Podcast
Your Money, Your Wealth
Making fun of finance. A US News & World Report "Top 9 Personal Finance Podcast" (2025) and "Top 12 Retirement Podcast" (2023). One of the "10 Best Personal Finance YouTube Channels" (CardRates, 2023). "Best Retirement Podcast With Humor" (FIPhysician, 2020-2024). Learn strategies that can help you retire successfully. Financial advisor Joe Anderson, CFP® and certified public accountant Big Al Clopine, CPA answer your money questions and spitball on your 401k, IRA, Roth conversions and backdoor Roth IRA, how to pay less taxes, asset allocation, stocks and bonds, real estate, and other investments, Social Security benefits, capital gains tax, 1031 exchange, early retirement, expenses and withdrawals, and more money and wealth management strategies. YMYW is retirement planning, investing, and tax reduction made fun, presented by Pure Financial Advisors - a fee-only financial planning firm. Pure Financial adheres to the fiduciary standard of care, in which we are required by law to act in the best interest of our clients at all times. Access free financial resources and episode transcripts, Ask Joe & Big Al On Air to get your Retirement Plan Spitball Analysis: http://YourMoneyYourWealth.com
- Investing chart
- #55
- Episodes
- 601
- Releases
- Weekly
- Typical length
- 44 min
- On air since
- 2016
- Latest episode
- 1 day ago
Episodes
601 episodes, newest first
-
48 min
Give Up a $76K Federal Pension and Retire Early: Worth It?
Episode 606
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Financial situations around early retirement today on YMYW: Shane and Ilya are 38 and 37. Ilya has a big federal pension and lifetime health insurance waiting for him at age 50, but he needs out of his job now. Can they still retire early? Rip and Beth are 35 and 33, and Beth can sell her business for $1.8 million. Is that enough for her to be done for good, or would she end up back at work anyway? Leeroy and Belle are teachers with just shy of a million dollars saved at age 34 and 33. Is it crazy for them to take a gap year? Finally, Jake is in his early 50s with $1.1 million, planning to Coast FIRE his way out at age 58. Does the math hold up? We’ll find out today on Your Money, Your Wealth® podcast number 606 with Joe Anderson, CFP® and Big Al Clopine, CPA.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-606 (full show notes & episode transcript)
LIMITED-TIME SPECIAL OFFER | DIY Retirement Guide: download by Friday, November 6, 2026!
https://purefinancial.com/ymyw/#specialoffer
WATCH Un-Retirement: Why Retirees Are Going Back to Work (And How to Avoid It) - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:58 - Quitting Kills My $76K Pension and Health Insurance. Can We Stop Working at 50 Anyway? (Shane & Ilya)
12:23 - Should I Sell My Business for $1.8M and Quit at Age 33? (Rip & Beth, KY)
24:24 - Two Teachers, $1M Saved, and a Gap Year at 34. Is That Crazy? (Leeroy & Belle, IA)
34:21 - Coast FIRE at 52: Can I Stop Saving Now and Retire at 58? (Jake, MI)
42:37 - Outro: Next Week on the YMYW Podcast
43:37 - The Derails: Giant Ice Cube, Dutton Ranch, Wisconsin's Brandy Old-Fashioned
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44 min
Can You Afford Early Retirement AND Millions for Your Kids?
