I first met Travis and the rest of the InCrowd team at their office party in February 2014. They were celebrating their move out of rented incubator space and into a space of their own. Framed software trademarks met guests as they entered through the glass double doors, just in front of the conference room where a huge company logo hung over a table of hors d’oeuvres. Most employees wore orange and black InCrowd tees, with streamers in the same colors flying above. Beer and cocktails flowed from an impromptu bar set up in the back next to the DJ booth, and a magician roamed the halls doing card tricks. Founder Travis gave a tour to anyone who asked. In his usual blunt fashion, he noted that this was as much a recruitment event as anything else, showing that InCrowd had arrived and was ready to act on his “number one operating principle”: “being an employer of choice for the right people.” A developer led me toward the Wall of Awesome Ideas, which recorded brainstorms for outlandish products. It was filling up fast. I shared a toast with a new hire, who said she was celebrating her own transition: from the slow, predictable pace of nonprofit work to a tech startup, where every day brought a new challenge and demanded new skills.
It was a night of hopeful transitions: new space, new careers, and a new identity for the startup. The move coincided with InCrowd’s pivot from a business-to-consumer (B2C) company, with software that supported anyone planning a party, to a business-to-business (B2B) company building software that specifically supported caterers in planning how food, drink, and place settings for large events were bought, scheduled, prepared, presented, and stored. It was a tough transition. Beyond fundamental changes to the software, all of the company’s marketing and training materials had to be substantially revised, but everyone was still excited. The company was supported in the change by a $2 million seed-funding round from the previous summer, an amount that would be quadrupled with its Series A investment at the end of the year.1
For Travis, the welcome party was about supporting this shift and changing the public perception of his startup. More than anyone else, he internalized the change. As the CEO and cofounder, he felt he needed to campaign for this big change, especially for potential investors, customers, and employees: “People buy me. Especially when they choose to work here, they want to believe in who I am.”
In startup land, this is called a pivot. It’s a gut-check moment for a company, where survival depends on fundamentally reorienting how you do business, with whom, and why. This idea is everywhere in tech, but its most powerful formulation comes from Eric Ries’s The Lean Startup (2011). Inspired by the lean production model pioneered by Toyota in the 1970s, Ries says startups should be constantly iterating new prototypes, pushing them out the door as soon as they are ready. For Ries, a startup doesn’t necessarily produce software. It’s bigger than that, “a human institution designed to create a new product or service under conditions of extreme uncertainty” (27). Extreme uncertainty and how to manage it—and the thrill of doing so—is a theme throughout. Unlike traditional businesses, startups don’t necessarily know who their customers are, what their best products are, or how to bring the two together. This environment where the work process changes constantly based on the data is not only accepted but embraced.
This is life on the “right” side of Clinton and Gore’s digital divide. In startups, the access doctrine appears to come true: the right tools and skills give you a chance at weathering this environment of radical uncertainty. With the right data, and the right mindset to make use of it, organizations can not only survive the economic storm winds but master them, using the momentum to reach new and greater heights of opportunity.
The access doctrine tells us that those on the margins of contemporary capitalism will move to its center if they have the right digital tools and skills. As we saw in the previous chapter, this political common sense emerged out of the Clinton administration’s attempts to manage the persistent poverty of the information economy. The access doctrine is a hopeful story that justifies both the reduction of the welfare state (because it held human capital back from full utilization) and the expansion of the carceral state (because threats to regional or national productivity must be contained). The world is divided into digital haves and have-nots, but the opportunity available through the internet promises to close that gap.
This idea holds special power in moments of economic instability, and so the high-tech people and organizations who thrive in these moments become models for everyone else. (Not coincidentally, they are largely White professionals who are also an important part of the new Democratic political coalition.) For individuals, the access doctrine presents a clear path out of poverty: learn to code like InCrowd employees and become an entrepreneur like Travis. For organizations that address the problem of poverty and embrace the access doctrine, InCrowd’s flexibility becomes a script for success. I use bootstrapping to describe schools’ and libraries’ attempts to follow this script. Bootstrapping is the process of rapid organizational restructuring that occurs when public service organizations define the problem of poverty as a problem of technology and the skills to use it. Bootstrapping begins when public service organizations are faced with overwhelming problems, limited resources, and diminished legitimacy. They rapidly change their identity and operations to provide the people they serve with digital opportunities. This process is modeled on startups’ pivots, but schools and libraries are simply different types of organizations, ones that cannot pivot like startups.
Beyond individual organizations, startups also offer hope to cities scared of falling behind in the global economy. Because of their cultural dynamism and their employees’ disposable income, startups appear to be a route to regional economic security. And so cities compete to remake themselves in tech’s image, in an effort to grow tech at home and attract it from elsewhere. At each scale—individual, organizational, and structural—the startup and the entrepreneurial citizens (Irani 2019) it employs become models of success in moments of extreme economic uncertainty. This chapter describes the internal functions of that model, showing how central the pivot is to the cultural life of startups—for individuals, firms, and the sector as a whole—so that later chapters can explore attempts to generalize it.
The moment of the pivot is where all this uncertainty comes to a head. It is, in Ries’s (2011) words, “a structured course correction designed to test a new fundamental hypothesis about the product, strategy and engine of growth” (149). InCrowd was undergoing a “customer segment pivot.” Travis and his team had realized that their product best served enterprise customers—professional caterers and event planners—rather than regular consumers planning the occasional graduation party or quinceañera. But. the pivot meant much more than a change in who the company sold software to. It also meant a fundamental reconsideration of what the company was and where and how it worked.
