Degrossing: Raising Cash During Shocks

This episode explores Harris “Kuppy” Kupperman’s framework for “inflection investing” and how he identifies asymmetric opportunities across global markets. The conversation dives into why he believes U.S. equities are structurally challenged, where he sees better opportunities globally, and how macro, politics, and capital flows drive major investing inflections.

Inflection investing and identifying asymmetric opportunities
How macro and politics create winners and losers in markets
The Argentina case study and why the stock exchange may outperform the country
How to structure trades with limited downside and multi-bagger upside
Time horizon advantages versus short-term Wall Street thinking
Portfolio construction, capital allocation, and when to sell positions
Managing risk, leverage, and liquidity during crises and wars
Building a “shopping list” during market dislocations
Country ETFs vs individual securities in global investing
Why Kuppy prefers international markets over the U.S.
The structural imbalances in the U.S. economy and stock market
Why AI may lead to profitless growth and economic disruption
The impact of AI on jobs, margins, and economic demand
How inflation distorts economic data and investor perception
Finding opportunities in “left for dead” markets like Brazil
The role of elections and policy shifts in market inflections
How to think probabilistically about investments
Avoiding unforced errors and emotional decision-making
The importance of long-term thinking in volatile markets
Psychology and discipline in global macro investing

Harris Kupperman Twitter
https://twitter.com/HedgeyeKuppy

Praetorian Capital Website
https://praetorian-capital.com

Timestamps
00:00 Why the U.S. stock market is structurally overvalued
01:14 What “inflection investing” means
02:54 Top-down vs bottom-up investing framework
04:31 Using politics to identify winning trades
05:00 Argentina trade setup and execution
06:20 Why the Argentine stock exchange is the best play
08:00 Earnings inflection and multiple expansion potential
10:37 Time horizon and holding period strategy
13:00 When to exit positions and recycle capital
18:41 How and when to raise cash
19:41 De-grossing the portfolio during crises
23:14 Real-time decision making during war scenarios
27:00 Building a shopping list during dislocations
29:32 ETF vs individual stock decision process
33:22 Why the U.S. is less attractive than global markets
38:17 The problem with AI-driven “growth”
43:31 Monitoring vs acting across global opportunities
48:14 The psychology of long-term investing and edge