• 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

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

3

'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

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

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

3

'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
TechA Boom With A View

When Software Tries to Eat Regulation

By
Erin Griffith
Erin Griffith
Down Arrow Button Icon
By
Erin Griffith
Erin Griffith
Down Arrow Button Icon
February 9, 2016, 1:33 PM ET
ZENEFITS Insurance Broker, Parker Conrad
Pickup Armin HarrisPhotograph by Jim Wilson—The New York Times/Redux
Add Fortune on Google for similar content.

Last night Zenefits, the corporate benefits software company, announced that its CEO and founder Parker Conrad had stepped down. Chief operating officer David Sacks became CEO. In an email to employees provided to media, Sacks wrote, “The fact is that many of our internal processes, controls, and actions around compliance have been inadequate, and some decisions have just been plain wrong. As a result, Parker has resigned.”

The message was clear: Zenefits was in legal trouble, and it was Conrad’s fault. He was not given a ceremonial title. He was not given a board seat. He was not spared the blame.

Until last night, Conrad played the role of the disruptive underdog going after the big, evil corporation. As I wrote last year, Zenefits brought a buzzy excitement to an otherwise dull sector. Just two years into its life, Zenefits had already been banned, demonized, and sued. A competitor called its PR strategy “manipulative and malicious,” and insurance brokers called its business model a “threat.”

Through it all, Conrad, colorfully defended his company’s right to disrupt. I wrote at the time:

Insurance brokers? “Fucked,” he told Fortune. Regulators in Utah, which temporarily banned the company’s services? “Blatant overreaching,” Conrad says. The legislation itself? “Kafkaesque.” When Automatic Data Processing, the $40 billion HR services company, sued Zenefits in June, Conrad launched the Twitter hashtag #ADPeeved.

It created a compelling narrative to root for. Conrad himself is a bit of an underdog. He graduated from Harvard after flunking out, beat testicular cancer at 24, and was pushed out of his previous startup, SigFig, by his own co-founder. He compared Zenefits’ mission of fixing employee benefits administration to the rebel alliance in Star Wars. (Zenefits’ conference rooms even have Star Wars themes.) Today, some those fights look more like red flags than positive attributes.

When the company raised an early round of funding, it was called “the hottest deal in Silicon Valley.” When its valuation jumped 9x to $4.5 billion in one year, the company had already amassed 10,000 customers. Conrad complained he couldn’t grow the company fast enough to keep up with demand. By the end of this year, Zenefits stumbled on missed targets, layoffs, and major write-downs from its investors.

The Zenefits meltdown follows a similar pattern at other startups in highly regulated categories. First a media report raises questions about a company’s business practices. Then regulators take a closer look. Then we find out that the disruption wasn’t quite as magical—or at least, not as legal—as it seemed. It happened at blood testing startup Theranos, worth $9 billion. It happened at fantasy sports betting sites DraftKings and FanDuel, worth respective $1.2 billion and $1.3 billion. It happened at DNA testing kit 23andMe, valued at $1 billion.

How does Silicon Valley keep letting this happen?

Get Data Sheet, Fortune’s technology newsletter.

It’s safe to say Silicon Valley worships at the altar of disruption. TechCrunch has a whole conference named after it. Disruption is an important part of Silicon Valley’s history: Innovative companies rise and turn into giant, slow-moving bureaucratic conglomerates. New, faster-moving startups emerge to unseat them. Cue “Circle of Life.”

But the definition of disruption has changed as we’ve entered the era of “software is eating the world.” If, as prominent venture investor (and Zenefits backer) Marc Andreessen posits, every industry we know will be disrupted by software, the opportunities are all around us. Transportation, blood testing, pizza delivery, shipping containers, bras—everything is fair game for disruption!

Except the stakes are a lot higher when startups disrupt highly regulated industries like health care, lending, insurance, or investing than they are for advertising, shopping, or music.

That hasn’t stopped startup founders from going for it. Some of the hottest startups of recent years have taken on those industries. Uber is disrupting transportation. Theranos is disrupting blood testing. Zenefits and Gusto are disrupting employee benefits. Oscar is disrupting health insurance. SoFi and Credit Karma are disrupting lending. Wealthfront and Betterment are disrupting investing. The list goes on.

