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Entrepreneur, Author, Business Consultant, & Digital Music Artist

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Month: November 2025

Arizona Adventures: From the Desert Trails to the Stars Above

Posted on November 7, 2025May 31, 2026 by Justin Calabrese

There’s something about Arizona that makes you feel both grounded and limitless at the same time. Maybe it’s the way the desert stretches endlessly in every direction or how the sunsets seem to set the whole sky on fire. Either way, it’s a place that stays with you long after you’ve left. When I traveled…

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Giving Back to the Community That Built You

Posted on November 7, 2025June 1, 2026 by Justin Calabrese

If you had asked me ten years ago whether I planned on going to college, I probably would’ve laughed and said, “No way — I’m too busy building my empire.” I was one of those people who believed that real experience beat textbooks any day of the week. At the time, I was knee-deep in entrepreneurship —…

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The Sandwich Approach: Serving Up Feedback Without the Burn

Posted on November 7, 2025May 31, 2026 by Justin Calabrese

If there’s one universal truth in management, it’s that delivering feedback can feel a lot like defusing a bomb — one wrong word and boom, there goes morale for the week. Early in my career, I used to think the best approach was just to be “honest and direct.” Turns out, “honest and direct” sounds a…

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Clear Skies and Jet Trails: My Visit to the Udvar-Hazy Control Tower

Posted on November 4, 2025May 31, 2026 by Justin Calabrese

It wasn’t originally on my itinerary. I had planned my trip to Washington D.C. last year with the usual patriotic hits — Smithsonian museums, the National Mall, cherry blossoms if I could catch them. But somewhere between planning my Metro routes and booking a monument night tour, a friend texted: “Don’t skip the Udvar-Hazy Center. Trust…

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Thriving When Life Gets Tough: Real Tips To Grow Through Challenges

Posted on November 4, 2025June 1, 2026 by Justin Calabrese

There have been times in my life when everything seemed to fall apart all at once. Whether it was a business failure, personal loss, or simply feeling overwhelmed by the daily grind, those moments felt like being caught in a storm with no clear way out. I’m sure you’ve been there too — when the…

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Where the Heck Do You Even Start as an Entrepreneur? (Spoiler: Probably Not Where You Think)

Posted on November 4, 2025June 1, 2026 by Justin Calabrese

If you’ve ever stared at a blank notebook or laptop screen thinking, I want to start a business, but what the heck should I do first?, welcome to the club — I’ve been there. Actually, I’ve had season tickets to that club. Starting out as an entrepreneur is both exhilarating and terrifying. It feels like skydiving…

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Why the Porter Five Forces Should Be in Every Entrepreneur’s Toolbelt

Posted on November 4, 2025June 1, 2026 by Justin Calabrese

Starting a business feels a bit like standing at the edge of a diving board for the first time — exciting, terrifying, and loaded with potential. I’ve been there more than once, and every time I’ve launched something new, whether it was a full-scale e-commerce operation or a local consulting gig, one framework has never…

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From Dream Cars to Handmade Legends: How I Ended Up in a Lotus Emira (And Why You Should Too)

Posted on November 4, 2025May 31, 2026 by Justin Calabrese

Let me just start with this: I love cars. Not in the casual, “Oh yeah, I like fast cars” kind of way — but in the kind of way that results in owning 27 of them. Yes. Twenty. Seven. I’ve basically lived in a permanent test drive for the last decade or so. It all…

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Entrepreneur-Turned-Artist: Justin Calabrese Announces Debut Album “Baptized in Regret”

Posted on November 4, 2025June 1, 2026 by Justin Calabrese

Justin Calabrese, most widely recognized as an American entrepreneur, author, and business consultant, is adding a new dimension to his already dynamic career — music. Calabrese has announced the upcoming release of his first full-length musical album, Baptized in Regret, a deeply personal project born from years of overcoming childhood and young adult trauma. Unlike his…

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Baptized in Regret — My Journey into Music, Healing, and Hope

Posted on November 4, 2025May 31, 2026 by Justin Calabrese

I never thought I’d release a music album. To be honest, I never even planned on writing one. But life has a funny way of handing you pain and then, if you’re lucky, offering you a melody to carry it. This album — Baptized in Regret — was born out of a very personal place. It’s not…

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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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