In the post on X he wrote that Wall Street dismissed Amazon as an absurdly expensive online bookseller, while Bezos laid out a logistics-first strategy built around shipping uniform products to map out warehouse placement. Scaramucci said he filled pages of notes and felt certain he should invest, but tore them up after Buffett’s remarks.

He also pointed to the punchline: Sears is gone, while he calculated that a $10,000 Amazon investment made that day would have been worth $16.5 million by Saturday morning. Scaramucci said the ride would have included eight separate drawdowns of 50% and one collapse of 90%, but the key was staying in.

Scaramucci said he’s telling the story because he thinks artificial intelligence is sitting at an early-stage moment that feels like the mid-1990s. He described a setup defined by big swings, unclear outcomes and plenty of skeptics, and said he’s buying anyway.

That appetite for messy price action also shows up in his market-cycle framework, where he has argued that bottoms can take shape while pessimism is still loud because many investors remain positioned too cautiously. Scaramucci has said he has lived through nine bear markets and has watched sentiment overshoot what underlying conditions warrant.

In that lens, the Amazon episode becomes less about a single stock pick and more about endurance through violent drawdowns. His AI comparison leans on the same idea: early narratives can sound implausible, yet the long-term winners can still be built in plain sight.

Scaramucci has also tied volatility to geopolitics, arguing that markets and Donald Trump can operate in a feedback loop where each side reacts to the other’s signals. He has described an “off-ramp” where Trump could declare victory and set the stage for de-escalation.

In that scenario, Scaramucci outlined steps aimed at calming oil markets: reopening the Strait, naval escorts involving France and the U.S., and an insurance backstop designed to reduce shipping risk and help pull crude prices down. He has argued that oil flows don’t truly normalize until the fighting stops, making energy the main transmission channel into broader market sentiment.

Back in 1999, Scaramucci said Bezos wasn’t just selling books; he was using standardized shipments to reverse-engineer a distribution network, a strategy Scaramucci characterized as a trojan horse for much bigger ambitions. He said Buffett’s comparison to Sears’ brick-and-mortar footprint pushed him to abandon the trade.

Scaramucci’s post treated the missed Amazon buy as a reminder that the hardest part of a transformative trend can be sitting through the drawdowns, according to X. He connected that lesson to his AI stance: when uncertainty is the headline, he’d rather accept the volatility than repeat the mistake of letting a popular critique override his own work.