#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. :) Sponsors: MUD\WTR energy-boosting coffee alternative—without the jitters: https://MUDWTR.com/Tim (between 15% and 43% off) Helix Sleep premium mattresses: https://HelixSleep.com/Tim (Between 20% and 27% off all mattress orders and two free pillows) AG1 all-in-one nutritional supplement: https://DrinkAG1.com/Tim (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) 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]