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When to HOLD OFF on Doing Roth Conversions

John in Boston is in the 32% tax bracket. Should he do Roth conversions? Flight Deck Dad and Irish Girl in Pensacola have a lot of tax-free pension income. Should they do Roth conversions? Bert and Ernie in New Jersey wonder if they should convert to Roth or take advantage of zero percent capital gains tax rates. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for all of them today. Plus, Michael and his wife in Bellevue are 34, in the 24% tax bracket and wonder if they should contribute to tax-free or tax-deferred accounts, and if they should slow down on retirement savings and start a bridging account for the years between when they want to punch the clock in their early to mid-50s, and when they can access their retirement savings. Then, for something completely different, Frenchie from Maine writes back in: What are the disadvantages to paying off her mortgage ASAP, and what’s the tax efficiency of a money market compared to bond funds?

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13
MAY
2025
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Market Hype vs. Reality: Take Control of Your Investment Risk

Pure’s Executive Vice President & Chief Investment Officer, Brian Perry, CFP®, CFA, AIF®, and Senior Investment Strategist & Financial Advisor, Brian Fahey, CFA, provide updates on tariffs, the economy, and financial markets, as well as insight into what might come next. Outline 00:00 Intro 00:36 What are Tariffs and Why do We Care? 3:20 How […]

06
MAY
2025
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Mutual Funds vs. ETFs, Bonds to Bourbon

What are the benefits and differences between exchange-traded funds and mutual funds? Mike in Colorado wants to know. How should Lauren in Florida approach the fixed-income portion of her investment portfolio? Would a balanced fund be good for asset allocation in the decumulation phase for DJ in Missouri? Plus, Karen wants to make a one-time roulette investment. Should she hire a broker or do it herself? But first, something for YMYW’s legion of Old-Fashioned drinkers: find out how you can put your money where your mouth is with our special guest Jeremy Kasler, the founder and CEO of CaskX, making investing in whiskey and bourbon more accessible and transparent for investors.

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11
FEB
2025
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Investing Basics Guide

Updated for 2025: How investment savvy are you? Do you know the difference between asset allocation and asset location? Many Americans don’t have a solid understanding of basic investing terms and concepts, and their lack of financial literacy can cost them! It can be difficult to grow your wealth if you don’t know what tools […]

03
JAN
2025
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Bonds and Annuities, Social Security and Retirement Spending

John in Pennsylvania doesn’t have bonds in his investment portfolio. Should he add them, and if so, where? The fellas also spitball on retirement plans for James in Tierrasanta, California, who has $4 million plus annuities, Esther in the San Francisco Bay Area, who has nearly $12M net worth, and Tiger and Lioness, who wonder about a safe level of lifestyle creep. Also, Charlie in Castlerock, Colorado asks Joe and Al to spitball on how to balance collecting Social Security with making withdrawals from his pre-tax retirement account for living expenses. Finally, a Worrywart Mom in Seattle wonders whether her 27-year-old daughter should focus on paying off her student loans or saving for the future.

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17
DEC
2024
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401(k) vs. Roth: Where to Save for Retirement

Kyle and his fiancée are in their 30s, have done a great job saving, and are in a high tax bracket. Would it make more sense for them to contribute to their 401(k)s or Roth 401(k)s for retirement? Mick’s wife Pam has both W-2 and sole proprietor income – where should she save for retirement? Plus, Joe and Big Al spitball for Janet on where junk bonds belong in a portfolio, they untangle the pro-rata and aggregation rules concerning 401(k) to Roth conversions for Nancy, and they spitball on whether Cary and Mark should retire now or work for two more years when pensions will provide them an extra $50K a year. 

