Jeffrey Gundlach, Bond Savant

DoubleLine Capital’s new office is high up in a downtown Los Angeles skyscraper, with unobstructed views of the famous Hollywood sign. As you walk out of the elevator, a huge canvas with the firm’s logo greets you; DoubleLine founder Jeffrey Gundlach painted it himself. Pass a six-foot-tall faux terra-cotta Chinese warrior and you’ll find a conference office called the Van Gogh Room. The Van Gogh Room has no Van Goghs, though it does display a pair of landscape paintings and looks out to a reception area adorned with other paintings Gundlach won at auction. It also, on this visit, contains Gundlach, sitting at the end of the conference table in a crisp button-down shirt, with a goatee and rust-colored hair, cut short.

The idea was to interview Gundlach, whose company is the fastest-growing mutual fund startup in history, but the conversation quickly turns into a kind of test. Gundlach wants you to know he is a connoisseur of fine art. He also wants you to know you don’t know squat.