At a glance
WHAT IT’S REALLY ABOUT
Jason Calacanis’ scrappy Brooklyn origins to New York internet kingmaker
- Calacanis describes a formative financial shock—his father’s bar being seized by federal authorities—that forced him to work full-time while attending Brooklyn College at night.
- Early fascination with home computers and modems evolved into entrepreneurial (and sometimes gray-area) hustles like copying/cracking software and phone phreaking.
- He chose tech media over becoming a hands-on technologist, influenced by DIY “zine” culture that foreshadowed blogging and independent publishing.
- A chance connection introduced him to Jerry Colonna and Fred Wilson, where he informally evaluated business plans and witnessed landmark NYC venture wins like GeoCities.
- He scaled Silicon Alley-era publications and events into a ~$10M revenue operation financed via credit cards, becoming a visible “New York internet guy” across major media outlets.
IDEAS WORTH REMEMBERING
5 ideasConstraint can become a forcing function for self-reliance.
Losing expected family support for college pushed Calacanis into a work-plus-night-school regimen that shaped his comfort with risk, hustle, and learning on the job.
Early technology access creates lifelong compounding advantages.
Being among the first generation with home computers/modems gave him both curiosity and practical skills that later translated into opportunities in tech and media.
Media can be a strategic path into tech ecosystems—not just commentary.
By publishing about emerging companies and investors, he gained proximity to deal flow, influential relationships, and credibility before he “knew what a VC is.”
Mentors can force pivotal career clarity through simple tradeoff questions.
Fred Wilson’s “which would you rather do?” prompted Calacanis to commit to the magazine path—an early example of choosing identity and focus over optionality.
DIY publishing models anticipate platform shifts (zines → blogs).
His zine background mirrored the later blog era: low-cost distribution, niche authority, and community-driven content—an enduring playbook for media builders.
WORDS WORTH SAVING
5 quotesHey, son, I can't help you with college. Good luck. Uh, and, uh, I might be going to jail, so take care of your mom.
— Jason Calacanis
I decided to work during the day, and then I went to school four nights a week, 6:00 to 9:00 PM.
— Jason Calacanis
I ran a lot of scams.
— Jason Calacanis
So there was a concept of a zine... Blogs before blogs.
— Jason Calacanis
I grew that business to $10 million in revenue off my credit cards.
— Jason Calacanis
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