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A ‘bulldog’ who ‘cuts through the bulls—‘: Here’s how insiders describe early Robinhood investor Jason Calacanis

Jason Calacanis has had several incarnations during his more than two decades in tech, making waves as a publisher, a blogger and an entrepreneur. 

Today, he’s living his latest, and seemingly most successful, life as a startup investor. He was among the first VC investors in Uber, Calm and Robinhood, among others, and he runs the boot-camp-like Launch “accelerator” to help startups founders make it to the big leagues.

And, almost every day, he’s preaching his philosophy and broadcasting his opinions through various podcasts and newsletters. 

If there’s one thing the peers, portfolio company founders, friends and frenemies of Calacanis all agree on, it’s his default setting as a polarizing lightning rod. People close to Calacanis describe him as impulsive, brilliant, opinionated, and brash — sometimes all in the same conversation.

Calacanis doesn’t disagree. “Most folks think I’m lucky, some…

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