Hugh Forrest, Chief of Programming at South by Southwest, interviewed Lyons Tuesday evening at WeWork Barton Springs at a PowerUp Austin event put on by the Greater Austin Chamber of Commerce. He started off with a somber discussion about the hate crime last Saturday when a gunman killed 11 individuals and wounded two others at the Tree of Life Synagogue. It is believed to be the deadliest attack on the Jewish community in the history of the United States, according to a statement from the Anti-Defamation League.
“It hit close to home for me,” said Lyons, who is Jewish. “Thoughts and prayers have been with the city of Pittsburgh.”
It’s incredibly sad, Lyons said.
Forrest asked Lyons about the effect social media and technology have had on fueling hateful discussions and actions.
Lyons said he thinks a lot about free speech online, but he doesn’t have the answers. Technology has made it easy for people to manipulate others. They can create fake stories, video, and audio today, he said.
“Now you’ve got a situation where you can literally have anybody saying anything on video,” Lyons said. “And I think folks, especially who aren’t in tech, are just going to look at that and think that’s real. And that’s today. Fast forward five, ten years and I think at this rate it’s going to be very hard to distinguish what’s real and what’s not.”
Some regulation would be good, Lyons said. At the same time, it gets to be tricky and dangerous if you start to edit people. It’s very subjective, he said.
Forrest asked Lyons if there were opportunities to create better social media platforms in which subscribers paid to participate instead of the technology companies selling data on its users to make a profit.
“The traditional media model is a challenge especially if you are starting something new today,” Lyons said.
There are some organizations that are doing cool things charging subscriptions for content, Lyons said. He went to the Middle East two years ago and a group of teenagers, half were from Palestine and half were from Israel, were involved in a project to create a news site with both sides of news stories. Over time, they became close friends.
“There is a need to get the conversation going in a way that both sides are there,” Lyons said.
In 2012, Lyons launched The Zebra, an aggregation and comparison site for insurance, in Pittsburgh.
Lyons’ took an unusual path to entrepreneurship. At 15, he dropped out of high school. A year later, he left home and worked several odd jobs and had no idea what he wanted to do.
“A lot of folks in my life brushed me off and said he’s not going to do anything,” Lyons said.
He got fired from bagging groceries. He got fired from packing boxes.
“I didn’t really have a choice, I had to go figure out how to school myself at this point,” Lyons said. He ended up realizing he wanted to do business. He snuck back into community college and then transferred to Temple University. He graduated and got an internship in London and ended up working in insurance. He saw how massive and antiquated the industry was, he said.
Lyons didn’t know anything about tech, managing people or venture capital. But he knew he needed to modernize the insurance industry. He quit his job and took a trip around the world. He came back and moved into his friend’s basement and started working on what would become The Zebra. He got into a five-month Alpha Lab Incubator program there.
One day, Lyons was scraping websites to get data on the insurance industry for his startup and the Pittsburgh police visited him to shut him down after one company complained. He took that as an opportunity to land the insurance company as a customer. And today, they are one of The Zebra’s biggest customers, Lyons said.
The Zebra is now the most visited auto insurance comparison site in the U.S. and the company has raised more than $70 million and it has 100 employees, Lyons said.
“I’m very proud of what we’ve built,” Lyons said. “It’s been named the best place to work in Austin five years in a row now.”
Lyons is also famous for cold emailing Billionaire Mark Cuban and getting an investment sight unseen. He sent a very short and to the point email with the subject “Wanna Disrupt the Auto Insurance Market?”
Cuban only took 20 minutes to respond. And he’s been an investor in the company ever since Lyons said. The first time they met was when Cuban gave a talk at the Longhorn Startup Lab at the University of Texas at Austin in 2013.
Forrest asked Lyons to talk about the fundraising process.
“It’s never fun to go around begging for money,” Lyons said.
At the end of the day, no one prepares an entrepreneur for the fundraising process, Lyons said. It’s incredibly challenging to run the day to day operations of the business and grow the business while also trying to raise funds, Lyons said.
“There is a lot of stress,” he said.
Over the summer, Lyons announced that he was leaving The Zebra. He’s now out of the day to day operations. His next venture will not be focused on the insurance industry, Lyons said. He is not ready yet to announce what he plans to do, he said. He said he likes consumer businesses and building new brands. And he does plan to launch his next venture in Austin.
“There’s one opportunity I’m incredibly excited about,” Lyons said.
Correction: An earlier version of this story referred to Lyons as the co-founder of The Zebra. He is the sole founder. We regret the error.