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Robert A. Klein

Retirement, Insurance, Lifestage Based Planning
“Robert A. Klein is a leading expert on reducing healthcare costs in retirement. Health costs are mandatory, even if you are healthy. Rob believes that ignoring the role of health costs in retirement planning may lead to greater costs, higher taxes and less net retirement income.”

Jester Financial

Job Title:

Managing Partner


Rob Klein is a financial services industry veteran. After the collapse of Lehman Brothers and the ensuing financial panic in 2008, he worked on developing a more meaningful and value added service he could provide his clients and future clients. Instead of the decades old conversations about dollar cost averaging, asset allocation, time in the market, etc., he and his colleagues focused on explaining the one mandatory cost in retirement - health.

What they discovered was the following reality. Never mind clients, most financial advisors do not understand there is mandatory cost of healthcare in retirement - Medicare. The financial planning the advisors help their clients implement may be used against their clients. The wrong type of retirement income may lead to higher insurance premiums,  higher taxes and reduced Social Security benefits. In some situations, the entire Social Security retirement benefit may be consumed by health costs.

Another risk in retirement is long term care planning. The average advisor believes the only solutions is traditional long-term care insurance. Long-term care planning is far more comprehensive than that. A comprehensive plan should include some of the following where one will live, who will take care of them, etc. Advisors who care about this risk for their clients and their clients' families, need to work with a specialist and partner who understands the aging and health needs of their clients, not someone who just wants to sell insurance.

It is his belief that healthcare is a major component of retirement planning. It must also include long-term care planning, which for many will be the modern day estate planning. If a financial advisor cannot explain to a client what happens when the client gets sick, it's time for the client to find one who can.

Additionally, Rob is a Long-Term Care Planning Specialist for INERTIA / Advisor Services Group. He works with advisors and their clients to ensure Long-Term Care planning and Healthcare in Retirement are addressed as part of comprehensive planning.


BS, Biology, University at Albany

Insurance License:



The topics and concepts discussed are general information based on public information from Social Security, Medicare and the IRS regarding health premiums, non-security linked insurance and annuity contracts, and income taxes.  Never the less, you should still seek advice of legal, tax, or financial advisors to help you with specific issues pertaining to your situation. The views, comments and positions taken are not an offer, solicitation or endorsement of any financial product or investment. 

  • 4 Rules of Retirement
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August 2017
    Retirement Living
April 2017
    Insurance, Senior Care, Retirement Living, Social Security
February 2018
    Retirement Savings, Senior Care, Retirement, Social Security
May 2017
    Insurance, Retirement Living, Senior Care
January 2018
    Estate Planning, Personal Finance, Long-Term Care Insurance, Senior Care, Retirement Living

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    Retirement, 401(k), IRAs
Can I convert my 401k into a Roth IRA account after I've retired?
33% of people found this answer helpful

Yes. But you want to pay attention to your age and modified adjusted gross income. While a Roth IRA may be wonderful for a variety of planning reasons, converting to one is not only a taxable even but it may also increase your health costs. Medicare premiums are based on your modified adjusted gross income. Remember, the greater your Medicare premiums are the greater the chances are you will get less net Social Security income.

January 2018
    Financial Planning, Retirement, Pensions, Social Security, 401(k)
How do I set up an 401(h) account for an S corporation?
0% of people found this answer helpful
January 2018
    Retirement, Social Security
Is it better to wait to withdraw from your Social Security benefits and your 401(k)/457(k) account?
0% of people found this answer helpful
January 2018