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Justin Calabrese

Entrepreneur, Author, Business Consultant, & Digital Music Artist

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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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Time Well Spent: My Love for Watches and the Stories They Tell

Posted on November 3, 2025May 31, 2026 by Justin Calabrese

For as long as I can remember, watches have been more than accessories — they’ve been storytellers. Each timepiece I own captures a chapter of my life: a success, a journey, a moment worth remembering. Some people mark milestones with photos or trophies; I mark mine in hours, minutes, and seconds. Over the years, my…

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How I Learned to Stop Winging It and Love the Business Plan

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

If you had asked me in the early days of my entrepreneurial journey whether I thought a business plan was necessary, I would have laughed and said something like, “Why plan when you can just *do*?” I was the poster child for the dive-right-in mentality, brimming with enthusiasm and confidence, convinced that sheer passion and…

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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

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

A great time in Hudson Yards New York watching the A great time in Hudson Yards New York watching the #America250 fireworks. ❤️
Sometimes the best way to reset is to pack a bag, Sometimes the best way to reset is to pack a bag, hit the road, and embrace a change of scenery. Here’s to a weekend filled with new places, unforgettable moments, and memories worth bringing home.
Today’s view from this beautiful park looking up t Today’s view from this beautiful park looking up the East River. #NewYork #CityLife
Beautiful #butterfly on a #summer afternoon hike. Beautiful #butterfly on a #summer afternoon hike.
Sunday morning workout. #fitness #workout #run Sunday morning workout. #fitness #workout #run
Happy #FathersDayWeekend to a wonderful and suppor Happy #FathersDayWeekend to a wonderful and supportive father. Always there for me, day and night. #FathersDay #Weekend #Holiday #Family
Late nights. Clear mind. No excuses—just putting i Late nights. Clear mind. No excuses—just putting in the work. 💪🌙

#WorkoutMotivation #FitnessJourney #GymLife #SelfImprovement #NightWorkout
It’s #race day in the #Poconos. #NASCAR #poconorac It’s #race day in the #Poconos. #NASCAR #poconoraceway
Today’s hiking adventure brought incredible views, Today’s hiking adventure brought incredible views, fresh air, and memories worth every step. 🥾⛰️ #explorepage #hiking #travel #summer
It’s way too hot to be hiking today… so naturally, It’s way too hot to be hiking today… so naturally, that’s exactly what I’m doing. 🥵🥾🌲 #HikingLife #TrailLife #GetOutside #SummerVibes #AdventureAwaits ExploreMore NatureLover WeekendAdventure HikeMoreWorryLess OutdoorLife
There is always time for a workout after a long da There is always time for a workout after a long day.  The weekend is almost here.
Good memories, amazing food, and beautiful weather Good memories, amazing food, and beautiful weather in Quebec City. A trip filled with unforgettable moments, charming streets, and views that never get old. #QuebecCity #MemorialDayWeekend #Travel #Canada
12 hours of travel but we made it. Nothing like a 12 hours of travel but we made it. Nothing like a weekend getaway for the Memorial Day holiday.  Time to check emails and relax before dinner. Happy #MemorialDayWeekend
The moments you live for. #kittpeak #Arizona #Suns The moments you live for. #kittpeak #Arizona #Sunset
On the road again… On the road again…
Always been into #tech and figuring things out as Always been into #tech and figuring things out as I go. Still learning every day. The #Tesla is just a cool part of the #journey.
#LakeComo is beautiful in every way. #LakeComo is beautiful in every way.
Two years ago from today I started my weight loss Two years ago from today I started my weight loss journey. Diabetes, liver disease, high blood pressure and more. Today, 60+ lbs lost and still keeping the weight off with no health conditions. The journey has been life changing to say the least.  #weightloss #health #happiness #life
This is us, exploring the historic temples of Delp This is us, exploring the historic temples of Delphi, Greece—where ancient history meets breathtaking views. What an amazing day ❤️. 

#Delphi #Greece #AncientHistory #TravelDiaries #ExploreGreece
Standing before the Parthenon in Athens is a power Standing before the Parthenon in Athens is a powerful reminder that true greatness is built with vision, patience, and purpose. What we create today has the potential to become tomorrow’s legacy.

#Athens #Parthenon #Acropolis #TravelInspiration #Legacy
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