Best Socialsecurity Podcasts (2025)

1
Will Buying Your Dream Home Ruin Early Retirement? - 559 48:06

Play Pause

2h ago48:06

48:06

Today on Your Money, Your Wealth® podcast 559 with Joe Anderson, CFP®, and Big Al Clopine, CPA, David wants to know if he and his wife (ages 47 and 53) are actually on track for retirement - without realizing they're creeping toward that .01% crowd that David swears he is not part of. Mia and Jessie from Seattle want to retire and still pick up a d…

1
The Federal Income Tax: Coming to an End? 31:19

2h ago31:19

31:19

In this episode, we break down the headlines about eliminating the federal income tax, $2,000 tariff-funded checks, and "no taxes below $150,000." We look at the math, the Supreme Court challenges, and what these proposals would actually mean for retirees. Although this show does not provide specific tax, legal, or financial advice, you can engage …

1
Inbox Question | Managing Allocation Across Many Accounts 9:04

22h ago9:04

9:04

Scott finds it difficult to manage asset allocation and buckets across multiple accounts and asks for an efficient way to coordinate everything. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin's team at https://carrolladvisory.co/podcast1 📍Cont…

1
Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558 51:52

3d ago51:52

51:52

McDreamy Dempsey wants to know if converting to Roth in the 37% tax bracket ever makes sense, and Gary in La Crosse warns Joe Anderson, CFP® and Big Al Clopine, CPA about Roth conversion "lag" and when it DOESN'T make sense to convert, today on Your Money, Your Wealth® podcast 558. Plus, Wine Guy and Gal in Northern California want a spitball on wh…

1
Key Changes for 2026 36:13

4d ago36:13

36:13

In this episode, Devin and John break down the key tax and retirement planning changes coming in 2026 and what they mean for your income, benefits, and long term strategy. We cover the latest Social Security COLA update, the expected increase to Medicare Part B premiums, and the new Social Security earnings test thresholds. We also walk through the…

1
092: The Emergence of Private Equity, Private Credit & Alternatives with BlackRock's Jon Diorio 38:46

9d ago38:46

38:46

For many investors approaching or navigating retirement, the world of private markets can feel intimidating. Over the past 30 years, the number of public companies in the capital markets has declined by 30% while private markets have grown at the same rate. This means failing to understand the rapidly growing asset class of private markets and alte…

1
UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557 41:20

10d ago41:20

41:20

Joe Anderson, CFP® and Big Al Clopine, CPA are defusing some confusing tax time bombs today on Your Money, Your Wealth® podcast number 557. George in Torrance wants to know the smartest way to deal with the giant UGMA account set up by his kids' grandparents. Suzanne in Detroit has a twist on the new 529 plan to Roth rollover rule. Homer and Marge …

51
5 Things Your Attorney Doesn't Want to Hear 34:01

11d ago34:01

34:01

In this episode, John talks about the 5 things that he hates to hear from his clients. You will learn why certain statements (and thinking) slow everything down, what your attorney wishes you understood before walking into the meeting, and how to approach your plan with clarity, calm thinking, and realistic expectations. If you want to make better …

1
Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap? - 556 31:20

20d ago31:20

31:20

Joe Anderson, CFP® and Big Al Clopine, CPA spitball Roth conversions, capital gains, and retirement readiness from every angle, today on Your Money, Your Wealth® podcast number 556. Joe Momma from Virginia wants to know if his zero percent capital-gains strategy is too good to be true, if he can trust his advisor, and if it's finally time to start …

1
Inbox Question | Roth Conversion Strategy for High Earners 8:30

25d ago8:30

8:30

Meera and her husband have $4.5 million in retirement accounts and a $430K income. They want guidance on when to start Roth conversions, how much to convert each year, and whether to continue 401(k) contributions. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firm…

1
091: Estate Planning Essentials: How Trusts & Gifting Protect Your Legacy with Attorney David Chaves 42:59

27d ago42:59

42:59

For many families, estate planning creates a feeling of anxiety, which is a big reason why they put it off for another day. From probate costs to nursing home spend-downs, failing to plan can leave loved ones vulnerable to unnecessary taxes, legal fees, and stress. In this episode, SHP's Laura Russo is joined by returning guest Attorney David Chave…

1
Retiring Before Social Security? Consider These Portfolio Changes - 555 41:24

28d ago41:24

41:24

Joe Anderson, CFP® and Big Al Clopine, CPA spitball withdrawal strategies, Roth conversion timing, and saving priorities for every stage of life, today on Your Money, Your Wealth® podcast number 555. Christine just retired at 59 and wants the smartest way to draw income before Social Security, without letting taxes take a third of it. Prickly Richa…

