The Upside of Humility

This willingness to listen to a founder’s unique knowledge instead of relying on his own experience distinguishes Maples from many lesser VCs. When economists talk of asymmetric information, they almost always view it as a problem: the risk that the party with more information will take advantage of the less informed party, which in turn causes suspicion, skepticism, and distrust by the other party. But Maples shows us that a middleman who keeps an open mind can benefit from the superior information of the entrepreneurs seeking funding.³⁹ For example, when he listened to the pitch from Chegg, the textbook rental company, he realized that the founders knew what they were talking about when they predicted that college students will rent textbooks. New college textbooks are notoriously expensive;⁴⁰ Chegg’s founders believed that if they did for textbooks what Netflix did for movies, students would eagerly sign up—and the company’s eventual success showed that they were right. But most VCs didn’t get it because they’re wealthy enough to pay for their kids’ textbooks. “A VC has no visceral understanding of why a debt-strapped college kid is going to rent a textbook—it just didn’t compute in a VC’s world,” Maples says. Maples seems too nice to say this outright, but this story and others like it paint a picture of many VCs as people who are not only out of touch with reality, but also too arrogant to realize that they are out of touch; they are too sure of themselves to consider that someone with less business experience might know something they don’t. Maples’s story about Chegg reminded me of the pushback SitterCity founder Genevieve Thiers faced when pitching her idea to VCs, some of whom said dismissively, “My wife handles that stuff.”⁴¹

The dismissive attitude seems to be an occupational hazard of gatekeeping middlemen, and one that Maples appears to have so far avoided. When a big part of your job involves saying no, and when you have the authority to write a large check, some of this power can go to your head. Psychologists have found that people in power actually see, think, and behave differently, having trouble adjusting their view to encompass alternative perspectives. We are all biased toward our own experience, of course, but research has shown that the powerful are more so. The most vivid illustration of this tendency is the “Letter E ” experiment by psychologist Adam Galinsky and colleagues, in which the researchers asked participants to quickly write the letter E on their own foreheads after being made to feel either powerful or powerless. Those who had been made to feel powerful (by recalling a time they had dominated others) were three times more likely to draw the E in a self-oriented direction—as if they themselves were looking at it—than those who’d been told to recall a time they felt low power. The low-power participants tended to write the letter so it faced the audience, a more empathic approach to the task.⁴² Maples has gained considerable power, too, but has somehow managed to maintain a healthy humility, which keeps him open to good ideas from founders.

Nowhere is this more apparent than in his openness to ideas from female founders. Recent studies have shown people to be more likely to accept business proposals from men (especially goodlooking men)—even when the proposals were identical.⁴³ It is the sort of coarse decision-making shortcut that may actually have once served investors well—but it is ill-suited to an environment in which anyone can become an entrepreneur. “When I was a kid, the tech industry was really geeks selling to geeks,” Maples recalls. “Then it was geeks selling to the rest of the world because the world is connected. But what Ann and I are seeing are new types of entrepreneurs emerging,” he says. “In the last decade, to be an entrepreneur you had to raise money, and Sand Hill Road had a preconceived idea of what a tech entrepreneur looked like—they were usually an early-twenties white dude, who was an alpha-geek computer hacker. And that was kind of the canonical person you’d invest in.” In B2B ventures, companies that sell products to other companies, the prototypical entrepreneur looked a little different, but it was still typically a he. “We believe that the low cost of starting a company is democratizing entrepreneurship itself,” Maples says, “and now entrepreneurs can emerge from any location and they can be any gender and any ethnicity, and so rather than a high priest on Sand Hill Road deciding what a start-up entrepreneur is, people can just do entrepreneurship, and whoever gets traction is an entrepreneur. That’s going to fundamentally change the nature of entrepreneurship and who starts companies and succeeds.” As entrepreneurship becomes accessible to more people and more different types of people, Maples says, he and Miura-Ko want to be accelerants of that trend; even in this climate, entrepreneurs need VCs for access to capital markets. “If you’re Leah Busque and you’re starting TaskRabbit, it doesn’t matter how good the idea is if you can’t raise a dime.”