Making It Easy

Easy Street Insurance Takes the Stress Out of the Medicare Process

Writer / Christy Heitger-Ewing
Photography Provided

Let’s face it. The internet is both a blessing and a curse. Sure, it offers a wealth of information at our fingertips, but Googling is not the way to go when trying to select a Medicare plan.

“It’s tempting for folks to get online and search around, thinking they can pick the right plan without having to talk to anyone about it,” says Jess Carrasquillo, co-owner of Easy Street Insurance. “While that may seem like the better route, it’s likely just going to leave you confused and overwhelmed.”    Easy Street Insurance

The better choice is to keep the laptop closed, and instead create a file with all those Medicare pamphlets that have been piling up in your mailbox. Bring that file with you when you meet with an agent from Easy Street, who promises no cost and no pressure, just sound advice.

During Medicare open enrollment, which runs from October 15 to December 7, seniors are bombarded with commercials, billboards and mail. They need help sorting through the mire. At that first meeting, which typically lasts an hour, the Easy Street agent presents a client with several plan options. When it comes to plan selection, agents need to know three things: the client’s hospital preference, a list of the client’s doctors, and a list of the client’s current medications.

“Those three things help direct us to the plan that’s going to provide the most benefits for your money,” says Carrasquillo, who co-owns the business with his wife, Sandra. The pair has been working in the health insurance industry for more than 20 years, and exclusively in Medicare since 2005. They work with seniors as well as those seeking underage disability.

Many people assume that once you select a plan, you stay on it forever, but that’s not the case. Variables change each year. This is why every fall, Jess and Sandra send out a letter to their clients to let them know that they are available to meet and help them determine if a plan change is in the clients’ best interest.

“Companies are so competitive these days,” Carrasquillo says. “The plan you picked five years ago might not be the best fit, as now there could be other plans that offer richer benefits with more perks and value.”

Just as you would consult an attorney for legal advice or check with an accountant during tax season, it’s wise to talk to a seasoned expert who knows the Medicare field inside and out. Not only do the Carrasquillos take recertification tests each year, but they also work with most companies represented in Indiana.  This allows them to know the differences in benefits between plans.

“You wouldn’t know that by Googling,” Carrasquillo says.

Remember that when it comes to Medicare plans, one size does not fit all. One size doesn’t even necessarily fit one couple, as it’s not unusual for a husband and wife to be on different plans after age 65.

“There are so many options, so many carriers and so many plans, but each client is unique,” Carrasquillo says. “Some of them are completely unaware how to navigate the industry.  That’s where we shine.”

The Carrasquillos, who have lived in Center Grove for nearly 50 years, are a blended family, as Sandra’s first husband passed away from a brain tumor years ago. Jess and Sandra, who have been married for 22 years, have five children between them, four of whom work in the Medicare business.

“Two of them work for us, two of them have agencies in other cities, and the fifth is planning to join the business next fall,” Carrasquillo says.

Three of their agents who work in Indianapolis and central Indiana are Avery Miller (a Center Grove graduate), Julie Corcoran, and Justin Kozlowski. Each agent takes time to carefully explain how Medicare works in a very simple manner.  They all care deeply about their clients and will ensure the client understands all the options available.  In addition to Medicare plans, Justin, a Finance and Business Management major, is well versed in Final-Expense insurance and ‘safe money’ planning for retirement.

In addition to Medicare supplements, Medicare Advantage Plans and prescription plans, there’s also Immediate Care and Extended Care that clients can acquire. Immediate Care, as the name implies, is for those injuries that require immediate attention, such as a broken bone. Extended Care is about protecting your life, health and wealth.Easy Street Insurance

“There are indemnity products like cancer plans or hospital plans, as well as long-term care and final-expense plans,” Carrasquillo says. “It’s one of those things where people may not know if they need it, but when they do end up needing it, they’re glad they had it.”

In January 2023, Jess and Sandra partnered with Integrity Marketing Group.  This partnership allows them to have access to a network of experienced, caring agents in all states, which is helpful if you have a parent or loved one who lives elsewhere.

“You want to have somebody local that you can go to for your Medicare and health care so that if you have a problem, they can resolve it for you,” Carrasquillo says.

Occasionally, clients have a question or situation they cannot navigate with the insurance company on their own so the agents at Easy Street Insurance get involved to help resolve them.  Jess, Sandra, and their team provide excellent, ongoing customer service, which is hard to come by in many industries today. Easy Street Insurance

Through the years, the team at Easy Street Insurance has saved people hundreds and even thousands of dollars. Just last year, Sandra met with a 90-year-old veteran who had a supplement that he really didn’t need because he got all his care through a Veterans hospital.

“He was paying $745 a month, which, when you multiply times 12, is $8,940,” Carrasquillo says. “He and his daughter were happy they met with us.”

The agents at Easy Street Insurance go to bat for their clients because they love seniors. “We treat them like they’re all our moms and dads,” Carrasquillo says. “It’s our passion and our mission to help seniors make the right decision.”

For the past 15 years, Carrasquillo has recruited and trained more than 80 agents throughout Indiana.  “My passion is helping others grow and develop so they can multiply our vision of helping seniors,” he says.

Easy Street’s main office is located at 8000 South Meridian Street in Indianapolis. They also have offices in Fishers, Brownsburg and Fort Wayne. For more information or to set an appointment, call 317-882-9602 or visit

The Centers for Medicare and Medicaid (CMS) require the following disclaimer:

We do not offer every plan available in your area. Currently we represent 8 organizations which offer 45 products in your area.  Please contact or 1-800-Medicare to get information on all your options.

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If your Medicare supplement has increased significantly in cost, you have other options?

Several carriers offer household discounts on their Medicare supplement plans.

That there are plans that offer a monthly Part B premium reduction?

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