1
Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case) 31:11

29d ago31:11

31:11

Everyone's wondering if this is the worst time to retire. With high valuations, stubborn inflation, and constant uncertainty, it's easy to feel uneasy about your timing. In this episode, we look at what history teaches from past "lost decades," why the order of returns matters, and how to protect your plan without panic. You'll learn three ways to …

1
Inbox Question | Typical Costs of Estate Planning 9:22

1M ago9:22

9:22

David asks for a general idea of what estate planning services typically cost, following up on the six-part podcast series. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin's team at https://carrolladvisory.co/podcast1 📍Contact John's team at ht…

1
Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins? - 554 34:47

1M ago34:47

34:47

Should the new temporary senior tax deduction change your Roth conversion strategy? Joe and Big Al spitball for Chris in Maple Grove, Minnesota, who wonders whether to keep converting to Roth now that the $6,000 Senior Bonus deduction phases out with higher income, today on Your Money, Your Wealth® podcast 554 with Joe Anderson, CFP®, and Big Al Cl…

1
The Hidden Cost of Delaying Social Security 33:22

1M ago33:22

33:22

You've heard it a thousand times: "Wait until 70 to file for Social Security." But if that's such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of waiting and the trade-offs most experts ignore. You'll learn how early withdrawals, taxes, and real-life emotions all change the math—and why the "right" …

1
Inbox Question | What's the Big Deal with HSAs 8:13

1M ago8:13

8:13

Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin's team at https://carrolladvisory.co/podcast1 📍Contact John's t…

1
090: Going Beyond the Portfolio: Transitioning Into Retirement with Confidence with Kyle Britton 26:20

1M ago26:20

26:20

For most of your life, retirement planning has likely centered around saving and building wealth. But what happens when the paychecks stop and it's time to start replacing your income withdrawing from your retirement savings and investments? In this episode, SHP Financial Co-Founder Derek Gregoire is joined by Kyle Britton, Lead Advisor at SHP Fina…

1
Should You Convert to Roth Before or After You Retire? - 553 40:41

1M ago40:41

40:41

Joe Anderson, CFP® and Big Al Clopine, CPA tackle one of the trickiest timing questions in retirement planning, today on Your Money, Your Wealth podcast number 553: when should you convert to Roth, while you're still earning, or after retirement? First, James from Texas wonders if it's worth maxing out his high-fee 457 plan, or if he's better off i…

1
Don't Let Money Anxiety Ruin Your Retirement - 552 36:30

2M ago36:30

36:30

Joe Anderson, CFP® and Big Al Clopine, CPA tackle the fears that mess with even the best-laid financial plans, today on Your Money, Your Wealth® podcast 552. Big Wallet Barbie and Ken from the Midwest have saved millions, but Barbie's still worried about retiring early, buying a new house, and converting to Roth. Is she second-guessing her plans? T…

1
Inbox Question | Using IRA Withdrawals to Fund Daughter's Roth 7:08

2M ago7:08

7:08

John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter's Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin's team a…

1
Where Should You Take Retirement Money First If You've Saved $2M? - 551 49:59

2M ago49:59

49:59

We're playing "which comes first" today on Your Money, Your Wealth® podcast number 551 with Joe Anderson, CFP® and Big Al Clopine, CPA. "Retired G-Man and Nurse Ratched" from Pennsylvania have saved $2 million. Should they withdraw money first from their IRA or their taxable accounts in retirement? "Mike and Carol in Florida" want to know when and …

1
Matt's Markets on the Move Q3: October 2025 36:16

2M ago36:16

36:16

1
089: The Future of Fannie Mae and Freddie Mac and What Privatization Could Mean for Homebuyers with Nathan Hartseil 25:07

2M ago25:07

25:07

The housing market has undergone significant changes in recent years, leaving many homeowners and prospective buyers feeling uncertain about its future direction. Interest rates have risen from historic lows, making affordability a pressing issue, and discussions about the possible privatization of Fannie Mae and Freddie Mac are sparking new concer…

1
Is Your Roth Conversion Timing All Wrong? (Financial Blunders) - 550 49:13

2M ago49:13

49:13

Joe and Big Al spitball on how to avoid screwing up the timing of your Roth conversions, today on Your Money, Your Wealth® podcast number 550. Barrie from New York is 62 and single, and she's been diligently converting pre-tax money each year for lifetime tax-free Roth growth. Should she continue after she retires next year? "Jerry and Elaine" want…

