So here's a story that will make any investor wince. Anthony Scaramucci recently revisited a moment from 1999 that, frankly, still stings. He was at Sun Valley, he says, and watched Jeff Bezos pitch Amazon (AMZN). He was impressed. He took pages of notes. He decided he needed to buy. And then... he heard Warren Buffett question Amazon's valuation compared to Sears.
And just like that, Scaramucci tore up his notes and abandoned the idea. You can probably guess the punchline. Sears is gone. Amazon is, well, Amazon. Scaramucci did the math: a $10,000 investment in Amazon that day would have been worth roughly $16.5 million by last Saturday morning. Ouch.
But here's the part that really makes you think: that ride to $16.5 million wasn't a smooth one. Scaramucci points out it would have included eight separate drawdowns of 50% and one gut-wrenching collapse of 90%. The key, he says, wasn't just picking the stock; it was staying in through all that chaos.
Why This Old Story Matters for AI Right Now
Scaramucci isn't just telling this story to torture himself (or us). He's telling it because he thinks artificial intelligence is sitting at a moment that feels eerily similar to the mid-to-late 1990s. It's defined by big price swings, unclear ultimate winners, and, yes, plenty of skeptics who think it's all hype.
His view is that this is exactly the kind of messy, volatile setup where long-term fortunes can be built. He's buying AI investments anyway, applying a lesson learned the hard way. In his framework, market bottoms often form while pessimism is still screaming, because too many investors remain positioned too cautiously, waiting for perfect clarity that never arrives.
So the Amazon story transforms. It's less about a single missed stock pick and more about the endurance required to hold through the violent drawdowns of a truly transformative trend. The early narrative for Amazon sounded implausible to many—an absurdly expensive online bookseller. Bezos, as Scaramucci recalls, wasn't just selling books; he was using the logistics of shipping uniform products to secretly map out a nationwide distribution network, a "trojan horse" for far bigger ambitions. The AI comparison leans on the same idea: the winning long-term plays can be right there in plain sight, even when the early headlines are all about uncertainty.
Politics, Markets, and the Feedback Loop
Scaramucci has also been connecting current market volatility to geopolitics, arguing that markets and President Donald Trump can operate in a feedback loop where each reacts to the other's signals. He's described a potential "off-ramp" scenario where a political declaration could set the stage for de-escalation.
In that case, he outlines steps aimed at calming oil markets—reopening key shipping straits, naval escorts involving France and the U.S., and an insurance backstop to reduce shipping risk. The idea is that energy is the main channel through which this kind of conflict feeds into broader market sentiment; oil flows don't fully normalize until the fighting stops.
He tied this sensitivity to a timeline from Mike Novogratz, suggesting the conflict could be broadly finished within a week, and that a political victory lap could spark a market rally that looks "like that was the plan all along." He's also warned previously that a U.S. strike on Iran could jolt energy prices higher and create knock-on effects, like pressure to loosen constraints on Russian oil—a move he said could aid Moscow and complicate U.S. operations.
The One Investment Lesson From a $16.5 Million Miss
Circling back to 1999, the core failure wasn't a lack of research. Scaramucci did the work, filled those pages of notes, and felt certain. The failure was letting a popular critique—even one from Warren Buffett—override his own analysis. Buffett's comparison to Sears' vast brick-and-mortar footprint pushed him to abandon the trade, missing the point that Bezos was building something entirely new.
Scaramucci's post treats the missed Amazon buy as a stark reminder: the hardest part of catching a transformative trend is often just sitting through the drawdowns. He's connecting that lesson directly to his AI stance today. When uncertainty is the headline, he'd rather accept the volatility than repeat the mistake of walking away because the skeptical chorus got too loud.
It's a lesson in conviction, endurance, and the high cost of consensus thinking. And for anyone looking at the wild swings in AI stocks today, wondering if it's all too risky, it's probably a lesson worth remembering.
