Your Money, Your Wealth

Your Money, Your Wealth
  • 4.6 (805)
  • Investing
  • Updated Weekly

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

  1. 1d ago ·  Video

    Got a Pre-Tax Fortune? Nobody Warns You About the Retirement Tax Bomb

    Schedule a Free Financial Assessment with an experienced professional: https://bit.ly/YMYWassessC 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: https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep590-description-whitepaper Financial Blueprint (free, self-guided): https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep590-description-blueprint Retirement Checklist: Check Off These 7 Things Before You Retire - YMYW TV: https://purefinancial.com/ymyw/episodes/retirement-checklist-check-off-these-7-things-before-you-retire/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep590-description-tv-s12e05 REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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 - $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

    Got a Pre-Tax Fortune? Nobody Warns You About the Retirement Tax Bomb

  2. Jul 7 ·  Video

    Retirement Margin Loans: Is Buy, Borrow, Die Worth the Risk?

    Schedule a Free Financial Assessment with an experienced professional: https://bit.ly/YMYWassessC 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): https://bit.ly/YMYWblueprintC REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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 01:53 - 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

    Retirement Margin Loans: Is Buy, Borrow, Die Worth the Risk?

  3. Jun 30 ·  Video

    $500K Income, $900K Saved: Will FIRE at 55 Work?

    Schedule a Free Financial Assessment with an experienced professional: https://bit.ly/YMYWassessC 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: https://purefinancial.com/white-papers/retirement-income-strategies/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-income-strategies&utm_content=ymyw-pod-ep588-description-whitepaper Financial Planning at Every Age: Retirement Planning for Millennials, Gen-X & Baby Boomers - YMYW TV: https://purefinancial.com/ymyw/episodes/financial-planning-at-every-age-retirement-planning-millennials-gen-x-baby-boomers/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep588-description-tv-s10e7 Retirement Readiness Guide - free download: https://purefinancial.com/white-papers/retirement-readiness-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-readiness-guide&utm_content=ymyw-pod-ep588-description-whitepaper Financial Blueprint (free, self-guided): https://bit.ly/YMYWblueprintC REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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

    $500K Income, $900K Saved: Will FIRE at 55 Work?

  4. Jun 23 ·  Video

    Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587

    Financial Assessment (Meet with an experienced professional): https://bit.ly/YMYWassessC 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: https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep587-description-whitepaper 401(k) vs. IRA vs. Equity Compensation: The Real Math - YMYW TV: https://purefinancial.com/ymyw/episodes/recipe-for-retirement-retirement-plans-explained/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep587-description-tv-s10e12 Financial Blueprint (free, self-guided): https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep587-description-blueprint REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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

    Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587

  5. Jun 16 ·  Video

    Roth Conversions: When to Pay Taxes NOW

    Schedule a free financial assessment with an experienced professional at Pure Financial Advsiors: https://purefinancial.com/lp/free-assessment/?utm_source=captivate&utm_medium=podcast&utm_campaign=free-assessment&utm_content=ymyw-pod-ep586-description-free-assessment “Walter and Skyler” in Iowa ask if they’re on track to retire early, or if they’re just "cooking up overconfidence?" And how aggressively should they convert their retirement savings to tax-free Roth money before the pension and Social Security kick in? California Dreamin’ has it down to one decision: convert to the top of the 22 percent tax bracket, or push into the 24? “Mike and Carol” in Florida ask, when you're weighing a conversion, should you be looking at your tax bracket, or your actual effective tax rate? Finally, is it worth the cost for “Westley and Buttercup” to use the brand new option to turn a big employer contribution into Roth money? Joe Anderson, CFP® and Big Al Clopine, CPA from Pure Financial Advisors spitball on all of these questions, today on YMYW podcast 586. Free Financial Resources in This Episode: https://bit.ly/ymyw-586 (full show notes & episode transcript) 10 Common Roth IRA Mistakes That Can Cost You $50,000 (or More!) - YMYW TV: https://purefinancial.com/white-papers/roth-ira-white-paper/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-guide-to-roth-iras&utm_content=ymyw-pod-ep586-description-whitepaper The Ultimate Guide to Roth IRAs - free download: https://purefinancial.com/ymyw/episodes/10-common-roth-ira-mistakes-that-can-cost-you-50000-or-more/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep586-description-tv-s12e04 Financial Blueprint (free, self-guided): https://bit.ly/YMYWblueprintC REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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 - Early Retirement Overconfidence? Aggressive Roth Conversions? (Walter & Skyler, Iowa) 13:25 - Roth Conversion Bracket Call: 22% or 24%? (CA Dreamin', Central Coast) 22:27 - Tax Bracket vs. Effective Rate: The Roth Math Most People Get Wrong (Mike & Carol, FL) 32:16 - Should the NEC Go to the Roth? The 401(k) Decision (Westley & Buttercup, TX) 42:28 - Outro: Next Week on the YMYW Podcast

