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Justin Calabrese

Entrepreneur, Author, Business Consultant, & Digital Music Artist

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Tag: business

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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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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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 Teen Visionary to Serial Entrepreneur: How Justin Calabrese Built Seven Businesses Before 30

Posted on November 3, 2025June 1, 2026 by Justin Calabrese

Long before most teenagers could decide on a college major, Connecticut native Justin Calabrese was already building an entrepreneurial legacy. Barely old enough to drive, Calabrese began transforming his ideas into thriving companies — coding websites in his parents’ basement and shipping products across the country while his peers were still studying for their driving tests. Calabrese’s…

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The Top 5 Ways to Make Side Income in 2025

Posted on November 1, 2025May 31, 2026 by Justin Calabrese

In an ever-evolving economy, finding ways to earn additional income has never been more accessible. With advancements in technology, shifting market trends, and increased opportunities for remote work, 2025 is brimming with possibilities for generating side income. Whether you’re looking to pad your savings, pay off debt, or simply diversify your income streams, there are…

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Why Every Business Needs a Plan (And Not Just in Your Head)

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

I’ve started more businesses than I can count on one hand — seven, to be exact — and each one taught me something new. From the thrill of launching to the grind of daily operations, no two ventures were the same. Yet, there’s one thing I’ve never skipped: writing a business plan. Not the back-of-a-napkin…

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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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