Mastering Medicare for Long-Term Wealth | Dan Pascone with Rosie Paulsen, SNR Services | Ep #8

Rosie Paulsen is the owner of SNR Services, a firm focused on Medicare and health insurance. Her first career was in business travel, where she spent about 10 years in a call center booking trips. A newspaper ad about helping seniors with their Medicare options led her to Humana. She says the interviewers compared the many screens she used to book travel with the single screen used to review Medicare options, and because she was bilingual, she was hired on the spot.

After 4 years in that corporate role, Rosie realized she had a gift for connecting people. She started networking, joined Business Network International (BNI) for a year, and says she became rookie of the year without ever having sold insurance or owned a company. She then expanded to offer plans from multiple companies. She now has 21 years of total experience and has personally trained about 15 people to do the same work. She has also written a book on resilience. [VERIFY: book title and spelling before any mention.]

Rosie's current focus is coaching insurance professionals, such as people with property and casualty or life licenses, who want to serve clients turning 65 instead of referring them elsewhere. Her argument is that these professionals already have the relationship, and adding another policy to a household strengthens retention.

She also makes a longevity point: if people are living to about 90, someone who enrolls at 65 could stay a client for 20 years or more, and she notes that Medicare commissions continue for as long as the client stays enrolled. In her view, that kind of recurring income could help fund a professional's own retirement or be invested elsewhere. [VERIFY: compensation and retention claims are Rosie's, specific to her industry, and are not a recommendation.] She also encourages business owners to think about an exit strategy and to work toward a business that runs without them.

Rosie says people are scared and confused, and that she would not be in business otherwise. Around age 64½, she says, people are flooded with postcards, calls and texts. Her approach is to get into people's lives before they have to decide, so that when they turn 65, they already know whom they plan to call.

Once someone selects a plan, she says she reviews it every year. Insurers can remove or add benefits and change networks, so she studies the changes and walks clients through them: if the client is comfortable, the policy renews, and if not, they look at other options. She also tracks clients' health over time and, when needs change, may suggest moving from a plan that worked while they were healthy to one with broader access to care. She reports a 99% client retention rate. [VERIFY: retention figure is Rosie's claim.] Medicare options and costs vary, so these are her practices, not a recommendation for any plan.

Rosie tells a story about a financial advisor friend who kept sending Medicare clients to her for years. After about 15 years of friendship, he added Medicare to his own practice once he saw that clients he had helped prepare for retirement at 55 or 60 were now reaching Medicare age. Her takeaway is that the work of building trust happens years before the decision.

She calls this relationship currency, a phrase she credits to John Maxwell. [VERIFY: attribution.] As an example, she describes a client who stayed in touch for 12 years after meeting her at a networking event, waiting until she turned 65 to become a client. That is why Rosie looks for people at 55, 59 or 60, so the relationship is already in place when the time comes.

Rosie says some people in the industry are uneasy about changes at the federal level and comments about there being too many brokers. She describes herself as an optimist. Her view is that the industry will change, but that the issue is not too many good brokers, meaning people who see this as a calling and not a quick way to make money. [VERIFY: regulatory commentary is Rosie's opinion, attributed to her.]

She also describes Medicare as a slow-growth career: the first 6 months to a year are about building relationships. After 21 years, she says she receives 5 to 10 leads a month and that people in her market in Tampa tend to associate Medicare with her name.

Rosie names resilience as her superpower. She says a flexible business allowed her to be present for her family during a difficult period, which she could not have done with a typical office job. That is why her heart is with caregivers, parents of young children and single parents who want meaningful work and a good income without giving up time at home.

She also encourages entrepreneurs to be authentic and visible. In her view, people who want to help small businesses will find you, get to know you and trust you if you put your voice out there.