Episode 605
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to build your own retirement AND support your kids financially, today on Your Money, Your Wealth® podcast number 605. Lloyd and Diane in Montgomery County are 50 with $8.4 million. Can they retire early and still be generous with their kids? E and T in Missouri are 34 and 31 with $255K, and hopefully some big inheritances in the future. Can they fund the kids' college, and help them buy their first homes, AND retire early? Kent in Kansas City is 73 with 12 million bucks and $2 million in life insurance. Do Joe and Big Al back up his plan to buy an annuity, gift money to his kids now, and still spend freely in retirement, Die With Zero style? Finally, should John in the San Francisco Bay Area sell the family home and move to Nevada, or hold the house for his autistic daughters to inherit later? We’ll have a brand-new episode of tax strategies, retirement planning, and making fun of finance for you next week, but in the meantime, enjoy this encore presentation of an episode from March of this year.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-605 (full show notes & episode transcript)
Estate Plan Organizer - free download:
Retirement Readiness Guide - free download:
Retirement Won't Look Like You Planned: Four Hard Truths About Retirement You Need to Face - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:10 - 50 with $8.4M. Can We Retire Early and Still Give to Our Kids? (Lloyd Dobler and Diane, Montgomery County, MD)
11:41 - Die With Zero: Spend My $12M or Buy an Annuity? (Kent, 73 & 70, Kansas City)
25:08 - Can We Afford Kids’ College AND Houses AND Our Own Early Retirement? (E & T, 34 & 31, Missouri)
34:17 - Should We Move to Save Money or Keep the House for Our Autistic Kids? (John, 68 & 66, San Francisco Bay Area)
42:29 - Outro: Next Week on the YMYW Podcast
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1 hr
Is 4% Too Conservative? How Much You Can Really Spend in Retirement
Episode 604
Show notes
Schedule a Free Financial Assessment with an experienced professional:
How much can you actually spend in retirement without running out of money? That’s today on Your Money, Your Wealth® podcast 604 with Joe Anderson, CFP® and Big Al Clopine, CPA. Longtime listener E-Dog built a fifty-year backtest spreadsheet to call out Big Al and prove the famous four percent rule is way too cautious. Hot stuff “Donna Summer” wonders if her biggest problem with her $13 million dollar portfolio is going to be the distributions she’ll be required to take from it and how to manage them. “Hansel and Gretel” in Minnesota are trying to figure out now what a lot of good savers never do: how to permit themselves to spend their $4.3 million dollar portfolio? James in Texas needs a spitball on how much to convert to Roth before Social Security and Medicare kick in, and Mark needs a spitball on whether he should save for retirement to his pre-tax 401(k) or his post-tax Roth.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-604 (full show notes & episode transcript)
Withdrawal Strategy Guide - free download:
Financial Blueprint - free, self-guided:
Retirement Panic? Here’s Your 7-Step Escape Plan - YMYW TV:
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:05 - Is 4% Too Conservative? A Listener’s 50-Year Backtest (E-Dog)
17:10 - Roth Conversion to the Top of 24% Tax Bracket, or Protect My ACA Subsidy? (James, TX)
27:53 - Will RMDs Be My Biggest Problem on a $13M Portfolio? (Donna Summer, CA)
36:47 - $4.35M and Scared to Spend It. What’s Our YOLO Number? (Hansel & Gretel, MN)
44:30 - In My Late 30s With $750K Income: Save to Roth or Pretax 401(k)? (Mark)
49:40 - Outro: Next Week on the YMYW Podcast
51:05 - The Derails: Donna Summer, Hansel & Gretel, Joe's six fridges, and TV
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46 min
Is a $400K Roth Conversion at Peak Income a Mistake?
Episode 603
Show notes
Schedule a Free Financial Assessment with an experienced professional:
George and Louise in Queens bring in $600,000 a year. Should they keep working just to do Roth conversions? Cher and Sonny in Oregon wonder if they can retire in a couple years at 59 and 60, and whether the mega backdoor Roth belongs in their plans. Joe Anderson, CFP® and Big Al Clopine, CPA spitball retirement planning and Roth conversion strategies for them, today on Your Money, Your Wealth® podcast number 603. Plus, Michelle in Vienna, Virginia, is 56 and ready to retire, but what about her brand-new mortgage? Finally, our friend Marion in Fresno asks about Vanguard's suggestion of an annuity to cover fixed expenses.
LIMITED-TIME SPECIAL OFFER | DIY Retirement Guide - download by Friday, October 16, 2026!
https://purefinancial.com/ymyw/#specialoffer
Free Financial Resources in This Episode:
https://bit.ly/ymyw-603 (full show notes & episode transcript)
Do You Have These 10 Habits of the Quietly Wealthy? - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:50 - Should I Keep Working Just to Do Roth Conversions? (George & Louise, Queens, NY)
13:50 - Convert to Roth Now or Wait Until We Leave Oregon? (Cher & Sonny, Oregon)
30:29 - We Built a Dream House. Can I Still Retire? (Michelle, Vienna, VA)
38:38 - Should an Annuity Cover Your Fixed Expenses? (Marion, Fresno, CA)
39:56 - Outro: Next Week on the YMYW Podcast
41:02 - The Derails: Cher, blue cheese olives, Joe's Escalade, iPhone, and new lifestyle
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29 min
Should You Do Roth Conversions in a Down Market?
