# Why Uncertainty Is an Opportunity (and some Wall Street players don't want you to know that) SB1847

Page: https://stenobird.com/podcast/the-stacking-benjamins-show-745268/why-uncertainty-is-an-opportunity-and-some-wall-street-players-don-t-want-you-to-know-that-sb1847
Text version: https://stenobird.com/podcast/the-stacking-benjamins-show-745268/why-uncertainty-is-an-opportunity-and-some-wall-street-players-don-t-want-you-to-know-that-sb1847.md
Podcast: [The Stacking Benjamins Show](https://stenobird.com/podcast/the-stacking-benjamins-show-745268)
Published: 2026-05-27T08:01:00+00:00
Episode link: https://pscrb.fm/rss/p/mgln.ai/e/345/rss.art19.com/episodes/cac0c974-5d24-4576-b3c7-6bb5a323ae49.mp3?rss_browser=BAhJIg90cmFuc2NyaWJyBjoGRVQ%3D--952c5701c84ad333c69d5faa668f8177091704f0
Audio file: https://pscrb.fm/rss/p/mgln.ai/e/345/rss.art19.com/episodes/cac0c974-5d24-4576-b3c7-6bb5a323ae49.mp3?rss_browser=BAhJIg90cmFuc2NyaWJyBjoGRVQ%3D--952c5701c84ad333c69d5faa668f8177091704f0
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Duration seconds: 3696

## Resource

The five highest global uncertainty readings since the 1980s have all occurred in the last five years. And yet the answer Wall Street keeps selling -- products that promise upside without downside -- is mathematically impossible and provably underperforms over time. Simone Stolzoff, author of How to Not Know, spent years studying how people, companies, and investors navigate uncertainty well. His findings are the opposite of what the financial industry is selling you right now. What You'll Walk Away With Why our tolerance for uncertainty is declining -- and the specific role smartphones and real-time data have played in making investors more anxious and worse at decision-making The anchor framework: how certainty in some areas of your life makes it dramatically easier to hold uncertainty in others -- and what that means for how you build a financial plan The Slack origin story -- how a gaming company at the peak of its success chose to shut down and pivot into the unknown, and what that teaches about staying open to what might emerge Why Warren Buffett and the best venture capitalists actively seek uncertainty -- and how confusion between uncertainty and danger costs most investors real money The kill criteria concept borrowed from mountain climbing -- and how pre-committing to rules before the emotion hits is the only reliable way to prevent catastrophic decisions One-way doors versus two-way doors: the Jeff Bezos framework for knowing when to agonize over a decision and when to just act Why buffer ETFs are mathematically required to underperform broad index funds over time -- and the one question that exposes every "downside protection" pitch instantly OG's case for looking at your portfolio as rarely as possible -- and the surprising thing that happened when he chec…

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