Money Matters by Allworth Financial

When markets reach new highs and tech stocks lead the charge, it’s tempting to let winners ride. But if you have accumulated significant wealth, when does high concentration stop building your future and start threatening it?

In this episode of Money Matters, Scott and Pat break down why the S&P’s massive tech weighting could leave near-retirees vulnerable, why rebalancing feels so emotionally difficult, and how to insulate the next 5 to 10 years of your cash needs from an extended market pullback.

Plus, Scott and Pat take listener calls:

The $800K Inheritance Dile...

What happens when an early retirement success story hits an unexpected tax wall? In this episode of Money Matters, Scott and Pat dive straight into real-life retirement dilemmas, starting with a 55-year-old caller sitting on a $4M+ nest egg who was hit with a major tax surprise.

Ron’s taxable brokerage account is generating $75,000 in unexpected annual capital gains distributions—threatening his Affordable Care Act (ACA) health insurance subsidies and throwing off his early retirement plans. Scott and Pat break down why "ripping off the Band-Aid," taking a one-time tax hit, and shifting to direct indexing might be t...

Worried about how the upcoming election will impact your investments? In this special bonus episode of Money Matters, Scott and Pat are joined by Apollo Lupescu, Vice President at Dimensional Fund Advisors (known as the "Secretary of Explaining Stuff"), to look past the political noise and examine what decades of market history actually reveal.

In this episode, they discuss:

Emotions vs. Evidence: Why politics triggers strong emotional reactions, and why successful investing requires separating those feelings from portfolio decisions.

Midterms & Market History: What typically happens to the stock market during election months—and wh...

When your retirement savings cross the seven-figure mark, the simple strategies that got you there might actually cost you money in taxes. In this episode, Scott and Pat explain why a high earner with a $1.8M portfolio needs to move beyond basic target-date funds and ETFs into direct indexing—plus when to pay off low-interest debt, how to pass down wealth, and when you can finally afford to spend more.

Scott and Pat also cover:

The 3.25% Mortgage Dilemma: Should you accelerate payoff on low-interest debt when Treasuries yield 5%?

Transitioning from Saving to Spending: A...

Is retiring at 55 with a $2M nest egg realistic? On this episode of Money Matters, Scott and Pat break down the numbers with a caller aiming for an early exit from the corporate grind. They discuss how to balance pre-tax 401(k)s, Roths, RSUs, and taxable brokerage accounts—plus how to front-load 529 plans without triggering unnecessary taxes.

Scott and Pat also dive into:

The Rise of Private Equity: What proposed SEC changes mean for everyday investors, and the hidden risks, lack of liquidity, and valuation pitfalls of alternative investments in 401(k) plans.

Bu...

How do you turn a lifetime of saving into reliable, tax-smart retirement income? In this episode of Money Matters, Scott and Pat break down what investors with $1M+ need to know when transitioning from building wealth to generating income in today’s market.

In this episode, Scott and Pat tackle real listener situations:

-Caller Case Study 1: Retiring with a 401(k), a solid pension, and a paid-off home—how do you stress-test your plan against inflation and potential Social Security shifts?

-Caller Case Study 2: Buying a second home in Texas while keeping California property—which...

Can you truly "Die with Zero" when you’ve built a multi-million-dollar portfolio? On this episode of Money Matters, Scott and Pat dive into real-world retirement scenarios covering aggressive tax strategies, spend-down plans, and smart estate transfers.

In this episode, Scott and Pat cover:

The "Die with Zero" Strategy: A 49-year-old entrepreneur with $5.5M in savings wants to know how to safely spend down assets without jeopardizing long-term security.

Solo 401(k)s & Roth Conversions: Navigating tax-efficient withdrawals alongside non-qualified brokerage assets and ongoing business income.

The Short-Term Rental Tax Trap: Can bu...

Is it possible to do a Roth conversion too early? In this episode of Money Matters, Scott and Pat break down why the timing of your tax planning matters just as much as the strategy itself.

They answer real listener questions on navigating the retirement transition—from managing adjusted gross income, to understanding how a great financial advisor provides value beyond just managing a portfolio.

Plus, Allworth Chief Investment Officer Andy Stout joins to discuss the 10-year Treasury yield hitting 5%, putting rising interest rates and government debt into historical perspective.

In this episode, Sco...

Should you use permanent life insurance to cover long-term care? Does converting a $1M pre-tax account before you stop working make mathematical sense? In this episode of Allworth’s Money Matters, Scott and Pat walk through real-world portfolio case studies, dissect common tax myths, and break down where aggressive financial pitches fall short.

Topics covered in this episode:

The Rise of Prediction Markets: Why momentum traders are shifting from crypto to event betting, and how speculative traps disguise themselves as investing.