    Roth Conversions: When to Pay Taxes NOW

  6. Jun 8 ·  Video

    Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes

    Financial Assessment (Meet with an experienced professional): https://bit.ly/YMYWassessC Free Financial Resources in This Episode: https://bit.ly/ymyw-585 (full show notes & episode transcript) Today on Your Money, Your Wealth® podcast number 585, Joe and Big Al spitball for folks who are already winning and thinking about getting fancy with it. Reno in Oregon is 50, and his pension is so big he's not sure how to invest or why he would need to convert to Roth. Michael is considering taking out a half-million-dollar margin loan to juice investment returns. What do the fellas think? Tune in for the surprising debate. Husker Fans just pocketed two million from selling their business here come the product pitches: should they buy annuities, set up a charitable trust, or just swallow the tax? What do the fellas think of whole life insurance? And finally, John and Lib on Waltons Mountain - or rather, the Catskills - aren’t sure if they’ve saved too little or too much. Can they bridge the gap until their pension? Emotionless Investing Guide - free download: https://purefinancial.com/white-papers/emotionless-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-emotionless-investing-guide&utm_content=ymyw-pod-ep585-description-whitepaper Financial Blueprint - free, self-guided: https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep585-description-blueprint Retirement Rebound: 5 Plays to Help You Score a Comeback - YMYW TV: https://purefinancial.com/ymyw/episodes/retirement-rebound-5-plays-help-score-comeback/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep585-description-tv-s10e11 REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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 - How Should a Pension-Rich 50-Year-Old Invest? Should They Even Bother with Roth Conversions? (Reno, OR) 10:30 - Should I Borrow $500K in a Margin Loan to Invest? (Michael, VA) 23:01 - We're Getting $2M From Selling the Business. Annuity, Charitable Trust, or Bite the Tax? What About Whole Life Insurance? (Husker Fans, Nebraska) 34:14 - Can a Frugal Mountain Couple Bridge the Gap to a $60K Pension? (John & Lib, NY Catskills) 41:13 - Outro: Next Week on the YMYW Podcast

    Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes

  7. Jun 2 ·  Video

    These Tax Strategies Let You Spend More in Retirement

    Schedule a Free Financial Assessment with an experienced professional: https://bit.ly/YMYWassessC Heidi from the Space Coast of Florida found a money-saving tidbit in a past episode that completely changed how she thinks about her financial advisor's fee. Joe Anderson, CFP® and Big Al Clopine, CPA expand on the strategy, today on Your Money, Your Wealth® podcast number 584. Laverne and Shirley have four million bucks, Roth conversion questions, annuity questions, and a retirement plan so detailed it may require a diagram. Finally, Bess and George from Pure Michigan are already retired, already on Social Security, and already losing sleep over their investments. So why are they so stressed? Joe and Big Al’s a debate about a 1% advisory fee gets a little spicy in that one. Retirement Accounts Guide - free download: https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep584-description-whitepaper Financial Blueprint - free, self-guided retirement plan check-in: https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep584-description-blueprint Retirement Course: Can You Hit a Hole in One? With PGA Pro Chris Riley - YMYW TV: https://purefinancial.com/ymyw/episodes/retirement-course-hole-in-one-pga-pro-chris-riley/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep584-description-tv-s11e02 REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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 - Can Financial Advisor AUM Fees Come Out of Pre-Tax Money? (Heidi, Space Coast, FL) 09:54 - Are We Converting Enough Before RMDs? What to Do With Annuities? (Laverne & Shirley, Cleveland, OH) 30:23 - Target Date Funds and a Sad Brokerage: Good Enough? Can't See Ever Paying an Advisor (Bess & George, MI) 45:37 - Outro: Next Week on the YMYW Podcast