Many startup founders are unapologetic in their ignorance of regulations. Not knowing or purposely flouting “the rules” of an industry used to be an advantage because you brought new perspective that insiders were blind to. (The hospitality industry, for example, dismissed Airbnb as a ridiculous idea. The TV industry still likes to snub Internet advertising.)

The writer Paul Carr memorably described the phenomenon in 2012:

Increasingly, though, the conference stage was filled with brash, Millennial entrepreneurs vowing to “Disrupt” real-world laws and regulations in the same way that me stealing your dog is Disrupting the idea of pet ownership. On more than one occasion a judge would ask an entrepreneur “Is this legal?” to which the reply would inevitably come: “Not yet.” The audience would laugh and applaud. What chutzpah! So Disruptive!

It’s easy to shrug off a startup that operates in the gray area of the law when it’s just a few people and an idea. We assume they’ll figure out the regulations and comply before they get big enough to cause any real problems. But in the so-called Age of Unicorns, startups can go from zero to $1 billion in the blink of an eye. It’s become very clear we can’t assume a billion-dollar company is legit just because some venture investors said so.

But these companies are private, so information on how they work is hard to come by. It’s possible that if BuzzFeed hadn’t first revealed that Zenefits was selling insurance without the proper licenses, the company wouldn’t have come under investigation by Washington State, which ultimately led to Conrad’s ouster. Or if The Wall Street Journal hadn’t revealed problems with Theranos’ blood tests, Walgreens (WAG) may not have suspended its lab testing with the company in California. But when reporters ask hard questions, Silicon Valley’s response is to call them “haters.”

Software is trying to eat some of the thornier parts of the world. I have no doubt that incredible, world-changing innovations will come out of it. But until founders figure out a way to disrupt within the existing legal framework, there will be some some ugly fights, and plenty of “haters,” along the way.

About the Author
By Erin Griffith
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

kalshi
CryptoKalshi
Kalshi’s ‘chronically online’ war room figured out World Cup virality — and realized AI might be bringing back the monoculture
By Nick LichtenbergJuly 21, 2026
2 hours ago
fl
North AmericaElections
Trump-backed hopeful to succeed DeSantis unveils plan to protect local water, electricity from data centers
By Matt Brown and The Associated PressJuly 21, 2026
2 hours ago
Bolt CEO Ryan Breslow
CommentaryHuman resources
The CEO who fired HR was right. About the wrong thing.
By KeyAnna SchmiedlJuly 21, 2026
3 hours ago
‘We all failed’: Former Disney CEO Michael Eisner on Hollywood, video games and the big question of IP
Arts & EntertainmentDisney
‘We all failed’: Former Disney CEO Michael Eisner on Hollywood, video games and the big question of IP
By Joshua HongJuly 21, 2026
3 hours ago
Jersey Mike's Subs restaurant.
C-SuiteCFO Daily
Jersey Mike’s tests how far investors will stretch on restaurant IPO valuations
By Sheryl EstradaJuly 21, 2026
3 hours ago
all five founders of SkyPilot pose for a photo
Startups & VentureTerm Sheet
SkyPilot, from Databricks’ cofounder, raises $20M to be the Switzerland of AI compute
By Lily Mae LazarusJuly 21, 2026
3 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
21 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
1 day 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
3 days ago
Current price of silver as of Monday, July 20, 2026
Personal Finance
Current price of silver as of Monday, July 20, 2026
By Joseph HostetlerJuly 20, 2026
1 day ago
It’s not just Taco Bell lettuce and possible glass in Pillsbury rolls: Food and drink recall events reached a 6-year year-over-year high
Retail
It’s not just Taco Bell lettuce and possible glass in Pillsbury rolls: Food and drink recall events reached a 6-year year-over-year high
By Sasha RogelbergJuly 20, 2026
1 day ago
Current price of oil as of July 20, 2026
Personal Finance
Current price of oil as of July 20, 2026
By Joseph HostetlerJuly 20, 2026
1 day 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.