You Can Win in Business Without Being Unhinged

I’ve read and watched many stories about the most heralded business leaders of the past few centuries. I’m not immune to the inherent drama of an arrogant rise, a spectacular fall or both. But usually — especially with books like Walter Isaacson’s biographies of Steve Jobs and Elon Musk and the screenwriter Aaron Sorkin’s portrayals of Jobs and Mark Zuckerberg — I’m so appalled by the gratuitous cruelty of these (usually) men that I need to hit pause on the movie or put the book down in disgust.

In too many narratives, the “move fast and break things” ethos of Silicon Valley is taken as gospel, and the things are often people who are being tormented for sadistic pleasure. (For example, harassing job interviewees, firing people in front of crowds, attacking former employees of companies they purchased. Sometimes even animals are treated horribly in the pursuit of innovation.)

As Jill Lepore pointed out in her delicious review of Isaacson’s Musk biography, these accounts have the tendency to suggest that you need to be a jerk to get anything done as a founder or leader:

I was thinking of Lepore’s take when I read Marisa Meltzer’s new best seller, “Glossy: Ambition, Beauty and the Inside Story of Emily Weiss’s Glossier.” While Meltzer doesn’t argue that building a new beauty company is the same thing as, say, revolutionizing telephone technology, she manages to portray a balanced vision of leadership and burning ambition without falling into empty rah-rah clichés. Meltzer neither demonizes nor valorizes Weiss, showing that it’s possible to create a readable and propulsive book that admires a founder’s business acumen and market strategy without excusing her missteps as somehow a necessary byproduct of success.

If you’re unfamiliar with Glossier, you are probably not a woman under 45. Weiss emerged in the public consciousness as an industrious intern on several episodes of the mid-aughts reality show “The Hills.” Her intimidating East Coast competence as a Teen Vogue underling made her “the capable foil to the jejune Lauren Conrad and Whitney Port,” as Hunter Harris explained in her review of “Glossy” for The Times.

Weiss didn’t parlay that appearance into a reality TV career. Instead, after working briefly in the fashion media industry, she started her own beauty website, Into the Gloss, and used the success of that site to start her beauty brand, Glossier.

According to Meltzer, what Weiss intuited was that there was a “dwindling divide between the expert versus the customer” in the beauty space, and the brand she started was appealingly approachable. It was “no-makeup makeup,” meant to look natural and effortless. “The brand’s voice was that of your older sister,” Meltzer explains, “or, more accurately, the coolest friend who knew that trying too hard was antithetical to being cool.”

Meltzer says that on the strength of “hero products” — “the signature best sellers of a company” — like the cream blush Cloud Paint and the eyebrow gel Boy Brow (both of which I own), by 2019, Glossier had over a billion-dollar valuation. Considering that “less than 2 percent of venture capital investment went to all-female founding teams in 2021 (itself a five-year low),” as Meltzer writes, this was a tremendous feat.

So how did Weiss get there? In Meltzer’s telling, she has a “stupendously type-A personality,” and she was never afraid to ask people for exactly what she wanted in a sometimes startlingly — even off-puttingly — direct manner. As a manager, Weiss seemed fine. There was the pressure that comes with working for a start-up, and Meltzer catalogs the legitimate gripes that especially the retail workers at Glossier’s brick-and-mortar shops had with management’s lack of support concerning obnoxious, sometimes racist, customer behavior. But, Meltzer told me on the phone, “most people seemed pretty happy with working there.”

The corporate employees had to contend with a lot of fickleness about the direction of the company. But having worked for start-ups myself, I think it’s fair to say that comes with the territory for a new brand and that most white-collar workers signing up for a new company know there will be less stability but more opportunity. Weiss was also learning on the job — she had very little work experience when she started her own companies — and sometimes that showed, Meltzer told me. Weiss could be melodramatic, bursting into tears occasionally when interviewing candidates because of how demanding and important she felt the work was. But she wasn’t a jerk and didn’t seem to revel in tormenting her staff, Meltzer said.

The retail staff experience at Glossier was more of a mixed bag, Meltzer said, but that can be the case for many service sector workers contending with entitled nightmare shoppers. Still, when Glossier had to furlough and then lay off retail staff members during the shutdown summer of 2020, a retail employee told Meltzer, “Glossier actually handled it better than any company I read about,” adding: “They kept us on payroll until August. They paid us normally until July and furloughed us until the end of August, and then we could file for unemployment, and they gave us severance — even for part-time employees — and all of our sick and vacation hours.”

It’s notable, even if we shouldn’t be too ecstatic in praising a company for what should be the bare minimum in terms of treatment of its work force.

Weiss left her perch as Glossier’s chief executive in 2022, but the brand remains powerful, and some of its products are staples for many women. She wasn’t deposed like some of her fellow girlbosses (a condescending term I hate) — a “raft of mediagenic women with their own venture-capital-backed, millennial-focused products” who moved aside amid “allegations of racism and toxic leadership,” as Alisha Haridasani Gupta reported for The Times in an article about Weiss’s resignation.

While Weiss spoke to Meltzer for “Glossy,” she seemed allergic or unwilling to introspect about her role as an executive — but that may be because she knows that whatever she says will be scrutinized to death and she wants to preserve the ability to get funding for her next act. “Female founders are under unbearably hard pressure to be seen as powerful and perfect,” Meltzer writes. “Which is not to say that the bad behavior of the girlbosses or the behavior of their companies is OK — it’s not; I believe they were terrible managers and behaved badly. Bad behavior is still a cardinal sin for women if it is exposed.”

Somehow, for famous (or infamous) male C.E.O.s, capriciousness can add a gloss to their legend.

Perhaps if we see fewer hagiographies about male executives and tycoons, we might begin to hold them to the same standards we seem to hold female captains of industry to. We shouldn’t continue to accept the fiction that there’s some mystical correlation between being a great leader or highly successful in business and being mercurial or an outright brute.

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