Commercial Real Estate Realities: A look at how major leveraged properties can co...

Are your retirement assumptions realistic, or is your financial plan relying on best-case scenarios? In this episode of Money Matters, Scott and Pat dive into the practical realities of long-term planning—from preparing for market volatility to navigating complex estate and tax rules. Plus, Scott and Pat answer caller questions on managing a multi-million-dollar portfolio, strategic gifting, and what it really takes to achieve financial independence in your 40s.

In this episode, we cover:

Stress-Testing Your Portfolio: Why planning for bear markets matters, how to avoid overly optimistic return assumptions, and why keeping 5–7 years of income...

When can you retire? It’s one of the biggest financial questions you’ll ever answer—and knowing you have enough is about more than reaching a certain number.

In this episode of Allworth’s Money Matters, Scott and Pat help a 57-year-old teacher determine whether she can afford to leave the classroom after 33 years. They break down her pension, retirement savings and spending needs, and discuss whether taking a pension supplement as a lump sum or an annuity makes more sense.

Then, a young couple earning a strong income wonders whether they should keep maximizi...

Can you retire early with private equity, direct indexing, and a mega backdoor Roth? In this episode of Money Matters, Scott and Pat help one investor weigh big decisions—from helping adult children buy homes to managing portfolio risk—before an aggressive retirement. Then, they follow up with a high-income saver who put their "mega backdoor" advice into action and is now looking at direct indexing for better tax efficiency.

From choosing the right advisor to making smarter investment moves, early retirement planning means getting the details right. Because a secure retirement isn’t just about how much y...

How do you protect a lifetime of savings when tax laws and changing life goals shift your priorities? In this episode of Money Matters, Scott and Pat explore wealth preservation, from managing concentrated stock positions and real estate decisions to sophisticated tax planning.

In this episode:

The $5.6M Property Test: Scott and Pat analyze a caller’s plan to carry three homes in retirement. They discuss “carry risk” and why even a $5.6 million net worth doesn’t automatically justify expanding a real estate portfolio.

Savings Trade-Offs at 52: A caller asks how to balance college...

Are you prepared for the complexities of a high-value retirement? In this episode of Allworth’s Money Matters, Scott and Pat break down real-world case studies for a $3M+ retirement, specifically focusing on the math behind long-term care, the tax implications of early inheritances, and a powerful framework for tax efficiency known as the "3 C's."

In this episode, Scott and Pat discuss:

The Long-Term Care Dilemma: They analyze a $3.7M case study where the caller is retiring abroad. Does she actually need long-term care insurance, or can she "self-insure"? Scott and Pat explain the "elimination period" s...

In an economy where AI is reshaping the landscape, how should a sophisticated investor respond? In this episode of Money Matters, Scott and Pat are joined by Dr. Apollo Lupescu from Dimensional Fund Advisors to discuss the "AI Ownership Machine" and how to manage portfolio concentration. Plus, Scott and Pat answer a caller’s questions on maximizing RSUs and utilizing advanced tax-saving vehicles.

What You’ll Learn:

The "Ownership Machine" vs. Gambling: Learn why shifting your mindset from "betting" on stocks to becoming a part-owner of a business is the key to long-term rational decis...

In this episode of Allworth’s Money Matters, Scott and Pat take a deep dive into two real-world case studies that highlight the critical difference between being sold a product and receiving fiduciary advice. First, they talk with a caller managing a $4.5 million estate who has been pitched a complex whole-life insurance strategy. Then, they address a $1.4 million retirement dilemma involving inherited assets and the "liquidity gap."

What you’ll learn in this episode:

The Whole Life Red Flag: Why insurance "leverage" strategies often benefit the advisor more than the client.

Inherited IRA Maste...

What does it take to manage a multi-million dollar portfolio once you’ve stopped adding to it? In this episode of Money Matters, Scott and Pat dive into the complexities of high-net-worth retirement, focusing on the critical shift from "saving" to "strategic spending."

Through real-world case studies, they explore why "tax location" is often more important than "tax allocation," particularly when it comes to bonds and individual stocks. They also tackle the psychological side of wealth—learning how to upgrade your standard of living and find joy in charitable giving through "warm hand" estate planning.

In t...

How do you turn a "jackpot moment" into a lasting family legacy? In this episode of Allworth’s Money Matters, Scott is joined by partner advisor Richard Del Monte (while Pat is on vacation) to tackle the complexities of wealth transitions and family gifting.

Through a $2.1 million case study, the team discusses how to support adult children through "giving while living" without creating family conflict. Then, Simone Devenny, Allworth’s Head of Private Wealth Strategies, joins to share a masterclass in succession planning for business owners. Using a multi-million dollar business exit as a guide, she breaks down...

