One afternoon in late March, Kevin Nazemi stood along a wall of the small, sweltering offices of the health insurance start-up Oscar in downtown New York, trying to rally the troops.
Noting that so far more than 10,600 New Yorkers had signed up for health insurance through Oscar, Mr. Nazemi, 32, a former Microsoft marketer who was a co-founder of Oscar last year, predicted long hours as individuals raced to meet the March 31 deadline for insurance coverage this year.
As Mr. Nazemi wrapped up, the 50 or so people in the room — most of whom appeared to be wilting in the heat thanks to a malfunctioning thermostat and in dire need of a Red Bull — clapped weakly before returning to their phones or computer screens.
Nearby, another founder, Joshua Kushner, 28, the scion of a New York area real estate dynasty whose venture capital firm has placed a sizable bet on Oscar, watched silently as he pulled his bright purple hoodie up over his head.
Oscar is Silicon Alley’s challenge to the staid business of health insurance. It is trying to use its tech-world skills to provide an easier experience to consumers. Its snazzy website is extremely easy to navigate (typing in “I have a stomachache” will pull up many options of types of doctors or facilities to visit). But what sets it apart, at least for now, is telemedicine, or unlimited phone calls with physicians, and greater price transparency.
It was dreamed up by a group of Harvard Business School tech entrepreneurs and investors and built by whiz-kid engineers and designers from Facebook, Google and Tumblr. With financing from big venture capital names and a cutesy ad campaign splashed all over New York City’s subways, Oscar has the new-era tech pedigree to become the Spotify, Airbnb or Uber of health insurance.
But what Oscar doesn’t have — yet — is the numbers. Depending on how you slice and dice the data, the 10,600 New Yorkers who had signed up as of late March represent anywhere from 2 to 5 percent of all individuals who enrolled in plans.
The New York insurance market — like many others across the country — is highly competitive and fragmented. Oscar and other new entrants have discovered that many individuals are buying insurance through established, brand-name companies. After that, they are going for price, choosing plans that charge smaller monthly premiums.
Oscar is neither a household name nor the cheapest plan out there.
But its founders are quick to paint Oscar’s small customer base as a victory. Those numbers, which they expect to grow to about 13,000 before the deadline, have far exceeded their expectations, they say. Moreover, they say, it’s not all about the numbers.
“We’re not a social app that is trying to chase the most hits. We’re trying to build something that’s going to turn the industry on its head,” says Mr. Kushner from Oscar’s offices in the landmark Puck Building, which is owned by his family.
Tall and lanky with a boyish face that is highlighted by brown hair that tends to shoot in different directions, Mr. Kushner is a spinning star in the constellation of young entrepreneurs and investors leading the latest wave of tech start-ups.
He is the youngest son of Charles Kushner, a real estate tycoon, philanthropist and major Democratic political donor, who spent time in jail nearly a decade ago for tax evasion, witness-tampering and other charges.
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