Making Medicare Simple
Do you need to sign up for Medicare when you turn 65?
Not everyone does.
Answer a few quick questions and find out exactly what you need to do — and when.
Free · No obligation · Instant results
🔒 Your info is never sold
⏱️ Takes under 2 minutes
📞 (253) 275-1413
When is your birthday?
Just the month and year — we use this to calculate your exact Medicare enrollment window.
Month
Year
🔒 We use this only to calculate your enrollment window. Your information is never sold — ever.
Question 1 of 3
What health coverage do you currently have?
This is the most important factor in your Medicare timing.
Question 2 of 3
Tell us about your employer
This determines whether Medicare or your employer plan pays first — which affects your entire enrollment timeline.
Question 2 of 3
When do you plan to retire?
Your retirement date is your Medicare enrollment deadline — this helps us calculate your exact window.
Question 2 of 3
Are you currently collecting Social Security benefits?
This determines whether you’ll be automatically enrolled in Medicare or need to sign up yourself.
You can delay — but you might not want to.
You’re not required to sign up right now and won’t face a penalty while your employer coverage is active. But here’s something most people don’t know: turning 65 sometimes opens up options that cost less and cover more than your employer plan.
Worth knowing
Medicare as a competitor to your employer plan
At 65, Medicare becomes available to you whether or not you take it. Some people find that a Medicare Supplement or Medicare Advantage plan — even with the Part B premium — comes out ahead of their employer plan when you add up payroll deductions and out-of-pocket costs. A 20-minute comparison costs nothing and could save you a lot.
We do not offer every plan available in your area. Currently we represent [1 to 12] organizations which offer [3 to 85] products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. Note: The plan and carrier ranges represent our entire multi-state footprint (WA, OR, ID, CA, AZ, TX). Actual availability varies by state and ZIP code. WhatSupp Insurance Solutions is not affiliated with or endorsed by the U.S. government or the federal Medicare program. This is a solicitation for insurance.
Heads up — your timing is more urgent than you might think.
Because your employer has fewer than 20 employees, Medicare becomes your primary insurance at 65 — meaning Medicare pays first and your employer plan only picks up what’s left. If you don’t enroll on time, you could face a coverage gap and bills your employer plan won’t cover.
The good news is this is completely fixable — and Dane can walk you through exactly what to do in a single 20-minute call.
Late enrollment = permanent penalty. Missing your Part B enrollment window results in a permanent premium penalty that stays with you for as long as you have Medicare.
We do not offer every plan available in your area. Currently we represent [1 to 12] organizations which offer [3 to 85] products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. Note: The plan and carrier ranges represent our entire multi-state footprint (WA, OR, ID, CA, AZ, TX). Actual availability varies by state and ZIP code. WhatSupp Insurance Solutions is not affiliated with or endorsed by the U.S. government or the federal Medicare program. This is a solicitation for insurance.
You’re in the right place at exactly the right time.
Getting set up on Medicare has two steps. Here’s what each looks like — and what we’ll cover on your call.
1
Original Medicare — The Government Side
Part A
Hospital Coverage
Inpatient stays, skilled nursing care, hospice, and some home health services.
$0 for most peoplePart B
Doctor & Outpatient Coverage
Doctor visits, outpatient care, lab tests, and preventive services.
$202.90 / month in 2026The 80/20 Problem: Medicare Part B pays 80% of approved outpatient costs — you owe the remaining 20% with no cap. On a $100,000 procedure, that’s $20,000 out of pocket. That’s exactly why Step 2 matters.
2
Your Healthcare Plan — The Coverage Side
The $202.90 Part B premium goes to the government no matter what. Step 2 costs are on top of that. Your two main options:
Pay Now
Medicare Supplement (Medigap)
✓Any doctor who takes Medicare — no networks
✓Predictable out-of-pocket expenses
✓Works anywhere in the country
↑Higher monthly premium
Pay Later
Medicare Advantage (Part C)
✓Often $0 monthly premium
✓Dental, vision, hearing, OTC extras
✓Annual out-of-pocket maximum
↕Provider network required
⚠️ One chance to get this right: When you first turn 65 you have a one-time 6-month window to get a Supplement plan with no health questions — no one can turn you down. After that, switching may require underwriting and a pre-existing condition can result in denial. In California a birthday rule gives added flexibility — but it does not apply to switching from Advantage to a Supplement. This is exactly why this decision deserves a real conversation.
Because Dane is an independent agent, his help costs you nothing — paid by the carrier only if you enroll, and your premium is the same whether you use an agent or go direct.
We do not offer every plan available in your area. Currently we represent [1 to 12] organizations which offer [3 to 85] products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. Note: The plan and carrier ranges listed above represent our entire multi-state footprint (WA, OR, ID, CA, AZ, TX) for Medicare Advantage and Part D plans. Actual availability varies strictly by state and ZIP code. Premium amounts reflect 2026 federal figures and are subject to annual change. WhatSupp Insurance Solutions is not affiliated with or endorsed by the U.S. government or the federal Medicare program. Medicare has neither reviewed nor endorsed this information. This is a solicitation for insurance.
Veterans have a unique situation — and you deserve a specialist.
VA health care covers you for service-connected conditions, but it doesn’t cover everything — and there are gaps that Medicare can fill. Coordinating the two correctly can save you significant money and make sure you’re never caught without coverage.
PB
Perry Baycroft
WhatSupp Insurance Solutions · Licensed Medicare Agent
Thank you for your service — you deserve every benefit you’ve earned.
WhatSupp Insurance Solutions is not affiliated with or endorsed by the U.S. government, the federal Medicare program, or the Department of Veterans Affairs. This is general information only.
Turning 65 on Medicaid? There may be more waiting for you than you know.
Here’s something a lot of people in your situation don’t realize: turning 65 opens up options that could seriously upgrade what you’re already getting. There are plans designed specifically for people who have both Medicare and Medicaid — with extra benefits most people don’t know exist.
Enrollment Window
Your timing matters
Just like anyone turning 65, you have an Initial Enrollment Period — a window to sign up for Medicare that opens 3 months before your birthday month and closes 3 months after. Getting this timing right matters.
Worth knowing
Dual Special Needs Plans (D-SNPs)
If you qualify for both Medicare and Medicaid, you may be eligible for a Dual Special Needs Plan — a Medicare Advantage plan built specifically for people in your situation. These plans can include benefits like help with groceries, utilities, over-the-counter items, dental, vision, and hearing. These supplemental benefits vary by plan and location — finding out what’s available in your ZIP code costs nothing and takes about 20 minutes.
We do not offer every plan available in your area. Currently we represent [1 to 12] organizations which offer [3 to 85] products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. Note: The plan and carrier ranges represent our entire multi-state footprint (WA, OR, ID, CA, AZ, TX). Actual availability varies by state and ZIP code. WhatSupp Insurance Solutions is not affiliated with or endorsed by the U.S. government or the federal Medicare program. This is a solicitation for insurance.
We do not offer every plan available in your area. Currently we represent [1 to 12] organizations which offer [3 to 85] products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. Note: The plan and carrier ranges represent our entire multi-state footprint (WA, OR, ID, CA, AZ, TX). Actual availability varies by state and ZIP code. WhatSupp Insurance Solutions is not affiliated with or endorsed by the U.S. government or the federal Medicare program. This is a solicitation for insurance.