Episode 602
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing on whether Roth conversions actually pay off as part of your retirement tax strategies, today on Your Money, Your Wealth® podcast number 602. “Ozzie and Harriet” in Lafayette, Louisiana are 67, and Ozzie's spreadsheet says converting from their $7 million IRA costs more than just taking the RMDs. He challenges the fellas to change his mind. They also address BondBeer’s many YouTube comments telling them that their favorite guidance to convert when the market drops is flat wrong. Finally, Alan on Daufuskie Island, South Carolina asks for clarification on paying the tax to pay the tax when you pull money from an IRA, and whether it matters if the tax comes out of the account or out of your brokerage.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-602 (full show notes & episode transcript)
Retirement Accounts Guide - free download:
Financial Blueprint - free, self-guided:
5 Years From Retirement? Do These Things Now - YMYW TV:
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:04 - Do Roth Conversions Actually Lose You Money? (Ozzie & Harriet, Lafayette, LA)
12:08 - Is a Market Downturn Really the Best Time for a Roth Conversion? (bondbeer, YouTube)
23:00 - Do You Pay Tax on the Tax? Roth Withdrawals vs. Roth Conversions Clarified (Alan, Daufuskie Island, SC)
28:04 - Outro: Next Week on the YMYW Podcast
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41 min
Can You Retire Early? With $475K at 42, You Need a Gap Plan
Episode 601
Show notes
Schedule a Free Financial Assessment with an experienced professional:
How do you know if you're really on track to retire, especially if you're hoping to get out early? Fred and Wilma in Denver are 33 and 31, earning a small fortune, but sitting on nearly two million dollars in debt. Should they focus on paying it down faster or saving more? Jeremy, in Summerville, South Carolina, is 42 with a hefty military pension. Is that his green light to go all-in on stocks for the next 20 years? And finally, Saver and Spender in Saratoga Springs, New York are 41 and 42 and hoping an early exit. Can part-time work can carry them through their gap years? Joe Anderson, CFP® and Big Al Clopine, CPA spitball for all of them, today on Your Money, Your Wealth® podcast number 601.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-601 (full show notes & episode transcript)
Ultimate Investing Guide - free download:
Financial Blueprint - free, self-guided:
$1M Retirement Savings: Is It Enough to Retire? - YMYW TV:
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:01 - $1.8M in Debt at 33: Pay It Down or Keep Investing? (Fred & Wilma, Denver, CO)
17:07 - My $97K Military Pension: Can I Go 100% Stocks for 20 Years? (Jeremy, Summerville, SC)
26:49 - Can We Bridge Ages 56 to 62 With Part-Time Work? (Saver & Spender, Saratoga Springs, NY)
40:01 - Outro: Next Week on the YMYW Podcast
41:03 - The Derails: The Flintstones, Project Hail Mary
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50 min
Retirement Withdrawal Strategy: Is $100K a Year at 63 Wrong?
Episode 600
Show notes
Schedule a Free Financial Assessment with an experienced professional:
63-year-old Kevin in Denver is pulling $100K a year out of his portfolio. What’s the tax-smart way for him to structure these retirement withdrawals? Tim in Pennsylvania was forced into early retirement, and his wife Jill may be facing a layoff. They have over $2.5M saved, but what about health insurance? And Rocky and Adrian in Tucson have $4M in pre-tax at ages 68 and 69. If they convert to Roth, are they just picking up nickels in front of a steamroller? But first, Jeffrey’s YouTube comment lit a fire when he called a recent episode of YMYW TV on Social Security claiming strategies "cookie-cutter with zero real info." Joe and Big Al have some thoughts!
Free Financial Resources in This Episode:
https://bit.ly/ymyw-600 (full show notes & episode transcript)
2026 Tax Planning Guide - free download:
Withdrawal Strategy Guide - free download:
Escape These 11 Tax Traps and Save in Retirement - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:54 - Claiming Social Security: Is Planning for a 40-Year Retirement a Waste of Time? (jeffreylevin9728, YouTube)
12:31 - How Do I Turn My IRA Into a Monthly Paycheck? (Kevin, Denver)
23:42 - I’m Retired Early Due to Illness and My Wife May be Laid Off. What About Health Insurance? (Tim & Jill, rural PA)
32:30 - Roth Conversions on a $4M IRA at 68: Picking up Nickels in Front of a Steamroller? (Rocky & Adrian, Tucson, AZ)
40:27 - Outro: Next Week on the YMYW Podcast
42:16 - The Derails: Frontier Crucible, The Punisher, Disclosure Day, etc.
-
37 min
Retirement vs. House Down Payment: Are You Getting the Timing Wrong?
