Bloomberg Creative Photos/Getty Images
Investor’s Guild
Investor’s Guild

Umbrellas for a summer market

Umbrellas for a summer market

Friday, June 5, 2026 by Stephanie Guild, CFA and Maddie MahoneySteph is Chief Investment Officer. Maddie is an investment strategist. Both are Wall Street alums.
Bloomberg Creative Photos/Getty Images
Bloomberg Creative Photos/Getty Images

Here in NYC the weather is finally looking up. Just like investing in the market has felt since the end of March, it feels good to walk the streets in a t-shirt and let the sun warm you up. Of course, we haven’t yet gotten to the dog days of summer. These are days when the humidity smacks you in the face as you walk outside, and the only relief is when a late afternoon thunderstorm clears it away.

And because of that humidity, it's often a good idea to carry an umbrella with you in the summer. But these are easily forgotten. And then you find yourself buying one from the guy who came out of nowhere standing by the subway stairs as you see the rain pouring down, conveniently charging you $20 for one. 

Should have bought that umbrella when it was sunny. 

Lately, the cost of caution has been visible. In our own proprietary factors, we’ve seen a great disparity in the types of US stocks. 

The gap between stocks exhibiting strong momentum and nearly everything else, particularly stocks that exhibit low volatility, as defined by MSCI’s indices, has been extremely wide over the last three months.

While for the previous 3 months (Dec 2025 to Feb 2026), for example, the difference in return between quality and momentum factors was 2.4%, not 24%. We believe that gap is worth considering, not as a trade, but as a market-behavior observation. The discipline lesson for long-term portfolios may not be to abandon balance. It's to recognize that diversification has a cost in (narrow-ish) rallies, and that cost is the price of being there, if and when leadership eventually rotates.

And narrow is the operative word. Of the AI-oriented companies we track, not including the materials and industrial names that benefit from the build out of AI, they are up on an average weighted basis, 28% in the last month, versus the 5.5% or so from the S&P 500 (both through June 4th).

The dominant question among investors has been FOMO, instead of fear—from "how do I protect against losing money?" to "how do I avoid missing more upside?"

Until today, the VIX has stayed near the lower end of its recent range through May, even as the S&P 500 has hit new highs. So it’s no wonder the cost of protection against a sudden crash dropped to its lowest level this year. 

The CBOE Skew Index measures the perceived tail risk of the S&P 500. It focuses on "out-of-the-money" (OTM) put options that investors tend to buy to insure their portfolios against a severe crash. Current levels are the lowest in 3 months and similar to February, prior to the conflict in the Middle East. On the other hand, demand for bullish calls has proved relentless, as the market’s optimism remains.

It's understandable. Fundamentals look strong: forward S&P 500 EPS estimates are up roughly 15% YTD through May, a revision pace more typical of a post-recession rebound than a mature expansion. Per Factset, Q1 earnings grew 29% year-over-year—more than double the 13% expected at the end of March. Net profit margins hit 14.8%, the highest the S&P 500 has reported since FactSet began tracking the metric in 2009. But there are real headwinds: inflation worries are resurfacing, “Middle East” mentions on Q1 earnings calls hit a decade high, and 30-year mortgage rates just made a fresh nine-month high.

It’s not a terrible time to consider buying that umbrella.

For portfolios, the 3 Rs still frame how we're thinking. We are still focused on the Receivers of AI capex; semis, networking, electrification, and Resources. Recoveries, such as in select software and healthcare, are the umbrellas for us. 

Make sure the FOMO doesn’t catch you in the rain without $20 cash.

More from Investor's Guild
The information provided here is for general informational purposes only and is not an individualized recommendation of any security, digital asset, or investment strategy. Expressions of opinion are as of this date and are subject to change without notice. There is no guarantee that these statements or opinions provided herein will prove to be correct. Past performance is no guarantee of future results. Investing involves risk including loss of principal. Diversification does not ensure a profit or guarantee against a loss. Information shown is as of a certain date and represents a point in time. Data will generally not be updated after publishing. Data is obtained from what are considered reliable sources. However, its accuracy, completeness, or reliability cannot be guaranteed. Supporting documentation for any claims or statistical information is available upon request. Keep in mind that individuals cannot invest directly in any index, and index performance does not include transaction costs or other fees, which will affect actual investment performance. Options trading entails significant risk and is not appropriate for all investors. Customers must read and understand the Characteristics and Risks of Standardized Options before engaging in any options trading strategies. Certain complex options strategies (including multi-leg) carry additional risk and complexities including the potential for losses that may exceed the original investment amount. Robinhood Financial does not guarantee favorable investment outcomes. The past performance of a security or financial product does not guarantee future results or returns. Customers should consider their investment objectives and risks carefully before investing in options. Because of the importance of tax considerations to all options transactions, the customer considering options should consult their tax advisor as to how taxes affect the outcome of each options strategy. Supporting documentation for any claims, if applicable, will be furnished upon request. 5557204