In the name of progress, internet entrepreneurs like Travis—indeed, all of InCrowd—must be prepared to discard their old tools and ideas, or at least radically restructure them based on the data. Ries even goes so far as to redefine a company’s survival prospects—its runway, usually defined as the amount of cash on hand divided by the rate of spending—as the number of pivots it has left: its remaining chances to learn, rebuild, and radically reinvent. The pivot is not just a corporate strategy, it is an identity. This capacity for reinvention is important for the internal and external legitimacy of these firms, generating buy-in from the employees that put in long hours and the cities that put in tax breaks. Ahead, I explore this legitimation process at the level of founders, firms, and cities. Startups today serve as an “ideal type” for public service organizations under pressure. But, of course, ideal types do not correspond to empirical reality; they are abstractions built for explanatory purposes. This abstraction—focused on the ability to pivot—serves different purposes at different scales of the tech sector.
This chapter builds on pioneering ethnographies of the startup scene during the turn-of-the-millennium dot-com boom, particularly Gina Neff’s (2012) exploration of venture labor. For Neff, venture labor is a strategy that professionals follow for managing the risks inherent to the contemporary labor market. They take an entrepreneurial approach to their own careers, viewing their work in a particular company that may not be long for this world as an investment in their creative portfolio, human capital, or financial security. In many ways, this chapter documents the normalization of what Neff identified as an emergent strategy in 1990s and early 2000s Silicon Alley, New York (see also Marwick 2013; Ross 2004). These are now accepted ways of living and working, with their own ecosystems of cultural and educational organizations to train new entrants to the sector.
Founders internalize the identity of their startups in order to demonstrate the vitality of the firm to powerful outsiders and uncertain insiders. They learn to do this from their peers, from financial pressures on the firm, and from the bridging organizations that tie local, national, and transnational tech communities together. Travis was always up front in saying, “the company is a reflection of me.” This was not self-aggrandizement. Angel investors conduct their due diligence on a founder’s background and management style as much as the fundamentals of an early-stage company with great promise but little to show for it. Founders also act as the firm’s ambassadors to politicians, clients, and partners. Identifying with one’s firm and performing that for outsiders necessarily means that pivots are deeply felt—as questions not just of business strategy but identity. Travis was not the only founder I met that went through this process.
I kept up with entrepreneur Ji for several years as she built Hearth, a matchmaking app for conversation partners. She knew monetization was inevitable—you have to pay the bills—but she worried that generating coupons to draw conversation partners to a bar or restaurant, and all the sales work that would require, would necessarily distract her from solving our “problematic decline in connectivity.” Ji was just as invested in researching connections she saw between “gun violence or digital divide issues or political chaos” as she was in bringing Hearth to market. Monetization was a necessary pivot, something that sullied Ji’s mission even as she knew it was necessary for her app’s long-term health.
Ji’s other pivot was geographic. Hearth had grown in DC, piloted with a series of group dialogue sessions hosted by local high-end restaurants in rapidly gentrifying areas like Shaw, curated around themes like trust. There, Ji tested out some of the prompts Hearth would use for in-person conversations and the curated group of mostly White professionals who repeatedly voiced a desire for more unplanned social connection in lives marked by eighty-hour work weeks, constant internet use, and frequent travel. It remains a cliché that White professionals in DC are rarely from DC, and that made the city the perfect venue for Hearth. The hopeful, cultural mission of the startup was thus perfectly aligned with Ji and her social network, who said, “For the first time in my life I really felt like I was among my people here in DC.” But she knew the investment networks for consumer technology were stronger in San Francisco, and a move was on the horizon. It hurt because she was leaving her “tribe,” the cultural geography that had birthed Hearth.
Founders like Ji and Travis do not learn to internalize their firm in a vacuum. They are trained to think of themselves as equivalent to their company by the bridging organizations2 of the startup ecosystem. These organizations are not startups themselves but build a sector for them. In DC, the 1776 startup incubator in Logan Circle is one of the most important sites of sector-building, as well as something of a meeting point for various smaller communities within the scene. Evan Burfield and Donna Harris founded 1776 in 2013. Their office space was secured by Mayor Vincent Gray, who often framed 1776 as a cornerstone of his five-year economic development plan. David Zipper, who became a key economic development advisor for Gray after holding a similar role for Michael Bloomberg in New York, led the creation of the DC Tech Incentives program, along with 1776’s dedicated $380,000 grant from the city. Later, 1776 would hire Zipper to lead its cities and transportation portfolio. In this role, he advised startups focused on urban problems, and lobbied municipal governments on 1776’s behalf.
Burfield made his name as an executive in consulting firms. Harris began her career as a serial entrepreneur in Detroit. She said that she “knew then that startups like mine could have been critical job creators to a city in decline. But I didn’t have data to prove it, and I didn’t have a platform to convince anyone I was right or strategies to bring about change” (Harris 2016). After working in enterprise software sales, she was appointed managing director of the Obama White House’s Startup America initiative, a public-private partnership to fund, train, and lobby on behalf of startups and cities recruiting them. The 1776 incubator rents office space to startups lacking it, provides training and resources to them, and hosts parties and informational events for the larger startup community.
