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

High School Dropout Raises $17 Million After Cold Emailing Mark Cuban

By
Erin Griffith
Erin Griffith
Down Arrow Button Icon
By
Erin Griffith
Erin Griffith
Down Arrow Button Icon
January 26, 2016, 9:15 AM ET
Courtesy The Zebra

Some of the country’s most successful entrepreneurs are college dropouts. But Adam Lyons, the founder and CEO of Austin-based insurance comparison startup The Zebra, might be the first high school dropout founder I’ve ever met.

Lyons left school at age 15 and embarked on a series of odd jobs, which included car flipping. That led him to the insurance industry, where he spent time working as an underwriter at Lloyd’s of London. (He eventually got a college degree from Temple University.)

In 2012 he launched The Zebra, a site that allows insurance customers to compare prices before they purchase. He sent cold emails to investors, including Mark Cuban, who was surprised a comparison-shopping site for insurance didn’t already exist. Cuban later invested, alongside Floodgate and other venture funds.

Today the company announced it raised $17 million in venture funding led by Ballast Point Ventures and Daher Capital. Cuban and other angel investors also participated.

“The Zebra is innovating a stodgy $220 billion industry by providing consumers the transparency they’ve needed for a long time,” says Cuban.

Cuban was correct ​in his initial disbelief​ that the startup’s business model had never been attempted before. Leaky, a graduate of Y Combinator, shut down in 2013 saying that it had been difficult to “get a foothold in the industry, which proved difficult as industry outsiders with a disruptive business model.”

Sign up for Data Sheet, Fortune’s technology newsletter.

The Zebra has managed to avoid that fate by embracing the insurance industry rather than trying to totally disrupt it. The company works with more than 200 insurance providers across all 50 states in the country, Lyons says. “The challenge is underestimating insurance,” he says. “It’s a very complex product. We want to help simplify everything for consumers, and one of the biggest challenges is a lack of transparency.”

Although, wouldn’t insurance companies benefit from that lack of transparency? Lyons notes that there is mistrust between consumers and insurance companies, but he doesn’t think they’re “evil.” “They don’t view any risk as a bad risk, they just need to price it correctly,” he says.

The Zebra makes money when someone buys insurance from its site, and in some states it also sells insurance on behalf of insurance providers. (About half of its customers buy directly through The Zebra.)

In 2015 the site helped 3.5 million people choose their insurance and the company grew its user base 35% each month last year, says the founder. Lyons plans to spend the new funding raised on marketing, and expanding its team of engineers and insurance agents. The company is building the capability to fulfill policies completely online, avoiding phone calls with agents that most insurers require. Although, with 50 employees, the site is still not yet profitable.

The Zebra faces competition from Google (GOOG), which announced its own insurance comparison product in March. Most other competitors are focused on lead-generation, which doesn’t benefit customers because they don’t compare all insurance options in one place.

The startup also faces competition from insurance companies, which are among the most aggressive advertisers in the country. The competition has the potential to drown out any message The Zebra wants to share with consumers. “It’s a pretty noisy space,” Lyons says. “We’re trying to cut through the noise.”

About the Author
By Erin Griffith
See full bioRight Arrow Button Icon

Latest in

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
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
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
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in

President Donald Trump delivers the State of the Union address during a joint session of Congress at the Capitol on February 24, 2026 in Washington, DC.
Economynational debt
The next generation of senators has a ticking time bomb in its lap: Social Security’s impending insolvency and no plan for the national debt
By Eleanor PringleApril 10, 2026
35 seconds ago
Who’s really in control as AI and Big Tech race ahead?
MagazineEurope
Who’s really in control as AI and Big Tech race ahead?
By Francesca CassidyApril 10, 2026
12 minutes ago
Today’s top high-yield savings rates: Up to 5.00% on April 10, 2026
Personal FinanceSavings accounts
Today’s top high-yield savings rates: Up to 5.00% on April 10, 2026
By Glen Luke FlanaganApril 10, 2026
53 minutes ago
Top CD rates today, April 10, 2026: Lock in up to up to 4.20%
Personal FinanceCertificates of Deposit (CDs)
Top CD rates today, April 10, 2026: Lock in up to up to 4.20%
By Glen Luke FlanaganApril 10, 2026
53 minutes ago
Photo: Donald Trump
EconomyMarkets
U.S. and Iran begin peace talks as Trump’s White House goes to war against the media, insider traders, and the Pope
By Jim EdwardsApril 10, 2026
57 minutes ago
Defense executives worry Trump’s proposed military splurge could backfire
NewslettersCEO Daily
Defense executives worry Trump’s proposed military splurge could backfire
By Diane BradyApril 10, 2026
1 hour ago

Most Popular

The U.S. government is spending $88 billion a month in interest on national debt—equal to spending on defense and education combined
Economy
The U.S. government is spending $88 billion a month in interest on national debt—equal to spending on defense and education combined
By Fortune EditorsApril 9, 2026
24 hours ago
A Meta employee created a dashboard so coworkers can compete to be the company's No. 1 AI token user—and Zuckerberg doesn't even rank in the top 250
AI
A Meta employee created a dashboard so coworkers can compete to be the company's No. 1 AI token user—and Zuckerberg doesn't even rank in the top 250
By Fortune EditorsApril 9, 2026
1 day ago
Gen Z doesn't want your full-time job. They want several part-time roles, and it's reshaping the entire workforce
Success
Gen Z doesn't want your full-time job. They want several part-time roles, and it's reshaping the entire workforce
By Fortune EditorsApril 9, 2026
1 day ago
White-collar workers are quietly rebelling against AI as 80% outright refuse adoption mandates
AI
White-collar workers are quietly rebelling against AI as 80% outright refuse adoption mandates
By Fortune EditorsApril 9, 2026
1 day ago
Gen Z workers are so fearful AI will take their job they’re intentionally sabotaging their company’s AI rollout
AI
Gen Z workers are so fearful AI will take their job they’re intentionally sabotaging their company’s AI rollout
By Fortune EditorsApril 8, 2026
2 days ago
Current price of oil as of April 9, 2026
Personal Finance
Current price of oil as of April 9, 2026
By Fortune EditorsApril 9, 2026
23 hours 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.