CHAPTERS
- 0:00 – 0:31
Brooklyn upbringing and a family financial crisis before college
Jason Calacanis recounts growing up in Brooklyn and the pivotal moment when his father’s bar was seized by federal authorities over unpaid taxes. The sudden crisis forced him to rethink college funding and take on adult responsibilities quickly.
- •Father’s bar seized by the feds after falling behind on taxes post-1987 crash
- •Timing: weeks before Jason was set to start college
- •Family pressure: told to take care of his mom and prepare for worst-case outcomes
- •Early lesson in instability, risk, and self-reliance
- 0:31 – 1:28
Working by day, college at night: learning hustle through laser printers
With no financial help available, Calacanis works during the day and attends Brooklyn College at night. He describes fixing laser printers as a lucrative early job that supported his education.
- •Attended Brooklyn College while working full-time
- •Night-school schedule: 4 nights/week, heavy course load
- •Job: fixing laser printers during an early boom period for HP printers
- •Self-assessment as an underperforming student despite strong drive outside class
- 1:28 – 1:59
Early exposure to computers, modems, and the conviction tech would change everything
Calacanis explains how having early access to home computing and video games shaped his worldview. He became more interested in exploring technology than traditional academics.
- •First-generation home-computer exposure (PCjr era) and early modems
- •Atari 2600 and early arcade-style experiences
- •Father had early Pong machine in his bar, reinforcing tech fascination
- •Developing a strong belief that computers would transform society
- 1:59 – 3:02
Teenage entrepreneurship and gray-area tech: copying software and phone phreaking
He describes early “scams” and side hustles, including selling copied software and experimenting with phone phreaking. The conversation highlights the practical technical skills required at the time.
- •“Jason’s Hot Tapes” referenced as an early business
- •Copying/cracking software (e.g., Chess Master) and selling copies
- •Phone phreaking as a hands-on exploration of telecom systems
- •Hardware-era skills: soldering, swapping chips, physically installing memory
- 3:02 – 3:36
Choosing media over engineering: discovering zines as proto-blogs
Calacanis traces the origin of his media identity to zine culture in New York’s music and art scenes. He frames zines as the precursor to blogs and decides he wants to be a publisher.
- •Hanging out in NYC’s Village scenes; browsing Tower Records’ zine section
- •Zines as DIY publishing: friends writing, photocopying, distributing
- •Decision point: telling himself he would become a magazine publisher
- •Launch of “CyberSurfer” focused on dial-up services and CD-ROMs
- 3:36 – 3:51
Early collaborators and future internet-media lineage (Brian Alvey and beyond)
He connects his early work with longtime collaborator Brian Alvey to later well-known internet media projects. The hosts tie the lineage to properties associated with Weblogs Inc. and AOL acquisitions.
- •Created early publication work with Brian Alvey (high school connection)
- •Mentions later-era projects: Weblogs, Engadget, and related properties
- •Frames these as part of a long arc from zines to blogs to scaled media
- •Signals how early media instincts became a repeatable career pattern
- 3:51 – 4:38
Breaking into venture orbit: meeting Jerry Colonna and Fred Wilson (future Flatiron)
Calacanis tells the story of meeting Jerry Colonna via the early Internet World conference and being introduced to Fred Wilson. He’s recruited informally to read business plans as the firm takes shape.
- •Internet World conference as a networking inflection point
- •Jerry Colonna consulting for Lycos/CMGI before becoming a VC figure
- •Invitation to help by reading business plans for a new venture effort
- •Origin story of what became Flatiron Partners
- 4:38 – 5:14
The Flatiron backing story and the GeoCities moment
He describes Flatiron’s early funding structure and how he encountered GeoCities as a business plan. Though young and inexperienced in venture, he recommends investing—one of Flatiron’s biggest wins.
- •Flatiron’s anchor backing: JP Morgan plus SoftBank (Masayoshi Son)
- •Calacanis paid to review plans (sushi + $1,000 per plan)
- •Reads plan for a Beverly Hills internet company later branded GeoCities
- •Recommends investment while not yet understanding VC mechanics
- 5:14 – 6:15
Mentorship and the fork: Fred Wilson challenges him to choose a path
Calacanis reflects on mentorship from Jerry Colonna and especially Fred Wilson, who pressures him to decide between covering startups and being closer to investing. Jason chooses building the magazine—foreshadowing his later ‘do both’ approach.
- •Jerry Colonna as early mentor; later life shift toward coaching/founder support
- •Fred Wilson becomes the deeper ongoing mentor
- •Fred’s challenge: stop straddling writing about investors/companies and pick a lane
- •Jason chooses the magazine path (later evolves into doing both)
- 6:15 – 6:49
Owning New York’s internet beat: scaling niche publishing into a real business
Calacanis explains how he positioned his publications as the New York counterpart to Bay Area tech media. He expands into multiple titles and events, scaling rapidly despite limited operational experience.
- •Market positioning vs. Red Herring/Upside: “I own New York”
- •Publishes Silicon Alley Reporter and launches Digital Coast Reporter in LA
- •Adds conferences and email newsletters to create an ecosystem
- •Bootstraps growth to ~$10M revenue largely on credit cards
- 6:49 – 7:46
Sudden prominence in the dot-com era: media fame and the ‘New York internet guy’
He describes the cultural moment when tech became the hottest thing in New York, propelling him into mainstream visibility. Calacanis compares the era’s hype to modern crypto mania and notes the intensity of being a central figure.
- •Team scale: ~75–100 employees by age 27; learning ad sales and ops on the fly
- •Major media validation: New York Times cover, Charlie Rose, New Yorker feature
- •NYC context: traditionally dominated by media, finance, art—tech felt new and scarce
- •Analogy: dot-com peak attention comparable to crypto’s peak fascination
