Staples

When the board and management fight, nobody serves the customer

Segal's first million came from a private equity deal with Tom Stemberg (Staples founder) at Highland Capital, but the partnership soured as his cousin wanted family members in while Segal wanted a meritocracy. The company went public partly so the PE group could exit and the warring parties could separate.

“And when your management team and your board are fighting with each other, you're not focused on creating value for your customers. And I just want to get out of there. There are too many bullets flying.”