20VC: Michael Dearing on 5 Key Principles He Uses To Assess Startup Founders, Why Benevolent Dictatorship Is A Beautiful Thing & Why Markets Are Better Capital Allocators Than CEOs

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Michael Dearing has established himself as an icon of early-stage venture over the last decade. With his founding of Harrison Metal in 2006, he has backed the likes of AdMob, MoPub, Heroku, TellApart and Harry’s just to name a few of his incredible companies. Prior to being in VC, Michael spent 6 years at eBay across numerous roles and before that held positions at Shoe Warehouse as CEO, The Walt Disney Company in corporate strategy and then Bain & Co as a consultant.

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In Today’s Episode You Will Learn:

1.) How Michael made his way into the world of venture from selling shoes with Shoe Warehouse to eBay to founding his own fund?

2.) Michael has said before that he looks for “personal exceptionalism” within the teams he backs, what does that really mean? How does he distinguish brilliance from arrogance? What is the balance between vision and stubbornness?

3.) How does Michael think about price sensitivity? How does he use it as a determining factor to test his level of conviction in the deal? More broadly, how does Michael view pricing in the market today? Why are the convertible debt markets so toxic?

4.) How does Michael view strategy around reserve allocation? Why does Michael believe reserves are where he has made the biggest mistakes? What are his takeaways from those mistakes? Why does recycling not feature as a core tenet of his strategy?

5.) Why does Michael believe that “benevolent dictatorship” is a beautiful thing? Does this thesis change in the debate over founder vs company first? How does Michael use McCallum’s 5 key principles to assess founders and their ability?

Items Mentioned In Today’s Show:

Michael’s Fave Book: Confederacy of Dunces

Michael’s Most Recent Investment: Astro

As always you can follow HarryThe Twenty Minute VC and Michael on Twitter here!

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

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