Episode 599
Show notes
Schedule a Free Financial Assessment with an experienced professional:
How do you buy a house as a young person, without wrecking your long-term retirement plan? That’s today on Your Money, Your Wealth® podcast 599, as Joe Anderson, CFP® and Big Al Clopine, CPA spitball for 35-year-old Gord in New York City. He's got $300,000 saved, and a home purchase is coming soon thanks to a new relationship. Should he liquidate his brokerage account and pull the trigger? Carrie Bradshaw in California is 33 and wants to buy a roughly $1.5M home. When should she move the down payment money out of the market, and can she avoid derailing early retirement? Finally, Archie and Veronica in Missouri are 41 and 34, pulling in $600,000 a year and saving close to $200,000 of it. Are they saving too much? Should they pay off their mortgage or keep investing?
Free Financial Resources in This Episode:
https://bit.ly/ymyw-599 (full show notes & episode transcript)
Financial Blueprint (free, self-guided):
10 Big Retirement Regrets to Avoid (Before It's Too Late) - YMYW TV:
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:02 - I’m 35 in NYC. Do I Cash Out My ETFs to Buy a House? (Gord, NYC)
15:21 - How Much of My $900K Goes to the Down Payment? ("Carrie Bradshaw", CA)
24:12 - We Make $600K With a $1.1M Mortgage. Pay It Off or Keep Investing? ("Archie & Veronica", MO)
35:55 - Outro: Next Week on the YMYW Podcast
-
40 min
Can You Retire with $1M at 42? The Early Retirement Lie
Episode 598
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Today on Your Money, Your Wealth® podcast 598, Joe Anderson, CFP® and Big Al Clopine, CPA spitball early retirement planning for Shua in Phoenix, who has a million dollars saved at age 42. Can he stop saving right now, coast until age 55, and still spend $170,000 a year in retirement? But first, Michael in Texas is a stay-at-home dad who does the stock market. His wife wants out of her job at age 47. Will their $5 million last through retirement? And then Homer and Marge in North Carolina make 640K in sales and want to spend up to 25K a month, and Seth in Illinois wants to retire at 58 on a pension and a Roth. Some of these plans work and some of ‘em aren't even close.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-598 (full show notes & episode transcript)
Withdrawal Strategy Guide - free download:
Retirement Readiness Guide - free download:
10 Assumptions Pre-Retirees Get Wrong About Retirement - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:52 - Wife Wants to Retire at 47. What Are We Missing? (Michael, TX)
14:03 - $3M Saved, $640K Income: Can We Retire at 50? (Homer & Marge, Northern California)
21:19 - Pension + $1.45M: Can I Retire at 58 and Spend $11K a Month? (Seth, North Central IL)
26:51 - Can We Stop Saving Now at 42 and 45 and Still Retire at 55? (Shua, Phoenix, AZ)
36:07 - Outro: Next Week on the YMYW Podcast
37:19 - The Derails: Big Al Canoeing on the Russian River
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41 min
We Have $12 Million. Should We Do Roth Conversions?
Episode 597
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing Roth conversions from every angle today on Your Money, Your Wealth® podcast number 597. John in Oklahoma is 75, sitting on a million dollars in traditional IRAs, and he's got a whole list of reasons NOT to convert to Roth. Is he right? Is it worth it as part of his retirement strategy? Jonathan and Jennifer in Phoenix have over six million dollars in tax-deferred accounts. How much should they convert, and where should they stop? J and C in Hawaii are both 38 and want to walk away from work at 55. How do they bridge the gap? And finally, are Bonnie and Clyde working for nothing if it all just turns into a giant tax bill?
Free Financial Resources in This Episode:
https://bit.ly/ymyw-597 (full show notes & episode transcript)
Retirement Accounts Guide - free download:
Ultimate Investing Guide - free download:
Once Retirees See This Data, They Stop Worrying About Investing - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:55 - Roth at 75: Does the Math Actually Work? (John, OK)
10:03 - 12M and Still Worried About Taxes: Roth Conversion Spitball (Jonathan & Jennifer, Phoenix AZ)
16:47 - Retiring at 55 in Hawaii: When Do We Start the Taxable Account? (J & C, Hawaii)
27:26 - Am I Just Working to Create a Bigger Tax Problem? (Bonnie & Clyde)
34:20 - Outro: Next Week on the YMYW Podcast
36:53 - The Derails: Hart to Hart, Minutiae, and Levels of Fame
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44 min
4 Retirement Questions That Expose Real Money Risks
Episode 596
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Each of the questions Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing today on Your Money, Your Wealth® podcast 596 has a real retirement risk attached to it. Philip and Elizabeth in DC have $7M. Philip's dying to quit a job he hates, but he's loading up on bonds to protect the nest egg. At 56, could playing it too safe be his real risk? Mr. Mojo Risin wants to retire in three years, but $1.7M of his nest egg is riding on one stock, and he needs a good CPA to help defuse it. BB and Shell got pitched a slick new AI crypto investment promising 15% a month. Too good to be true? And Huggy Bear in New Hampshire has $450K in cash value life insurance. Should he grab it now, or wait 20 years until he’s 80?
