#790: Chris Sacca — How to Succeed by Living on Your Own Terms and Getting Into Good Trouble

Chris Sacca is the co-founder of Lowercarbon Capital and manages a portfolio of countless startups in energy, industrial materials, and carbon removal. If it's unf**king the planet, he's probably working on it. Previously, Chris founded Lowercase Capital, one of history's most successful funds ever, primarily known for its very early investments in companies like Twitter, Uber, Instagram, Twilio, Docker, Optimizely, Blue Bottle Coffee, and Stripe. But you might just know him as the guy who wore those ridiculous cowboy shirts for a few seasons of Shark Tank. To purchase Chris's ranch, schedule a viewing at FivePondsRanch.com.

P.S. This episode features a special, one-of-a-kind introduction that Chris recorded of yours truly. :)

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Timestamps:

[00:00] Coming up

[06:47] Chris introduces me.

[11:07] Some Sacca background.

[18:32] Raising pre-teen gamblers and tailgating troublemakers.

[19:54] Conscious changes and rethoughts since our first interview.

[26:12] The personal and professional influence of Rich and Sarah Barton.

[30:18] Property management and the Zen of Kevin Rose.

[35:12] Zillow Gone Wild.

[36:58] Simplifications.

[45:03] Remaining optimistic despite being in the business of saying no.

[51:33] Living in the finite without +1 obligations.

[56:54] “Wait, what’s hustle culture?”

[59:48] The (lack of) trouble with kids today.

[01:09:53] Raising kids to solve problems and eschew smartphones.

[01:14:15] Rawdogging? You keep using that word. I do not think it means what you think it means.

[01:16:05] An Andy Goldsworthy aside.

[01:16:30] Taking advice from R. Buckminster Fuller GPT.

[01:19:13] Assigned reading.

[01:20:10] Humans vs. AI.

[01:26:20] What happens to people stuck between AI job displacement and a broken social contract?

[01:42:38] Counting on the human craving to convene and connect.

[01:56:30] What kind of business would a younger Chris start today?

[02:00:44] The prescience of The Medium is the Massage.

[02:01:39] What does Lowercarbon Capital do?

[02:08:44] Projects Chris is most excited about.

[02:18:59] Youthful mischief and flim-flammery.

[02:24:51] The premise for Chris’ upcoming No Permanent Record.

[02:35:25] Cultivating the ability to face (and maybe win over) a tough crowd.