Medicare Supplement guidance, from someone you can call.
Hi, I'm Jake. If you're approaching 65 or thinking about a Medicare Supplement, I believe you deserve a real conversation—not another comparison site. I'll help you sort through your questions at your pace.
WHAT WORKING WITH ME FEELS LIKE
You'll be heard.
We start with what matters to you, not a product.
You'll understand.
Clear explanations and time to ask questions.
You'll decide.
No rushing, no pressure, and no obligation.
MY STARTING POINT
Curious about Medicare Supplement?
Medicare Supplement Insurance—also called Medigap—works alongside Original Medicare and can help with certain deductibles, copayments, and coinsurance.
It isn't for everyone, and the timing can be important. My approach is to help you understand the tradeoffs before you make a decision.
Ask Jake about MedigapWorks with Original Medicare
You generally need Medicare Parts A and B to purchase Medigap.
May reduce cost surprises
Standardized plans help pay certain out-of-pocket Medicare costs.
Timing deserves attention
Your Medigap open enrollment window and other rights can affect your options.
LET'S START WITH YOU
Where are you right now?
There's no complicated questionnaire. Just tell me where you're starting and we'll take it from there.
I'm turning 65
I want to understand Medicare and when to consider a Supplement.
Let's prepare ↗ 02 →I'm exploring Medigap
I have questions about how Medicare Supplement coverage works.
Let's talk it through ↗ 03 →I already have coverage
I'd like help understanding what I have and what questions to ask.
Let's connect ↗starts with listening.
Clear answers.
Thoughtful options.
Your decision.
NICE TO MEET YOU
I'm Jake.
Let's keep this human.
I believe insurance decisions deserve patience, clear answers, and someone who will pick up the conversation where you left off. I'm an Arizona-licensed insurance agent, and I created Enroll With Jake to make Medicare conversations feel more personal.
You won't be pushed into a decision in a five-minute call. Start with your questions. We'll take it one step at a time.
LET'S HAVE A CONVERSATION
It's okay to have questions.
Tell me a little about where you are with Medicare. I'll respond personally using the method you choose. No automated marketing subscription. Please do not include Medicare numbers or health information.
Talk with Jake
A few simple details, and we'll go from there.
THE ESSENTIALS
Just a few good questions.
And if yours isn't here, I'd rather talk it through with you.
Is Medicare Supplement the same as Medicare Advantage?
No. Medicare Supplement (Medigap) works with Original Medicare. Medicare Advantage is another way to receive Medicare benefits through a private plan. You can't have both at the same time.
When can I get Medicare Supplement coverage?
For many people, the six-month Medigap open enrollment period begins when they're at least 65 and have Medicare Part B. Other rights may apply; outside protected windows, underwriting may affect availability. Timing is worth checking carefully.
Does Medicare Supplement include prescriptions?
Modern Medigap policies generally don't include outpatient prescription drug coverage. A separate Part D plan may be appropriate, depending on your situation.
Are you Medicare or part of the government?
No. Enroll With Jake is an independent insurance service. It is not connected with or endorsed by the U.S. government or Medicare.