20VC: Khosla’s Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square

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Keith Rabois is an investment partner at Khosla Ventures where he has led investments in Stripe, Thoughtspot, HealthTap and Teespring among many others. He also started OpenDoor, which aims to transform the process of selling a home through technology. Keith’s unparalleled operational track record does not stop there as he has forged several of the most important new social and commerce platforms over the last decade holding key roles at LinkedIn, Paypal and being COO at Square. As a board member, Keith guided Yelp [NYSE: YELP] and Xoom [NASDAQ: XOOM] from inception to successful IPOs. Simultaneously, he also invested in other like-minded entrepreneurs with early stakes in YouTube [acquired by GOOG], Yammer [acquired by MSFT], Palantir, Lyft, AirBnB, Eventbrite and Quora.

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In Today’s Episode You Will Learn:

1.) How Keith made the move from key executive at LinkedIn, Paypal and Square to being a VC with Khosla?

2.) Question from Lee Hower: What were the biggest learnings from playing a key role at LinkedIn, Paypal and Square? How do they compare to learning from Slide, a not so successful project? Does one learn more from success or failure?

3.) Question from Jason Lemkin: How can founders assess the potential of their teams? How long is it possible to allow individuals to stretch to their roles? What are the signs that people are either exceeding or falling below expectations?

4.) Eric Yuan @ Zoom has previously illustrated the importance to me of sustainable growth. What is Keith’s view of this? Why does he not like this term? What are his thoughts on the key constraints on growth for most startups?

Items Mentioned In Today’s Show:

Keith’s Fave Book: The Upside of Stress

Keith’s Fave Blog: Stratechery

Keith’s Most Recent Investment: Forward 

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

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

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