There were other training venues that established the rules of the game besides 1776. The various WeWork coworking spaces were important here. One way that WeWork justifies its rental costs—$400 to $550 per month for a dedicated bullpen desk—is through the events (e.g., “How to Properly Offer Unpaid Internships”) and networking opportunities available to tenants. Tech Cocktail, run by former AOL employees, ran an industry news website and sponsored events, like pitch competitions in the style of the Shark Tank reality TV show. Various bootcamps like General Assembly promised to quickly reskill people for the information economy, taking disgruntled bureaucrats and turning them into in-demand developers. Mentoring also occurred in informal meetups, where founders or developers with particular skill sets got together once a month. Or it occurred through designated advisors who brought their years of experience to younger founders—sometimes in exchange for equity, sometimes not. And though DC tech workers and executives often bemoaned the lack of a large technical university like Stanford or MIT around which the scene could orbit, local universities (e.g., George Washington, American, Maryland) still brought entrepreneurs together for hackathons, networking, recruitment, and more.
Tech Cocktail cofounder Frank Gruber released a book in 2014 entitled Startup Mixology: Tech Cocktail’s Guide to Building, Growing, & Celebrating Startup Success, blending business advice with self-help for budding founders. Although it lacks the scientific pretensions of Lean Startup, it was similarly meant to help readers get into an entrepreneurial mindset. At one event held at Crystal City incubator Disruption Corp, Gruber pitched the book as a twenty-first-century successor to the self-help classic How to Win Friends and Influence People. He invited several founders on stage to discuss their failures and successes. Each was greeted with a cocktail personalized to them and their firm. Mixologists made the drink, passed it up to the founder on stage, and then passed samples throughout the crowd.
I was in the audience with Travis, who had waved at me from across the room as I entered, furiously typing emails on his laptop before the panel began, clad in his usual jeans, sportscoat, and InCrowd t-shirt. As people mingled after the event, he related InCrowd’s origin story to a small group. Travis told them he’d been frustrated with overcrowded, understaffed parties in his native New York during the dot-com boom years, when he was working as a web developer. He omitted the portion of the story he had told me in an earlier interview, where he joked about first wanting to design an app that would make sure he always sat next to the prettiest girl at friends’ weddings. That was a few pivots ago.
Travis was a rising star in the scene. He was one of the first graduates of The Fort, another incubator and predecessor to 1776. And 1776 had cut InCrowd a deal on rent before it moved to its current location, something Travis described it as a mutually beneficial relationship because InCrowd’s fast growth lent the new incubator an air of respectability. InCrowd had been a side project while he worked on his MBA and then for a government contractor, whose impersonal bureaucracy frustrated him to no end.
This story was important to InCrowd. Travis’s identification with the firm was not just a performance for outsiders, it was also a management practice. Everyone needed to identify with the company’s pivots. Travis told me in an interview, “I’m a majority owner, everybody here is an owner [i.e., all InCrowd employees received a small amount of equity] so everybody here is an entrepreneur. I know it sounds cheesy, but everybody here is an entrepreneur. Everybody is entrepreneurial. … My goal is to make it everybody’s baby, but I might have the head. They might have a finger.”
Travis needed to be a role model in an environment of extreme uncertainty, and he told mid-level managers he expected the same from them, because he wanted his employees to commit to their new business model, and all the various smaller challenges that would arise from it. The idea of the pivot was central to the InCrowd’s identity and operations. Employees circulated the idea as part of their efforts to build a company culture, and in the process learned to embrace a great deal of flexibility not just in the organization’s structure and purpose, but in their day-to-day or even minute-to-minute work habits.
When I asked Christopher, a bootcamp founder, what he was trying to teach his students, he didn’t hesitate to say “entrepreneurialism.” I asked what that meant. He replied: “I think to be an entrepreneur really encompasses an orientation towards being able to think on your feet, to constantly pivot, to work in constantly changing dynamic environments, to observe the world and the changes going on around you and come up with solutions and business ideas that take advantage of the opportunities in front of you—not necessarily shorter term, but very quickly growing business ideas.” There is nothing in this definition about technology. “Business ideas,” Christopher would make clear, could be a new approach to a design problem or a particular way of handling customers. This is a philosophy of work: surviving and thriving in an environment of extreme uncertainty by taking in new data and using that data to quickly change your work habits. The problem he was hoping to solve, to return to the access doctrine, was much bigger than a skills gap. It was a culture gap.
This is exactly what Travis hoped to instill in his employees. Indeed, he hired some of his first employees from these sorts of bootcamps precisely because they had the correct mix of skills and philosophy—and so didn’t need a lot of on-the-job training. The company grew quickly, but there was every indication that Travis’s cultural project worked, and not because they blindly accepted his instruction. InCrowd’s culture was something everyone was self-consciously engaged in building. Organizational culture within startups is built on an embrace of large-scale strategic pivots, in the sense in which Ries described them, as well as a sort of daily pivot between different work tasks and the different mindsets that support them. Embracing flexibility legitimates an environment of economic uncertainty and the long hours and unclear prospects that entails. Who teaches techies to embrace flexibility? The previous section discussed sector-building organizations outside the firm. Within the firm, women encourage this embrace as part of the startup’s general culture-building project. Such assignments either occur in the formal capacity of nontechnical roles, as one part of their regular duty to manage the emotions of peers and clients, or in the informal capacity of unwaged emotional labor women are expected to carry out in waged work because of the regular, unstated assumption that they are naturally good at it (Hochschild 2012; James 1989).
Beneath Travis and his assistant Karen, InCrowd was made up of three teams: Design developed the software; Sales secured new clients; and Contact trained clients in the use of InCrowd software, designed templates for them, answered and managed customer complaints and questions, collected outstanding bills, and sold existing customers on new products and bigger contracts. Beth led Contact. She had conducted her own personal pivot away from her dreams of being a speech pathologist and into a career in tech. InCrowd was her second startup. She told me, “I’ve been here for seven months, but on a day-to-day basis, my job has probably changed four or five times. It’s really exciting.” She would never dream of leaving tech now, largely because she had learned to embrace the environment of extreme uncertainty and the personal and professional pivots it required of her: “With startups, you do a lot of personal growth because you kind of are thrown into a role that’s sink or swim. You’re either going be able to do the path and then some and move with the pace of the company or you’re not going to be able to handle it. It’s pretty ambiguous.”