1
The Great Retirement Plan Illusion 26:14

2M ago26:14

26:14

Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and how to spot the difference between true planning and portfolio sales. Although this show does not provide specific tax, legal, or financial advice, you…

1
What Retiring With $6 Million Really Looks Like - 549 36:00

2M ago36:00

36:00

Today on Your Money, Your Wealth® podcast number 549 with Joe Anderson, CFP® and Big Al Clopine, CPA, a comment on one of our YouTube videos sparks a dialogue between Joe and Big Al on the 4% rule vs. the "guardrails" withdrawal strategy. Joe at the Beach is managing his ~$6M portfolio on his own, but wants the fellas' take on his upper limit for y…

1
The Hidden Estate Tax Lesson in the $1.8 Billion Powerball 23:51

2M ago23:51

23:51

Winning the lottery may be rare, but estate tax mistakes aren't. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes and how tools like a BDIT can help protect growth assets. We'll also show why this strategy isn't just for lottery winners, but for anyone holding asset…

1
088: The Importance of Retirement Planning for Women and Widows with Alina Osokhovska, CFP® 23:03

3M ago23:03

23:03

Losing a spouse is one of life's most painful experiences, and in the midst of grief, surviving partners are often faced with overwhelming financial decisions. From settling estates to adjusting to changes in income, the process can feel like an impossible burden to carry alone. Without a plan in place, surviving spouses may find themselves vulnera…

1
Is Financial Software Giving You False Retirement Confidence? - 548 47:56

3M ago47:56

47:56

Wendy and Joe in Colorado ran the numbers, and their financial planning software says they'll have over $10 million when they pass. Wendy's wondering if they should continue converting to Roth while working, despite their high tax bracket. But has the software lulled them into a false sense of security? That's today on Your Money, Your Wealth® podc…

1
Why So Many Americans Are Claiming Social Security Early in 2025 24:48

3M ago24:48

24:48

So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they're doing so because they're worried about cuts. But will filing early really help? In this episode, we talk about what the data shows, what most people get wrong about Social Security cuts, and how to think about …

1
Roth Conversions: When to Make 'Em, When to Take 'Em - 547 43:20

3M ago43:20

43:20

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener's name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, …

1
087: How Death Doulas Help Families Navigate End-of-Life with Love & Compassion with Aimee Yawnick 38:35

3M ago38:35

38:35

Death is one of life's certainties, yet it remains one of the hardest subjects to talk about. Many families avoid end-of-life conversations out of fear, discomfort, or superstition. Unfortunately, this avoidance can lead to increased stress, resentment, and regret when the time comes to make critical decisions. So how do we make the process smoothe…

1
How to Accomplish Your Retirement Goals - Even Without a Fat Wallet - 546 51:07

3M ago51:07

51:07

We heard your feedback, and today on Your Money, Your Wealth® podcast number 546, Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing retirement for the not-so-fat wallets: Joe and Masako in Washington state and Reid in Indiana have less than a million saved. Can they still accomplish their retirement goals in their 60s? Mr Buckeye in Ohio a…

1
What The New Law Means For Your Roth IRA! - 545 38:04

3M ago38:04

38:04

One Big Beautiful Bill is now law. How does it impact your Roth conversion strategies and other financial decisions? Plus, you may have seen or heard other advisors talking about their strategies for getting your retirement savings into tax-free Roth accounts. How are these different from a good ol' Roth conversion, and what do Joe and Big Al think…

1
Three Priorities That Should Shape Your Social Security Decision 25:58

3M ago25:58

25:58

When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement plan. Devin begins by challenging the common belief that wealthy retirees do not need to think about Social Security. In realit…

1
What's the Tax Triangle and How to Find Out if Yours is Lopsided - 544 28:35

3M ago28:35

28:35

You've heard Joe and Big Al talk about the benefits of tax diversification in retirement. That is, having money in tax-deferred, tax-free, and taxable accounts. But what should you do if this tax triangle of yours is lopsided? Joe and our special guest co-host, Marc Horner, CFP®, spitball on this quandary for Rae and Roy in Central California, toda…

1
What Millionaire Retirees Fear Most (But Rarely Talk About) 41:22

3M ago41:22

41:22

For many affluent retirees, the biggest financial fear isn't market volatility or rising taxes. It's this simple question: What happens if I'm not the one here to manage the plan? In this episode, we talk about a deeply personal concern shared by countless couples. When one spouse manages the investment strategy, the tax planning, and the long-term…

