An analysis of Dash's various holdings, which range from fashion to entertainment, turns up more misses than hits.
Dash's CEO clothing line has yet to take off, reality TV show "Ultimate Hustler" aired for one season and bombed in the ratings, and his foray into Hollywood with the movies "State Property" and "The Woodsman" has not produced box office hits, though DVD sales have fared better.
Meanwhile, Dash has pulled the plug on his State Property sportswear line and fledgling record label Damon Dash Music Group, according to spokeswoman Amanda Silverman. "Music is not where the money is," she said.
While a line of designer clothing by wife Rachel Roy has garnered critical acclaim, and a higher profile after Roy appeared on "Oprah," it has yet to turn a profit.
Dash's biggest win so far has been Pro-Keds, a sneaker brand he licensed from Stride Rite in 2004 and which, according to industry estimates, has more than doubled sales in the past year to exceed $22 million.
"It's not that easy to hit a home run every time," said Izzy Ezrailson, a friend of Dash's, who operates a chain of specialty stores.
Nevertheless, those who know Dash say they are not counting him out.
"I think he'll come back strong," said Billy Rudnick, of the Dr. Jay's retail chain, which is considering buying the CEO line, but waiting for Dash to make some adjustments, such as shrinking the logos "so they are not so in your face." Other retailers also said they are holding off on carrying the line to see how it evolves.