Independent Medicare education and enrollment support

Medicare guidance made simple.

Personal Medicare guidance across 36 licensed states. From our California neighbors to clients across the country, we help you understand your options and plan your next steps.

Licensed in 36 states Napa Valley & Bay Area roots Personal guidance, near or far

Medicare Annual Enrollment

October 15–December 7

Is your Medicare coverage still a good fit?

Annual Enrollment is a chance to consider changes to Medicare Advantage and prescription drug coverage for the coming year. An appointment may help when you are considering your overall Medicare coverage.

A conversation may help if you are:

  • Considering a different Medicare Advantage plan.
  • Comparing Medicare Advantage with Original Medicare.
  • Sorting out how doctors, prescriptions, and costs fit together.

Start with a quick next-step check. No contact details needed.

How We Help

Medicare decisions feel easier when the steps are clear.

New to Medicare

Understand enrollment timing, Parts A and B, and how supplemental, Advantage, and Part D coverage fit together.

Supplement vs Advantage

Compare flexibility, networks, premiums, referrals, out-of-pocket costs, and travel considerations without pressure.

Part D Planning

When we help you plan for Medicare, we also review prescription drug coverage so your doctors, medications, pharmacies, and overall coverage fit together.

In our clients' words

What our clients are saying.

Location and licensing

Personal support across 36 licensed states.

Our office is in Napa, California, and our clients live across 36 licensed states. We serve Napa Valley, the Bay Area, and Northern California while bringing the same care and attention to clients beyond California. Availability and plan options vary by location.

  • AL
  • AK
  • AZ
  • AR
  • CA
  • CO
  • FL
  • GA
  • HI
  • ID
  • IL
  • IN
  • IA
  • KS
  • KY
  • LA
  • MA
  • MI
  • MT
  • NE
  • NV
  • NJ
  • NM
  • NC
  • OH
  • OK
  • OR
  • PA
  • SC
  • TN
  • TX
  • UT
  • VA
  • WA
  • WI
  • WY

Licensing does not guarantee plan availability. Plan options vary by county, ZIP code, carrier, and plan year.

U.S. map highlighting licensed states: AL, AK, AZ, AR, CA, CO, FL, GA, HI, ID, IL, IN, IA, KS, KY, LA, MA, MI, MT, NE, NV, NJ, NM, NC, OH, OK, OR, PA, SC, TN, TX, UT, VA, WA, WI, and WY.

A clear comparison

Medicare Supplement vs Medicare Advantage

Both paths can make sense. The right conversation starts with how you use care, how you feel about networks, how much flexibility matters, and what tradeoffs you are comfortable with.

Compare the two paths

New to Medicare?

Start with the basics: what Medicare covers, when to enroll, and what decisions usually come next.

Read the New to Medicare Guide

A simple process

From confusion to a clear next step.

Schedule a call

Start with a general Medicare planning conversation.

Complete the questionnaire

If you are preparing for an appointment, use the secure questionnaire when our office needs details before we meet.

Review your options

Compare the paths that fit your timing, coverage, and preferences.

Enroll with confidence

Get help with the next steps once you understand your choices.

Small local team

Meet Sam and Sarah.

When you work with Sam Olson Insurance Services, you are not dealing with a call center. Our small team gets to know you and follows through, whether you live nearby or in another state where we are licensed.

Sam Olson headshot

Sam Olson

Founder / Medicare Advisor

Sam founded the agency to make Medicare easier to understand, with clear explanations of Medicare Supplements, Medicare Advantage, Part D, and retirement-related Medicare decisions.

Sarah Krupa headshot

Sarah Krupa

Client Service / Medicare Support

Sarah is often the first point of contact for clients and brings more than 20 years of healthcare, care coordination, and administrative support experience.

Client words

Helpful, professional, and clear.

★★★★★
"Personable and expedient. Sam knows the answers or where to find them. He made the whole process straightforward."
James R.
★★★★★
"Professional, timely and helpful making the transition to Medicare seamless. Highly recommend using Sam."
Axel G.

Ready to feel more confident about Medicare?

Schedule a Medicare call with Sam Olson Insurance Services. If you are preparing for an appointment, use the secure questionnaire when our office asks for more detail.