New to Medicare
Understand enrollment timing, Parts A and B, and how supplemental, Advantage, and Part D coverage fit together.
Independent Medicare education and enrollment support
Medicare guidance made simple.
Based in Napa, serving clients throughout Northern California and in multiple licensed states, Sam Olson helps you understand Medicare options in plain English.
Napa Valley home base
Northern California Medicare help
Licensed Medicare guidance in multiple states
How We Help
Medicare decisions feel easier when the steps are clear.
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.
Location and licensing
Based in Napa. Licensed in Multiple States.
Sam Olson Insurance Services is based in Napa, California and serves clients throughout Napa Valley, Northern California, and multiple states where the agency is licensed. Availability and plan options vary by location.
- AK
- AR
- AZ
- CA
- CO
- CT
- FL
- GA
- HI
- ID
- IL
- IA
- IN
- KY
- MA
- MI
- MN
- MT
- NC
- NM
- NV
- OK
- OR
- PA
- SC
- TN
- TX
- UT
- VA
- WA
Licensing does not guarantee plan availability. Plan options vary by county, ZIP code, carrier, and plan year.
Plain-English 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 pathsNew to Medicare?
Start with the basics: what Medicare covers, when to enroll, and what decisions usually come next.
Read the New to Medicare GuideA 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. You are working with a Napa-based team focused on clear guidance and follow-through.
Sam Olson
Founder / Medicare Advisor
Sam founded the agency to make Medicare easier to understand, with plain-English education around Medicare Supplements, Medicare Advantage, Part D, and retirement-related Medicare decisions.
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 E.
★★★★★
"Professional, timely and helpful making the transition to Medicare seamless. Highly recommend using Sam."Axel G.
Ready for a calmer Medicare conversation?
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.