Her previous workplace had, if anything, more of the stereotypical startup aesthetic than InCrowd’s: games, frequent happy hours, a ball pit. But it didn’t feel like a startup to her because of the emergent bureaucracy that segregated employees into clearly defined roles and kept them there all day—itself an organizational shift made in an effort to sustain their early growth. That failed. Beth was eventually laid off as nontechnical roles were outsourced.
At InCrowd, Beth’s days were a series of pivots in the kind of work she did and the kind of relationships she had to maintain through that work. For her, this was largely about how she dealt with clients over the phone through careful choice of tone, words, and diction. The default was a breezy, instructional demeanor as she walked party planners through a particular piece of their software. There were no bad questions. She was inviting people to explore the product with her in order to build it into their routine: “This is going to make your life easier, I’m more of a visual person myself. … I’m very impressed, it looks like you have that tool down.” But this could change fast. Sometimes she had to finish one teacherly call only to turn around and play debt collector. This required a sterner reprimand. Throughout, she was also careful to request more information on various events, menus, and staffing arrangements that might be useful for future pitches to the client.
Variations on these strategies were also deployed internally. Beth would advise subordinates on key phrases (e.g., “Please advise …”) to deploy to get the desired effect and coach them on the strategy they would take for specific clients. Stiffer stuff was deployed to get InCrowd developers to follow up on a particular feature implementation or when graphic designers hadn’t fixed something to a client’s specification. She was a leader who liked leading, but the emotional pivots required of her were exhausting. It wasn’t rare to see her arrive at her desk at 8:00 a.m. and not leave until 9:00 or 10:00 p.m.
Vijay, a lead developer in Design, was also drawn to tech because of his romance with the atmosphere of constant change. He had tried his own startups and failed and was happy to now be mentored by Travis. “Because we’re all startup people,” he said, “we all do a bit of everything, from survey system administration, managing CAD infrastructure, to how many pixels wide this particular element should be, the whole thing.” Like many people in DC tech, he would favorably compare startup life with his prior experience in large corporate or federal bureaucracies. And in contrast to Christopher’s lofty philosophy that took entrepreneurialism beyond coding, startup culture was inseparable from software development for Vijay. For him, mastering the environment of extreme uncertainty was best achieved through the immediate feedback you got from building and implementing code. This is why he left policy work: “I thought that the opportunity to actually close that feedback loop, to actually have an effect on my job, on the world that I was living in, was much, much tighter if I were doing [software] development.”
Where Beth’s hour-to-hour changes were often about evincing particular emotions from clients and subordinates, Vijay’s were about corralling a quickly changing product. InCrowd sold catering software. New features were constantly added to support new needs, especially from big clients, or to solve unanticipated problems. Major redesigns had to be built with prospective clients in mind, and this required research and conversations with Sales about sectors they hadn’t yet reached and what sort of silverware, plumbing, waitstaff, and so on they might have.
Over the course of a day, Vijay might implement his own code, review a subordinate’s demo, teach a quick programming tutorial at an all-hands Lunch-and-Learn, interview a potential new hire, plan the next few months of product development with fellow Design members Travis and Tim, and walk a Contact team member through a particular feature built for a high-value client. It was a regular back-and-forth between putting out fires they hadn’t anticipated and building a product that scaled with their business. When our first interview ended at 7, he turned right around and went back into the office.
The Division of Emotional Labor
As Beth and Vijay made clear, there are a lot of different roles and statuses in tech; it’s not just a sea of developers tapping away at the keyboard. An important part of this story is that the work of producing that tech identity—training others to believe in the pivot—and the rewards from it are unevenly distributed across the firm, typically along gendered lines. Ji’s startup Hearth was too young for this division of labor to reveal itself. InCrowd, in contrast, had grown rapidly since its founding in 2011, and by the time I arrived in 2014 it employed over thirty people, with more being added every month. Travis took an instrumental approach to these challenges, building the cultural and physical space of InCrowd with exactly this work ethic in mind, telling me “One of the things you have to accept is that people don’t go to work these days, they go to sleepaway camp. The employer has to be more than a provider of salary but also an environment, continuing education, excitement.” A shared culture was essential to securing buy-in for long hours and an unpredictable work style.
Women in “nontechnical” roles—whether formally included in their duties or not—were most often responsible for training their coworkers to embrace the uncertainty inherent to tech. Beth was clear that this sort of extra work was required: “You may have a role on paper but if all you’re doing is what it says on that paper, then you’re not doing your job.” Beyond late-night conference calls or weekend reviews of potential new hires, this meant that time spent socializing at work and out of work became a research activity. She and the other Contact team members regularly coordinated brunches, concerts, hikes, and bar crawls for coworkers. It meant that her phone was filled not just with work emails, but Instagram photos, tweets, and Facebook posts from her coworkers.
Corporate identity became a social identity, an embrace of those community-building opportunities Travis mentioned alongside what Beth called “a mutual excitement for the product.” She admitted that was cheesy, but that didn’t make it less important. Beth drew on her friendships with members of other teams in order to put herself in the shoes of an engineer or salesperson and gain their buy-in on new projects. She also taught her team members to do the same. This instrumentalization of socialization by middle-management was not only encouraged by Travis but was one of the things InCrowd employees liked best about the company. That work friendships had a purpose was a sign that the company had a vision and that everything its employees did was bent toward that vision.