9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026/
The Ultimate Investing Guide - free download:
Retirement Readiness Guide - free download:
Retire at 62: Great Idea or Huge Mistake? - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:03 - We Have $7M and I Hate My Job. Why Am I Still Here? (Philip & Elizabeth, Washington DC)
10:20 - Retiring in 3 Years, $1.7M in One Stock. Where's the CPA for This? (Mr. Mojo Risin, GA)
19:33 - Is This AI Crypto Investment With 15% Monthly Return Too Good to Be True? (BB & Shell)
28:48 - Cash Out $450K in Life Insurance or Wait Until 80? (Huggy Bear, New Hampshire)
39:28 - Outro: Next Week on the YMYW Podcast
40:58 - The Derails: The Americans, Mr. Mojo Risin
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47 min
When to Claim Social Security and Why Full Roth Conversion Might be a Mistake
Episode 595
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Today on Your Money, Your Wealth® podcast number 595, Joe Anderson, CFP® and Big Al Clopine, CPA spitball for Eeyore and Nurse Kathi: retired in Orlando, both 65, and they swear they've never heard this one on the show before: is a full Roth conversion strategy the way to go, or is there a point where you should stop? Harry and Sally in New York potentially moving to Florida, have been living off their brokerage for retirement account withdrawal for two years, and Sally is getting nervous. Is this a tax efficient retirement plan? When should they claim Social Security? And “When Can I Retire From 12 Hour Days” in Virginia is 62, single, and faced with the same decision: collect Social Security benefits at full retirement age, or hold out for the bigger check at 70?
Free Financial Resources in This Episode:
https://bit.ly/ymyw-595 (full show notes & episode transcript)
9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026/
Social Security Handbook - free download:
Claim Social Security at 62 or Wait Until 70? Here's What Actually Matters - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:54 - Should We Convert All of Our Retirement to Roth? What About Selling Our Rental Property and Capital Gains? (Eeyore and Nurse Kathi, Orlando, FL)
14:56 - We've Lived Off Our Brokerage for 2 Years. Are We Crazy? When Should We Claim Social Security Benefits? (Harry & Sally, NY)
31:02 - Single, 62, $820K: Does My 2029 Retirement Plan Hold Up? When Should I Collect Social Security? (“When Can I Say Goodbye to 12 Hour Days?”, Virginia)
37:27 - Outro: Next Week on the YMYW Podcast
39:15 - The Derails: Winnie the Pooh and Eeyore, Smirnoff Ice, Childhood Stuffed Animals
-
45 min
He Has $10M and Can't Spend It. Here's Why.
Episode 594
Show notes
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Today on Your Money, Your Wealth® podcast number 594, Joe Anderson, CFP® and Big Al Clopine, CPA spitball retirement planning for high net worth couples: Gary in Pennsylvania is 54 with $10 million, and get this, he still can't decide whether he can walk away or if he needs to grind out a few more years. What is up with that? But before we get to Gary, Frida and Diego are 54 and 52 in California with $5.3 million, itching to start their go-go years. Can they both retire right now? And is $200,000 a year of spending pushing it? Stanley and Stella in New York have a pension decision to make. Choosing the wrong option could leave one of them exposed for life.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-594 (full show notes & episode transcript)
9th Annual YMYW Podcast Survey (password ymyw):
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Withdrawal Strategy Guide - free download:
Retirement Spending: How Much is Too Much? - YMYW TV:
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:56 - 54 and 52 with $5.3M. Can We Both Retire Now? (Frida & Diego, CA)
18:13 - Which Pension Option Protects Us Both? (Stanley & Stella, NY)
30:23 - Should We Retire at 54 with $10 Million? (Gary, PA)
40:51 - Outro: Next Week on the YMYW Podcast
42:14 - The Derails: Frida & Diego, Tesla, Kir Royale, Streetcar and Brando, Joe's pool remodel
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46 min
Roth vs. Traditional 401(k) at $275K Income: What's the Right Move?
