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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 stretch-band 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. 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. I guarantee it! 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.

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Bank , a previously discussed merger Zimmer had opposed. Bank could be repositioned as an upscale complement.

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But then the new numbers started coming in, and the stock crashed to the midteens, where it languishes today. Sales at Jos. Bank have plummeted since its new parent eliminated its aggressive buy-one-get-three-free suit promotion, and the heavy debt Men's Wearhouse took on to pay for the acquisition has hampered earnings. In February, the business announced it would restructure as a holding company called Tailored Brands , a move that could better insulate the chains from each other.

Though the Men's Wearhouse unit continues to perform well, Wall Streeters speculate that the company might be headed for bankruptcy. A Barclays analyst recently called it "uninvestable.

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To Zimmer, it's a great "I told you so" moment, made even sweeter by the prospect that he might build something special again with his new companies. But he's hardly moved on. Stifel analyst Richard Jaffe, who's followed Men's Wearhouse for 20 years, says Zimmer has "founder's regret"--a condition that sometimes afflicts entrepreneurs who let go of the reins, causing them to scramble to get hold of them again.

In fact, Zimmer tells Inc. Don't get Zimmer started about those executives. It's impossible to understand Zimmer's journey without understanding his involvement with something called the Institute of Noetic Sciences , which studies "the intersection of science and spirit," as he puts it. It's easy to dismiss Zimmer's interest in noetics as more evidence of his inner stoner. Zimmer, who says he once smoked six joints in one hour with hippie icon Baba Ram Dass, used to inhale "anything that combusts.

But it always comes up as he explains key decisions. If the coldly analytical technocrat is today's model entrepreneur, Zimmer is the opposite. In business, the approach translates to making decisions based on humanistic values, rather than purely economic ones. To Zimmer, bigheartedness was the core of Men's Wearhouse; it was a company built as an extension of his psyche.

Zimmer started opening a store per year around that city for the next decade, and expanded to San Francisco in the early '80s. Apparel was a natural choice for him. His dad worked for a discount clothier, and later started a raincoat company called Royalad Apparel. Zimmer grew up hiding in the clothes racks as his dad visited stores around New York City, and spent summers packing coats in the warehouse.

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In college, he grew his hair into a bushy "Jewish Afro" and got involved with the Vietnam War protest movement. He also joined a fraternity and ran with a more conservative crowd.

In time, he realized that becoming an entrepreneur would allow him to continue nurturing his independent streak and have a respectable career. Zimmer started shaping the company with his philosophies. In the mid-'80s, he decided to break the traditional retail cycle of inflated prices and constant discounting, and establish everyday low prices instead. But by the second year, it started to turn around. Then came those ubiquitous commercials, and then an IPO in , which funded more aggressive expansion. Men's Wearhouse had about stores when it went public, and afterward, 50 or 60 new ones opened each year.

It was anything but a conventional public company: Zimmer's executive team included his brother, who retired last year after 35 years, and his dad, who joined as the head of real estate after Royalad failed. There were old friends, too, including Charlie Bresler, a psychologist in Fresno, California, who joined the company in without any particular job lined up.

Zimmer and Bresler had been tournament bridge players together as kids, and, Zimmer explains, "when you play bridge, you get an intuitive sense about your partner. Policies were designed around Zimmer's values. Eventually, the average store manager got as many shares as top executives. When Zimmer left, turnover among store managers had been around 10 percent for years, compared with an industry average of 25 percent. That message didn't always go over well on Wall Street--his bankers at Bear Stearns warned Zimmer not to talk about his "crazy ideas" on the road show before the IPO--but it didn't stop the company from dominating its category.

When Zimmer was fired, one in five suits purchased in the U. Jaffe, the Stifel analyst, calls Zimmer "lucky and smart," but says the company's success was a function less of Zimmer's management ideas and more of his having perfectly ridden the changing winds in mainstream men's retail. As mall department stores found they could make more money per square foot with in-store brand-name boutiques than they could with large suit departments, Men's Wearhouse swooped in with more convenient and cheaper locations, wider inventory at lower prices, onsite tailoring, and solid service.

Marshal Cohen, a longtime retail analyst with NPD Group who started his career in menswear competing against Men's Wearhouse, uses words like revolutionary for Zimmer.

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He was always saying, 'This is where we're going, folks,' even if it wasn't happening yet. Such a moment came in An employee suggested getting into tux rentals, a segment that had no big national chain. Zimmer saw it as a "minor league" for new customers, one revolving around proms and weddings. Men's Wearhouse already had real estate all over the country and a tailor in each of its stores, so a tux station could be added with little incremental cost. Zimmer was loved at his stores, because the rank and file made good money and he made high-profile efforts to connect with them.

Every year, the company would hold dozens of black-tie holiday balls all over the country, many of which Zimmer would attend, get on the dance floor, and play the fun, famous boss.

It's only going to get worse for Men's Wearhouse.

In the upper ranks, though, Zimmer was known as what one insider calls a "tough son of a bitch. Richie Goldman--one of Zimmer's first hires, who stayed for almost 30 years and ultimately ran marketing--says Zimmer often surprised him with his "sheer genius--his ability to take a step back and see the simple solution that others missed. Even the famous "I guarantee it" line is in dispute.