UNFINISHED BUSINESS
GEORGE ZIMMER, the Men’s Wearhouse founder and besuited TV pitchman, looks a little startled as I enter his office. “Oh!” he exclaims in that famous languid and gravelly voice, and his hand darts up to his desk and shoves something small into a drawer while his assistant stifles a laugh. There’s a distinctly skunky-smelling haze in the air, and the sounds of downtown Oakland, California, waft through the open windows.
It’s been almost three years since Zimmer was abruptly fired by the company he built from a single store into a multibillion-dollar empire, and he’s begun to settle into the world of tech startups. He’s wearing a charcoal suit—from his startup Generation Tux, an online formalwear-rental outfit—that hangs slightly loose in a way that’s breezy rather than ill-fitted, along with a looser-fitting floppy-collared shirt. He explains that the brilliance of this particular suit is a comfy little hidden stretchband on each side of the waist. Women don’t get it, he confides. But men love it.
As comfortable as Zimmer seems in his new life, he’s also tormented by the loss of his old one—and how his longtime boardroom colleagues, in his telling, ambushed and fired him two years after he turned over his CEO role to his handpicked successor, Doug Ewert. After battling with his former board over his ouster, Zimmer launched not one but two startups that compete with Men’s Wearhouse. In addition to Generation Tux, there’s zTailors (the z is for Zimmer)—essentially an Uber that summons tailors for house calls. He has a hundred-some employees and more than $30 million in funding from investors like Salesforce Ventures, and Workday and PeopleSoft co-founder David Duffield.
Zimmer, who’s now 67, says his new companies will utterly transform how people shop for clothes. Whether or not he’s right about that, there’s something comforting in knowing that he’s out there hawking suits again. His face was a near daily presence on TV for decades, and that reliable promise—“You’re gonna like the way you look. I guarantee it”—was a nice safety net. You knew he’d be there if you needed him.
Which is probably why his dismissal became such a sensation. Late-night host Jimmy Kimmel said it was like firing Santa Claus. “You lost my business. I guarantee it!” became a refrain on Facebook. At first, the board offered no public explanation for the firing. Eventually, it announced that Zimmer had left it no choice: He had become an obstructionist bent on retaking the authority he’d ceded to Ewert.
For a time, the board looked smart. The company paid $1.8 billion to acquire competitor Jos. A. Bank, a previously discussed merger Zimmer had opposed. From the time Zimmer was fired to mid-2015, the stock price nearly doubled,