Episode 593
Show notes
Paul and Angela in Florida are 52 and 45. What's the earliest the two of them can walk away from work at the same time, so Paul can spend a whole lot more time in the boat? That’s today on Your Money, Your Wealth podcast number 593. Then the fellas spitball for Mike in Riverside. His mom inherited his dad's IRA at age 84. Can she still roll it into her own? Edward in Illinois is watching his bond funds lose value even while they pay him interest, and he's wondering if treasuries are the fix. "Blanche Devereaux" in California is 55 with $1.1M in pre-tax. Should she go all Roth for her last five working years? And "Mr and Mrs Smith" on the Carolina coast want to know if they can afford to retire at age 59.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-593 (full show notes & episode transcript)
LIMITED TIME SPECIAL OFFER: The DIY Retirement Guide! Download yours before the Special Offer changes on Friday, August 7, 2026! https://purefinancial.com/ymyw/#specialoffer
9th Annual YMYW Podcast Survey (password ymyw):
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Your Favorite Money Influencer Might Be Wrong - YMYW TV:
Financial Blueprint (free, self-guided):
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:58 - Nearly $3M at 52 and 45. When Can We Retire Together? (Paul & Angela, FL)
12:56 - Mom Inherited Dad's IRA at 84. Can She Still Roll It Into Her Own? (Mike, Riverside, CA)
18:13 - Bond Funds Keep Losing Value Despite Paying Interest. Treasuries Instead? (Edward, IL)
25:06 - $1.1M Pre-Tax: Roth for the Last 5 Years? (Blanche Devereaux, CA)
35:10 - How Much Will We Have by 2030? Is It Enough to Retire at 59? (Mr. & Mrs. Smith, Coastal NC)
39:26 - Comment: No NUA Step-Up at Death (Jeff)
42:20 - MYGA vs. Immediate Annuity. Is MYGA a CD in Disguise? (Holly, San Francisco)
44:18 - Outro: Next Week on the YMYW Podcast
-
45 min
We Reverse-Engineered Their $6.5M Retirement. Here's What We Found
Episode 592
Show notes
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Michael, K & J, and Tracy all need retirement spitballs and Roth conversion plans, but they didn't share one of the most important numbers in retirement planning: how much they actually want to spend. Today on Your Money, Your Wealth® podcast number 592, Joe Anderson, CFP® and Big Al Clopine, CPA reverse-engineer their spitballs to back into what might be the same numbers missing from your own plan. Plus, Sean wants to retire in two years at age 56 with $4.4M without handing half of it to the tax man, and Dallas and Leeloo are wondering if there's such a thing as too much Roth - they’re 48 and on track for $1M in theirs. Plus we’ll talk about some charitable giving strategies: what's the difference between a DAF and a CRUT?
Free Financial Resources in This Episode:
https://bit.ly/ymyw-592 (full show notes & episode transcript)
9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026
Is There a Formula for Retirement? - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - The 9th Annual YMYW Podcast Survey is now open!
00:44 - Intro: This Week on the YMYW Podcast
01:39 - Working Until 70 With $6.5M Saved. Do I Need Roth Conversions? (Michael, Pittsburgh, PA)
09:25 - How Aggressively Should We Drain Our $2.6M IRA Before RMDs Hit? (K & J, the Cascades)
16:46 - Can I Retire Single at 63 With $1.5M? (Tracy, 63, CA)
20:15 - I'm 54, Single, With $4.4M. How Do I Retire at 56 Without Getting Crushed on Taxes? (Sean, Orlando, FL)
29:22 - How Much Roth is Too Much? We're 48, Heading for $1M in Roth. Did We Overshoot the Goal? (Dallas & Leeloo, 48, Brooklyn, NY)
36:15 - You Said CRTs Must Leave 10% to Charity. Let Me Correct the Record. (DG)
38:21 - DAF vs. CRUT: Which Charitable Tool is Better for $1M Company Stock That's Up 237%? (Fish Sean, 54, Winter Springs, FL)
44:22 - Outro: Next Week on the YMYW Podcast
-
34 min
Roth Conversions and RMDs: Are You Ready to Retire?