While Pat is on vacation, Scott and partner advisor Richard Del Monte break down two high-stakes financial scenarios that highlight the difference between "good on paper" and "good in practice."

Through two detailed caller case studies, they explore:

Case Study 1: The $450k New Doctor. After 15 years of medical training, a 32-year-old is finally hitting a massive salary. But with multiple retirement options like 403(b)s and non-governmental 457 plans, her father is worried about "tying her hands" too early. Scott and Richard explain why some retirement plans are actually "traps" for young high-earners and how to u...

In this episode of Money Matters, Scott and Pat dive into a $5M client case study on the hidden dangers of stock concentration and explain why a $1.5M Roth conversion might be your smartest tax move. They also tackle direct indexing and welcome Allworth partner advisor Victoria Bogner to share the story of "Jim and Karen." You’ll hear how this retired couple unknowingly had 35% of their $5 million portfolio tied up in just eight stocks—and how a shift in "asset location" saved them six figures in projected taxes.

Key Topics Included:

-Roth Conversion Strategies: Manag...

Can you support your adult children without derailing your retirement? In this episode of Money Matters, Scott and Pat dive into the financial realities of a caller with a nearly $10M net worth who is spending $75,000 a year to support his adult daughter. They break down the math on his retirement timeline and uncover a common "tax efficiency" mistake that could be costing him significant returns.

Also in this episode:

The "Shell Game" of State Budgets: How budget constraints in states like California could impact your long-term security.

Roth Conversions & Moving States: Why a...

Is the current AI boom a repeat of 1999? In this episode of Money Matters, Scott and Pat dive into the "irrational exuberance" surrounding tech IPOs and the hidden dangers of concentration risk in a high-net-worth portfolio. Plus, they break down real-world case studies on tax efficiency and retirement income.

What You’ll Learn:

The AI "Froth" Factor: Why 97x revenue valuations for new IPOs are a warning sign for diversified investors and how to manage concentration risk in big tech.

The Roth Conversion Reality Check: A $1.1M case study on why "pre-paying" taxes thro...

When does a Roth Conversion make sense—and when could it be a costly mistake? In this episode of Money Matters, Scott and Pat tackle one of the most common retirement planning questions: whether a Roth Conversion is the right move for your financial future. They break down a real-life caller’s situation involving IRAs, pensions, charitable giving, required minimum distributions (RMDs), and the tax implications of converting retirement assets.

The show also features an emotional conversation with Laura, a member of the “sandwich generation” who is balancing retirement planning while supporting aging parents and a special-needs child. S...

How do you make smart financial decisions after you've already built significant wealth?

In this week's episode of Allworth's Money Matters, Scott and Pat help a retired couple with an $11 million portfolio evaluate Roth conversions, estate planning, charitable giving, and strategies to improve tax efficiency. Then they speak with a 52-year-old listener navigating uncertainty in the alcohol industry while balancing retirement savings, college expenses, and cash reserves. Should he use taxable assets to maximize his 401(k) contributions? Scott and Pat weigh in.

The episode also features Allworth advisor Laurie Ingwersen, who explains how investors with...

After decades of saving and investing, how do you know when it’s okay to truly enjoy your money?

In this episode of Money Matters, Scott and Pat help a couple with nearly $8 million determine how much home they can comfortably afford after relocating to Florida, while another listener with more than $12 million asks whether Roth conversions still make sense given today’s tax rules and retirement tax planning environment.

They discuss retirement tax planning strategies, the dangers of chasing “popular” AI stocks, and how AI-powered scams are targeting investors and older Americans.

What You...

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 financia...

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 invest...

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 an...

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 red...

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’...

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 redu...

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 inste...

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:

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...

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:

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, ET...

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...

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.

Taxes can quietly shape some of the biggest financial decisions you’ll ever make — from choosing how to take a pension to deciding how to leave money to your heirs. On this week’s Money Matters, Scott and Pat take calls from listeners working through those exact issues. One caller is weighing a pension lump sum against monthly payments, and the tax consequences of that decision become central to the conversation. The guys also discuss how asset location affects tax efficiency, why different accounts are taxed differently, and how thoughtful planning can help reduce unnecessary taxes over time. They even e...

In this episode of Money Matters, Scott and Pat take calls from high-net-worth listeners who uncover the same wealthy tax mistake, despite very different financial situations. From retirees with most of their money in IRAs to investors weighing Roth conversions and income strategies, the conversations show how easy it is to pay more in taxes than expected. They explain how this wealthy tax mistake often comes from tax-deferred concentration, why paying taxes from retirement accounts can shrink cash flow, and how poor timing can quietly turn into a long-term wealthy tax mistake. If you’ve built significant assets and wa...