E603: Chris Sacca is back! The legendary investor hears pitches & talks Shark Tank, Twitter, education, climate change, politics, the state of fundraising, what’s next

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Legendary angel investor and “Shark Tank” star Chris Sacca returns to TWiST! Chris and Jason sit down to discuss everything from investing in relationships to Jack Dorsey as Twitter’s CEO (now and early on). He talks about what he looks for in an investment, how he met Matt Mazzeo, those early years with Twitter and selling people on the business, and how his dream job involved “a lot of being on the phone, a lot of yelling at people… high risk, high reward.” Chris shares his experiences on “Shark Tank,” how fun it is to bust the chops (he uses a different term…) of Mark Cuban and Kevin O’Leary, and how TV could be part of the next chapter of Chris’ life. Chris also listens to pitches from three companies that came out of Jason’s LAUNCH IncubatorRequested, LeadIQ and Benchmade Modern – offering feedback to each of the three founders about their businesses and how to move forward.

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0:00 – 3:03 “Legendary top 10 episode”

3:04 – 5:04 “Do you know who was coding 25 feet away at a desk? Kevin Systrom of Instagram.”

5:05 – 7:02 “I pick and choose those relationships that I really want to invest in.”

7:03 – 9:43 “What I do is impossible without real relationships with great people.”

9:44 – 11:14 “It’s pretty easy to be a VC, in terms of reputational management.”

11:15 -13:13 “He was smart. He knew what he was talking about. He knew all these company names we’d never heard of before.”

15:48 – 17:38 “I try to understand the idea, but particularly how I can help make the idea better.”

17:39 – 20:01 “I only invest in people who’ve had shitty jobs, or who’ve traveled or studied extensively abroad.”

20:02 – 29:50 Requested Pitch

31:51 – 36:04 “What I’m always looking for… are there insights or aspects of this particular product that are different.”

36:05 – 39:20 “The data insights that you get from a company like that can really focus the strategy.”

39:21 – 42:37 “I think they can be managed well as long as you’re super transparent about it and don’t let it cloud your judgement.”

42:38 – 45:40 “Ultimately, I’d like to be off the board and just have that informal advisory capacity.”

45:41 – 48:50 “I think Adam wanted to do it with Jack.”

48:51 – 53:15 “The hardest thing for him was asking for help.”

53:16 – 57:21 “One of the things that Jack has is that he’s an incredible curator of talent.”

57:22 – 1:11:34 LeadIQ Pitch

1:11:35 – 1:17:29 “There’s an abundance of money on the investor side and that’s gotta get put to work cause it’s in the investor’s incentives to put it to work.”

1:17:30 – 1:21:31 “Companies have to be different… they have to have a clear, unfair advantage.”

1:21:32 – 1:39:33 Benchmade Modern Pitch

1:39:24 – 1:40:27 “You know why it was the most fun? I made it about the other sharks rather than the company.”

1:40:28 – 1:44:22  “In the end, I’m gonna wrap it up by the time I’m 40 and do something else.”

1:44:23 – 1:47:22 “The inherent skepticism in Silicon Valley is kind of disgusting me at this point.”

1:47:23 – 1:51:07 “The climate is fucked. We as a planet do not have the global will to fix it.”

1:51:08 – 1:54:51 “The think the political realm has been just dopamine hacking… I think it’s an entire industry that’s been hacking the personal dopamine response of the mass citizenry.”

1:54:52 – 1:57:29 “The very best entrepreneurs have very unreasonable expectations of themselves… They just know it’s gonna work.”

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