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Bosker introduces readers to Elizabeth and Rob, owners of the Denny Dimin Gallery. Despite their contrasting personalities and backgrounds, the pair formed an unlikely partnership after their respective experiences in the art world: Elizabeth earned a master’s in art history and worked at galleries while Rob pursued performance art after obtaining his MFA.
The chapter centers on their preparation for Art Basel Miami Beach, a prestigious art fair. Unable to secure a spot at the main event due to its selective application process and opaque selection criteria, Elizabeth and Rob showcase their work at Untitled, one of two “acceptable” alternative fairs. This decision carries significant financial risk, requiring an investment of approximately $39,000—equivalent to a month’s operating costs for their gallery.
Bosker describes the intense pressure surrounding the fair preparations. Elizabeth and Rob need to sell around $70,000 worth of art just to break even, specifically targeting sales of about 13 photographs by artist Erin O’Keefe. The stakes extend beyond immediate financial concerns; the gallery’s expansion plans, including a new Tribeca space and Hong Kong location, hinge on their success in Miami.
The narrative illuminates the distinct artistic philosophy of Denny Dimin compared to other galleries. While many contemporary galleries favor provocative or challenging works, Elizabeth embraces formal beauty in art, rejecting the notion that artistic merit requires abrasiveness. This approach sets them apart, marking a potentially risky business strategy.
The chapter also explores the complex dynamics of gallery growth. Elizabeth and Rob face pressure to expand in order to retain their emerging artists, who increasingly demand more resources and prestigious exhibition opportunities. The ultimate goal, as expressed by Rob, centers on achieving museum recognition for their artists, particularly at institutions like the Whitney or MoMA.
Financial strain permeates the chapter’s conclusion. Elizabeth is anxious about their expansion plans, forcing difficult decisions about prioritization of art fairs, new space acquisition, and international expansion. Rob’s suggested approach to the Miami fair—maintaining some level of intoxication throughout—indicates the intense pressure of the art world’s high-stakes environment.
Bosker describes her experiences at Miami Art Week, a major gathering of art fairs, galleries, and collectors. The chapter begins with her efforts to manage an overwhelming schedule of exclusive events, parties, and viewings. As a gallery assistant for Denny Dimin Gallery, she attends Art Basel Miami Beach and its satellite fairs, learning about the complex hierarchy of VIP access and social status in the art world.
Bosker works at the Untitled art fair, helping gallerists Elizabeth and Rob sell photographs by artist Erin O’Keeffe. Initially unsuccessful at sales, Bosker struggles to discuss the artwork meaningfully, relying too heavily on historical references rather than engaging directly with the pieces. She gains insight into effective art sales techniques by observing her colleagues, including the importance of discussing the artwork itself before moving to contextual information about the artist.
Bosker explores the economic aspects of the art market, explaining how galleries price artwork and manage sales. She learns that prices often stem from comparisons with similar artists, and that galleries frequently offer different discounts to different buyers, such as museums or art advisors.
The narrative also examines the role of beauty in contemporary art. Bosker references scientific research suggesting humans have innate aesthetic preferences, such as favoring curved shapes and certain colors. This leads her to question the art world’s dismissal of beauty and to recognize its potential therapeutic value.
As Miami Art Week progresses, Bosker’s understanding of art deepens, and she successfully sells several pieces. She describes the transformation of her sales approach and her growing appreciation for challenging, unconventional artwork. She reflects on the art market’s imperfect but necessary role in supporting artists, illustrated by her colleague’s observation that each sale helps artists continue their work.
Bosker receives a promotion to Assistant Director at Denny Dimin Gallery following her successful work at Art Basel Miami. Her expanded responsibilities include managing client relationships, coordinating art fair applications, and continuing to learn from Elizabeth and Rob. Despite her growing comfort in the role, Bosker remains aware that her position might have been partially influenced by her status as a writer.
Seeking to broaden her understanding of contemporary art, Bosker attends an unconventional performance piece by artist Mandy ALLFIRE at a small gallery in Queens. The performance involves ALLFIRE sitting on audience members’ faces while reading messages from her social media followers. Despite initial hesitation, Bosker participated in the performance, an experience that prompts her to investigate the boundaries between art and non-art.
Through subsequent conversations with Elizabeth and meetings with ALLFIRE (whose real name was Amanda Alfieri), Bosker learns about the artist’s background and artistic intentions. Alfieri developed an online persona with hundreds of thousands of followers who appreciate photos of her butt. She views this social media presence as a form of performance art examining contemporary beauty standards and social media culture.
Bosker uses Alfieri’s work as a launching point to examine fundamental questions about art’s definition. She discovers that the distinction between “fine art” and “craft” emerged relatively recently in European culture, around the 1760s. Before this period, art encompassed any skilled human activity. The modern Western concept of art as something to be contemplated rather than used developed alongside social changes, including the rise of museums, art criticism, and a new middle class.
The chapter explores various theoretical approaches to defining art, from essentialist views focusing on formal properties to institutional theories dependent on expert recognition. Bosker considers evolutionary perspectives suggesting that artistic expression might serve biological and social functions, helping communities bond and survive. She engages with scholar Ellen Dissanayake’s theory that art emerges when ordinary experiences are transformed into extraordinary ones through specific creative processes.
