EPISODE · Apr 27, 2026 · 29 MIN
Ask the Advisor: Rapid-fire questions, real-world answers | Ep. 67
from Playbook of the Wealthy · host Playbook of the Wealthy
Rapid-fire questions, real-world answers.In this mailbag episode, Dave Grant and Heather Townsend go straight into “What Would You Do?” and tackle a stack of listener and client questions, from charitable giving and Roth conversions to AI in financial planning, inheritance tax strategy, and whether you should change your investing plan based on what markets might do next year. What you’ll learn… • QCDs explained simply, and why they don’t work the way many people think for Roth conversion “room” • 529 vs 529 ABLE: who they’re for and what the money can be used for • How Dave and Heather actually use AI, and where it still gets financial planning wrong • Market forecasts for 2026: why “big institutions” disagree, and why no one actually knows • The timeless advice when markets feel uncertain: keep contributing anyway • Inheritance strategy: step-up in basis explained, and which accounts can be best to leave to which people • HSA inheritance rules and why they treat HSAs differently in estate planning • Partnership buy-ins: when “buying in” is a bad idea if you don’t have the cash flow • How often a DIY plan should be reviewed (and why a periodic check-up can save you big money) Chapters00:00 Cold open: market predictions, noise, and why no one knows 01:12 Welcome: mailbag episode (straight into questions) 01:58 Q1: QCD strategy to “enable” a bigger Roth conversion 06:18 Q2: 529 vs 529 ABLE (who qualifies and what it’s for) 08:01 Q3: Do you use AI as a CFP? Pros, cons, and what it gets wrong 11:14 Q4: How will AI change investing and the role of a financial planner? 16:12 Market forecast chart: what big institutions think for 2026 (and why to ignore it) 19:00 Q5: Inheritance planning: step-up in basis and which accounts to leave to whom 21:50 Q6: Becoming a shareholder/partner without extra cash (should you go into debt?) 25:05 Highlights 29:14 Wrap up 29:38 Disclaimer I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover Social Security, tax strategies, IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected]: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast.
What this episode covers
Rapid-fire questions, real-world answers.In this mailbag episode, Dave Grant and Heather Townsend go straight into “What Would You Do?” and tackle a stack of listener and client questions, from charitable giving and Roth conversions to AI in financial planning, inheritance tax strategy, and whether you should change your investing plan based on what markets might do next year. What you’ll learn… • QCDs explained simply, and why they don’t work the way many people think for Roth conversion “room” • 529 vs 529 ABLE: who they’re for and what the money can be used for • How Dave and Heather actually use AI, and where it still gets financial planning wrong • Market forecasts for 2026: why “big institutions” disagree, and why no one actually knows • The timeless advice when markets feel uncertain: keep contributing anyway • Inheritance strategy: step-up in basis explained, and which accounts can be best to leave to which people • HSA inheritance rules and why they treat HSAs differently in estate planning • Partnership buy-ins: when “buying in” is a bad idea if you don’t have the cash flow • How often a DIY plan should be reviewed (and why a periodic check-up can save you big money) Chapters00:00 Cold open: market predictions, noise, and why no one knows 01:12 Welcome: mailbag episode (straight into questions) 01:58 Q1: QCD strategy to “enable” a bigger Roth conversion 06:18 Q2: 529 vs 529 ABLE (who qualifies and what it’s for) 08:01 Q3: Do you use AI as a CFP? Pros, cons, and what it gets wrong 11:14 Q4: How will AI change investing and the role of a financial planner? 16:12 Market forecast chart: what big institutions think for 2026 (and why to ignore it) 19:00 Q5: Inheritance planning: step-up in basis and which accounts to leave to whom 21:50 Q6: Becoming a shareholder/partner without extra cash (should you go into debt?) 25:05 Highlights 29:14 Wrap up 29:38 Disclaimer I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover Social Security, tax strategies, IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected]: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast.
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Ask the Advisor: Rapid-fire questions, real-world answers | Ep. 67
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