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Tag: failure

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

Posted on December 31, 2025June 1, 2026 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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What I Learned About Business Growth After Failing More Times Than I Can Count

Posted on December 31, 2025June 1, 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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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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