Jay Winestein, Founder of DeepDive Retirement, Interviewed on the Influential Entrepreneurs Podcast Discussing Taxes in Retirement

Jay Winestein discusses how to mitigate and lower taxes as much as possible to prepare for retirement. 

Listen to the interview on the Business Innovators Radio Network: 


The level of a retiree’s post-tax liabilities can have a large effect on the quality of retirement.

Utilizing pre-tax 401ks, 403b, Deferred comp plans, IRAs, etc. while working are good for tax deductibility and for those looking to lower their current taxable income and taxes.

Moving forward, however, the resultant future tax liabilities at retirement can be relatively quite large. Distributions from the pre-tax accounts will likely appear on the tax return as earned income and may also affect the taxability of  Social Security benefits negatively.

The taxes rates will be the current rates at the time of distribution, whether higher or lower – compared to the time deposits were made and deductions were received.

This podcast starts to delve into some of the key tax issues in retirement and what can be done to create a tax-free, or a mostly tax-free retirement. Some of them include funding Roths, Roth conversions, and using other post-tax savings and investment vehicles that offer tax advantages.

One key is to diversify tax-wise and to use all of the tax classes, so can there are more options to combat tax law changes and needed liquidity. Outmaneuvering taxes can be more easily accomplished if there are more places to access cash.

With careful planning and proactive effort, people can lower their taxes and enjoy the retirement of their dreams.

Jay shared: “The key to successful tax management when preparing for retirement is to take a current and detailed inventory of all positions. Next, it’s crucial to make projections to see where the tax liabilities will show up, given the current direction of the deposits made. Then different if/then scenarios to create more tax efficiency can be examined.

 With careful preparation and strategic planning, you can save more money on taxes and enjoy a more comfortable retirement.”

About Jay Winestein

Jay Winestein helps retirees get more income using several powerful and time-tested strategies. His unique message, based on his years in the small business pension space, uses the same actuarial (pension) tables and calculations that large corporate pension designers use. It can add peace of mind in retirement.

Book a Call with Jay:

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