Jason Calacanis on the Evolution of the Internet, Media & Investing

The Grow Wire Podcast

Angel investor and founder of the popular podcast, “This Week in Startups,” Jason Calacanis walks us through the evolution of the internet. He starts off with his own evolution, growing up in Brooklyn (5:07) and attending college at Fordham University where he originally intended to become an FBI agent but where he’d actually kickoff a lifelong obsession with the internet (9:15). He opens up about starting a Zine in the ‘90s (13:45), helping Sony realize the power of web pages for musicians (17:02) and landing major deals (like Uber) with Sequoia Capital (19:39). Calacanis also discusses the early years of blogging (21:30), its massive impact on journalism (29:21) and his thoughts on the future of media (32:10). He goes on to explain his philosophy on angel investing (40:27), including training his brain to better understand odds (49:36) and dealing with controversy amid the companies in which he’s invested (1:02:30). Finally, Calacanis notes that the next generation of great founders are going to look much different than ever before, warning investors that if they don’t represent that shift in their own firms, they’re inevitably going to miss out. Tune in for more!

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