This vision was distinct from that of other big names in DC tech. When I asked how InCrowd compared to other DC tech stalwarts, many complained about companies and colleagues in tech that turned their office into a playground or let their workdays be taken over by drinking and video games. LivingSocial often played the heel in these stories: a high-profile startup lured to DC with hefty subsidies, but with a business model that wasn’t helped by what InCrowders perceived as a party culture (Isaac and Benner 2015). Indeed, Beth preferred the InCrowd model to that of her previous startup, which “put these friendships first and that’s why people were there.”
Design was an all-male team led by Tim (who was Chinese American and nicknamed Captain Deploy) and Vijay (who was born in the United States but raised in Bangladesh and Britain), with largely South Asian subordinates except for Paul, who was White. Sales was split evenly between men and women and was led by Grayson (a White man Travis referred to as his second-in-command) and Suraj (an Iranian American, and the only non-White member of the Sales team). Contact was led by Beth (who was White) and was made up entirely of women of a mix of races, with the exception of three men—two White and one Black—two of whom exclusively focused on drawing up plans rather than on direct customer service. Sales secured customers, Contact maintained them, and Design almost never met them. Each team had its own office, though as InCrowd grew, it increasingly placed new employees in hallways or in the small corner spaces that used to be used for phone calls or one-on-one meetings. Travis tried to have a one-on-one with each employee every month.3
InCrowd’s division of emotional labor had specific roles for specific divisions, each enrolled in the production of a hopeful tech culture. Design certainly had a role to play, even if other divisions joked about the team doing nothing but drinking Red Bull and building Connect Four bots for fun. Tim would post live updates to social networking site Twitter about demos Design carried out in its office, sharing InCrowd’s business with the world. The clear glass wall around Design’s office was always marked up, usually by Vijay, as the team diagrammed designs it was working on or brainstormed ideal features the team would love to work on in the future. The Wall of Awesome Ideas became a fixture of debates at company happy hour—every Friday at six—and of tours given to new employees and interns, prospective investors, or just other tech entrepreneurs visiting the office at Travis’s invitation.4
But the bulk of this emotional work, the labor that led InCrowd employees to embrace the uncertainty of tech, was carried out by those in nontechnical roles. This happened formally, as part of the Contact and Sales teams’ regular duties, and informally, as unpaid labor on the part of women InCrowders who kept the social life of the firm going.
The cheery tones of the Contact team were background music to the rest of InCrowd’s work. Even as actual background music played softly from speakers in the middle of the office, you could hear the steady rhythm of their customer service scripts repeating over and over. Entry-level women working in Contact and Sales posted to the official company blog several times a week. This was the public face of the company and included everything from guides to popular Twitter hashtags used in the industry, to announcements of new features rolled out for customers, to core InCrowd values (hiring managers would be disappointed if interviewees had not researched these), to a breakdown of the annual InCrowd awards ceremony, where everyone received a funny certificate about their work personality. Contact members Jessica and Martine would regularly represent the firm at industry events or just fashionable DC parties, bringing InCrowd swag—t-shirts, toys, cards—with them. This was the face the firm showed to external stakeholders. Contact members kept that face up as part of their assigned duties.
But this work also happened internally, for the sake of their coworkers. Beyond coordinating InCrowd’s social calendar and mediating between teams, the women in Contact also decorated the office in the company’s orange and black colors, hung inspirational quotes, planned themed clothing days, and cheered the company on in their InCrowd t-shirts when it did public demos at DC tech events. They also brought a kiddie pool and coolers in to store beer for Friday happy hours, though men in Sales and Design were usually the ones going on beer runs. This work was not part of anyone’s formally assigned duties. But without it, InCrowd wouldn’t have felt like a startup, and its workers would not have bought into the flexibility the startup demanded of them.
Daily Pivots
The emotional labor that Beth and her colleagues undertook every day, and many nights, worked. InCrowd was a place where they not only wanted to work, but also embraced the extreme uncertainty and the daily pivots it required. When the company was much smaller, it relied on bootcamps like General Assembly and incubators like 1776 to provide employees with a startup mindset. That was what happened for Grayson, whom Travis praised for coming into the company at age twenty-three, ready to work around the clock and manage a team of his own and its rapidly shifting deadlines. By 2014, the vibrant company culture did that job for him. By then, Travis could joke with new hires about leaving behind the nine-to-five schedule that marked their old lives in government or nonprofits while he gave them a tour, and other employees would laugh along. Following Travis’s example, his employees learned to internalize the demands of the company and its shifting fortunes. As Sales member Allen told an interviewee over the phone: “Every day is a school day, work hard and play hard. We are a startup but we all own part of the company, so we need to operate on the day-to-day a bit like how we want the company to operate.”
“Every day is a school day” was a common refrain throughout DC tech, but especially at InCrowd. It signaled not just a commitment to lifelong training, but an openness to day-to-day changes in one’s job—because there was always something new to learn, some new challenge to face. Where Ries and similar business gurus described the pivot primarily in terms of organizational strategies, the idea of embracing flexibility was important to InCrowd employees not just in terms of periodic gut-check moments for the firm as a whole but in terms of the changes individuals expected to see in their workdays. This meant not just a demanding schedule—long days, lots of different things to accomplish in them—but flexibility in how they organized their workplace and responded to incoming data.