Episode 591
Show notes
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B and S in Maryland are in their mid-40s with $425,000 and a couple of rental properties. Can they retire early at 62? Vee in Oregon came to the US as a refugee with nothing and built a three and three-quarter million dollar portfolio from the ground up. Is his Roth conversion plan solid? And finally, Chandler and Monica in Texas are sitting on $1.4 million and hope they can walk away from work in 3 years. Will Roth conversions keep the tax man from taking a giant bite on their way out? That’s all today on Your Money, Your Wealth® podcast 591 with Joe Anderson, CFP® and Big Al Clopine, CPA.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-591 (full show notes & episode transcript)
Withdrawal Strategy Guide - free download
The Number One Spending Mistake Ruining Retirements - YMYW TV
Financial Blueprint (free, self-guided):
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WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
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Connect With Us:
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Leave your honest reviews and ratings in Apple Podcasts:
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
00:57 - Half a Million and Rental Properties in Our Mid-40s. Can We Retire Early? (B & S, Westminster, MD)
12:48 - Refugee to $3.75M: Is My Roth Conversion Plan Actually Solid? (Vee, OR)
25:55 - Can Friends with $1.4M and a Roth Conversion Puzzle Retire in 3 Years? (Chandler & Monica, TX)
33:05 - Outro: Next Week on YMYW Podcast
-
45 min
Got a Pre-Tax Fortune? Nobody Warns You About the Retirement Tax Bomb
Episode 590
Show notes
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Today on Your Money, Your Wealth® podcast 590, Joe Anderson, CFP® and Big Al Clopine, CPA spitball for people with a small fortune sitting in pre-tax accounts turning into a tax bomb. We’ll find out how Roth conversions and careful tax liability management can optimize their retirement income strategy. Eric in California is 72 with nearly four million dollars in pre-tax accounts. How much should he transfer in Roth conversions? Is borrowing against his own house to pay the tax bill brilliant or bonkers? Rick and Kiani hoping they can quit sooner than they think. Mike just hit full retirement age. Should he claim Social Security benefits now or wait until age 70? And finally, Jeff wants to walk away at 59 with a roadmap for aggressive Roth conversions, assuming the tax cliff doesn't get him first.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-590 (full show notes & episode transcript)
Retirement Accounts Guide - free download:
Financial Blueprint (free, self-guided):
Retirement Checklist: Check Off These 7 Things Before You Retire - YMYW TV:
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
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Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:01 - $3.9M Pre-Tax at 72: How Do We Minimize Taxes Before RMDs Hit? (Eric, CA)
11:13 - We’re on One Salary. Can We Retire at 62 With $1.7M and a $56K SS Benefit? (Rick & Kiani, Southern CA)
23:16 - Just Hit Full Retirement Age. Should I Delay Social Security or Start Now? (Mike, 66, NV)
31:04 - Retiring With $4M and a Roth Conversion Roadmap at Age 59. Does Our Plan Hold Up? (Jeff & Amber, 55, Orlando, FL)
44:54 - Outro: Next Week on the YMYW Podcast
-
44 min
Retirement Margin Loans: Is Buy, Borrow, Die Worth the Risk?
Episode 589
Show notes
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The margin loan debate continues today on Your Money, Your Wealth® podcast number 589. Jack and Jill recently moved from the UAE to Australia and want a sanity check on using margin loans (AKA pledge loans) to build and live off their portfolio. Joe and Big Al spitball whether borrowing against stocks and never paying tax on the gains, the Buy Borrow Die strategy, is smart, or a fast way to blow yourself up. They also recap the spicy comments on the episode 585 margin loan discussion. Then the fellas flip the script for Forest and Jenni in Virginia: does a reverse glide path, investing conservatively now and getting more aggressive as you age, actually hold up? And finally, Jack and Diane in New Jersey are retiring this year, selling the house, and moving to Florida, so Joe and Big Al stress-test their Roth conversion plan before they pull the trigger. We're making fun of finance over here on YMYW, the financial planning podcast that won't put you to sleep. Tell a friend.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-589 (full show notes & episode transcript)
Withdrawal Strategy Guide - free download: https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep589-description-whitepaper
Retirement Sabotage! 12 Post-Retirement Money Mistakes to Avoid - YMYW TV: https://purefinancial.com/ymyw/episodes/retirement-sabotage-12-post-retirement-money-mistakes-to-avoid/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep589-description-tv-s10e08
Financial Blueprint (free, self-guided):
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DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
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Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:53 - Margin Loans, Buy-Borrow-Die, and PFIC Risk: Sanity Check (Jack & Jill, Australia)
13:11 - Why I Love Margin: NYC Tax Math (Bones1999, YouTube)
14:29 - 8% Margin Loans to Buy Stocks: Bad Math! (Tom, YouTube)
19:39 - Reverse Glide Path at Retirement: Does Starting Conservative Make Sense for Us? (Forest & Jenni, VA)
35:43 - Retiring to Florida: SEP IRA Bridge, Home Sale Timing, and Roth Conversions (Jack & Diane, NJ)
43:18 - Outro: Next Week on the YMYW Podcast
-
48 min
$500K Income, $900K Saved: Will FIRE at 55 Work?
