20VC: Jason Calacanis on The 4 Questions Investors Must Ask Founders, Whether YC Have Scaled Their Process Successfully & Why Early Founder Liquidity Is Good Not Bad

Jason Calacanis is arguably one of the world’s greatest angel investors, as he says he has “got lucky” 7 times and counting with a portfolio that includes the likes of Uber, Thumbtack, Evernote, Tumblr and more incredible companies. Jason has also previously been a scout for Sequoia Capital, where he made the original Uber investment. On the operational side, Jason was previously a Sequoia Founder with Weblogs, sold to AOL for a reported $25-40m. Today he is the Host of This Week In Startups and Founder of The Launch Festival, bringing entrepreneurs together with potential investors. You can buy his fantastic new book, Angel here!

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In Today’s Episode You Will Learn:

1.) How did Jason make his move into the world of angel investing? Why was now the right time to write, Angel?

2.) What does Jason believe are the 4 questions investors must ask founders? What response to those questions excited Jason to hear? What responses make him nervous?

3.) Why does Jason believe that founders having the option for early liquidity is good? Why does he believe it does the opposite of what VCs think and actually makes them continue to work? What are the dangers of offering early liquidity to those founders?

4.) Why does Jason believe that companies are always bought and not sold? Does VC access to corporate development teams then become a futile exercise?

5.) How does Jason view the scaling of Y Combinator? How does Jason evaluate the valuations placed on YC companies? Why does Jason believe that progressive term sheets are ridiculous?

As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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