E408: DFJ’s Josh Stein on his biggest losses – and wins

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Venture capitalists don’t always talk about regret. Especially when, like Josh Stein, you got in early on companies like Box, Chartbeat, AngelList, Redfin, Path and Twilio. But when Jason sat down with Josh, who’s been a VC for 10 years with Draper Fisher Jurvetson, he opened up about some of the big deals he and the firm missed. Facebook, for one.

Plus, what he looks for in an entrepreneur: fearless and headstrong, with an unwavering belief in their idea. An ability to execute on mile markers. And above all, resiliency.

Jason and Josh often play poker together. Here, Josh tips his hand just a bit. Don’t miss this opportunity to get inside the mind of a top VC.

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Highlights:

2:05 Thank you @WeWork and WeWork Golden Gate!
2:45 Josh, when did you start in venture capital and what did you do before that?
3:45 And then you decided to be a VC. Why?
4:00 So you were a founder-product manager turned VC. Most VCs then were MBAs right?
5:18 A fund takes 7-10 years to wind down?
5:53 The investors/limited partners expect to get a return realistically, when?
6:55 Why did you decide to be a VC and not keep being an entrepreneur?
8:13 Ten years of doing this, what have you learned about selecting companies to invest in?
9:55 What are the characteristics, what are your filters for the right people? I’ve heard hard to deal with entrepreneurs are sometimes a good signal that they’re edgy.
11:45 Thanks to our partner @NewRelic. Application performance monitoring for deep and actionable data. Free tshirt: http://newrelic.com/twist
13:37 You’re one of the first investors in Box. Aaron Levie has become a force in the industry. Do you remember the first meeting? When did you know it was something special?
15:18 That business is tremendous. What’s the status of that business?
15:30 People hold Box and Dropbox up side by side. Is that right or are they different?
16:30 Also you’re in Chartbeat, which I used and loved. How much about making great investments is seeing a great product?
18:12 How do you keep it positive?

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