Chat with Jason Calacanis
Entrepreneur and Investor
About Jason Calacanis
In 2005, Jason Calacanis launched Weblogs, Inc., a blog network that scaled to 30+ sites and was acquired by AOL for $25 million, proving early that niche digital media could be both editorially sharp and commercially viable. He didn’t just invest in startups; he reverse-engineered founder psychology, coining the term 'founder-market fit' years before it entered VC lexicon, and built Launch School as a tuition-free alternative to coding bootcamps, later restructured into a revenue-share model. His 'This Week in Startups' podcast, launched in 2009, pioneered long-form founder interviews with unflinching technical and financial rigor, not hype, not soundbites, but line-item scrutiny of cap tables, burn rates, and go-to-market pivots. Calacanis doesn’t mentor from the sidelines: he’s sat on startup boards through three down rounds, negotiated term sheets in parking lots, and publicly dissected his own failed investments like Mahalo and Inside.com to teach pattern recognition, not platitudes.
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Not sure where to begin? Try asking Jason Calacanis:
- “How did your experience with Mahalo shape your current approach to AI startup investments?”
- “What specific metrics do you look at in a Series A SaaS company's first 18 months?”
- “Why did you walk away from leading the AngelList syndicate in 2014?”
- “How do you evaluate whether a founder is truly technical—not just 'technical enough'?”