Roelof Botha, MBA'00, Partner of Sequoia Capital, discusses how taking risks led him to career payoffs first as PayPal's CFO and then as an investor in a series of hugely successful ventures such as YouTube, Tumblr, and Instagram, with candid revelation of flops and failures that come inevitably with the process.

(This is an episode of the Career Path Interview Series produced for the Career Management Center of Stanford University Graduate School of Business.)