Anthony Scaramucci has argued that his costliest habit in markets has been exiting positions too soon, and urged investors to stick with a simple plan: buy an S&P 500 index fund and hold it for decades. He has also pointed to his own missed Amazon call — where a $10,000 Amazon investment made that day could have grown to $16.5 million —t o show what patience can capture even after brutal drawdowns.
In his late-night post on Friday, Scaramucci said his advice is to let the S&P 500’s rules do the heavy lifting rather than trying to outsmart the cycle. he wrote that the index already filters for size and business strength, and that investors can focus on owning it instead of constantly trading around headlines.
He framed the index as a built-in upgrade mechanism, noting that companies can be removed when they no longer meet the bar. Scaramucci added that he bought his first S&P 500 index investment roughly 30 years ago and still owns it.
Why Timing The Market Is A Mistake
That message lines up with a separate regret he has described from 1999, when he said he listened to Jeff Bezos explain Amazon’s logistics-driven ambitions and left convinced he should invest. He later said he backed off after Warren Buffett criticized the valuation by comparing the company to Sears, and Scaramucci ultimately walked away from the idea.
Scaramucci has since run the numbers on what he passed up, saying $10,000 put into Amazon (NASDAQ:AMZN) at that moment would have been worth $16.5 million by Saturday morning. He has also said the path would not have been smooth, describing eight separate 50% drops and one plunge of about 90% along the way.
In that framing, the lesson isn’t about finding a perfect entry point as much as surviving the ugly stretches that test conviction. Scaramucci has said he has lived through nine bear markets, and that sentiment can swing far past what fundamentals justify while investors stay positioned too defensively.
Geopolitical Factors Shaping Market Recovery
Scaramucci has previously discussed the intricate relationship between markets and President Donald Trump, emphasizing that they influence each other in a reciprocal manner. He noted that Trump could declare victory at any moment, potentially leading to a market rally, as seen in past instances where such narratives significantly shifted sentiment, creating conditions for recovery. This dynamic illustrates how geopolitical factors, particularly concerning energy markets, can play a crucial role in shaping investor sentiment.
In earlier statements, Scaramucci pointed out that military actions may disturb energy supply, which could complicate market recovery efforts. He described scenarios where de-escalation could stabilize oil prices, underlining the importance of energy dynamics in his broader analysis of market sentiment and positioning during turbulent times.
Is Index Investing The Ultimate Strategy?
In the Friday post, Scaramucci’s core point was that the hardest mistakes often come from selling, not buying. He described a straightforward “formula” built around owning high-quality assets and resisting the urge to cash out early.
He has also connected that endurance mindset to what he sees as a new long-duration opportunity in artificial intelligence. Scaramucci has compared the current AI setup to an early-stage phase like the mid-1990s, with big price swings, loud skeptics, and outcomes that are still unclear.
Rather than waiting for certainty, he has said he is buying through the volatility anyway, aiming to avoid repeating the Amazon experience where a widely shared critique overpowered his own work. The throughline across both examples is that the long-term payoff can depend on staying invested when the tape looks chaotic.
How Geopolitics Shape Market Sentiment
Scaramucci has also tied market turbulence to political and geopolitical catalysts, arguing that markets and Trump can react to each other in a feedback loop. In that view, he has described an “off-ramp” where Trump could claim a win and shift the narrative toward de-escalation.
He has outlined steps he believes could cool energy risk quickly, including reopening the Strait, adding naval escorts involving France and the U.S., and creating an insurance backstop to reduce shipping risk and ease crude prices. He has also warned that oil flows may not normalize until fighting ends, making energy a key channel into broader investor sentiment.
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