The Identity Crisis of Sears: From Retail Giant to Bankruptcy

This chapter explores the history of Sears, from its beginnings as a successful catalog retailer to its decline and bankruptcy. It emphasizes the pivotal decisions made by the company, including the abandonment of profitable ventures in financial services as it tried to maintain its retail identity amidst growing competition.

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IN THIS EPISODE, YOU’LL LEARN:

12:49 - How Annie Duke got sick, quit academia, & became a professional poker player.
18:24 - How poker taught her to “embrace uncertainty” & recognize the limits of what we know.
27:26 - How a legendary poker champion taught her to think more rationally about luck & loss.
37:45 - Why it’s important to think probabilistically—and how to strengthen this skill.
41:49 - How Annie helped a venture capital firm to improve its decision-making process.
44:54 - What skills & insights can be transferred from the game of poker to the game of investing.
51:36 - Why Annie never owned Bitcoin or NFTs.
55:13 - How to develop “kill criteria” that will help you decide when to sell an investment.
1:00:31 - Why we tend to make terrible investment decisions when we’re losing money.
1:06:29 - How to think rationally about whether to quit your job.
1:12:11 - How our sense of identity & tribalism can wreck our ability to revise our beliefs.
1:27:53 - Why Daniel Kahneman has a “quitting coach”—and why you should have one, too.
1:42:18 - Why it’s invaluable to open your mind to other people’s dissenting views.

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members.
Annie Duke’s new book, “Quit: The Power of Knowing When to Walk Away.”
Annie’s previous bestsellers, “Thinking in Bets” & “How to Decide”
William Green’s book, “Richer, Wiser, Happier” – read the reviews of this book.
William Green’s Twitter.
Related Episode: The Mind Of A World Poker Champion W/ Annie Duke - TIP231.

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