While it might seem obvious, it’s important to note that a laptop connected to cloud services is essential to the startup work style: meetings can be taken anywhere, ad hoc teams can assemble in different rooms or on the road. While “Every day is a school day” is a little more high-minded, “Can I show you something real quick?” is probably just as common in the day-to-day work of the company. Beyond that baseline, each team had different accessories to facilitate its own quickly changing tasks. Sales wore Bluetooth earpieces and business casual, always ready to take a call or meet a client. Contact wore a mix of business casual and the unofficial startup uniform of t-shirt and jeans. Each Contact member had a laptop screen open for active tasks and a larger monitor displaying ambient data for reference (e.g., billing information, standing instructions). Design dressed the most casually—its members rarely saw clients—and had setups similar to Contact, but the contents were different: usually command-line interfaces on the laptop and wireframes or the InCrowd website on the larger monitor. They had the only office with a TV on the wall. They would all turn to it once or twice a day for a demo.
InCrowd’s office was flexible enough to accommodate new collaborations that emerged throughout the day. While long and narrow, it was a relatively open office. Individual employees had desks they usually used, teams had their own rooms with glass walls, and there were several unclaimed breakout rooms. That meant that these team dynamics would often spill over into adjacent rooms or hallways—Contact and Sales regularly took calls in closets—and this happened more and more as InCrowd grew. Travis and the team leaders kept the different teams abreast of each other, coordinating their different rhythms. Occasionally a big request from a large client or the rollout of updated software would force everyone to drop what they were doing, aligning their rhythms for the day.
These new rhythms were usually based on new data. Those data might be delivered by customers themselves, by InCrowd employees tracking their interaction with the product, by management tracking employees through the Salesforce software that recorded all client interactions, or by leadership’s decisions about what new client sectors looked promising. Organizations like InCrowd are, in Neff and Stark’s (2004) words, permanently beta: constantly testing new organizational forms because the firm’s product and the infrastructure supporting its operations are both based on software that is itself constantly updated in response to user feedback and steady drips of performance data. This was especially clear during the B2B transition, but manifested too in the startups’ growing pains as new roles were introduced that did not fit smoothly into the longstanding Sales-Design-Contact divisions: graphic designers, project managers, human resources, and so on.
It was also clear in the day-to-day work of the company, where riding the tide of constant feedback and performance data became a way to master the environment of extreme uncertainty. This was true both externally and internally. Contact team members regularly told clients that 75 percent of the InCrowd product was based on client feedback. This is a difficult thing to quantify, but the gist of it was surely true, for the simple reason that InCrowd needed to encourage more extensive and intensive use of its products to drive renewals and upsell existing clients on bigger software packages with additional user privileges or features (e.g., invoice management, client history pages).
Discussions within Contact about the problems a specific sector of clients—say, universities—faced would be relayed to Design and to Travis to prompt new technical solutions. Contact ensured a steady stream of client data by encouraging more active use of bells and whistles clients might not have noticed. Their activity could be tracked on InCrowd’s end and used as a measure of a feature’s success or failure. Sales would pick up new sorts of clients that drove new features, which created the demand for new client trainings. The feedback loop would also work in other directions, where the people supporting clients over time noticed new use cases that fed into new development, which encouraged Sales to go looking for more customers that fit the use case.
This permanently beta dynamic was also present internally. The customer relationship management software Salesforce tracked and aggregated every interaction an employee had with a client. This allowed for a birds-eye view of those relationships and made onboarding new employees, especially in Contact, faster because much of the “soft” work of relationship management was recorded, ready for review. InCrowd’s customer database pinged every employee when a new client was secured, along with the amount of the sale and the commission the salesperson received. Beth praised this as a sign of an “open culture” where everyone was equally committed to the cause.
The pivot was thus not just an irregular crisis in the startup’s life cycle, something that came up every year or two. InCrowd certainly went through a major gut-check moment as it became a B2B company. And it would experience several more moments like that, including when it was acquired several years later by a much-larger competitor for around $100 million. But there were many smaller pivots over the course of a day or month. Workers frequently changed tasks because incoming data changed, causing a cascade of other changes in roles, technologies, and office space. Buying into InCrowd’s mission and the lifestyle surrounding it would seem to wreck work-life balance. And Beth did worry about this for younger employees especially. But on both anonymous satisfaction surveys and in my months at their office, InCrowd employees reported loving their jobs and everything came with them. They embraced the pivot. This empowered Travis’s vision of his company: “If work is not part of your life or if you consider it two different things, then this is not the place for you. Because I want you to really believe in what you’re doing and be really committed to the company.”
Founders embraced the pivot as the defining feature of startup life because they had learned to identify with their firms. Startup workers embraced the pivot because it legitimated the long hours and quickly changing work practices required of them, even if the emotional work of teaching each other to embrace flexibility was not evenly distributed throughout the firm. Above the level of individual workers and firms, municipal elites in business and government positioned startups as a pivot for a city with an uncertain economic future.
Just as bridging organizations like 1776 or the various coding bootcamps taught individuals to pivot, they also built an identity for the sector as a whole in order to claim space in DC. This claim was built on tech’s ability to help the city pivot away from government jobs, as well as decades of racialized poverty. The sector worked with government to redevelop the city in tech’s flexible image. This included an activist cultural policy that legitimated the changes a flood of new, largely White professionals wrought on the city, as well as the city government’s support of them. The DC tech community represented, to insiders and outsiders, the ideal type of worker and workplace—the end result of the access doctrine.
