March Madness has more random outcomes than trying to pick a startup company to invest millions into, so filling out brackets takes more than just a bet on probability. The best minds in finance have very different approaches when it comes to picking the winners of the NCAA basketball tournament.
Some rely on pure luck and find it fun whether they end up on the bottom or not; some are really dedicated to their alma mater and pick them blindly no matter the seed.
And some choose to outsource their bracket "like any good PE manager, I just try to find the best talent to get the job done," said Jonathan Gray, Blackstone's president and chief operating officer.
Gray is competing in the 11th year of Bloomberg's Bracket for a Cause, where participants play for a charity of their choosing, pledging $20,000 each for a total of more than $1.2 million to be donated.
Even though they are playing for charity, the edge for hedge fund managers, CEOs and investment bankers are all similar: They want to win.
The men's bracket proved to be a minefield of upsets, leading to disappointment for executives whose favorites, like Duke, suffered early exits.
The women's side, however, saw a much more predictable Final Four, with all four No. 1 seeds advancing, validating the strategy of picking top-tier power programs. The semifinals begin with the women's tournament on Friday and culminate in the men's final on Monday.
"I went to a small school, so it helps that I'm not emotionally attached to any of the usual contenders," said David Solomon, chief executive officer of Goldman Sachs.
He entered the semifinals in the top four in both the men's and women's brackets. "I always consult the people around me to help me make my decisions and then I make my final picks. A lot of people told me to pick Duke, but I went with Florida. Turns out, we were all wrong."
Ryan Tolkin, CEO & Chief Investment Officer of Schonfeld Strategic Advisors, said that alma maters often prove to be a hindrance.
Regarding the men's side of the bracket, Tolkin, a Duke alum, stated: "I'm always going to go with Duke, my alma mater, whether they're number 1 or 64. Unfortunate outcome this year, but I fully expect they'll come back even stronger next year."
Debra Cafaro, Ventas Inc. chairman and CEO, brings an approach rooted in actually owning teams. Her passion for sports extends beyond basketball, as she is also an owner of the Pittsburgh Penguins, Baltimore Orioles and Chicago Stars FC.
"Women's basketball power programs are incredibly hard to topple, which is the philosophy behind my bracket picks," said Cafaro, who sits in third in the women's tournament and has Connecticut winning it all.
"Having Notre Dame, my alma mater, upset Ohio State and Vanderbilt gave my bracket a real boost. With all four No. 1 seeds in the Final Four, I just need Texas to beat the UCLA women for a second time this season and hope the UConn juggernaut can bring home another title to finish in the money for the Greater Chicago Food Depository," she added.
For many, the complexity of picking winners is secondary to the simple fun of participating, proving that even finance executives can take a loss more easily on a spreadsheet than they might on a bracket.
"I've been at the bottom of the pack; I've been at the middle of the pack; and this year I got lucky," said Solomon, who finished outside the top 40 on both sides of last year's Brackets for a Cause. "The bottom line is these brackets are all about luck but it's a lot of fun."
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