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This Week in Startups – Episode 218: Kevin Rose of Milk Inc

Does this guy need any introduction? Digg, Diggnation, Revision3, and tons more… Kevin Rose joins Jason this week to talk about their history in start-ups, Kevin’s career with web technology and his latest venture with Milk Inc.

0:00-1:00 Today we welcome Kevin Rose–serial entrepreneur, angel investor and founder of Milk.
1:00-3:00 We both started angel investing around the same time, we’re kind of the new kids on the block, right?
3:00-4:45 Who were the big players back then?
4:45-6:45 Thank you to MailChimp for sponsoring the program. Everyone thank @MailChimp for their support of independent media!
6:45-8:00 We’ve known each other for a long time. How did we meet, again?
8:00-11:30 What was the beginning of your career?
11:30-13:00 How did you build the first prototype of Digg?
13:00-15:45 Digg became such a huge site. Where did it peak?
15:45-17:00 How do you manage the user base becoming more powerful than the company?
17:00-19:45 So Digg is still chugging along?
19:45-20:30 And there’s a lot at Facebook that came out of Digg, right?
20:30-22:00 Diggnation became a real phenomenon.
22:00-23:30 Why are you turning it off? Is it just taking up too much time and energy?
23:30-25:15 You’re a performer, too, and you want to go out on top.
25:15-27:30 So how did you decide to go with Milk as your next project?
27:30-30:30 You went to your investors and you said what?
30:30-32:30 Do you now feel pressure to live up to expectations, now that you’ve had so many hits?
32:30-34:30 Thank you to SurveyMonkey for sponsoring the show. Kevin, have you ever used SurveyMonkey?
34:30-36:00 Was it ever publicly announced who was trying to buy Digg?
36:00-37:00 How do you reconcile that decision as a founder?
37:00-39:45 Tell us about Oink. What’s the mission?
39:45-43:00 There are shades of a lot of other sites like Foursquare, Gowalla and even Digg. How long did it take to build?
43:00-45:00 Based on this success, why go on to a second app if Oink is doing so well?
45:00-46:45 How are things different now for you as an entrepreneur?
46:45-48:30 Is there an advantage to doing apps?
48:30-54:00 As an entrepreneur, what’s your advice to young people starting today?
54:00-58:00 How scary is it having so much responsibility for a product? Do you get stressed?
58:00-1:00:00 How do you cope with the stress?
1:00:00-1:05:00 Tyler recounts how Jason attempted to hire people from Digg’s fanatical community.
1:05:00-1:07:00 Kevin: Were people at AOL mad at you for going after Digg?
1:07:00-1:08:30 What would you do with Yahoo, Kevin?
1:08:30-1:11:30 How would you overtake Gmail? Is your idea too good to say?
1:11:30-1:13:30 How re-charged could you be as a Yahoo employee when someone like Carol Bartz or Tim Armstrong shows up?
1:13:30-1:15:00 Kevin, congratulations on your new adventure. I think Oink might be a big success and you’ll be one and done.
1:15:00-1:16:15 Thank you to SurveyMonkey and MailChimp for helping make this show possible. If you’re a world class developer, Milk is hiring, so head to mi.lk and work for Kevin.
1:16:15-1:17:15 What was your latest angel investment? (They were Fab and Yardsale.)

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Jason: @jason
Tyler: @steepdecline
Kevin: @kevinrose
SurveyMonkey: @surveymonkey
MailChimp: @mailchimp