Work with Matt
Paid, one-on-one services for people who want professional help with their Medicare and retirement decisions.
Everything on this site is free. The guides, the comparisons, the data. Most people who visit here can figure out their Medicare situation on their own, and that's the point.
But some situations are genuinely complex. Multiple medications across different therapeutic classes. IRMAA brackets that change your premiums by hundreds of dollars a month. Employer coverage transitions with enrollment windows that don't forgive mistakes. Long-term care gaps that Medicare was never designed to fill.
If you've read the guides and still want someone to do the analysis with you, that's what these services are for.
What I Can Help With
Part D Drug Plan Analysis
A deep review of your specific medication list against every available Part D plan in your area. I run the numbers the way a financial analyst would: total annual cost including premiums, deductibles, copays, and the new $2,000 out-of-pocket cap.
- Full cost comparison across all available plans
- Formulary tier analysis for each medication
- Pharmacy network check (retail, mail-order, preferred)
- Written recommendation with reasoning
Medigap Plan Comparison
Turning 65, leaving a Medicare Advantage plan, or moving to a new state? I'll compare Medigap plans from every carrier available in your area and walk you through the trade-offs: Plan G vs. Plan N, rate stability, underwriting differences, and carrier financial strength.
- Side-by-side carrier comparison for your zip code
- Rate history and stability analysis
- Enrollment timing guidance (guaranteed issue, open enrollment, underwriting)
- Help with the application if you decide to move forward
Medicare Strategy Session
For situations that don't fit neatly into one category. IRMAA surcharges eating into your retirement income. Late enrollment penalties you're not sure how to resolve. Coordination of benefits between employer coverage and Medicare. If your question starts with "my situation is a little complicated," this is the right service.
- One-on-one consultation focused on your specific situation
- Review of your current coverage and costs
- Clear action steps with deadlines and enrollment windows
- Follow-up email summarizing the plan
Long-Term Care Planning
Medicare does not cover long-term custodial care. Not assisted living, not nursing homes, not in-home aides for daily activities. This is one of the biggest gaps in retirement planning, and most people don't discover it until they need it. I hold the CLTC (Certification in Long-Term Care) designation and can help you evaluate your actual risk and coverage options.
- Assessment of your long-term care risk factors
- Review of coverage options: traditional LTC, hybrid policies, self-funding
- Cost comparison across available products in your state
- Integration with your overall retirement and Medicare plan
Retirement Protection Review
The life insurance you bought at 40 might not make sense at 70. Term policies expire. Whole life policies may be underperforming. Some people are paying premiums on coverage they no longer need, while others have gaps they don't realize exist. I hold the CRPC (Chartered Retirement Planning Counselor) designation and can review whether your current coverage is still structured efficiently for retirement.
- Review of existing life insurance policies and their current value
- Analysis of whether your coverage matches your actual needs
- Options if your current coverage no longer fits (keep, reduce, replace, settle)
- Integration with your Medicare and long-term care strategy
Flat rate. All services. No hidden fees, no tiered pricing, no "premium package" upsell. You're paying for my time and expertise, and you'll know the cost before we start.
Most sessions run 45 to 90 minutes depending on complexity. If your situation is straightforward, it takes less time and costs less. If it's complex, we take whatever time it needs.
Medigap plan comparisons are commission-based (the carrier pays, not you) and don't require a consultation fee. If you need Medigap help alongside another service, that portion is included at no extra charge.
How It Works
Tell me about your situation
Fill out the form below. It takes about two minutes. I use this to understand what you need help with and whether I'm the right person for it.
I'll send you an invoice
If I can help, I'll email you an invoice with the estimated time and cost. No payment is required until you're ready to proceed.
We schedule and meet
Once payment is received, you'll get a link to book a time that works for you. Video or phone, your choice. After our session, you'll receive a written summary with my recommendations.
Request a Consultation
Tell me a bit about your situation. I'll review your request and follow up within one business day.
Credentials
CRPC
Chartered Retirement Planning Counselor
Retirement income strategies, asset protection, and financial planning for people in or approaching retirement.
CLTC
Certification in Long-Term Care
Long-term care risk assessment, coverage evaluation, and planning for extended care needs that Medicare does not cover.
Licensed Agent
Medicare Insurance Agent
Licensed to sell Medicare Supplement (Medigap), Medicare Advantage, Part D, and related insurance products. Serving clients nationwide.
Common Questions
Why $250/hour?
You're paying for specialized analysis, not a sales call. I hold retirement planning and long-term care certifications, and the work I do requires reviewing your specific financial and coverage details. Fee-for-service means the advice is unbiased because I'm not incentivized to recommend one product over another.
Can I just ask a quick question without paying?
If it's genuinely quick, send an email to info@understandmymedicare.org. I answer what I can. For anything that requires me to look at your specific numbers, a paid session is the right path.
Do I need to live in a specific state?
I'm licensed in multiple states and can help most people nationwide. If your state requires a specific license I don't hold, I'll tell you upfront before any payment.
What if I just want to do this myself?
Good. That's why the rest of this site exists. Start with the Learn section, use the Compare Plans tool, and check the Resources page for official links. Everything you need to make your own decision is here for free.
What happens after I submit the form?
I'll review your information within one business day. If I can help, I'll send an invoice to the email you provided with the estimated time and total cost. You don't pay anything until you're ready. Once payment clears, you'll receive a scheduling link to book your session.