Case Study 22-1: The Wing — How a Co-working Space Used Social Media Visibility to Create Disproportionate Luck

DataField.Dev

Overview

In 2016, Audrey Gelman and Lauren Kassan launched The Wing: a network of co-working and community spaces designed exclusively for women. The concept was not novel — co-working spaces had been a growing market since WeWork's 2010 founding, and women-focused networking organizations had existed for decades. The market was saturated, the capital requirements were high, and the odds of success, by any conventional analysis, were not favorable.

Within three years, The Wing had raised $117 million in venture capital, opened locations in New York, San Francisco, Washington D.C., Boston, Chicago, London, and Toronto, and secured a valuation of approximately $375 million. It had a waitlist of thousands of potential members. Its name was recognized internationally by people who had never entered one of its spaces.

The Wing did not succeed primarily because it invented a better co-working space. It succeeded, in substantial part, because it understood — intuitively, strategically, and in practice — how social media visibility could create disproportionate luck in a saturated market.

The Starting Position: A Saturated Market

To understand how unusual The Wing's rise was, it's useful to start with the competitive landscape.

By 2016, the co-working market was genuinely crowded. WeWork, already a dominant player, had locations in dozens of cities and was on its way to becoming one of the most heavily funded startups in history. IWG (formerly Regus) had thousands of flexible workspace locations globally. Hundreds of independent co-working operators had carved out local niches. The barriers to entry were not technical — anyone could rent commercial space and furnish it. The barrier was differentiation, and the market had already seen every obvious form of it.

Women-focused professional networking organizations were similarly well-established: 85 Broads (now Ellevate), Lean In circles, PPWN (Professional and Personal Women's Network), and dozens of local organizations existed across the country. The problem these organizations addressed — women's professional community and advancement — was recognized and had attracted substantial organizational attention.

Entering both of these markets simultaneously with a premium-priced product (Wing membership cost hundreds of dollars per month) was, in business school terms, fighting on two fronts against entrenched competitors.

What Gelman and Kassan understood that their competitors didn't was how the luck physics of the social media era had changed the rules of brand-building.

The Wing's social media presence was not an afterthought to its physical spaces — it was co-designed with them.

The Aesthetic Signal: The Wing's interiors were designed specifically to be photographed. The deep rose color palette, the custom furniture, the neon signage (most famously, "Nevertheless, She Persisted"), the carefully curated library, the branded merchandise — every element was conceived not just for the in-person experience but for the visual language of Instagram in 2016–2018.

This was strategic aesthetic design for platform luck. Instagram's algorithmic distribution at the time rewarded distinctive visual content that generated high engagement. The Wing's spaces were intrinsically photogenic in a way that most co-working spaces (designed for function) were not. When members posted photos of themselves in The Wing, the images carried a strong aesthetic signal that differentiated The Wing instantly from every competitor.

The result: The Wing's Instagram presence was substantially built by its own members, without traditional advertising spend. Members who photographed themselves in the spaces effectively recruited other potential members — generating authentic word-of-mouth through a platform that could distribute it at scale.

The Community Signal: Gelman, as a media-world figure (she had been president of the company behind feminist magazine The Cut), had personal social capital in exactly the communities The Wing was targeting. She was credible to media women, to political women, to entrepreneurial women. Her existing network gave The Wing's social media presence an initial authority and reach that a founder without that network could not have manufactured.

This is structural hole bridging in action: Gelman spanned multiple professional communities (media, politics, entrepreneurship, venture capital) and used those bridges to simultaneously distribute The Wing's story to multiple high-value audiences.

Network Effects and Viral Growth

Once The Wing had achieved initial visibility through its aesthetic and founder network, a different luck mechanism kicked in: network effects.

Network effects occur when a product or service becomes more valuable as more people use it. For The Wing, the mechanism was community-based: the more prominent, high-achieving women became members, the more valuable membership became for other prominent, high-achieving women who wanted access to that community.

This created a self-reinforcing cycle: 1. Prominent women joined → membership gained status signal 2. Status signal attracted more prominent women → community quality increased 3. Increased community quality increased media coverage → attracted more prominent women 4. Media coverage increased institutional credibility → attracted venture capital 5. Venture capital enabled expansion → more locations → broader network effect

The Wing became, in a specific technical sense, a platform for social capital rather than merely a co-working space. It was a place where structural holes between different communities of high-achieving women were bridged — where a technology entrepreneur could meet a political operative, where a journalist could meet a nonprofit founder. The co-working aspect was real but secondary; the network effect of concentrated, cross-domain social capital was the primary value proposition.

Social media was the distribution mechanism for this network effect. Every time a prominent member posted about The Wing, or was photographed at a Wing event, or mentioned membership in an interview, the social signal of "this is where interesting women are" was amplified to their audiences — who were themselves potential members.

The Long Tail of PR Luck

The Wing also benefited from a form of long-tail media luck that was specific to the social media era.