1
086: Career Insights for New Grads Aspiring to Become Financial Advisors with Raphael Hanna 31:18

4M ago31:18

31:18

Graduation marks an exciting new chapter for young professionals, but for those eyeing a career in financial planning, the path forward can feel uncertain. What are the skills that investment firms are looking for? Which licenses and designations matter most? And how do you land that first opportunity in a highly competitive field? Today, Matthew P…

1
Can You Retire at Age 57 and Spend Big? - 543 38:58

4M ago38:58

38:58

Is it possible, common even, to spend a lot early in retirement to celebrate your financial freedom? How do Roth conversions and withdrawals work if you do plan to call it quits around age 57, and spend big early on? Should you convert retirement funds to tax-free Roth after you stop working? Joe Anderson CFP® and our special guest co-host, Marc Ho…

1
Private Equity Meets Your 401(k) 24:07

4M ago24:07

24:07

Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications of this move, especially for retirement savers who may not be equipped to handle the risks. We start with a quick quiz that hi…

1
Are You Cutting Retirement Too Close? - 542 35:49

4M ago35:49

35:49

"Rubble and Skye" in Minnesota want to spend $65,000 a year in retirement, and they'll have $67K in annual fixed income. Are they cutting it too close? "Atouk and Tala" in New Jersey will have retirement money, Social Security, and "Lumpy," their lump sum pension - will they be okay? We'll find out today on Your Money, Your Wealth® podcast number 5…

1
085: How Donor-Advised Funds Simplifies Charitable Giving And Maximizes Tax Benefits with Kyle Casserino 43:15

4M ago43:15

43:15

Many retirees want to give back—but aren't sure how to do it in a way that's financially savvy and tax-efficient. If you've ever wondered how to streamline your charitable giving, take advantage of smart tax strategies, or leave a lasting legacy without the administrative burden, we have the perfect guest to help with those important decisions. Tod…

1
Are These Millennials Saving Enough to Retire Before 60? - 541 49:29

4M ago49:29

49:29

Pam and Jim in Phoenix are 38 and 41 and want to retire at 59 and 62. Matt and his wife in Pennsylvania are both 39 and want to retire at 57. Are these millennials on the right financial path, or have they brunched and YOLO'd away their retirement dreams? That's today on Your Money, Your Wealth® podcast number 541 with Joe Anderson, CFP® and Big Al…

1
Smart Strategies to Retire Early and Spend More - 540 33:14

4M ago33:14

33:14

Can Beth and Rip retire early, spend more, and Die with Zero? When should they claim Social Security? Forrest and Jenny have 10 rental properties at age 31. Can they retire at age 50? (And what makes you a real estate professional from a tax perspective?) Plus, what are the rules for spousal IRA contributions and required minimum distributions? Mem…

1
084: Examining the Big Beautiful Tax Bill & What it Means for Your Retirement with Alina Osokhovska 41:43

5M ago41:43

41:43

The "One Big Beautiful Bill Act" has just become law, bringing sweeping tax changes that will directly impact retirees and pre-retirees. From changes to itemized deductions and charitable giving to updates on Social Security taxation and estate planning, the impact is far-reaching. Today, Matthew Peck is joined by one of SHP Financial's Certified F…

1
Where to Invest for Pre-Retirement and a GO-GO Lifestyle? - 539 27:02

5M ago27:02

27:02

Roger in Canton, Ohio, is burnt out. Can he and his wife Jane pre-retire next year in their mid-50s with $2.8 million? Joe and Big Al spitball on whether they'll still have enough money for their Go-Go years, Joe's favorite, today on Your Money, Your Wealth® podcast number 539. Roger also has an employee stock purchase plan. For the best asset loca…

1
5 Mistake Most Millionaire Retirees Make 31:05

5M ago31:05

31:05

You've done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares the five most common retirement mistakes he sees among high-net-worth clients. These include missing long-term tax planning …

1
How Much Money Do You Need to Retire in 2026? - 538 35:10

5M ago35:10

35:10

George and Weezy in the land of Lincoln will have deferred compensation and wonder if they can retire in mid-2026, or even earlier. Will they have enough? Should Jenn in Ohio move with work, take a break, or just retire? She asks Joe Anderson, CFP® and Big Al Clopine, CPA for a brutally honest spitball, today on Your Money, Your Wealth® podcast 538…

1
Overview of the One, Big, Beautiful Bill 32:11

5M ago32:11

32:11

In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a brand-new "Senior Deduction"—there's a lot packed into this legislation. We'll walk you through the major provisions, highlig…