Buying VOO Near All-Time Highs Could Still Be a Smart Move

The article argues that despite the S&P 500 being near record highs (early June), investors face greater risk from staying on the sidelines than from entering near highs. Using Invesco research, a $100,000 S&P 500 investment (1995-2025) could fall from ~$1.9M to ~$855k if it missed the market’s 10 biggest single-day gains, implying the cost of absent best days can be more severe than short-term pullbacks. The piece expects any weakness after stepping in to be temporary and emphasizes staying invested.

Analysis

This is a flow story more than a fundamental one: when benchmark indexes grind to highs, the mechanical bid from retirement contributions, model portfolios, and trend-following sleeves tends to outweigh valuation anxiety. That favors the most liquid momentum beneficiaries — mega-cap growth and index heavyweights such as NVDA and NFLX — while leaving less-liquid segments more exposed to any air pocket because they do not have the same passive demand cushion.

The second-order risk is crowding, not exhaustion. Advising investors to stay fully invested works until a macro surprise forces a synchronized de-risking, at which point the same "best days" logic flips into a violent squeeze higher after the drawdown. In practice, that means the market can look resilient for weeks, then gap lower on a single inflation/jobs miss; the near-term downside is days to a few weeks, but the structural bull case for index ownership remains 6-18 months.

Contrarian take: this kind of message usually appears when cash balances are already low and fear-of-missing-out is doing the heavy lifting. The consensus may be underestimating how narrow leadership can get before breadth breaks, which is why equal-weight and small caps can lag even if SPY holds up. If breadth broadens, the article is right; if not, it is a late-cycle sentiment tell rather than a green light to add aggressively at any price.

Key Decisions for Investors

• Keep core SPY/VOO exposure intact; add only on 1-2% pullbacks over the next 2-4 weeks rather than chasing highs. Thesis fails if SPY loses its 50-day moving average on rising volume.
• Express the leadership-breadth view with a 1-3 month pair: long QQQ / short IWM. Works if mega-cap momentum stays dominant; invalidate if Russell 2000 reclaims its 200-day average and breadth improves.
• Buy limited-cost downside protection via 1-2 month SPY put spreads when implied vol is cheap. This is a hedge against the crowded-position unwind, not a directional bearish bet; expect decay if the tape stays orderly.