Community//

“Understanding your options.” With Penny Bauder & George Kalogeropoulos

At HealthSherpa, we’re trying to improve access to health care. We help people understand their options and enroll in affordable, comprehensive health insurance with ease. We connect people with Affordable Care Act and Medicaid plans, which all offer comprehensive coverage with consumer protections, and we help people understand which subsidies they might be eligible for […]

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At HealthSherpa, we’re trying to improve access to health care. We help people understand their options and enroll in affordable, comprehensive health insurance with ease. We connect people with Affordable Care Act and Medicaid plans, which all offer comprehensive coverage with consumer protections, and we help people understand which subsidies they might be eligible for based on their income.


As part of my series about young people who are making an important social impact”, I had the pleasure of interviewing George Kalogeropoulos.

George is the CEO of HealthSherpa, a mission-driven company and partner to HealthCare.gov that helps people find and enroll in high quality, affordable health coverage and use that coverage throughout the year. Since George co-founded HealthSherpa in 2014, HealthSherpa has enrolled over 3 million Americans in Affordable Care Act coverage. George has a B.A. in Political Science from Yale University.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit. Can you tell us a bit how you grew up?

I grew up in Greece. My father was a sculptor and my mother was a tutor, so money was very tight growing up. We were lower middle class. We moved to the United States for a year, from 1990 to 1991, and we benefited from Medicaid and the programs that we at HealthSherpa now help people enroll in. Even though I work in tech now, as a kid I never really used computers until a 7th grade computer class — and I wasn’t great at them then.

You are currently leading a social impact organization. Can you tell us a bit about what you and your organization are trying to change in our world today?

At HealthSherpa, we’re trying to improve access to health care. We help people understand their options and enroll in affordable, comprehensive health insurance with ease. We connect people with Affordable Care Act and Medicaid plans, which all offer comprehensive coverage with consumer protections, and we help people understand which subsidies they might be eligible for based on their income.

We enrolled over a million people in affordable health insurance last Open Enrollment Period, and we hope to enroll even more this Open Enrollment Period. With so many people losing their health insurance due to COVID-19, it’s more important than ever that we help as many people as possible get insured and avoid predatory plans.

Can you tell us the backstory about what inspired you to originally feel passionate about this cause?

Growing up in Greece, I was used to having universal health care. When I briefly lived in the United States as a child, my family was on Medicaid. I’ve always been interested in access to health care. When the Affordable Care Act was passed, my co-founders and I were inspired to do what we could do to support the legislation, so we built a website to help people enroll in Affordable Care Act health plans.

My passion for this cause increased when I started talking directly to the consumers we were helping during the early stages of starting the company. I remember in particular talking to an older man in Texas who was living in the Medicaid gap — that’s when a state has not expanded their Medicaid coverage, so you make too much to qualify for Medicaid but too little to qualify for Affordable Care Act subsidies. This man was suffering from cancer and unable to get affordable health insurance. I realized just how complicated, unintuitive, and broken the health care system was. My passion for this cause has further increased during COVID-19 — our society depends on employment for health insurance, and we’re hitting record unemployment during a deadly pandemic.

I want to continue working on these problems for years to maximize the number of people we enroll, until the country at some point implements some kind of universal health care.

Many of us have ideas, dreams, and passions, but never manifest it. They don’t get up and just do it. But you did. Was there an “Aha Moment” that made you decide that you were actually going to step up and do it? What was that final trigger?

After growing up lower middle class, I felt a lot of insecurity about money after graduating from school. I immediately started working at a hedge fund after college. I hated it. But after a couple years, I had enough financial security to finally feel comfortable asking myself what I really wanted to do every day.

When HealthCare.gov first launched, the website couldn’t handle the traffic and crashed immediately. They brought in experts to fix the site, and there was a ton of press about the disastrous launch. As fans of the Affordable Care Act and accessible health insurance, we wanted to help people get more information on these health plans, so we spent a couple days building an alternative to HealthCare.gov that could handle high traffic and gave people the information they needed. And that’s how HealthSherpa was born.

Many young people don’t know the steps to take to start a new organization. But you did. What are some of the things or steps you took to get your project started?

The first step toward starting your project is finding the right partner(s). I knew Ning Liang from college and we realized we had very similar values. Then we met Cat Perez, who had just won a hackathon after doing a similar project. I found two people with integrity, talent, and skills that complemented mine, and we were able to challenge and support each other.

Can you share the most interesting story that happened to you since you began leading your company or organization?

I once talked to a 77 year old man to help him get health insurance. A scammy insurance agent had signed him up for a paid health insurance plan — but he was 77 years old and therefore Medicare-eligible! We helped him sign up, and that experience taught me how high-stakes this business was. There’s no one watching out for you to make sure you get the most affordable health plan. If you enroll in the wrong plan, you’ll just lose money.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson or take away you learned from that?

