Jason Calacanis


Jason Calacanis is best known for his podcast This Week In Startups and for investing in unicorn companies such as Uber, Thumbtack and Robin Hood; as well as selling shares in Facebook (whilst telling Mark Zuckerberg what he thought of him) and working alongside investors such as Elon Musk.

But it took him awhile to get here.

Jason was the Founder and CEO of Rising Tide Studios and Weblogs Inc (which he sold to AOL in 2005 for $25m), before turning his hand to angel investing. Jason is the dinner party guest you want to have at your table - he would entertain and delight because he favours candidness over honesty, and believes that the secret to success is the ability to get on with difficult people.

An early investor in calm.com, Jason could see the benefit it would bring to the world and credits the founder, Alex Tew, for having the same levels of creativity as Elon Musk and Steve Jobs.

Jason says he loves angel investing because he gets to hang out with the smartest people in the world who tell him how the world is going to change, how they're going to do it and then they invite him along for the ride.

So to that end, join us on our ride as we chat with Jason about:

  • Whether he’s marmite or fungus.

  • Getting trolled for investing in calm.com and why you should never underestimate anyone.

  • The secret to angel investing.

  • Why the people who are going to change the world aren’t always easily likeable.

  • His favourite book of 2018 (hint, it isn’t Shoe Dog).

  • Who his all-time favourite guest on TWIST (this week in startups - his podcast) has been.

  • The impact of the realisation that the person who picked the Times cover model was the most powerful person in the room, not the model themselves, had on him.


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