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Justin Calabrese

Entrepreneur, Author, Business Consultant, Digital Music Artist

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The Hard Truth About Entrepreneurship No One Told Me Until I Lived It

Posted on December 31, 2025December 31, 2025 by Justin Calabrese

Entrepreneurship is often sold as freedom: flexible schedules, independence, control over your future. What rarely gets mentioned is the weight that comes with it. The responsibility. The isolation. The quiet pressure of knowing that every decision—good or bad—rests on your shoulders. No one told me how lonely it can feel to be the one making…

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Why I Stopped Chasing Revenue and Started Building Real Value

Posted on December 31, 2025December 31, 2025 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, 2025December 31, 2025 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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Where the Best Business Ideas Come From: Turning Real Problems into Purpose

Posted on November 3, 2025November 12, 2025 by Justin Calabrese

The Myth of the “Big Idea” People often ask me, “Where do you find your business ideas?” They expect me to say something about reading industry reports, scrolling through startup blogs, or brainstorming the next big tech disruption. But the truth is — most great ideas don’t come from boardrooms or business plans. They come from real…

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The Top 5 Ways to Make Side Income in 2025

Posted on November 1, 2025November 12, 2025 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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Justin Calabrese

Justin Calabrese, MSM is an American entrepreneur, author, digital musical artist & creator, and small business consultant originally from Hartford, Connecticut. 

  • January 31, 2026 by Justin Calabrese How I Earned a Rare Double Lifetime Induction Into a Prestigious Business Honor Society
  • January 24, 2026 by Justin Calabrese Justin Calabrese Begins Doctor of Business Administration at South College
  • January 5, 2026 by Justin Calabrese The Most Expensive Message I’ve Ever Paid For In New York City — And Why It Was Worth It
  • January 4, 2026 by Justin Calabrese The moment I realized success doesn’t feel the way it’s advertised
  • January 3, 2026 by Justin Calabrese Stepping Into 2026: Creating What Matters, On My Terms
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