Very early on in the company, before we even had product-market fit, we hired a VP of Sales. What we didn’t realize is that sales at an early stage is really just the founders talking to potential buyers to figure out product-market fit. It was definitely a mistake — we tried to outsource something that should have been our job, and we didn’t set that person up for success in that role.

None of us can be successful without some help along the way. Did you have mentors or cheerleaders who helped you to succeed? Can you tell us a story about their influence?

I’ve honestly never had a real mentor, but it’s something I’m trying to do for other people. I did read lots of Paul Graham’s essays, so I used readings to make up for a lack of a mentor.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

We’ve helped over 3 million people enroll in Affordable Care Act health plans, and we’ve helped over 10,000 people apply for Medicaid. And for the last couple days of Open Enrollment every year, we have all hands on deck at the company doing customer support. I’m a licensed insurance agent, and I get on the phone and talk to people calling in for help choosing a health insurance plan and understanding their eligibility for subsidies. So through that I’ve talked to a lot of people looking for insurance, and I talk to more every year. One particular individual that stands out is a car salesman I talked to who was caught in a vicious cycle where he didn’t have the money to pay for insurance, so he wasn’t able to get the diabetes and blood pressure medications he needed, and in turn he wasn’t able to work as much because he was feeling so sick from missing his medications. I helped him apply, and when I worked with him on estimating his income accurately, he was eligible for a huge subsidy that made his monthly premium very low. He was so excited to get the medications he needed so that he would be able to work and earn money.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

Our goal is to help people understand their health insurance options so that they can enroll in the best plan for them — one that’s affordable and meets their health care needs.

One thing employers can do to help address this problem is provide information on Affordable Care Act plans when someone leaves their company. Employees often think that COBRA is their only option, but oftentimes they’ll qualify for subsidized ACA plans. The average person on our site can save 90% by opting for an ACA plan instead of COBRA — our users pay an average of $48 per month instead of the average of $599 per month for a COBRA plan.

One thing that the government could do would be to increase the subsidies they offer to people looking for Affordable Care Act plans. Currently, you can get a subsidy if you make between 100% and 400% of the federal poverty line. This applies across the entire country, so it doesn’t account for the huge cost of living differences — making $60,000 for a family of 4 means you’re ineligible for subsidies, but that living off of that salary is very different experience in New York City than it is in rural Alabama.

Another thing we could do is make people more aware of the government programs that exist to help them, and plug the gaps in those programs. Many people end up caught in the Medicaid Gap, which occurs in the 14 states that have not expanded their Medicaid programs. The Affordable Care Act intended to cover all low-income people by giving subsidies to those making between 100% and 400% of the federal poverty line, and giving Medicaid to those below those limits. However, some states did not expand their Medicaid programs to accommodate those people, so we’ve ended up with 2.5 million people who fall into the Medicaid Gap, meaning they make too little money to qualify for Affordable Care Act subsidies, but they also don’t qualify for Medicaid.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. How broken and complicated the US health care system is.: The Medicaid Gap is a great example of this: in the 14 states that did not expand their Medicaid programs, 2.5 million people make too little to qualify for Affordable Care Act subsidies and yet they don’t qualify for Medicaid. They are typically uninsured.
  2. Bad incentives in the health care system: Insurance agents get paid on commission from insurers, and they get higher commissions to sell what is known as “short-term health insurance.” These plans are not comprehensive, do not qualify for subsidies, and typically don’t cover pre-existing conditions. We work with many ethical insurance agents who put their clients into the best plans for their needs and budget, but they are also some agents who show clients plans that give the agent the highest commission.
  3. Decentralized health care system: There are often different rules for each state, and eligibility for programs varies by state.
  4. How political health care is: Decisions are often made with political motives.
  5. How disconnected tech culture is from the needs of the rest of america: In the Bay Area, we have a multitude of startups to pick up your laundry, but HealthSherpa is the only one that can help you apply for Medicaid, which covers 1 in 5 Americans.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

After college, I worked for 3 years at Bridgewater, a hedge fund. I had anxiety every hour I spent there. I constantly questioned why I was doing what I was doing and who it was imapcting.

That anxiety melted away once I started doing entrepreneurship.

My advice to young people is that your decision-making process should include evaluating the impact your work has on others and the impact your work has on yourself. Are you making new skills? Are yu pushing yourself? I wasn’t looking for a finish line or an exit. I found something i genuinely like doing every day.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

I would love to have lunch with the Prime Minister of Greece, Kyriakos Mitsotakis. He completely saved Greece from COVID-19 with his quick response. Very few people died in Greece, and I didn’t have to worry about my parents. He may have saved my parents’ lives. His management and leadership has been incredible.

