Why do so many successful investors struggle to actually enjoy the wealth they’ve built? In this Memorial Day weekend episode of Allworth’s Money Matters, Scott and Pat talk with UCLA professor and behavioral expert Hal Hershfield and explore the emotional side of money, retirement, and investing.

From fear of running out of money to recency bias and loss aversion, this episode dives deep into the hidden psychological forces that shape financial decisions — even for millionaires. If you’ve ever wondered why investors panic during market drops, hesitate to spend in retirement, or obsess over past financial mistakes, this conversation about investing will completely change how you think about money.

Scott, Pat, and Hal unpack why wealthy retirees often struggle to spend confidently, how emotions influence investing decisions, and why understanding investor psychology may be just as important as understanding the stock market itself. They also discuss longevity insurance, risk tolerance, mental accounting, and how advisors can help clients align money with purpose and happiness.

Whether you're approaching retirement or simply want to become a smarter long-term investor, this episode offers powerful insights into the psychology behind successful investing and financial decision-making.

What You’ll Learn:

-Why many wealthy retirees are afraid to spend money

-How loss aversion impacts investing decisions

-The dangers of recency bias in the stock market

-Why financial regrets stick with us longer than successes

-How psychology shapes investing behavior

-The emotional side of risk tolerance and market volatility

-How “mental accounting” affects spending habits

-Why longevity insurance hasn’t caught on with investors

-How financial advisors help clients align money with life 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.

 

When it comes to investing, the most important decisions aren’t made in theory—they happen in real life. In this episode of Allworth’s Money Matters, Scott and Pat answer real listener calls and break down how smart investing decisions actually play out.

Martha, a 79-year-old retiree with $4–5 million, considers a complex investing strategy involving direct indexing to generate tax losses and improve tax efficient investing strategies. But does this level of complexity actually benefit her portfolio—or just add unnecessary risk?

Then Dennis, age 51, with nearly $2.3 million saved and major expenses ahead, faces key investing decisions around portfolio allocation, college funding, and building a sustainable retirement income plan.

Through these real-world financial questions, Scott and Pat show that successful investing isn’t about chasing complexity—it’s about simplifying your strategy, aligning with your goals, and making confident decisions over time.

What You’ll Learn:

-When complex investing strategies like direct indexing are actually worth it

-How to approach tax efficient investing strategies without unnecessary risk

-Smart ways to think about portfolio allocation as you near retirement

-How to build reliable retirement income from your investments

-How to evaluate real-world financial questions with confidence

-Why simpler investing strategies often lead to better long-term results

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.

 

A good financial plan isn’t just about retirement—it’s about how all the pieces of your financial life fit together. In this episode of Money Matters, Scott and Pat talk with a caller who already has about $2 million and expects a much larger inheritance—but still struggles to spend any of it. They walk through why that happens and how a financial plan can help ease into actually using the money.

They also take a call from a high-income couple earning around $600,000 a year. Even with strong savings, there are still areas being overlooked, so Scott and Pat explain what a complete financial plan should cover—from retirement to insurance to college planning—and where people often miss.

It’s a reminder that a financial plan isn’t just about how much you have—it’s how everything fits together.

What You’ll Learn: -Why having millions doesn’t always make spending easier -How to start using wealth without feeling uncomfortable -What high-income families often overlook -How to think about retirement when income is strong -What a real financial plan actually ties together

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.

 

If you’ve built significant wealth, knowing how to reduce taxes in retirement can have a major impact on what you keep—and what your kids ultimately receive. In this episode, Scott and Pat walk through two real-life situations: one caller facing large tax exposure from millions in pre-tax accounts, and another trying to make sure their children don’t quickly spend an inheritance.  Along the way, they also touch on how areas like private credit and private equity are evolving—and what that means for investors thinking about risk, transparency, and long-term planning.

If your goal is to reduce taxes in retirement while being more intentional about your legacy, this episode gives you a clear and practical framework.

What You’ll Learn:

-How to reduce taxes in retirement with large pre-tax accounts

-When Roth conversions work—and when they don’t

-Why RMDs can create long-term tax challenges

-How to structure a trust to protect your kids’ inheritance

-The role of trustees and distribution strategies

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.

 

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.