Nostalgia and Reflection on Relationships

In this chapter, a lively dinner conversation at ZZ's Clam Bar unfolds, filled with nostalgic anecdotes about family and humorous stories, particularly involving Crocs. The speakers reflect on the complexities of parenting and friendships, delving into the bittersweet nature of watching children grow independent. The dialogue further explores the theme of authenticity in relationships, the challenges of dating later in life, and how personal growth shapes one's understanding of healthy partnerships.

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Episode notes

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.