Episode 588
Show notes
Schedule a Free Financial Assessment with an experienced professional:
Joe Anderson, CFP® and Big Al Clopine, CPA spitball for three people planning for early retirement and wondering, can I really pull this off? How much risk can you take, and how much do you really need to? That’s today on Your Money, Your Wealth® podcast 588. Dr. Kickass Seabass and his wife are both 41 and they got a late start on savings. Can they still hit FIRE - that is, financial independence, retire early - by 55? Get your salt shakers ready. Aang and Katara have military pensions and a big thrift savings plan. Should they invest it aggressively or play it safe over the next decade? Finally, Steph has a mandatory retirement at 56 but wants out even sooner, at age 50… if his wife Ayesha doesn't kill him first for quitting seven years before her.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-588 (full show notes & episode transcript)
Retirement Income Strategies Guide - free download:
Financial Planning at Every Age: Retirement Planning for Millennials, Gen-X & Baby Boomers - YMYW TV:
Retirement Readiness Guide - free download:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:00 - High-Earning Doc With a Late Start: Can I Actually FIRE at 55? (Kickass Seabass, NJ)
13:39 - Military Pension + TSP: How Aggressive Should We Stay for the Next Decade? (Aang & Katara, VA)
25:10 - Mandatory Retirement at 56, But Can I Punch at 50? (Steph & Ayesha, SF Bay Area)
46:54 - Outro: Next Week on the YMYW Podcast
-
44 min
Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587
Episode 587
Show notes
Financial Assessment (Meet with an experienced professional):
11 rapid-fire spitballs today from Joe Anderson, CFP®, and Big Al Clopine, CPA, on Your Money, Your Wealth® podcast number 587, on everything from Roth conversions and RMDs to whether a guy named Wayne can finally treat himself to a seventy-five-thousand-dollar Audi. Aaron in Syracuse just hit a million bucks in his 401(k) and realizes he needs a spitball on keeping his RMDs low. Do new Roth conversions restart the 5-year clock? 72-year-old Mike in Texas wants to know. Marion inherited a not-yet-five-year-old Roth, and an IRMAA problem along with it. Lu and Stephen each argue that the fellas’ conversion and retirement spitball math might be misleading. Teachers Tony and his wife have pensions that cover everything, so should they even keep saving? John and Peggy need a retirement spitball, Rajesh wonders if he should pay off his mortgage or convert to Roth, and Mike in San Marcos asks about funding a Roth with pension money.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-587 (full show notes & episode transcript)
Retirement Accounts Guide - free download:
401(k) vs. IRA vs. Equity Compensation: The Real Math - YMYW TV:
Financial Blueprint (free, self-guided):
REQUEST your Retirement Spitball Analysis:
DOWNLOAD more free guides:
READ financial blogs:
WATCH educational videos:
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
Connect With Us:
Subscribe on YouTube and join the conversation in the comments:
Subscribe or follow YMYW in your favorite podcast app:
Leave your honest reviews and ratings in Apple Podcasts:
https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254
Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:32 - $1.1 Million in My 401(k) at 56: Should I Do Roth Conversions Before RMDs Hit? (Aaron, Syracuse, NY
04:51 - Can You Fund a Roth IRA With Pension Money? (Mike, San Marcos, CA)
06:14 - Can You Roll an UTMA Into a 529 for Tax-Free Education Savings? (Bob the Builder, Westchester, NY)
10:29 - I'm 72 With a 25-Year-Old Roth. Do New Conversions Trigger the 5-Year Clock for Roth Withdrawals? (Mike, TX)
11:43 - Inherited a Roth Less Than 5 Years Old: Are the Earnings Taxable? Can IRMAA Be Avoided? (Marion)
15:59 - You Ignore Future Income! How to Spitball Spending When a Pension and Social Security Are Coming (Stephen)
21:02 - Are Your Roth Conversion Calculations Misleading? Why Future RMDs Need an Inflation Check (Lu)
24:57 - We're Teachers With Pensions That Cover Everything. Should We Stop Saving and Fund the 529s? (Tony, NY
28:23 - $4 Million and Ready to Exit the Rat Race at 61. Do the Numbers Work? (John and Peggy, San Jose, CA
34:37 - $4 Million 401(k) and a 6.5% Rental Mortgage: Pay It Off or Convert to Roth? (Rajesh)
38:42 - We're 62 With $1 Million. Can I Finally Buy the $75K Audi, or Should I Lease? (Wayne, Long Beach, NY)
43:17 - Outro: Next Week on the YMYW Podcast
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