The Rise of Calacanis
Jason Calacanis (guest), Ben Gilbert (host), David Rosenthal (host)
In this episode of Acquired, featuring Jason Calacanis and Ben Gilbert, The Rise of Calacanis explores 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.
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.
Key Takeaways
Constraint 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.
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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.
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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.”
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Mentors can force pivotal career clarity through simple tradeoff questions.
Fred Wilson’s “which would you rather do? ...
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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.
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Scaling a business before knowing ‘how’ is possible, but inherently risky.
He grew to 75–100 employees and ~$10M revenue while self-teaching operations and ad sales, funded by credit cards—highlighting both audacity and fragility.
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Geography matters less when a local scene is under-covered and hungry.
He positioned New York as his beat while the Bay had Red Herring/Upside, becoming a central node in a rapidly forming Silicon Alley network.
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Notable Quotes
“Hey, 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
Questions Answered in This Episode
What did reading business plans for Colonna/Wilson actually involve, and how did you decide what was investable at age 24?
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.
Get the full analysis with uListen AI
You mentioned cracking software and phone phreaking—what did that teach you about systems, incentives, and ethics that carried into your career?
Early fascination with home computers and modems evolved into entrepreneurial (and sometimes gray-area) hustles like copying/cracking software and phone phreaking.
Get the full analysis with uListen AI
Why did you choose publishing over becoming a builder/engineer, and do you think that decision limited or amplified your long-term upside?
He chose tech media over becoming a hands-on technologist, influenced by DIY “zine” culture that foreshadowed blogging and independent publishing.
Get the full analysis with uListen AI
How did you structure ad sales and conference revenue to get to ~$10M, and what were the most important distribution channels (newsletter, events, print)?
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.
Get the full analysis with uListen AI
What were the biggest operational mistakes you made managing 75–100 people with no prior training, and how would you avoid them today?
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.
Get the full analysis with uListen AI
Transcript Preview
In the '90s, um, I, you know, I grew up in Brooklyn. Um, my dad had his bar, uh, seized by the feds because he didn't pay his taxes during the 1987 crash. He became, like, he got behind, and, uh, the feds showed up one day, and this was the maybe six weeks before I was set to go to college. And he said, "Hey, 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." So he was, like, really behind on his taxes, and, you know, state liquor authority, they kind of take it serious. So feds come, shotguns, the whole thing. They seize the place. They seize everything in it. And, uh, I was like, "Wow, I guess I'm going to school at night, and I'm gonna work during the day." And I worked, uh, fixing laser printers, and, uh, that was, like, a really good racket. The HP had just come out and-
Were you set to go to college somewhere else?
Well, that's another story. But I was set to go to Brooklyn College. I had gotten into that. I had also taken the police exam to be a police officer. So my brother went into the force, and then I said, "You know what? I'm gonna see if I can go to college and make that work. So I'm gonna go to Brooklyn College." So I decided to work during the day, and then I went to school four nights a week, 6:00 to 9:00 PM, carried full credit, 16 credits a semester, and, uh, I would work fixing laser printers all day. I was a bad student. Uh, I was always that student who underperformed. I didn't find great meaning in academics, but I had a computer when I was in high school, and I was more interested in playing with my 300 baud modem, which then became a 1200 baud modem in my PC junior. So it kinda, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home. Uh, I actually had an Atari 2600-
What-
And it could play Tank, was the game that came with it, and Pong. And so my dad bought this for us when I was six or seven years old in 1976, 1977, and he had one of the first Pongs in Brooklyn in his bar.
Oh.
So-
He, he must have cleaned up on that.
Oh my God, it was crazy. Um, and so we, uh, I, I just got exposure to video games and computers, and I was like, "Wow, this is incredible." Like, computers are gonna change everything. And then I happened to hack some software. We used to... I ran a lot of scams. Uh, but, uh, [laughs] that-
You told us about the, the VHS-
So VHS-
... relay
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