Entrepreneur Jason Calacanis on the Evolution of the Internet, Media, Investing and More

Entrepreneur Jason Calacanis on the Evolution of the Internet, Media, Investing and More

Entrepreneur Jason Calacanis on the Evolution of the Internet, Media, Investing and More

By Kendall Fisher, executive producer at Grow Wire

We can argue that Jason Calacanis was one of the first people to become truly and fully obsessed with the internet: He was one of the early reporters to cover the “internet industry” (as it was called in the ‘90s); he was one of the first people to commercialize blogs in the early ‘00s; he was one of the first people on Twitter (his handle is @Jason for goodness sake!); he was one of the early investors in Uber and one of the original believers in podcasting (his increasingly popular podcast, “This Week in Startups,” is 10 years old). 

Needless to say, Calacanis has a grasp on the internet. His insight is not only valuable but genuinely intriguing, and that’s precisely why we’re so excited he joined us on this episode of “The Grow Wire Podcast.” 

Calacanis walks us through his own evolution alongside the evolution of the web, taking us back to his childhood in Brooklyn and into his college years at Fordham University where he originally intended to become an FBI agent. However, while working at the university’s computer lab, a co-worker began messaging his girlfriend in Argentina and that sparked what would become Calacanis’ lifelong obsession with the internet. 

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He’d go on to write for the New York Times, reporting on the internet, and eventually build his own publication and blogging companies—one of which was the Silicon Alley Reporter—shortly thereafter. Calacanis was hired to scout for Sequoia Capital, helping land deals with companies like Uber, and then set off down his own path in angel and seed investing, placing bets on companies like Robin Hood and apps like Calm.

He discusses his fundraising tips for entrepreneurs, his top advice for investors, his vision on the future of media and his overall outlook on the world, business and startups. 

Suffice to say, you’ll want to tune into this episode. Listen now on Apple Podcasts, SoundCloud and YouTube.