Cultural Diversity and Learning Through Mistakes, with Meetesh Karia

By Published On: December 11, 2018Categories: Blog, Podcasts, The CTO Studio

Both cultural diversity and learning through mistakes are important topics in the tech world. Hiring people from diverse backgrounds can help a company grow in a myriad of ways, and here to tell us what some of those ways are is Meetesh Karia. Meetesh is the CTO of The Zebra, a company that is the equivalent of Kayak to the car insurance space.

In his role as CTO and in his jobs prior, Meetesh has also found the benefits of learning through mistakes. He shares a few he has made, what he has learned from them and how he approaches failures with his team now as a result. You’ll hear those valuable lessons and more on today’s CTO Studio with Meetesh Karia.

In this episode, you’ll hear:

  • How can you create a culture where people aren’t afraid of failure?
  • What does it tell you if the same mistake continues to happen again and again?
  • How did becoming a parent make him a better leader?
  • Why are so many of his staff from non-STEM education backgrounds?
  • Why cultural diversity hiring benefits everyone, and isn’t a passing fad.
  • And so much more!

We share stories about our first jobs post-college to kick off the show. My story is about begging my supervisor for the root password, and doing so for weeks before he finally gave in. Once I was in I decided to change the root password, just temporarily because I anticipated a couple of switchs, and within seconds of changing it I forgot it!

So I had to go back to him and tell him he was right, I had done all the things he thought I was going to do and even went a step further by locking him out because I had forgotten the password!

Meetesh has a similar story. In his first job out of college, he was put in charge of things that he says no 21-year old should’ve been put in charge of. Some of those things involved pricing all of the cars for a site called

Take into consideration he was six months out of college at this point and he has tons of data to input (like MSRP list prices, etc). So he decided to get a temp to help him, even though he had never managed anyone before. He didn’t know he had to double check she was doing the work correctly.

Inadvertently, she had transposed the prices for a Cavalier and a Camaro – very different in price!! A Cavalier at the time, on the low end, was $18,000-$20,000 range. A Camaro, on the other hand, was $50,000-$60,000. Then he applied dynamic pricing algorithms based off the list prices (the wrong ones) so they went out into production and were offering to sell a Camaro for the price of a Cavalier!

Suddenly people were flocking to the site and placing orders, they didn’t know what was going on at first. Then they realized they had sold some Camaros with a $30k-$40k loss on each. That was a sobering lesson for him.

Along those same lines is another story he shares. He had access to the company’s pricing model (the same company), and whenever you made changes to the model it would effect the prices directly on the site. One day he made a change to the pricing model that he thought was correct and it wasn’t. The change he had made had set all the prices on the web site to -$1, which was not what he had intended. He made that change at 5:30pm one night, and then proceeded to leave the office.

He was away from his phone for the next few hours, but when he came back he had 7 voicemails from people trying to revert his change. His co-workers had figured out the pricing model was not revertable and they had to reconstruct it from scratch. He learned very quickly the importance of a staging model!

After hearing those stories, I asked Meetesh as a CTO now how does he deal with his employees when they make mistakes like that? He says honestly both of those experiences taught him things he couldn’t have learned faster if someone else had told him. Those mistakes were probably some of the best things for him.

As a result, he now wants to create a culture where people are not afraid of failure. People should be able to fail within reason, and our jobs as leaders is to create the balance so they don’t fail spectacularly and they learn from those failures. He tells his team no one gets punished for making an honest mistake. If the mistake is made out of negligence or if continues to be repeated then he will talk with them, but no one is punished for making an honest mistake.

From there we move on to talk about his company, The Zebra. He describes the company as being Kayak for insurance. They started in the car insurance vertical. They are a search engine to help connect consumers who are looking for auto insurance with insurance carriers. Surprisingly there hasn’t been a real player in this space even though other industries have had something similar for 15 years now.

Prior to The Zebra, insurance had primarily been a lead gen, spam-filled space without price transparency. What they are trying to do is cut through all of that and provide value to consumers by educating them much the way Turbo Tax or Credit Karma did on complicated subjects.

In addition, they are striving to connect these same consumers, now better educated on insurance, with insurance carriers that are the best for them without them having to call and/or enter all their data in four or five different places. These educated consumers are now more valuable to the carriers because they are the right match for the carriers, and the carriers retain these consumers as customers longer and they are happier.

Today we talk more about how they work with carriers before we switch to diversity in hiring, a topic that is important to Meetesh and to his staff at Zebra. Tune in to hear him talk about how they hire non-STEM staff, how it benefits them and much more on this edition of CTO Studio.

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