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Does Oscar Sound Cooler Than Aetna?

From left, Kristina Berger, 39, dancer and choreographer; JD Sharpe, 24, real-estate broker; Yoni Weiss, 24, graphic designer   

“When I first got here, I was head-to-toe in Brooks Brothers, with a tie,” Dave Henderson, the head of insurance, confessed sheepishly. “That was the world I’d come from. Now take a look at me.” He pointed down at an open-collared oxford. “Sometimes I’ll even wear jeans.”

Behind Henderson, on an LCD display, blinked the enrollment figures for Oscar: roughly 16,000 subscribers, good enough for an estimated year-end revenue of $72 million. That’s more than double the number of subscribers Oscar had originally forecast, and considering what industry expert Gary Claxton calls “the high barriers for entry for new insurers”—the networks to build, the reserves you’ve got to have in the bank (Oscar needed $25 million for New York alone), the Byzantine ­licensing—the company was off to a respectable start.

I followed Kushner, Nazemi, and Schlosser into a conference room overlooking Houston Street. Kushner grabbed a keyboard and pulled up his personal Oscar profile on a projection screen. In interviews, he often says that the idea for the company was born when he attempted to parse a particularly complicated bill from his old insurer. “I’m overeducated,” he told me, “and I had no idea what it all meant. So I thought, Okay, how can we take technology, data, and design and make this transparent and easy to understand?

He gave an example: A few weeks earlier, he’d felt some rawness in his throat that he was worried might be strep. Using his Oscar iPhone app, he put in a request with his doctor, who phoned him back in 15 minutes. The doctor, Kushner recalled, “asked me to stand in front of a mirror and look at the back of my throat. Did I have white spots on the back of my throat? I did. He said, ‘I’m going to prescribe you Amoxicillin.’ ” (Oscar has stressed that the call feature is not intended for ongoing care nor major ­medical conditions. “We’re not going to treat diabetes by phone,” Nazemi told me.)

Kushner’s profile displayed the details of his “visit,” along with notes from the doctor, reminders about follow-ups, and warnings about possible drug interactions. “Health insurers, in the past, signed up customers and then did everything they could to avoid them,” Kushner concluded, handing off the controls to Schlosser. “Our ambition is to do the opposite.”

Schlosser and Kushner met at Harvard Business School and, in 2007, along with a few other friends, started Vostu, a Latin American gaming company—a kind of south-of-the-border Zynga. At Oscar, Schlosser’s role is one of chief programmer and designer—the leader of the hoodies. As he pointed out to me, the types of technology that Oscar utilizes are well established, if historically siloed. For instance, an individual might sign up for a service like MyMediConnect or Microsoft HealthVault, platforms that can be used to track and store personal medical data. “In those cases, though, you go to your doctor and ask him for your records or your claims, and then you’ve got to plug it all in,” Schlosser says. “The nice thing here is that you don’t have to do anything—you go to the doctor, and it all comes back to us directly and seamlessly.”

It was impossible not to be impressed by the presentation in the same stunned and respectful way you’d be impressed by any number of cutting-edge technologies, from a smartwatch to a newfangled video-­sharing portal—it was pretty, and it looked like the future. But it was also impossible not to be a bit unsettled by the implications. For instance, is it wise to trust so much of our health history to the cloud? Is the Silicon Valley ethos, with its premium on sharing and openness—and as a corollary, the steady monetization of personal information—really compatible with the health-care system? (Schlosser told me that the servers that store Oscar’s subscriber information are several times more secure than regulators mandate; he added that Oscar would never sell user data in any way.)

Perhaps most vitally, is the whole thing stable? No matter how much is said about big insurance companies and their garbled paper bills and their bad allergy to innovation, those same big insurers are durable. They have deep foundations. Oscar, on the other hand, has had to cobble together its operation from preexisting bricks: Dave Henderson (he of the open-collared oxford shirt) brought in lawyers with Albany connections to help navigate the certification process; claims are being processed by a company out in Cincinnati; in-house software crawls the state database for pricing info on local doctors. And rather than attempt to build its own network of providers, Oscar has piggybacked onto the shoulders of MagnaCare, a network that extends across New York and New Jersey.