This episode of Money Matters explores advanced tax strategies that go beyond traditional investing to help high earners and retirees maximize efficiency, reduce taxes, and create smarter, more tax-efficient income streams.

With Pat out this week, Scott and Allworth advisor Mark Shone break down how strategies like direct indexing, long/short investing, and tax-loss harvesting can unlock new opportunities—especially for those with larger, more complex portfolios.

Plus, Scott and Allworth’s Head of Private Wealth Strategies, Simone Devenny, dive into trusts, from simple living trusts to more sophisticated estate planning tools.

What You’ll Learn:

-How direct indexing works—and when it can outperform traditional index funds

-Strategies to generate tax losses and offset future gains

-Smart ways to manage concentrated stock positions

-How options strategies can help increase portfolio income

-The key differences between revocable and irrevocable trusts (and when to use them)

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

How do you manage a concentrated stock position without getting crushed by taxes? In this episode of Money Matters, Scott is joined by Allworth advisor Mark Shone, who steps in while Pat is away to break down smart, tax-efficient strategies for handling highly appreciated stock positions. They use a real-life case of a recent retiree with nearly $2 million in Apple stock to explore how to reduce risk, diversify, and balance income and legacy goals. Plus, they touch on private credit and real estate trends shaping today’s investment landscape.

What You’ll Learn:

-How to reduce risk in a concentrated stock position-

-Strategies to diversify without triggering large capital gains

-Tax-efficient ways to manage highly appreciated stock

-How to balance income needs with long-term legacy goals

 

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

For many investors, the big question is whether $5 million is enough to retire—and this real-life case study shows how to answer it. With Pat out this week, Scott is joined by Allworth advisor Mark Shone to walk through a $5–6 million household navigating retirement while raising kids, funding college, and managing a second marriage. Scott and Mark break down what really matters when asking if you can retire with $5 million—and how to make that decision with confidence.

Plus, a physician with $6M+ asks if being all-in on the S&P 500 is a mistake—and what to do instead.

What You’ll Learn:

• How to evaluate if you can retire with $5M
• How to fund college without derailing retirement
• When sequence of returns risk actually matters
• Smart withdrawal strategies for complex situations
• Why diversification goes beyond the S&P 500

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

 

In this episode of Money Matters, Scott and Pat react to a listener being pitched a complex direct indexing strategy using margin, while another wrestles with whether setting up trusts for their grandchildren is worth the hassle—breaking down what actually adds value and what doesn’t.

They expand into tax strategies for larger portfolios, including when more sophisticated approaches create more cost and complexity than benefit. You’ll also hear practical guidance on estate planning, gifting, RMDs, and charitable giving through QCDs.

What You’ll Learn:

• When a direct indexing strategy using margin may do more harm than good
• How to approach tax strategies for larger portfolios without overcomplicating your plan
• When trusts make sense for gifting—and when they don’t
• Smarter ways to handle RMDs and reduce taxes with QCDs
• Why some strategies are driven more by firm incentives than investor outcomes

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

In this episode of Money Matters, Scott and Pat take calls from high-income listeners facing real financial crossroads—from deciding whether to return to work to navigating major portfolio and tax decisions. Along the way, they break down when a Roth conversion strategy makes sense, how taxes impact big financial decisions, and why timing and sequencing can have a long-term effect on wealth.

The conversation also covers portfolio risk, income needs, and how to approach leaving money to the next generation without overcomplicating the process. Scott and Pat explain how a well-thought-out Roth conversion strategy fits into a broader financial plan that balances flexibility, taxes, and long-term goals.

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

In this episode of Money Matters, Scott and Pat break down real-world tax strategies for high net worth investors dealing with multi-million dollar IRAs, brokerage accounts, and rising future tax liabilities. They walk through detailed listener cases—including a couple with over $18 million in assets trying to minimize RMD taxes, IRMAA surcharges, and legacy tax burdens—while sharing actionable tax strategies for high net worth investors.

Here’s what you’ll learn:

• How to handle upcoming RMDs on multi-million dollar retirement accounts
• Why Roth conversions may have limited impact at higher income levels
• How gifting appreciated assets can reduce your taxable estate
• When to use a donor-advised fund instead of giving cash
• Why you should stop reinvesting dividends in taxable accounts
• How tax-loss harvesting technology can improve portfolio efficiency
• The importance of asset location (and how mistakes can cost you)
• How to better prepare large portfolios for generational wealth transfer
• Why AI can assist—but not replace—real financial advice

If you’re serious about optimizing your wealth, understanding the right tax strategies for high net worth investors can help you reduce taxes, protect your assets, and build a more efficient long-term plan.

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

 

In this episode of Money Matters, Scott and Pat break down smart Roth conversion strategies for retirees who want to reduce lifetime taxes, manage future RMDs, and avoid costly bracket mistakes. A caller with $4+ million asks how much to convert each year — and whether moving IRA withdrawals into a brokerage account makes sense as part of a long-term Roth conversion plan.

They also discuss direct indexing, including how it works, whether low-cost providers are safe, and when direct indexing makes sense compared to backdoor Roth contributions.

Plus, a real client case study highlights asset location, ETF overconcentration, muni bond mistakes, and how coordinated Roth conversion and tax planning can potentially add six figures over time.

What You’ll Learn:

-How to structure a Roth conversion tax-efficiently

-When direct indexing makes sense — and when it doesn’t

-Why asset location matters more than most investors realize

-How to reduce future RMD and IRMAA surprises

-The hidden risks inside “diversified” ETF portfolios

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

In this episode of Money Matters, Scott and Pat unpack why tax diversification is one of the most overlooked strategies in retirement planning. From a 70-year-old investor with $3.6 million mostly in traditional IRAs to a 55-year-old looking to retire early and start Roth conversions, they explore how tax diversification can help reduce lifetime taxes and create flexibility in retirement income.

You’ll hear discussions about:

-When Roth conversions make sense — and which tax bracket to target

-How much cash and bond exposure you really need before retiring

-The realities of the 4% rule

-401(k) vs. brokerage — and where bonds and equities should actually live

-How diversification protects your lifestyle, not just your portfolio

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.

 

 

 

In this episode of Money Matters, Scott and Pat walk through smart decisions around Roth vs. pre-tax savings, pension lump sums, and when it actually makes sense to use your HSA. They help a high-earning family think through life insurance gaps and special needs planning, guide a soon-to-be retiree through a $1 million pension decision, and revisit a multi-million-dollar couple debating whether to spend or preserve a large HSA. From tax diversification to retirement income strategy to how certain accounts are treated at death, this episode shows the difference between surface-level investing and true financial planning for $2M+ portfolios.

Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain. Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com.

Download and rate our podcast here.