Behind the Startup: A Conversation with Benjamin Shestakofsky

We are thrilled to welcome Benjamin Shestakofsky to the Contexts Blog to celebrate the publication of his new book, Behind the Startup: How Venture Capital Shapes Work, Innovation, and Inequality. In this post, blog editor Elena van Stee chats with Ben about everyday life inside a tech startup and the consequences of venture capital funding. You can watch the full interview above and find lightly edited excerpts from their conversation below.

Elena van Stee: Can you tell us about the startup you studied and what prompted your initial interest in it?

Benjamin Shestakofsky: I call the startup “AllDone” (that’s a pseudonym). It provided a digital platform for local services. If you wanted to hire a house cleaner, math tutor, or wedding photographer, you could log into this platform as a customer, and they would connect you with providers of that service in their database.

I worked at a startup prior to grad school—not in a technical role but in a content generation and managerial role. And I didn’t think that that’s what I was going to end up studying, but it ended up making a lot of sense to me. I was always fascinated by this idea that rich people give these young folks a lot of money, and all of a sudden, they’re starting a company. What was going on there?

So I knew I wanted to study startups in general, and I knew that I wanted to do participant observation research. And so I went to my network—as most novice ethnographers do—to look for connections. In this case, I had a friend who had gone to high school with one of the co-founders of AllDone, and she was able to broker an introduction.

I explained that I was interested in studying their company and offered free labor in exchange […] At first, I was an unpaid intern, just coming in one day a week. But pretty soon, [my supervisor] asked me, “Could you come in twice a week, and we’d even pay you a little bit?” And I said, “Okay, seems like a win-win.”

EVS: What do you think [your position inside the company] helped you see that you might not have otherwise?

BS: Josh Seim wrote this great article about hybrid ethnography. In the article, he describes the spectrum of different ways of doing ethnography. On one end is participant observation, where the observation component is more emphasized. On the other end is observant participation, where an ethnographer is deeply involved in the activities of the field site. For me, the advantages of deep involvement (observant participation) were twofold. First, it gave me increased depth of access. The more involved I got with the company, the more I could see and understand. I got involved with all three of the company’s teams—San Francisco first, then the Philippines, and then Las Vegas. And I got to see not only what members of different groups were doing, but also the relationships between groups […] The other thing  Josh talks about in his article is that observant participants [have] the opportunity to engage in tacit learning through embodying an organizational role and experiences that are, if not exactly the same, at least in some way similar to what others in the field are going through.“The story I tell is about how the financing structure for startups shapes everything that happens inside them.”

EVS: Tell us a bit about what you found and what you hope others will take away from this book.

BS: In the popular press, there are a lot of startup exposes that are very sensationalized, and they portray tech founders as villains or fools. They’re always entertaining stories. But I think they don’t always tell the whole story. There’s also a lot of academic work on algorithms, and how technology itself contributes to inequalities. As I was writing this book, I realized I had a story to tell that was more about the structures that create the conditions that seem to systematically generate tech founders who do morally questionable things and algorithmic systems that can end up harming people. […] The story I tell is about how the financing structure for startups shapes everything that happens inside them.

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Benjamin Shestakofsky is in the Department of Sociology at the University of Pennsylvania. He is the author of Behind the Startup: How Venture Capital Shapes Work, Innovation, and Inequality. Elena van Stee is a graduate student in the Department of Sociology at the University of Pennsylvania. She studies culture and inequality, focusing on social class, families, and the transition to adulthood.