The Pomp Podcast: 95% Deal Wins, Diversification, and AI Investing Insights

Transcripted.ai (0:01)

When markets move fast, the biggest danger isn't just losing money—it's losing discipline. On this episode of The Pomp Podcast, Anthony Pompliano sits down with Christopher Zook, founder and CIO of CAZ Investments. Zook has a striking track record. Over 25 years, his firm has made money on 95% of its realized and unrealized private market investments. That's an incredible success rate. What's his secret? It's surprisingly simple. Remove emotion from the equation. And that brings us to a central theme of their conversation: diversification. Zook calls it "the only free lunch in investing," but he warns that conviction without proper sizing can become a trap. So being early isn't always good? Exactly. Being early can be the same as being wrong if your position is too large to survive volatility. And here's where it gets interesting—Zook pushes back on traditional diversification. If holdings are highly correlated, they're not truly diversified. What does he mean by that? He uses the "Magnificent Seven" tech stocks as an example. If you own all seven, you're still holding seven versions of the same trade. That's why he looks for uncorrelated assets—things that zig and zag differently. Like what specifically?

Professional sports, GP stakes, businesses with low correlation to public markets. He says a portfolio of 8 to 15 uncorrelated assets can dramatically reduce risk while improving returns. His crypto approach follows the same logic—focus on the infrastructure, the picks and shovels, not just speculating on which token wins. That framework sounds like it applies beyond crypto too. It does. In space and defense, Zook describes a shift from legacy primes to faster, cheaper neo-primes like Anduril. He says the era of using a million-dollar missile to destroy a 30,000-dollar drone is over. New defense technology has to be smarter, cheaper, and more autonomous.

And what about sports assets? Why does he see them as valuable? It's not just about owning something cool. Sports is scarce, protected by league structure, and tied to the rise of live streaming where advertisers still need live attention.

Plus, private markets are becoming more accessible. Investors can now own pieces of SpaceX, Anthropic, OpenAI, and sports teams through new fund structures with low minimums. That's quite a shift. What prompted his book with Tony Robbins? The Holy Grail of Investing makes risk management practical.

Fear and greed destroy returns, so the book helps investors think in percentages, not dollar amounts, making allocation mechanical rather than emotional. Did they discuss other sectors?

Energy came up. Zook says, "we are for energy and against poverty," investing across nuclear, storage, and batteries because the world needs more supply.

What's his take on AI and jobs? His warning is clear: "AI doesn't replace people, but people who use AI will replace people."

The real challenge is retraining workers for a future where human judgment, relationships, and creativity matter more than repetitive tasks.