How can our readers follow you online?

You can find me on Twitter at @GeorgeK_HS, and you can follow us at @healthsherpas.

This was very meaningful, thank you so much. We wish you only continued success on your great work!

At HealthSherpa, we’re trying to improve access to health care. We help people understand their options and enroll in affordable, comprehensive health insurance with ease. We connect people with Affordable Care Act and Medicaid plans, which all offer comprehensive coverage with consumer protections, and we help people understand which subsidies they might be eligible for based on their income.


As part of my series about young people who are making an important social impact”, I had the pleasure of interviewing George Kalogeropoulos.

George is the CEO of HealthSherpa, a mission-driven company and partner to HealthCare.gov that helps people find and enroll in high quality, affordable health coverage and use that coverage throughout the year. Since George co-founded HealthSherpa in 2014, HealthSherpa has enrolled over 3 million Americans in Affordable Care Act coverage. George has a B.A. in Political Science from Yale University.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit. Can you tell us a bit how you grew up?

Igrew up in Greece. My father was a sculptor and my mother was a tutor, so money was very tight growing up. We were lower middle class. We moved to the United States for a year, from 1990 to 1991, and we benefited from Medicaid and the programs that we at HealthSherpa now help people enroll in. Even though I work in tech now, as a kid I never really used computers until a 7th grade computer class — and I wasn’t great at them then.

You are currently leading a social impact organization. Can you tell us a bit about what you and your organization are trying to change in our world today?

At HealthSherpa, we’re trying to improve access to health care. We help people understand their options and enroll in affordable, comprehensive health insurance with ease. We connect people with Affordable Care Act and Medicaid plans, which all offer comprehensive coverage with consumer protections, and we help people understand which subsidies they might be eligible for based on their income.

We enrolled over a million people in affordable health insurance last Open Enrollment Period, and we hope to enroll even more this Open Enrollment Period. With so many people losing their health insurance due to COVID-19, it’s more important than ever that we help as many people as possible get insured and avoid predatory plans.

Can you tell us the backstory about what inspired you to originally feel passionate about this cause?

Growing up in Greece, I was used to having universal health care. When I briefly lived in the United States as a child, my family was on Medicaid. I’ve always been interested in access to health care. When the Affordable Care Act was passed, my co-founders and I were inspired to do what we could do to support the legislation, so we built a website to help people enroll in Affordable Care Act health plans.

My passion for this cause increased when I started talking directly to the consumers we were helping during the early stages of starting the company. I remember in particular talking to an older man in Texas who was living in the Medicaid gap — that’s when a state has not expanded their Medicaid coverage, so you make too much to qualify for Medicaid but too little to qualify for Affordable Care Act subsidies. This man was suffering from cancer and unable to get affordable health insurance. I realized just how complicated, unintuitive, and broken the health care system was. My passion for this cause has further increased during COVID-19 — our society depends on employment for health insurance, and we’re hitting record unemployment during a deadly pandemic.

I want to continue working on these problems for years to maximize the number of people we enroll, until the country at some point implements some kind of universal health care.

Many of us have ideas, dreams, and passions, but never manifest it. They don’t get up and just do it. But you did. Was there an “Aha Moment” that made you decide that you were actually going to step up and do it? What was that final trigger?

After growing up lower middle class, I felt a lot of insecurity about money after graduating from school. I immediately started working at a hedge fund after college. I hated it. But after a couple years, I had enough financial security to finally feel comfortable asking myself what I really wanted to do every day.

When HealthCare.gov first launched, the website couldn’t handle the traffic and crashed immediately. They brought in experts to fix the site, and there was a ton of press about the disastrous launch. As fans of the Affordable Care Act and accessible health insurance, we wanted to help people get more information on these health plans, so we spent a couple days building an alternative to HealthCare.gov that could handle high traffic and gave people the information they needed. And that’s how HealthSherpa was born.

Many young people don’t know the steps to take to start a new organization. But you did. What are some of the things or steps you took to get your project started?

The first step toward starting your project is finding the right partner(s). I knew Ning Liang from college and we realized we had very similar values. Then we met Cat Perez, who had just won a hackathon after doing a similar project. I found two people with integrity, talent, and skills that complemented mine, and we were able to challenge and support each other.

Can you share the most interesting story that happened to you since you began leading your company or organization?

I once talked to a 77 year old man to help him get health insurance. A scammy insurance agent had signed him up for a paid health insurance plan — but he was 77 years old and therefore Medicare-eligible! We helped him sign up, and that experience taught me how high-stakes this business was. There’s no one watching out for you to make sure you get the most affordable health plan. If you enroll in the wrong plan, you’ll just lose money.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson or take away you learned from that?