Through her investigation of Alfieri’s work and art theory, Bosker develops a more nuanced understanding of art’s nature. She concludes that art exists as an agreement between creator and audience, requiring both the artist’s intention and the viewer’s engagement. While she remains uncertain about judging art’s quality, she recognizes that work that prompts deep questioning about society, beauty, and human nature might qualify as meaningful art, regardless of its form or context.
Bosker works at art fairs and galleries during the winter and spring months. She discovers that art fairs, despite being criticized by industry insiders, remained crucial networking and sales events. Her boss Elizabeth struggles after an unsuccessful fair in San Francisco, noting that wealthy Silicon Valley residents aren’t engaging with the art market as expected.
During this period, Bosker develops an interest in curating exhibitions, though she feels uncertain about her ability to judge artistic quality. To address this uncertainty, she joins a critique group called Crit Club, in which artists discuss their work. Rather than focusing on whether pieces are “good” or “bad,” the artists explore nuanced aspects of their work’s meaning and impact.
The chapter provides insight into the financial realities of running an art gallery. Bosker learns that exhibitions often served as marketing tools rather than direct revenue sources. The gallery sustains itself by selling older inventory and prints that aren’t on display. She also observes that galleries frequently rely on sales from a small subset of their represented artists.
Bosker discusses privilege’s role in the art world, particularly regarding gallery ownership. Her colleague Rob acknowledges that his success stems partly from family wealth and social connections. The industry’s financial barriers contribute to racial disparities: Among the Art Dealers Association of America’s 176 members, only one is African American.
Bosker receives an opportunity to co-curate a show for Danny Dimin’s Hong Kong gallery space. While working on this project, she interviews Whitney Museum curator Rujeko Hockley about the curatorial process. Hockley emphasizes that curating is inherently subjective, challenging Bosker’s desire for objective criteria in evaluating art.
The chapter concludes with Bosker’s decision to leave the gallery and attend the School of the Alternative in North Carolina. This experimental art school offers unconventional approaches to artistic creation and thinking. Though initially uncomfortable, Bosker begins to appreciate their value in expanding her understanding of artistic practice. She realizes that comprehending artists’ creative processes requires more than just observing their work in galleries or during studio visits.
In these chapters, Bosker provides an intimate look at the complex dynamics of The Art World’s Culture of Exclusivity, Hierarchy, and Secrecy through her experience at Art Basel Miami and other major art fairs. The author details the elaborate VIP tier system at the event, where even “VIPs” are stratified into hierarchical access levels determining when they can enter fairs and preview artworks. Bosker comments, “What an innocent I was. Art Basel Miami Beach hosted not one but two invitation-only VIP days” (141). Her pass, “which got me in more than twenty-four hours later, should have been called ‘It’s Cute You Tried.’ There was a hierarchy of entrance times and a hierarchy of days of the week” (141). She notes that this system creates artificial scarcity that drives sales while simultaneously making participants feel perpetually like outsiders: “No matter where you were in line, someone was ahead of you. Jack had told me I was the outsider. But did anyone feel like an insider?” (143). The text illustrates how this culture of exclusivity serves economic purposes while also revealing its arbitrary and often absurd nature.
The narrative explores Why People Make and Buy Art through multiple lenses. Collectors’ motivations range from genuine passion to social status-seeking to financial investment, often blending all three. Bosker references sociologist Pierre Bourdieu’s theories about how collecting art allows the wealthy to convert economic capital into cultural and social capital:
These collectors obviously had oodles of what Bourdieu calls economic capital (a.k.a. cash money), which they’d used to buy art that in turn got them cultural capital (an aura of cool) as well as social capital (access to a clubby in-crowd of Heads and their wealthy patrons) (129).
Meanwhile, artists’ motivations span from pure creative expression to career advancement to financial survival. The author presents these various motivations without judgment, illustrating the complex interplay between art’s intrinsic and instrumental values.
A central theme of these chapters is Developing an Eye for Art, as Bosker documents her evolution from feeling intimidated to developing confidence in her aesthetic judgments. Her experience curating a show for Denny Dimin’s Hong Kong space represents a pivotal moment in this journey. Through conversations with curator Ru Hockley and others, Bosker comes to accept that while technical criteria matter, ultimately judging art quality involves embracing subjectivity rather than searching for absolute standards.
From an analytical framework perspective, Bosker draws on both academic theories (Bourdieu’s concepts of capital) and insider practical knowledge (gallery economics, art fair dynamics) to explain how the contemporary art market functions. Her investigation of what makes something “art” references historical and philosophical debates while remaining grounded in concrete examples like Amanda Alfieri’s performance art. This combination of theoretical and experiential knowledge aims to strengthen the book’s analytical rigor.
The historical and cultural context is effectively integrated throughout these chapters. Bosker traces how current art world practices evolved from earlier periods, explaining for instance how the concept of “fine art” as distinct from craft emerged in 18th century Europe. She also situates contemporary developments like Instagram art within broader cultural trends. This historical perspective helps convey how present-day art world dynamics reflect longer-running social and economic patterns.
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