Chris Sacca of Lowercase Capital, Part 1 #291

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Today on This Week in Startups, investor, entrepreneur and cyclist Chris Sacca of Lowercase Capital joined the program to discuss his investments in Facebook, Twitter, Uber and more. He also gave a candid account of how he hustled his way to the top.

Chris' interview was so incredible that we couldn't contain it in just one episode, so today is only part one--you'll have to check back soon for part two!

*Disclaimer: Chris has a potty mouth and we've attempted to bleep out all of his swear words. We apologize in advance if any snuck by our censors.

1:00 Welcome everyone! Today on TWiST we have Chris Sacca of Lowercase Capital.
2:30 Thank you to Hiscox for supporting the show. Everyone go to hiscoxusa.com/smallbiz to get a free quote online in less than 15 minutes.
5:00 Chris, welcome to the show.
6:15 What is it that you do on a daily basis?
9:15 Chris: There’s a lot of garbage getting funded today.
10:00 What does it mean to be a founder in your book?
12:15 Is fearlessness a good trait?
14:45 Has it become too easy to become a founder?
19:15 How did you wind up being an investor in companies like Facebook, Twitter and Uber?
20:00 Chris shares the story of how he found himself in a huge financial hole.
25:30 Thank you to Stamps.com for their support of the show! Everyone go to stamps.com and use the code TWIST for your free, 4-week trial.
28:15 Chris resumes his story of how he gambled and lost big.
29:45 What happens when people come to collect on the debt?
34:30 What was Speedera’s business?
35:00 How did you land at Google?
38:15 Chris: My first angel investment was in Photobucket.
40:00 Is it right that you once took over on the secondary market for most Twitter shares?
44:30 True or false: people in the Valley tend to be like “dude, I got you,”--until the money comes in.
47:45 Has VC behavior gotten better or worse in the last decade?
50:30 Tell me about Garrett Camp of Stumbleupon.
51:45 Twitter, some would say, is screwing over the developers that helped build it. What’s your take on that?
1:00:00 Are you slowing down on angel investing right now?
1:01:45 Chris reveals the existence of the fund Lowercase Stampede.
1:03:30 What gives you the ability to look at a new space with fresh eyes?
1:05:30 How did you get involved in Hollywood?
1:07:00 What do you think the impact of Kickstarter is on the entertainment business?
1:10:15 This concludes part one of Jason's interview with Chris--stay tuned for part two...

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