In a volatile, rapidly rising market, an 'options crawl' strategy allows investors to stay in the trade while managing risk. It involves selling expensive, high-strike calls that speculators are buying and using the proceeds to finance calls closer to the current price, thus maintaining directional exposure with a defined risk profile.
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Instead of making large initial bets, a more effective strategy is to take small, "junior varsity" positions. Investors then aggressively ramp up their size only when the thesis begins to demonstrably play out, a method described as "high conviction, inflection investing."
A portfolio's performance can be dramatically enhanced by combining traditionally separate strategies. A leveraged mix of equities (S&P), hedges (long volatility), and trend-following strategies can produce returns that are multiples higher (e.g., 40x) than equities alone (e.g., 6-7x) over the same period.
In an environment characterized by a series of sector-specific bull runs (e.g., from semis to metals), a winning strategy is to actively trade breakouts as they occur. This capitalizes on rotational leadership and momentum rather than relying on a static portfolio.
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.
Extremely low realized volatility is fueling systematic buying. Simultaneously, hedging demand has pushed implied volatility to 99th percentile highs. This creates a large premium for options sellers, turning short volatility strategies into a consistent yield-generating trade in the current market environment.
Investors should establish a baseline risk level on a 0-100 scale based on personal factors like age and wealth. This becomes their default posture. The more advanced skill is then to tactically deviate from this baseline—becoming more or less aggressive—based on whether the prevailing market environment is offering generous or precarious opportunities.
To manage the risk of volatile or 'bubble' stocks, investors should systematically take profits until their original cost basis is recovered. After this point, any remaining shares represent 'house money.' This simple mechanical rule removes emotion and protects principal while allowing for continued upside exposure.
The most important market shift isn't passive investing; it's the rise of retail traders using low-cost platforms and short-term options. This creates powerful feedback loops as market makers hedge their positions, leading to massive, fundamentals-defying stock swings of 20% or more in a single day.
Dan Sundheim argues that while retail-driven markets create more shorting opportunities, the risk of a coordinated squeeze makes concentrated shorts too dangerous. The modern strategy is to hold a much more diversified portfolio of smaller short positions to survive extreme, irrational price moves that can 10x or 20x.
In markets dominated by passive funds with low float, retail investors can create significant volatility by piling into call options in specific sectors. This collective action creates "synthetic gamma squeezes" as dealers hedge their positions, making positioning more important than fundamentals for short-term price moves.
