• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock

2

OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation

3

‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion

1

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock

2

OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation

3

‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
Tech

For health insurance startup Oscar, it’s get bought—or go bust

Andrew Nusca
By
Andrew Nusca
Andrew Nusca
Editorial Director, Brainstorm; author, Fortune Tech
Down Arrow Button Icon
Andrew Nusca
By
Andrew Nusca
Andrew Nusca
Editorial Director, Brainstorm; author, Fortune Tech
Down Arrow Button Icon
September 9, 2015, 11:37 AM ET
Oscar health insurance box gif
Oscar health insurance boxCourtesy: Oscar
Add Fortune on Google for similar content.

“Oscar has hundreds of millions in funding,” screams a September 3 article in Bloomberg Businessweek. “Now it needs customers.”

In this Age of Unicorns—that is, this age of privately-held technology companies valued at more than $1 billion—you could probably replace “Oscar” with the name of virtually any billion-dollar startup and get the same result.

“23andMe has hundreds of millions in funding. Now it needs [paying] customers.”

“Lyft has millions in funding. Now it needs customers.”

“Tinder has millions in funding. Now it needs customers.”

OK, maybe not that last one. But you get the drift. In today’s frothy market, it’s often easier to obtain venture capital than it is customers—let alone enough revenue from them to turn a profit. And that’s the case for many companies on Fortune’s Unicorn List.

Oscar, the two-year-old New York health insurance company, is quite clear that it’s trying to shake up a staid market. Its ads, for a time plastered across New York City’s public transit system, were illustrated and adorable and very much the last thing you’d expect from an insurance company. The message was clear: We’re different. What’s not clear is whether the business it’s in will allow it to be different enough to, well, make a difference.

The Businessweek article outlines why, right at the outset. The health insurance industry is highly regulated. It’s extremely competitive. Financial success requires scale—on the insured side, enough healthy people to support the fundamental insurance business model; on the provider side, enough hospitals and doctors willing to provide favorable prices.

With the 2010 Affordable Care Act at its back, Oscar is pushing its technology as a differentiator. It says its system connects doctors and patients faster than the rest of the pack and its consumer-facing products—mobile app, website, bills—are easier to use and understand, too. Behind the scenes, data collection from those health visits refines the physician search.

But it’s unclear whether those forward-thinking features will help it win in a market so strongly dominated by size. Can Oscar’s agility help it outmaneuver increasingly large competitors as it continues to lose tens of millions of dollars per year? In almost a single month this summer, Anthem and Cigna hooked up for nearly $48 billion; Aetna and Humana did the same for $37 billion; and Centene and Health Net recited vows to the tune of $6.8 billion. To the best of my knowledge, the only “billion” found in Oscar’s financials is its valuation. (It has raised about $300 million from investors.)

Moreover, the road so far hasn’t all been roses. From Fortune’s December 2014 report on the company:

[CEO Mario] Schlosser admits Oscar failed to properly communicate how deductibles and healthcare plans work to its members. “The healthcare system is astoundingly complex,” he says. Oscar customers can avoid unexpected payments by keeping in close contact with the company while receiving care. “There are uncontrollable traps in the healthcare system,” he says. “The complexity of this system is astounding and the immediate thing we can do to make sure none of this happens is have you come through us.”

The company has managed to become a serious competitor in New York (No. 4 U.S. state by population) and New Jersey, and it has serious plans to expand to Texas (No. 2) and California (No. 1) this fall. Recipe for disaster or risk worth taking? We’ll soon find out.

Sign up for Data Sheet, Fortune’s daily newsletter about the business of technology.

About the Author
Andrew Nusca
By Andrew NuscaEditorial Director, Brainstorm; author, Fortune Tech
Instagram iconLinkedIn iconTwitter icon

Andrew Nusca is the editorial director of Brainstorm, Fortune's innovation-obsessed community and event series. He also authors Fortune Tech, Fortune’s flagship tech newsletter.

See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Tech

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • TikTok icon
  • YouTube icon

Latest in Tech

orson
CommentaryOpenAI
We got California to intervene about OpenAI’s corporate switch from nonprofit status. It’s time for the SEC to come to the table
By Orson Aguilar and Catherine BracyJuly 22, 2026
36 minutes ago
A woman observes stock trends on her smartphone while a computer screen displays financial graphs.
NewslettersCFO Daily
Beyond SpaceX: Why great IPOs depend on more than first-day demand
By Sheryl EstradaJuly 22, 2026
44 minutes ago
Arrakis cofounder and CEO Rafael Quintanilla.
Startups & VentureVenture Capital
Exclusive: Arrakis, betting AI’s biggest payoff is in industrial sectors not office work, emerges from stealth with $38 million in venture funding
By Jeremy KahnJuly 22, 2026
1 hour ago
ls
Commentarybooks
Confessions of an award-winning AI memoirist — the ‘slop’ debate isn’t really about good writing, and you know it
By Luke StoffelJuly 22, 2026
2 hours ago
b
Commentarythe future of work
Manpower President: The future of work question that even CEOs can’t answer
By Becky FrankiewiczJuly 22, 2026
2 hours ago
nela
Successdisruption
Exclusive: Stanford and ADP have new payroll data on Gen Z women losing ground to men in the job market—and AI isn’t the main culprit
By Nick LichtenbergJuly 22, 2026
2 hours ago

Most Popular

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock
Success
Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock
By Sasha RogelbergJuly 20, 2026
2 days ago
OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation
Cybersecurity
OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation
By Jeremy Kahn and Emily ForliniJuly 21, 2026
17 hours ago
‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
Success
‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
By Sydney LakeJuly 20, 2026
2 days ago
Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
AI
Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
By Eva RoytburgJuly 21, 2026
21 hours ago
Despite a $156 million contract, Knicks star Jalen Brunson still calls his parents for financial advice any time he makes a big purchase
Success
Despite a $156 million contract, Knicks star Jalen Brunson still calls his parents for financial advice any time he makes a big purchase
By Emma BurleighJuly 21, 2026
22 hours ago
'Dr. Doom' Nouriel Roubini says we're headed for universal basic income or 'some form of socialism' as AI revolutionizes work—He calls that optimistic
AI
'Dr. Doom' Nouriel Roubini says we're headed for universal basic income or 'some form of socialism' as AI revolutionizes work—He calls that optimistic
By Jason MaJuly 18, 2026
4 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.