South by Southwest

How a 25-year-old high-school dropout cold-emailed Mark Cuban and got an investment

Adam Lyons, CEO of The Zebra
Photo courtesy The Zebra
Adam Lyons, CEO of The Zebra

When Adam Lyons completed a program at an intensive start-up accelerator in Pittsburgh, he had his insurance rate comparison start-up, The Zebra, in good shape, and he had also decided on a dream investor: Mark Cuban.

Lyons didn't know how to get in touch with Cuban, but he guessed the billionaire's email address and sent a short email with the subject line, "Wanna disrupt the insurance industry?"

Twenty minutes later, the 25-year-old got an email back. It was a response from the star of ABC's "Shark Tank" and owner of the Dallas Mavericks.

Adam Lyons (L) and Mark Cuban on stage at SXSW.
Photo by JEALEX Photo

For the next several weeks, Lyons and Cuban emailed back and forth about Lyons' business plan, which involved building a platform where customers could go and compare estimates for car insurance. Then, without ever meeting in person or talking on the phone, Cuban made an investment in Lyons.

Cuban, who is obsessed with email as a preferred method of doing business, says the email from Lyons was perfectly timed. It was 2012, and Cuban thought the insurance industry could be improved with more technology and transparency.

"I didn't know if he would respond. I was actually surprised when he did." -Adam Lyons, CEO of The Zebra

"He was talking about innovating and automating the process of comparing car insurance and it was an area that I thought was ready to be disrupted," says the investor, speaking at the SXSW Conferences and Festivals in Austin. Lyons, now 29, was on stage with Cuban for the talk.

Cuban invested an undisclosed amount in Zebra and serves as an advisor to its founder, who says the billionaire is very responsive on email and provides invaluable advice. Since launching in 2012, Austin-based Zebra has raised more than $21 million and has 70 employees.

Making it to a stage with Cuban at SXSW represents a radical transformation for Lyons. At 15, he dropped out of high school, and at 16, he left home, taking a series of low-skilled jobs like bagging groceries, washing dishes and packing boxes in warehouses. He was fired from most of those, he says.

Lyons started taking classes at the local community college and those credits allowed him to get into college, even without a high school diploma. He graduated from Temple University and got an internship at Lloyd's in London, which is how he became fascinated with insurance. He worked in insurance in Florida and then got a sales job in Philadelphia.

After getting fired, again, he changed course, bought a one way ticket to Colombia and backpacked for almost half a year. But when he returned from South America, he got serious: He started his insurance start-up from a friend's basement, where he crashed while living off his unemployment checks. He got accepted at and completed his training at the accelerator program, AlphaLab in Pittsburgh. Then he emailed Cuban.

"I didn't know if he would respond. I was actually surprised when he did," Lyons tells CNBC. But he was so inspired by Cuban that he decided to give it a try. He wanted to work with the best advice he could get as he built his company.

Zebra only operates for cars right now, but the plan is to expand to other sectors.

"It's been a really cool journey so far. I still feel like I am just getting started," says Lyons. "I have learned so much and come so far, but it's one of those things — the further you get or the more you learn, it's like, 'Wow, there is so much to do.'"

See also:

Mark Cuban says that his best life hack is saying yes to email and no to meetings

Mark Cuban: Why I regret not investing in Uber

Mark Cuban: The world's first trillionaire will be an artificial intelligence entrepreneur