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Justin Calabrese

Entrepreneur, Author, Business Consultant, Digital Music Artist

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Tag: business

How I Learned to Sell Before I Learned to Drive

Posted on February 14, 2026March 10, 2026 by Justin Calabrese

I learned how to close a sale before I ever held a driver’s license. That sentence still makes me smile — not because it sounds impressive, but because of how unlikely it was. Most teenagers are focused on passing their road test, saving for their first car, or figuring out weekend plans. I was learning…

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The moment I realized success doesn’t feel the way it’s advertised

Posted on January 4, 2026March 10, 2026 by Justin Calabrese

For most of my life, success had a very specific look. It was loud. Polished. Predictable. Success was supposed to feel like fireworks the moment you arrived. Like a standing ovation. Like relief mixed with pride, certainty, and maybe even a little smug satisfaction that said, “See? I told you so.” At least, that’s how…

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Stepping Into 2026: Creating What Matters, On My Terms

Posted on January 3, 2026March 10, 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, 2025March 10, 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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Why I Stopped Chasing Revenue and Started Building Real Value

Posted on December 31, 2025March 10, 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, 2025March 10, 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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What 150+ Businesses Taught Me About Entrepreneurship, Ego, and the Power of Being Teachable

Posted on November 22, 2025November 22, 2025 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, 2025November 7, 2025 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, 2025November 12, 2025 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, 2025November 12, 2025 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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justincalabrese

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

Another #cold weekend. Another #cold weekend.
Never too late for a workout. Never too late for a workout.
@wendys #tendys run in the @lotuscars @wendys #tendys run in the @lotuscars
Honored and grateful to be inducted into a double Honored and grateful to be inducted into a double lifetime membership with Beta Gamma Sigma, one of the top honor societies representing accredited business schools worldwide. This recognition reflects a journey shaped by learning, hard work, and the mentors who guided me along the way. Thank you to the University of Hartford and the Barney School of Business for the foundation and support. In just 2 days, I begin my doctoral journey—excited, humbled, and ready for what’s next. #LetsDoThis #Business #HonorsSociety #Honored
Winter storm #2026 #snowshoeing. Winter storm #2026 #snowshoeing.
The quiet before the storm. Stay safe everyone. The quiet before the storm. Stay safe everyone.
People watching in Chicago. #chicago #travel #golf People watching in Chicago. #chicago #travel #golfcart #funny #comedy
#stonehenge England. Amazing memories from our wee #stonehenge England. Amazing memories from our weekend trip across the world. #life #travelphotography #travelgram #viral
A quick #stockmarket update as #stocks start off t A quick #stockmarket update as #stocks start off the year on a high note and the U.S. faces uncertainty with #venezuela #2026 #DJIA
@johnlegere you have inspired me to make a #Sunday @johnlegere you have inspired me to make a #Sunday night #Chili. #crockpotsunday #crockpotmeals #crockpot
#Memories that shaped me. #Lessons that strengthen #Memories that shaped me. #Lessons that strengthened me. #Grateful for everything #2025 gave me. #viral
Thanks @thetinychefshow for helping me get through Thanks @thetinychefshow for helping me get through 2025. You always bring me smiles and laughs, even on the darkest of days. ❤️
Happy #2026! Let’s make this year a good one. #ne Happy #2026!  Let’s make this year a good one. #newyear
#winter fun in the #snow. #snowshoe #sunset #conne #winter fun in the #snow. #snowshoe #sunset #connecticut
I’m not sure who else needs to hear this today but I’m not sure who else needs to hear this today but @fivebelow got it right. Love who makes you happy. 🏳️‍🌈
#Fearless and #committed to personal growth. #2026 #Fearless and #committed to personal growth. #2026 #newyear
Let it #snow Let it #snow
If you’re #dating a narcissist at #Christmas (not If you’re #dating a narcissist at #Christmas (not my video).
Getting #old sucks. No cookies in this #holiday co Getting #old sucks. No cookies in this #holiday cookie jar. #comedy #viral #funny
Detours don’t mean defeat—they mean you’re still m Detours don’t mean defeat—they mean you’re still moving toward the #goal. #entrepreneurship #selfcareroutine #motivation #instagram
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  • Six Months Later: What Mental Health Means to Me
  • The Person In The Mirror Is The Only Person That Needs Your Approval: A Brave Story About Mental Health
  • A Humbling Drive: My Experience with the Lotus Emira (AMG Engine)
  • The Quiet Strength of Winter: Lessons from the Snowshoe Trail
  • The Long Way Around
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