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

Jason Calacanis
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 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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