Michael Bloomberg, the visionary entrepreneur, philanthropist and three-term New York City mayor, has a well-meaning, if mildly foolish, grandad-style oh-my-better-half-is-so-much-better joke that he used to utter in the company of close friends, sources who have heard the remark say. Referring to his elegant longtime domestic partner, Diana Taylor, the often gruff and blunt billionaire would lovingly quip about how he only wished that she could find someone else so that, at his advanced age, he could hit the market again. 

It was a silly and harmless joke, meant to get a knowing wink kind of a laugh. Indeed, as anyone in Manhattan society well knew, Taylor was the far more charming and telegenic member of the couple. But it also may have insinuated Bloomberg’s perpetually restless and youthful energy that has not ebbed since he built the Bloomberg L.P. empire forty years ago.

Preternaturally technocratic, now 81, Bloomberg remains one of the most tireless and ambitious people in the game to this day, and he does not sit still for long. Upon returning to his namesake company after 12 years as mayor, he forewent any sort of sinecure and took back the reins of his company, only to start floating the idea of a presidential bid two years later. He finally ran for president in 2020, at the end of a protracted and highly public will-he-or-won’t-he period, spending nearly $1 billion of his own money in the process before being cut down to size by Elizabeth Warren in Las Vegas. (Funny how fast you can lose a fortune in that town.)