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.

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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 say I'm a complete fraud, and a handful think I'm a brilliant hype man, and I don't agree with any of them - I agree with all of them," he wrote in his 2017 book, "Angel: How to Invest in Technology Startups."

To chart Calacanis's rise up Silicon Valley's clubby investor ranks, Insider spoke with more than 50 people close to him for the most in-depth profile of the investor to date.

Here are a few excerpts from those conversations that show just how polarizing of a figure Calacanis has become in Silicon Valley's venture capital and startup scene.

• "There is nobody out there that has not gone to war with Jason at some point. But the funny thing is, then, a year later, they are back on his podcast or back asking him for a job." - Brian Alvey, a former business partner and childhood friend.
• "Would I want him on my side? Absolutely. He's a bulldog." - Launch alum Jeremy Redman
• "He's the type of person who will give you blunt feedback and advice. It's going to hurt - a lot." - Launch alum Sheri Atwood
• "He cuts through the bull-- and gets right to the point. It was not like he needed to see a business plan, projections, all the paperwork." - Christy Liu, cofounder of Wanderfly, a travel recommendation startup that was acquired by TripAdvisor.
• "He's kind of earned the right" to make bold claims on Twitter and "his track record speaks for itself." - Launch alum George Charkviani

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