20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset

Reid Hoffman is a Silicon Valley stalwart in the modern technology world. On the investing side, he is a Partner @ Greylock, one of the leading venture firms of the last 2 decades with a portfolio including Facebook, Airbnb, Dropbox, Figma, Appdynamics and Okta to name a few. Reid has led investments in Airbnb, Convoy, Coda and Aurora to name a few. As an operator, Reid co-founded LinkedIn, the world’s largest professional network and before LinkedIn, Reid served as executive vice president at PayPal, where he was a founding board member. If that was not enough, Reid is the co-author of Blitzscaling and two New York Times best-selling books: The Start-up of You and The Alliance. 

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In Today’s Episode You Will Learn:

1.) How Reid made his way into the world of startups, came to found Linkedin and how that led to his joining Greylock?

2.) Does Reid consider himself an innate and natural leader today? How has his leadership style changed over time? What elements does Reid struggle with? How has he scaled to these leadership challenges? What does Reid believe are the different strands of leadership?

3.) How does Reid think about what separates the good from the great board members? What is the biggest danger for board members today? How do the very best founders manage their boards? How does Reid think about the weight of his words today?

4.) How does Reid think about the importance of ownership? How does Reid analyse price today? What was the story behind Greylock investing in Airbnb? What did Reid see so clearly and before anyone else saw it? What is the story with Stripe? Why did Reid turn Stripe down?

5.) How does Reid think about ensuring venture partnerships always have a learning mindset? What can be done deliberately to ensure this? Where do many people struggle here? How can partners develop trust within venture partnerships? Where does trust most often break down?

Item’s Mentioned In Today’s Episode

Reid’s Favourite Book: Thinking, Fast and Slow, Amusing Ourselves to Death: Public Discourse in the Age of Show Business

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