    These Tax Strategies Let You Spend More in Retirement

  8. May 26 ·  Video

    $1.6M in One Stock? Here's How to Get Out Without Getting Crushed

    Schedule a Free Financial Assessment with an experienced professional: https://bit.ly/YMYWassessC Joe Anderson, CFP® and Big Al Clopine, CPA spitball for people sitting on life-changing gains who are just one wrong move away from handing a third of it to the IRS. How should they diversify their concentrated stock positions? That’s today on Your Money, Your Wealth podcast number 583. First up, Walter's a software engineer who got lucky 15 years ago. Now he's got $1.6 million in company stock, and a retirement clock ticking down in six years. Richard from Staten Island listened to his son six years ago, went big on oil, saw a huge gain, and now 80% of his portfolio is in that one position. His custodian wants him to sell, but he’s not so sure. Finally, Doctors “Bones McCoy and Beverly Crusher” just discovered they’ll be inheriting millions still sitting in an old 401(k) loaded with company stock. Free Financial Resources in This Episode: https://bit.ly/ymyw-583 (full show notes & episode transcript) 2026 Tax Planning Guide - free download: https://purefinancial.com/white-papers/tax-planning-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-planning-guide&utm_content=ymyw-pod-ep583-description-whitepaper 10 Steps to Improve Investing Success - free download: https://purefinancial.com/white-papers/10-steps-to-improve-investing-success/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-10-steps-to-improve-investing-success&utm_content=ymyw-pod-ep583-description-whitepaper Once Retirees See This Data, They Stop Worrying About Investing - YMYW TV: https://purefinancial.com/ymyw/episodes/once-retirees-see-this-data-they-stop-worrying-about-investing/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep583-description-tv-s12e03 Strategies for Diversifying Concentrated Stock Positions - blog post: https://purefinancial.com/ask-pure/strategies-for-diversifying-concentrated-stock-positions/?utm_source=captivate&utm_medium=podcast&utm_campaign=learning-center&utm_content=ymyw-pod-ep583-description-learning-center Comic-Con 2014: https://www.youtube.com/watch?v=EQASw5viQPI 2016: https://www.youtube.com/watch?v=WcSRFo7W5ZQ Financial Blueprint (free, self-guided): https://bit.ly/YMYWblueprintC REQUEST your Retirement Spitball Analysis: https://bit.ly/YMYWaskC DOWNLOAD more free guides: https://bit.ly/YMYWguidesC READ financial blogs: https://bit.ly/YMYWblogC WATCH educational videos: https://bit.ly/YMYWvidsC SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWnewsletterC Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw 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 01:09 - How Do You Sell $1.6M in Company Stock Without Writing the IRS a Giant Check? (Walter & Jesse, NM) 13:04 - One Oil Stock is 80% of My Portfolio. My Financial Advisors Want Me to Sell It. I Don't Trust Them. (Richard, Staten Island, NY) 30:10 - We're Two Doctors About to Inherit a $1.35M Tax Bomb. What Now? (Bones & Beverly, MI) 45:23 - Outro: Next Week on the YMYW Podcast

    $1.6M in One Stock? Here's How to Get Out Without Getting Crushed
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4.6
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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

Information

  • Creator
    Your Money, Your Wealth
  • Years Active
    2009 - 2026
  • Episodes
    586
  • Rating
    Clean
  • Copyright
    © Pure Financial Advisors, LLC
  • Show Website
    Your Money, Your Wealth

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