of being child-free is the ability to pack a bag, book a flight, and jet…

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Our Alaskan Adventure: A Perfect Day in Juneau

Posted on November 12, 2025May 31, 2026 by Justin Calabrese

There are some days that feel like they were designed just for you—and our stop in Juneau, Alaska, was exactly that kind of day. As part of our Silversea Cruise from Vancouver to Anchorage, we had already been mesmerized by the endless glaciers, snow-dusted mountains, and calm ocean waters—but Juneau was something different. It was…

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Why The Rolex Submariner (With Date) Is My Go-To Watch

Posted on November 11, 2025June 1, 2026 by Justin Calabrese

When it comes to watches, I’ve owned my fair share of fine timepieces — Bovet, Jacob & Co, and a handful of ultra-luxury brands that would make any collector’s heart skip a beat. Each one has its own story, its own craftsmanship, its own soul. Yet somehow, no matter how many brands I explore, I…

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Taking Time for Yourself: The Art of Slowing Down and Truly Living

Posted on November 11, 2025May 31, 2026 by Justin Calabrese

Lately, I’ve been thinking about how easy it is to get caught up in the rhythm of constant doing — work, projects, deadlines, events, obligations. Life can feel like one long to-do list. And somewhere in between all that noise, we forget to simply be. To stop. To breathe. To reflect. There was a time when I…

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A Night Among the Stars: Our 5th Anniversary at Kitt Peak National Observatory

Posted on November 11, 2025May 31, 2026 by Justin Calabrese

Anniversaries are a time for reflection — a chance to look back on where you’ve been and dream about what’s ahead. For our 5th anniversary, we wanted to do something unforgettable, something that would take us out of the everyday and remind us just how small and miraculous this world (and universe) really is. That’s…

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Lighting Up Times Square: Why Mental Health Deserves the Biggest Stage of All

Posted on November 8, 2025May 31, 2026 by Justin Calabrese

When I decided to bring mental health awareness to the big screen in Times Square, people asked me, “Why there? Why spend so much?” My answer was simple—because there is no price tag on saving a life. There’s no cost too high for a message that might stop someone from ending their story too soon….

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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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