MEET Vivek

Vivek Garipalli is co-founder and CEO of Clover Health, which uses data analysis and preventive care to provide better insurance at better prices for Medicare patients. He began his career in finance, and founded Ensemble Health Partners and CarePoint Health, as well as serving as Board Member and Advisor to Flatiron Health since inception, before launching Clover Health in 2014.

What is something you’ve learned that you lean on daily?

I’ve learned to take the long view. Building a business takes a lot of time, and things will go wrong. That’s just the way it is. You have to get used to those undulations and realize you can work through them if you stay focused on what you want to achieve.

Part of that is choosing a business model closely tied to your mission. It’s not just about doing good while making money; it’s about making money by doing good. When I started out as an entrepreneur, I was very focused on economics. Healthcare was a means to an end. But now I can’t imagine being the CEO of a business that doesn’t directly help people. Adding value to the world—that’s the most satisfying thing. It’s what allows you and your team to push through all those short-term challenges.

What one piece of advice would you give someone starting a company?

The only way I know to start a business is to just hurry up and start a business. You can do financial models and end up with “analysis paralysis,” or you can just go. I bought my first business in healthcare the same week I quit my finance job.

My dad is a physician, and I was walking around the medical complex where he worked when I saw this tiny sleep center. I did some basic Googling on sleep disorder diagnostics, negotiated the deal, and two months later I was running it. Of course, I could have chosen a million other businesses, and I made plenty of mistakes with that one, but it put me on the path that eventually led to Clover Health nine years later. Quit your job and start something. Fail—because you will fail. Then start something else. It’s as simple as that.

What small change has made a big difference in your life?

As our company grows, I’m learning to stay out of the weeds more and more. When you start out as a founder, you have the vision and you understand the details, so your hands are in everything. But as you bring on more experienced people, I think it’s important to excuse yourself from some conversations. Ignore some emails. Resist the urge to give feedback on every strategy and tactic being discussed, even if someone asks for it—even if you think you can add value.

But old habits die hard, and you do have to level up your leadership team before you can afford to be more hands-off. You have to hire great people—and then you have to give them the freedom to do great work. I find that when I limit my involvement, the organization speeds up. When I don’t, things slow down. Every day, there’s something I’m glad I didn’t say, either because the team went in the same direction on their own, or because they came up with something even better.

You can build a company on your own back. I’ve done it. But that can only take you so far. If you want to create something massive and transformational, you need a team that’s functional from top to bottom, with or without your input.

What don't you know that you wish you knew?

I’m actually a huge believer in the idea that there are certain things you don’t need to know, at least not in the beginning. When I look back on my experiences as an entrepreneur, there are so many things I probably wouldn’t have done if I knew then what I know now. When we started Clover Health four years ago, for example, I funded it personally. If I’d understood more about Medicare insurance and realized how much that was going to cost, I might not have taken the risk.

And when I was helping to start the business before this one, Flatiron Health, I initially knew nothing about technology and they initially knew nothing about healthcare. But that allowed us to push each other. It’s the reason we were able to come up with a great idea and start to execute.

When I need to learn something, I’ll go learn it. But I’m fine with not knowing in the meantime, and figuring things out as I go.

What books are on your nightstand right now?

Creating alignment between your mission and business model is vital for the future success of today’s companies. There is a short read called Raving Fans, by Ken Blanchard and Sheldon Bowles that does a fantastic job of laying out powerful and simple stories of concepts around this.

I just picked up Net Gain, by John Hagel III and Arthur G. Armstrong, and Net Worth, by Hagel and Marc Singer. I haven’t read them yet, but I’m really interested in the idea of marketing by giving customers information to help them make decisions, rather than using advertising that’s designed to manipulate people.

There’s also a book my fiancé gave me that I’ve since recommended to a lot of people, called The Obstacle is the Way, by Ryan Holiday. It’s about taking every single obstacle in front of you and turning it into an asset, rather than something to overcome. When someone at Clover makes a big mistake, I’ll give them a call and say, “Get this book, read it over the weekend, and we’ll talk Monday.”

When did you realize you were wrong about something?

It’s a weekly occurrence. You make so many decisions on a daily, weekly, monthly basis—mostly small, some big—so I’ve gotten comfortable with the reality that being wrong is okay. One example happened a couple of years ago when Clover was moving into the private Medicare insurance space. We had this idea to offer the same cost-sharing in and out of network and remove that friction for customers. So we talked to a couple of law firms, got sign-off, got our marketing materials, and launched the plan. Then the Centers for Medicare and Medicaid Services, or CMS, had a very different interpretation, and we had to immediately cease the marketing approach.

We had great intent. But we also had a tiny compliance team, and we didn’t recognize the level of specialized expertise we needed. Because when you really examine the structure of the federal regulations and the precedents, it’s clear that CMS has a fundamentally different perspective. They just did not agree with our marketing framework, and after the fact it became obvious to us why. We realized their intent was clearly positive, and was aimed at benefiting and protecting consumers. But when you don’t understand the nuances, you can be blind to unintended consequences.

I’d been in healthcare for a while at that point, but that experience taught me the learning curve on compliance in Medicare Advantage was much steeper than I’d realized. It wasn’t something I was going to figure out quickly on my own. That’s when we hired our chief compliance officer, and she’s been phenomenal. That experience taught me the importance of hiring experts, even if it’s a space you believe you’re familiar with.

What unit of time matters the most and why?

Shower time—that 10 to 15 minutes when you’re in the shower, just staring at the ground. For whatever reason, that’s when ideas and solutions always come to me. Clover was a shower thought.

There are so few parts of your day when you’re doing a mindless, repetitive activity. It’s pretty much showering and brushing your teeth. You’re kind of stuck with your thoughts, and you might as well make some use out of them. There’s something about the place your mind goes at those moments that’s creative—and useful. It’s the time when I’m like, “Ah! That’s how I’m going to approach it.” I’ve made some mistakes based on those ideas, but I’ve solved a lot of problems, too.

Hard-won advice