Traditional PR (public relations) operates through a relatively limited number of major media outlets: a small number of national newspapers, magazines, and broadcast programs generate the majority of cultural authority in any given domain. Access to those outlets is a structural hole — controlled by editors and reporters who serve as gatekeepers.

The Wing's aesthetic and community narrative was particularly well-suited to the media landscape of 2015–2018, when publications like The Cut, Refinery29, The Atlantic, and The New Yorker were heavily covering the intersection of feminism, work, and entrepreneurship. The Wing was a perfect case study for that coverage — it was aesthetically interesting, culturally timely, and personally relevant to the journalists writing about it (many of whom became members).

The coverage created a virtuous cycle with social media: articles generated social media engagement, social media engagement demonstrated cultural relevance to the next round of editors considering coverage, coverage generated more social media content. The Wing didn't just benefit from media luck — it created a feedback loop between media attention and social media distribution that amplified both.

The Wing's story also illustrates the limits of social media-generated luck.

By 2020, The Wing faced a series of crises that social media could not resolve and in some cases amplified:

The brand promise/reality gap: As The Wing expanded rapidly, the gap between its aspirational brand (inclusive feminist community) and its operational reality (predominantly white, affluent membership; labor issues with its staff, who were predominantly women of color) became increasingly visible. Social media that had amplified The Wing's brand could equally amplify the criticisms — and did, with significant effect.

The COVID-19 collapse: A physical location business with a premium-priced product dependent on in-person community was particularly vulnerable to a pandemic that closed offices and social spaces. The Wing permanently closed all its locations in 2020, was sold in a fire sale, and eventually partially relaunched under new ownership.

The post-mortem illustrates a specific principle about social media luck: it is particularly effective at building initial visibility and community, but it cannot substitute for fundamental business model viability. The Wing used social media luck masterfully to acquire members, raise capital, and build a brand. But social media luck could not make its unit economics work at scale, could not resolve its operational contradictions, and could not protect it from external shocks.

What The Wing's Story Teaches About Platform-Era Luck

1. Aesthetic is algorithmic infrastructure. In the Instagram era, visual distinctiveness is not just a design choice — it is a distribution strategy. Spaces, products, and experiences that are intrinsically photogenic generate organic social media distribution that is worth significant advertising equivalent value.

2. Community × platform creates multiplicative luck. The combination of a genuine community (with real network effects) and a social platform (with algorithmic distribution) can produce growth curves that would be impossible through either element alone. The Wing's community generated social proof; the platform amplified that social proof to audiences that the community couldn't reach directly.

3. Founder network is a structural hole advantage. Gelman's existing bridges across media, politics, and entrepreneurship communities gave The Wing initial access to multiple high-value audiences simultaneously. A founder without those bridges would have needed to build them from scratch — a much slower process with less certain outcomes.

4. Social media luck has a trust dependency. Platform-era luck is particularly powerful for building brands that promise community and authenticity. But platforms also amplify the distance between promise and reality. Brands that build on social proof must be careful that the social reality they're building is consistent with the social image they're projecting — because the same platform that amplified the image will amplify the contradiction.

5. Luck is not a substitute for unit economics. The Wing's story is ultimately about a company that used social media luck brilliantly to solve the brand-building and capital-raising problems, but did not solve the fundamental economics of premium physical space at scale. This is an important limit case: luck can accelerate a business that works, but it cannot make a fundamentally broken business model viable.

Discussion Questions

The Wing's spaces were intentionally designed to be photogenic — what the chapter's framework would call "aesthetic luck infrastructure." What are the ethical dimensions of designing for social media virality? When is this authentic brand-building, and when is it manipulative?
Gelman's personal social capital (her bridging connections across media, politics, and entrepreneurship) was a major factor in The Wing's early success. To what extent can this be reproduced by founders without that inherited social capital? What would an equivalent strategy look like for someone without those connections?
The Wing's collapse illustrates that social media luck cannot fix fundamental business model problems. Can you identify current businesses or brands that have substantial social media-generated luck but appear to have fundamental underlying problems? What would need to change for those businesses to convert social media luck into durable success?
The Wing built a community that was genuinely valuable to many members while also failing to live up to its inclusive promises. How should we evaluate companies that create real value for some people through luck while reproducing existing inequalities in their practices?

Key Takeaways from This Case Study

The Wing used social media luck mechanisms (aesthetic distinctiveness, community network effects, platform amplification of authentic community) to build a brand in a saturated market that achieved scale and capital access that conventional business metrics would not have predicted.
Founder social capital (Gelman's bridging connections) was a structural advantage that provided initial access to multiple high-value communities simultaneously — a form of inherited positional luck converted into a business asset.
Network effects and social media distribution created multiplicative luck: genuine community quality generated social proof, which the platform amplified, which attracted more community quality.
The Wing's story also demonstrates the limits of social media luck: it could not resolve the gap between brand promise and operational reality, could not protect against external shocks, and could not make fundamentally difficult unit economics viable at scale.
In the platform era, aesthetic design is strategic infrastructure — spaces and products that generate organic social media distribution provide a disproportionate return relative to traditional advertising spending.