• Coffee or tea, cats or dogs: Coffee and dogs.
• Can't-live-without tech: Audible, which she calls her best friend.
• Favorite quotes: From The Slight Edge: “Difficult is what takes a little time. The impossible is what takes a little bit longer.” From 10X: “True transformation doesn't happen by chance. It happens by choice.” [VERIFY: exact wording and attributions.]
• Favorite book: The Slight Edge, along with her advice to pay yourself first. She says entrepreneurs tend to pay everyone else first, and that mindset has to change.
• Personal hack: Habit stacking, an idea she credits to Atomic Habits: attach a new habit to an existing one so it becomes automatic.
• Bucket list item already done: Spending the 4th of July on the lawn by the Lincoln Memorial watching fireworks, and visiting the White House 3 times.
• Financial milestone still ahead: A bigger career earnings goal, which she says is coming soon. Her coach's line is that he only makes millionaires, and she jokes, “Okay, billionaire next!”
• Advice to her younger self: Don't be afraid, be yourself. She says people notice you less than you think, and being bilingual and different can help you stand out.

The first thing people miss is timing. Medicare's Initial Enrollment Period is a 7-month window around your 65th birthday: the 3 months before, the month of, and the 3 months after. Missing it can have consequences, so it helps to know your dates early. Medicare.gov explains when you can sign up for Medicare, and your situation may differ if you or a spouse are still working and covered by an employer plan. [VERIFY: confirm enrollment-window wording against the Medicare.gov page.]

The second is that Medicare is not set and forget. Rosie's yearly review habit reflects the fact that benefits, networks and costs can change from year to year.

We'd add a third from the planning side. If you step back from full-time work before 65, you may need coverage for the years before Medicare begins, and that cost belongs in your plan. We cover the timing side of that decision in The Final Year Before Early Retirement: 7 Mistakes High Earners Make. Income in the years before 65 can also matter, because higher earners may pay income-related surcharges on Medicare premiums based on a tax return from 2 years earlier. [VERIFY: confirm IRMAA description before publishing.]

This example is hypothetical, uses assumed figures and is not a prediction. Suppose an executive moves to a Hybrid Retirement at age 60 and needs individual health coverage until Medicare starts at 65. Assume coverage costs $1,800 a month, or $21,600 a year, and ignore inflation and out-of-pocket costs.

• Years 1–2 (ages 60–62): $43,200 in total premiums.
• Years 3–5 (ages 62–65): $64,800 in total premiums.
• Total bridge period: $108,000.

Real costs vary by plan, location, age, health and eligibility for subsidies, so this is only a way to size the line item. The planning question is where that $108,000 should come from and when. Money needed in the next 2 years generally belongs in a different place than money needed 3–5 years out. Tax planning for the withdrawals matters too, so owners and executives should work with their CPA.

We use Life-Driven Planning, our 6-phase process (Cash Flow, Retirement & Hybrid Retirement, Risk, Expense & Goal, Tax and Legacy), to build a plan around how you want to live. A Hybrid Retirement is a phased approach where full-time work gives way to flexible, optional work rather than an abrupt stop. Healthcare touches several phases: Risk (coverage), Expense & Goal (the budget line) and Tax (how income can affect premiums). Our guide How Should a Corporate Executive Plan a Hybrid Retirement? covers the broader picture.

Our Life Driven Investing (LDI) approach builds the portfolio backward from your life, using the Four Liquidity Bands: money you'll need in 0–2 years, 3–5 years, 6–10 years and 10+ years. Bridge-year premiums sit in the nearer bands, so they shape how we position those dollars. We revisit all of it in our Quarterly Strategy Rhythm, a regular check-in each quarter where we review the plan against what has changed.

We are a fee-only fiduciary firm. We don't recommend specific Medicare or health plans, and we don't provide insurance, tax or legal advice. Plan selection and enrollment are best handled by a licensed insurance professional, and we work alongside them and your CPA.

This conversation is for executives and business owners in their 40s–50s with household income of $500,000 or more who want to understand how healthcare coverage fits into a retirement that may start before 65. If you hold equity compensation, run a company, or are considering a Hybrid Retirement, building the Medicare and bridge-year costs into your plan early can help you avoid surprises.

If you're thinking about stepping back before 65, or you want to see how healthcare costs fit into your retirement, tax and equity picture, we're happy to talk it through. The Free Wealth Strategy Call is a low-pressure conversation about your situation. Book a Free Wealth Strategy Call.