Agent Careers
Jason Sherman Clearwater

For anyone who is a “freelancer” or self-employed, going without health insurance can be a scary and risky road. Austin, Texas-based entrepreneur Jason Sherman, who started companies in real estate development and the mortgage industry, saw that first-hand.

Jason Sherman, co-founder of Clearwater.

“In 2006, I co-founded Aspen Heights Partners and it was my first taste in seeing how agents were affected. Being self employed and not having benefits are the biggest struggles.”

Jason recognized that “1099s lack affordable coverage” and set out to do something about it. He started Clearwater Healthcare, which he describes as “owning the whole ecosystem for how to provide affordable healthcare.”

“Clearwater can customize plans and control the price a little better. That’s because we make the plans, distribute them and administer them,” said Jason. “Big insurers don’t do that and therefore, don’t do well in the smaller space. We are not trying to compete with them.”

From Airline Pilot to Entrepreneur

What’s unique about Jason is that he always wanted to be a commercial airline pilot, getting his degree from Baylor University in aviation science. But when his first flight check happened on 9/11, it set his career in a different direction, eventually into a world of entrepreneurship where his creative side can solve problems instead of flying a plane from Point A to Point B.

Fortunately for eXp Realty and its agents, eXp Executive Vice President of People, Mike Vein, heard Jason giving a speech at an Inman conference about Clearwater and was quickly inspired.

“We were looking for a healthcare solution for our agents – one that was affordable and provided the close customer care and service we expect. When I heard Jason talk about what his company could offer, we quickly explored it and sure enough – it’s better than anything we imagined. Clearwater has been a huge, important partner for us and our agents,” said Mike.  

We asked Jason more about Clearwater Healthcare. Here’s what he had to say:

Give me the pitch. What is Clearwater Benefits?

“Clearwater Benefits is a healthcare vendor that offers a wide variety of high quality, highly affordable healthcare solutions tailored to meet individuals’ unique needs. The company was started four years ago. I set out to build a company that truly cared about the members over profits. We have grown exponentially. Our main office is located in beautiful Austin, Texas, but we have people that work all over the country.” 

How did you get the idea to start Clearwater?

I have a lot of experience in the real estate industry, and a few years ago, I kept noticing how the major carriers treated self-employed people. It was truly awful because to these brokers, the pay out from selling to 1099s was not worth their time, and the lack of compassion astounded me. Clearwater was started to offer a strong healthcare plan that is still affordable and places people over profits. We will always hold these values.”

How is Clearwater affiliated with eXp Realty?

“Clearwater is the official healthcare partner for eXp Realty. This partnership is truly the perfect fit. Our values and eXp’s values line up perfectly. We both care deeply about the people we serve. Also, eXp agents have an exclusive discount on their plans. Currently, we have over 10,000 eXp Realty agents and their family members signed up, and I hear about how people were able to use their plan to get the treatment they needed while saving thousands, in some cases hundreds of thousands of dollars in out-of-pocket costs.  I’ll admit, I’ve teared up. There was one member who was in the ICU for several days, and without coverage, that bill would have been in the hundreds of thousands, if not millions. This member only paid $1,000.”

> Read how 4 eXp Realty Agents have saved thousands using Clearwater

What sets Clearwater apart from other healthcare companies?

“I don’t want to sound braggadocious, but I could go on for an hour on what separates Clearwater from the other major carriers. I know I’m repeating myself, but truly caring about our members is the number one difference. Another is that we give our members two nationwide PPO networks. Most plans in numerous states don’t offer any PPO network plans. Our monthly costs and out-of-pocket costs are significantly less, agents save an average of $10,000 every year. One part of Clearwater that is revolutionary, is our care coordination service. We help agents navigate their major procedures, and in many cases, we will be able to get them $0 on surgeries, cancer treatment, and so much more!” 

What are some of the biggest challenges in healthcare that you are trying to tackle with Clearwater?

“The healthcare industry is very complicated, especially for 1099s. And, a lot of challenges happen behind the scenes with how bills are coded, network and pricing contracts with providers, and so much more. For us, we want to address the confusion that everyone faces. Confusion around scenarios such as:

  • Why is my bill this amount?
  • How can I get approval for this procedure?
  • If I have to go to a hospital, what will I owe?
  • I have a very specific medication, how do I get the prescription covered?
  • Which doctors are in-network?

“A huge mission for Clearwater is to provide that clarity for people. I embrace these challenges, because I know what my goal is, and meeting these challenges head on to truly provide the best plans possible is my passion.” 

What is your vision of where Clearwater can go?

“The vision is limitless. We have found a model that works, and people are taking notice. Huge names in the benefits industry that are pioneers themselves, are coming to us, wanting to work with us because they see how we operate and what we will accomplish. I can say that I see in the not so distant future, 1099s from multiple verticals coming to us as their first choice for benefits.” 

Where will I find Clearwater at EXPCON?

“Our booth will be No. 100 – the first booth when people walk into the Expo Hall. Our team is always so thrilled to meet everyone in person!”


Jason resides in Austin, Texas, with his wife and their five children, including a daughter, twin boys and two adopted from Ethiopia. You can meet Jason and Clearwater representatives at EXPCON Oct. 11-14 in the Expo Hall at Mandalay Bay Convention Center in Las Vegas between the hours of 9 a.m. to 5 p.m. Or learn more about Clearwater Healthcare here.


These figures are not a guarantee, representation or projection of earnings or profits you can or should expect. They also do not include expenses incurred by Agents in operating their businesses. eXp Realty makes no guarantee of financial success. Success with eXp Realty results only from successful sales efforts, which require hard work, diligence, skill, persistence, competence, and leadership. Your success will depend upon how well you exercise these qualities.

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