In finance circles, Tom Lee has built a reputation for bullish, audacious and arguably fantastical bets—the S&P 500 index more than doubling by 2030 or Bitcoin reaching $3 million (versus roughly $90,000 today) during that same stretch. But when it comes time for us to make our way from his Midtown Manhattan office to the New York Stock Exchange, on the island’s southernmost tip, Lee is undeniably a realist. At this late-afternoon hour, he knows a brisk 10-block walk to the express train is a much better bet than the hired car his chief marketing officer has suggested we hail. “The train’s always faster,” Lee says.

It’s a chilly November day, and Lee—sporting his trademark dark suit, black-rimmed glasses and famously voluminous hair—has just wrapped up a jam-packed day of meetings at his research firm, Fundstrat Global Advisors LLC, including a tight 50 minutes with me. His office is flanked by a quartet of 6-foot camera lights for his frequent appearances as a contributor on CNBC, but I’m more surprised by a different furnishing: Tucked into a corner is a small bed, added four years ago as a refuge after long-haul flights.