Very early on in the company, before we even had product-market fit, we hired a VP of Sales. What we didn’t realize is that sales at an early stage is really just the founders talking to potential buyers to figure out product-market fit. It was definitely a mistake — we tried to outsource something that should have been our job, and we didn’t set that person up for success in that role.

None of us can be successful without some help along the way. Did you have mentors or cheerleaders who helped you to succeed? Can you tell us a story about their influence?

I’ve honestly never had a real mentor, but it’s something I’m trying to do for other people. I did read lots of Paul Graham’s essays, so I used readings to make up for a lack of a mentor.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

We’ve helped over 3 million people enroll in Affordable Care Act health plans, and we’ve helped over 10,000 people apply for Medicaid. And for the last couple days of Open Enrollment every year, we have all hands on deck at the company doing customer support. I’m a licensed insurance agent, and I get on the phone and talk to people calling in for help choosing a health insurance plan and understanding their eligibility for subsidies. So through that I’ve talked to a lot of people looking for insurance, and I talk to more every year. One particular individual that stands out is a car salesman I talked to who was caught in a vicious cycle where he didn’t have the money to pay for insurance, so he wasn’t able to get the diabetes and blood pressure medications he needed, and in turn he wasn’t able to work as much because he was feeling so sick from missing his medications. I helped him apply, and when I worked with him on estimating his income accurately, he was eligible for a huge subsidy that made his monthly premium very low. He was so excited to get the medications he needed so that he would be able to work and earn money.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

Our goal is to help people understand their health insurance options so that they can enroll in the best plan for them — one that’s affordable and meets their health care needs.

One thing employers can do to help address this problem is provide information on Affordable Care Act plans when someone leaves their company. Employees often think that COBRA is their only option, but oftentimes they’ll qualify for subsidized ACA plans. The average person on our site can save 90% by opting for an ACA plan instead of COBRA — our users pay an average of $48 per month instead of the average of $599 per month for a COBRA plan.

One thing that the government could do would be to increase the subsidies they offer to people looking for Affordable Care Act plans. Currently, you can get a subsidy if you make between 100% and 400% of the federal poverty line. This applies across the entire country, so it doesn’t account for the huge cost of living differences — making $60,000 for a family of 4 means you’re ineligible for subsidies, but that living off of that salary is very different experience in New York City than it is in rural Alabama.

Another thing we could do is make people more aware of the government programs that exist to help them, and plug the gaps in those programs. Many people end up caught in the Medicaid Gap, which occurs in the 14 states that have not expanded their Medicaid programs. The Affordable Care Act intended to cover all low-income people by giving subsidies to those making between 100% and 400% of the federal poverty line, and giving Medicaid to those below those limits. However, some states did not expand their Medicaid programs to accommodate those people, so we’ve ended up with 2.5 million people who fall into the Medicaid Gap, meaning they make too little money to qualify for Affordable Care Act subsidies, but they also don’t qualify for Medicaid.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. How broken and complicated the US health care system is.: The Medicaid Gap is a great example of this: in the 14 states that did not expand their Medicaid programs, 2.5 million people make too little to qualify for Affordable Care Act subsidies and yet they don’t qualify for Medicaid. They are typically uninsured.
  2. Bad incentives in the health care system: Insurance agents get paid on commission from insurers, and they get higher commissions to sell what is known as “short-term health insurance.” These plans are not comprehensive, do not qualify for subsidies, and typically don’t cover pre-existing conditions. We work with many ethical insurance agents who put their clients into the best plans for their needs and budget, but they are also some agents who show clients plans that give the agent the highest commission.
  3. Decentralized health care system: There are often different rules for each state, and eligibility for programs varies by state.
  4. How political health care is: Decisions are often made with political motives.
  5. How disconnected tech culture is from the needs of the rest of america: In the Bay Area, we have a multitude of startups to pick up your laundry, but HealthSherpa is the only one that can help you apply for Medicaid, which covers 1 in 5 Americans.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

After college, I worked for 3 years at Bridgewater, a hedge fund. I had anxiety every hour I spent there. I constantly questioned why I was doing what I was doing and who it was imapcting.

That anxiety melted away once I started doing entrepreneurship.

My advice to young people is that your decision-making process should include evaluating the impact your work has on others and the impact your work has on yourself. Are you making new skills? Are yu pushing yourself? I wasn’t looking for a finish line or an exit. I found something i genuinely like doing every day.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

I would love to have lunch with the Prime Minister of Greece, Kyriakos Mitsotakis. He completely saved Greece from COVID-19 with his quick response. Very few people died in Greece, and I didn’t have to worry about my parents. He may have saved my parents’ lives. His management and leadership has been incredible.

How can our readers follow you online?

You can find me on Twitter at @GeorgeK_HS, and you can follow us at @healthsherpas.

This was very meaningful, thank you so much. We wish you only continued success on your great work!

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