300% Gains in a Week: My Asymmetric Portfolio Strategy Revealed

Markets Are Crashing, But Here’s Why I’m Sleeping Peacefully

I was fortunate enough to read Taleb during one of the most pivotal and challenging moments of my life. As Naval Ravikant aptly puts it, Taleb possesses one of the best mental models out there, a framework that helps you see the world more clearly and make decisions with greater conviction. His ideas are not just intellectually stimulating—they are profoundly practical, especially in times of uncertainty.

Reading his work during these moments of market panic—where everything seems dire and headlines scream doom—has proven invaluable. As of April 9, 2025, my asymmetric portfolio has been in positive territory for the past week. This outcome is not due to luck but to a deliberate strategy rooted in Taleb’s principles, which emphasize resilience, optionality, and preparing for the unexpected.

It’s quite simple: humans are riddled with biases, and one of the most pervasive is mass bias. This bias manifests when your close circle starts discussing a particular topic—whether it’s the latest investment trend or a "surefire" opportunity—leading you to consider it seriously. Eventually, you may come to believe it’s the best decision possible, even if it goes against your better judgment or long-term strategy.

This phenomenon has driven many people to invest in tech stocks or Bitcoin at the end of 2021, Bitcoin again in 2017, real estate in 2007, and perhaps now into positions like NVIDIA or similar assets. It’s a cycle that repeats itself: when everyone around you is convinced they’ve found the next big thing, it’s easy to get swept up in the excitement. But history shows us that these moments often precede significant corrections.

This makes me wonder: what’s next? Gold? Perhaps. It’s hard to say with certainty. What I do know is that there is an overwhelming amount of blood in the markets right now—perhaps more than ever before. Fear is palpable, and uncertainty reigns supreme.

Yesterday marked the largest directional shift in market percentage terms in history, moving from +3% to -4% (approximately) within a single session. These are relative numbers, not absolute ones, but they highlight the extreme volatility we’re experiencing.

This intensifies my concern as it underscores just how precarious this environment is. Such dramatic swings are not just numbers on a screen; they reflect deep structural issues and heightened emotional reactions from market participants.

Taleb’s assertion that things which haven’t happened before can indeed occur seems increasingly accurate in light of recent events. His concept of "black swans"—unpredictable events with massive impact—feels more relevant than ever. It’s interesting to note that those who once criticized us for buying deeply out-of-the-money (OTM) options are now asking why they didn’t follow our lead. The tables have turned, and it’s a reminder that unconventional strategies often only make sense in hindsight.

Beyond all this market chaos, there’s a sense of calm that comes with knowing I’m sleeping more peacefully than ever. Holding a substantial gold position alongside an even larger cash reserve is proving effective—not just financially but psychologically as well. In times like these, peace of mind is priceless.

This week, we’re sending out our newsletter today, Wednesday, instead of Sunday. You won’t receive another until next Wednesday. The reason is simple: we want to share some of our portfolio movements and provide you with timely updates on how we’re navigating this turbulent period. Additionally, we’re excited to report that our options have appreciated by 300-400%. Keep in mind that today’s market hasn’t opened yet, and Trump’s tariffs on China have just been signed—a development that could further shake things up.

As I mentioned on Monday, I believe this will amount to nothing in the long term. Markets have a way of absorbing shocks and moving forward over time. However, in the short term, there’s no denying that there’s significant blood on the streets. Fear-driven sell-offs are creating opportunities for those who can remain patient and disciplined.

Here’s our portfolio performance as of today:

Portfolio Movements