Mayor Vincent Gray, for example, never missed an opportunity to compare the influx of startup workers, and the real estate boom catering to them, with an older DC that was majority Black and, in his telling, crime-ridden, bereft of private investment, and dependent on the federal government for any job creation. “I could only think about what O Street used to be,” he said at the Digital DC Thank You, held at the brand-new City Market on O condominium building in 2014. Gray then joked about how any apartment or hotel built here twenty years ago would have just been used for sex workers, before reviewing the benchmarks of his 2011–2016 economic development plan. The mayor himself thus participated in building up tech as a coherent sector, assisting the work companies like InCrowd conducted within their walls or the work organizations like 1776 did to bring entrepreneurs and startups across the city together.
Gray’s economic development proposals contained the usual financial incentives to help kick-start incubators like 1776 or reduce taxes on passive income to incentivize venture capitalists, as well as a host of proposed changes that would improve the human capital stock of the city—both by reskilling the people already here and by incentivizing creatives to come and stay. The goal of his Creative Economy Strategy was one hundred thousand new jobs and a further $1 billion in tax revenue. Its cover depicted Black musicians alongside a majority-White cast of chefs, cameramen, and tech workers pointing hopefully at each other’s screens. The creative economy included all these disparate jobs, linking them together through the ability to pivot: “In a Creative Economy, organizations are agile, continually offering new value to customers through innovations in products and delivery methods” (ODMPED 2014, 10). Pablum perhaps, but deployed in concert with very real economic development proposals and very real gentrification. As noted previously, and while there are of course many contributors, the rise of DC tech coincided with a demographic shift wherein Chocolate City lost its Black majority. What fruit did this bear for tech? As we’ve seen, networks of startups work with each other, related services (e.g., law, real estate, finance), and local government to create a local tech identity. They do this to attract a pool of talent (e.g., software developers who require little on-the-job training) multiple firms can draw from, to secure continued support from local and state governments, and to legitimate the social mission of a sector that is dominated by the White upper and middle classes and frequently indicted as an agent of gentrification and displacement (Stehlin 2016). In meetups and industry branding materials, this network was usually called DC Tech. The city government used other labels, enrolling the city as a whole in branding efforts such as Digital DC.
Building up a majority-White sector in a historically majority-Black city meant that leaders in tech and government needed to pose the influx of tech workers as a positive development for Black Washingtonians. It was a hard sell, but one Gray regularly tried to pitch at events like the March 2014 opening of the WeWork coworking space in Shaw. Douglas Development Corp. had long been seeking a tenant for the abandoned Wonder Bread factory it had gutted and renovated—one of the few remaining industrial spaces downtown. The space was overflowing by the time Mayor Gray arrived for the ribbon cutting downstairs, an empty warehouse space that would be leased to iStrategyLabs some months later. Black middle-schoolers from a STEM-focused charter school managed by Howard University wandered through in a line behind their teacher. They were the only signal of the historically Black university’s presence nearby, the anchor of the neighborhood and one of the most important Black cultural institutions in the country.
“The District has come a long way,” Gray announced. He ran down the list of successes from his tech-oriented economic development plan: growing the city’s population from its historic low in the 1990s, bringing in more tax revenue, and moving it away from the federal government as the primary employer. Shout-outs were given to 1776’s Challenge Cup competition, local startup TrackMaven’s new founding round, and Blackboard founder Michael Chasen’s foundational role in DC tech. They were helping the city pivot.
The mayor delivered a prize to the charter school students. Their technical accomplishments proved, he said, that they could go toe-to-toe with Sidwell Friends, the historically elite, majority-White private school to which Presidents Clinton and Obama had sent their children. Gray and WeWork CEO Adam Neumann stood on stage together to cut the ribbon, echoing the economic and social mission of tech, but also the personal one, with Neumann adding a motto that would resonate with InCrowd employees: “If you love what you do, you never have to work another day in your life.”5 Gray wore a tie, but every other CEO present—Travis included—went without.
A few weeks after the ribbon cutting, Travis and I sat down for our first formal interview, in one of InCrowd’s breakout rooms. We spent our final twenty minutes together reviewing the financial incentives DC offered startups, and founders especially. He praised a since-canceled city program for paying the first $10,000 of a new hire’s salary if they’d been unemployed in DC beforehand but were training for a new skill at their new employer.6 “That is an awesome program! It does not dilute capital for entrepreneurs to put to work.” But in general, he said the municipal government’s incentives for startups to relocate to DC were “totally misaligned” with what founders needed, mere “lip service.”
Regarding tax credits for hardware purchased in DC: “Who the fuck buys hardware in the store?” And: “This other thing where they have a real estate credit if you move to some shithole [the city-designated tech corridor along the gentrifying Seventh Street NW and Georgia Avenue NW strip]. No! I need to live here; I need to work here.” Gray had unveiled that program at WeWork, and a few weeks later banners hung from streetlights along the strip: “Digital DC: The Innovation Capital.” What Travis said he really needed were tax breaks, not so much for business expenses, because startups didn’t make many big fixed-capital purchases, but from income and capital gains taxes so that he could save his profits and pump them back into InCrowd.
Despite working in the national Democratic party in the past, Travis confessed, now that he was a business owner, “I don’t even know what government does. I just try to stay far from it.” Still, I was a little taken aback when I asked if he thought the incentives package might change since Gray had lost the Democratic primary7 to Muriel Bowser yesterday, and he raised an eyebrow, confused. He popped his head out of the conference room to shout down the hall, “Did anyone know there was an election yesterday?” and was met with shrugs and laughs. “Is she also African American?” he asked. I said she was and related a bit of her political history in Ward 4. Travis thanked me for the information and went about the interview. InCrowd had a mission; mayors would come and go. They would work around it.