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07
MAY
2024
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Mega Backdoor Roth Conversion 5-Year Rule and Bond Investing

Should Jim in New Jersey do the YMYW-infamous Megatron (the Mega Backdoor Roth IRA) or use his Roth 401(k) – and how can he keep bonds out of his Roth accounts? Joe and Big Al discuss the January first start date when it comes to the 5-year rule on Roth conversions for Nancy in Wisconsin, and they spitball on those Roth clocks for withdrawals and tax-efficient investments for Johnny Mercer in Savannah, GA, who also wants to know the pros and cons of bonds vs. bond funds vs. CDs. Plus, should Brad in St. Louis incorporate bonds into his investment portfolio, given the fact that he will have pensions and Social Security providing 5 streams of fixed income in retirement? 

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17
OCT
2023
LISTEN NOW
SEASON 9, EPISODE 10

Financial Boot Camp: Investing Basics

Stocks and bonds, 401(k)s and IRAs – how investment savvy are you? Less than half of Americans have a solid understanding of basic investing terms and concepts. It can be difficult to grow your wealth if you don’t know what tools and strategies are available, much less know how to use them to develop a […]

01
OCT
2023
WATCH NOW

Investing 101: Get Serious About Your Financial Future

Do you want to understand how to get the most amount of return for the amount of risk you’re willing to tolerate? Pure’s Financial Planner, Sumit Mehta, CFP®, AIF®, provides insight into what investing strategies can help you improve your odds of success and establish a foundation to achieve long-term goals. FREE GUIDE | 10 […]

29
SEP
2023
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RSU, Mutual Funds, Bonds, and Annuities

What’s the best strategy for E-Dog’s restricted stock units with his employer, how are RSUs taxed, and how do Roth conversions fit into the mix? Should Jay in Raleigh liquidate his annuities or follow “Stan the Annuity Man’s” advice and take the annual payments? Elisa wants to know how a mutual fund portfolio would work in retirement, and what’s a good way for listener Joe to invest in bonds in a taxable account to bring his portfolio back into proper balance? Finally, the fellas spitball on Medicare savings vs. Roth conversions for David, and an unrealized gain strategy on an UTMA education savings account for Jay in California.

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15
AUG
2023
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HSA to Roth, RMD Investing, and Social Security Strategies

Can you convert your health savings account (HSA) to Roth, and do the five-year Roth withdrawal clocks apply? What should you do with money you’d been putting to your student loan debt if you’re part of the student loan forgiveness program? What’s the best way to invest your RMDs, or required minimum distributions? How does IRMAA, the income-related monthly adjustment amount for Medicare, apply to zero-coupon municipal bonds? And finally, strategies for collecting survivor Social Security benefits.

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16
MAY
2023
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Mutual Funds vs. ETFs, SECURE 2.0, & Capital Gains Strategies

Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account that’s better than a SEP IRA. Plus, will municipal bond income bump you into a higher tax bracket? Can you avoid capital gains tax by investing less aggressively over time?

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14
MAR
2023
LISTEN NOW

Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security & Medicare

Joe and Big Al spitball on set-and-forget brokerage investments for 30-something investors, real estate as a substitute for bonds in a diversified portfolio, and options for taking a state pension with or without sick time pay. The fellas also discuss how to bridge the gap until collecting Social Security, strategies for claiming spousal Social Security benefits, and whether you need to sign up for Medicare if you’d rather keep the healthcare you already have. 

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14
FEB
2023
LISTEN NOW

Diversification Vs. Fees: What’s More Important for Retirement Investing?

Is it better to choose low-cost index funds or to diversify investments, even if it means paying higher fees? What causes mutual fund price fluctuation? Are mid-cap funds necessary in a balanced portfolio? Joe and Big Al also talk about real estate funds vs. real estate investment trusts (REITs), and annuities vs. bonds in a retirement portfolio. Finally, we revisit some investing strategy questions from earlier in the year that are still relevant in today’s volatile markets, on moving to cash in tough times, analyzing your asset allocation, and rebalancing your retirement portfolio. 

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27
DEC
2022
LISTEN NOW

Life Insurance, Muni Bonds, and Dividend Stocks in Retirement

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman’s Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds?

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22
NOV
2022
LISTEN NOW
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