The term "trend following" misrepresents how managed futures generate alpha. Their value lies in identifying and taking early, contrarian positions on major macroeconomic shifts—like rising rates or currency devaluations—before they become consensus, allowing them to profit when the world changes significantly.

The most profitable periods for trend following occur when market trends extend far beyond what seems rational or fundamentally justified. The strategy is designed to stay disciplined as prices move to levels few can imagine, long after others have exited.

Investors frequently give up on trend-following strategies after a few flat years, right before they rebound. This is attributed to a deeply ingrained behavioral bias to chase recent performance, which causes them to sell low and miss the subsequent recovery, ensuring they underperform the strategy.

Investors mistakenly view trend following solely as a defensive 'crisis alpha' tool. Its primary benefit is actually offensive: providing dynamic exposure to the significant upside trends (the 'right tail') in asset classes most portfolios lack, like commodities, currencies, and foreign bonds.

Many trend followers only trade stock market indices, which dilutes performance by averaging all constituents. Trading individual stocks provides far greater potential for capturing extreme outlier moves, both long and short. An index, by definition, mutes the very trends the strategy seeks to exploit.

“Crisis Alpha” is not a guaranteed hedge but the result of a managed futures strategy successfully capturing extreme macroeconomic shifts. The strategy is fundamentally about following major macro themes, with a crisis simply being one of the most intense themes it can follow.

Unlike other sources of alpha, trend following is difficult to arbitrage away. The guest argues that as more people adopt the strategy, their collective actions tend to amplify and extend existing trends, creating a self-reinforcing dynamic rather than a diminishing one.

A core tension in systematic trading is that while the rules are profitable over thousands of instances, they offer no specific insight for the single trade you're focused on now. Trend following is explicitly bad at satisfying the psychological need to optimize the present moment, which is why it's so hard to follow.

Combining managed futures with equities in a single product makes the strategy easier for investors to hold behaviorally. However, this “smoother ride” comes at a cost: it dilutes the powerful, anti-correlated impact that a pure-play managed futures strategy can have during a significant market downturn.