DC was grounds for DC tech’s various pivots, but not every part of the city could embrace the environment of radical uncertainty and transform itself in the same way. Both commercial and residential real estate developers were wholly on board, as were the bigger corporations represented by the DC Chamber of Commerce (motto: “Delivering the Capital”). They appreciated the influx of human capital and potential partners and acquisitions. The city’s changing culture was a draw too. At industry events, I frequently met older investors and executives new to the tech scene, but unabashedly addicted to its culture. Some sections of city government were equally enthusiastic.
This love was not unconditional. Travis’s ignoring the election was emblematic of the larger relationship between the sector and the city. DC tech needed the city’s cultural cache and robust public infrastructure to attract talent and produce the agglomeration effects that characterize any growing sector (Audretsch 1998; Sassen 2001). The city needed DC tech to pivot away from the federal government and would pay for the privilege. But DC tech did not, of course, invest evenly across the city. Startup offices were overwhelmingly concentrated in wealthy, majority-White neighborhoods in Wards 1 and 2, with only a small percentage in other wards and none in the majority-Black neighborhoods east of the river (Taylor 2016).
Even the biggest players in DC tech were ready to leave, no matter the incentives on the table. Educational technology giant Blackboard booked around $700 million in annual revenue. After a long search for a new headquarters, in 2015 it announced a new 71,000 sq. ft. office in the city in which it was founded. The twelve-year lease was rewarded by the city with an annual subsidy of around $500,000. Those funds drew from DC’s Qualified High Technology Company incentive program, which distributed around $40 million annually, largely to companies already in DC and without any dedicated agency to review the success of those or similar tax breaks (Bowser and DeWitt 2018). In 2019, only four years into its lease, Blackboard moved across the Potomac to Reston. The Virginia government did not provide any incentives, raising the question of whether DC’s incentives mattered in the first place (Medici 2019; see also Jansa 2020).
The benefits of the city’s pivot were unevenly distributed. But this new model of development, based in a citywide embrace of tech, forced other organizations, especially those concerned with poverty, to adopt the startup model of work and culture exemplified by InCrowd. Hoping to save themselves and the people they serve—both, the story goes, on the wrong side of the digital divide—places like schools and libraries attempted to pivot to a new identity and a new way of organizing their mission. They wanted a piece of tech’s hope for themselves and the people they served. But older political commitments and harsh economic realities prevented a startup-style pivot and end up forcing impossible choices on these community spaces. This is the dynamic I call bootstrapping, and to see it in action we have to move a few blocks away from InCrowd’s offices—to the MLK central library branch.
1. InCrowd and Hearth are both pseudonyms. Elements of the startups’ business strategies and branding have been altered to preserve anonymity, while still retaining the core features of their revenue models, operations, and identities.
2. Bridging organizations was originally a term used in the development literature (Brown 1991) to describe those nongovernmental organizations that link scattered antipoverty initiatives and their constituencies into a broader movement. I use it to describe those organizations devoted to sharing resources and ideas among similar organizations and advancing the cause of a sector more generally (Reveley and Ville 2010). In the private sector, this may mean voluntary industry associations in which business leaders participate, professional associations in which workers participate, regulatory agencies that promote local development of a field or define its credentials, or training organizations that bring newcomers into the field. In the public sector, we may add to this list those philanthropies that fund new initiatives in the field, convene discussions on the field, and thus shape its priorities. It is important too to recognize the role that private sector bridging organizations play in remolding the public sector.
3. Two persistent myths obscure the division of emotional labor in startups. First, the very real sexism in the industry and the declining presence of women in computer engineering and computer science majors since the 1980s (NSF 2013) leads to the assumption that women are largely absent from the tech sector or at least inessential to it (e.g., Khazan 2015). Women may be undervalued in tech, but exploitation is not absence. It is, rather, a sign of the many types of paid and unpaid labor that are crucial to the maintenance of the company but are not paid fairly because this work is perceived to be either unskilled, in comparison to software development, or the sort of caring, interpersonal work women are supposed to take to naturally. As Kate Losse’s (2012) history of Facebook’s early years showed, women in startups find themselves playing a variety of roles beyond those listed in their official duties (e.g., planning events, mediating disputes), many of which are crucial to the continued success of the firm (e.g., Losse’s work as Zuckerberg’s ghost writer) but do not match the cultural ideal of the young, White, male software developer. Second, the very real focus in the very competitive industry on quick-moving business plans and computer science skills leads to the assumption that tech does not care about or think deeply about culture. Of course, everyone has culture and all organizations build a specific—if sometimes implicit—internal cultural in order to keep themselves going. Startup engineers may have a very different understanding of culture from humanists, but they still research it, act on it, and actively promote it in their organizations (Seaver 2015).
4. Office tours were a fixture of the DC startup scene—so much so that DC Inno, the local industry news portal, ran a regular Office Envy column with breathless photo tours of startup offices.
5. Five years later, WeWork would become the face of tech excess. Multibillion dollar losses and no clear path to profitability meant its business model—subleasing office space to entrepreneurs—collapsed and its IPO unraveled (Platt and Edgecliffe-Johnson 2020).
6. Since the 1990s, DC has been notoriously bad at maintaining its jobs programs. The Department of Labor ranked it dead last among “states” in terms of effectively using federal job training funds. Since 2012, Labor has classified DC as a high-risk partner for job-training programs (McCartney 2015).
7. DC is effectively a one-party city, so the Democratic primary in spring is the de facto general election for mayor.