Simply Money by Allworth Financial

The 5 Key Times to Call Your Financial Advisor

On this episode of Simply Money, Bob and Brian break down the key life moments when calling your financial advisor can make—or cost—you thousands. They also tackle a surprising trend: why retirees with millions saved still feel financially insecure, and how shifting from pension-style income to managing a “pile of money” has changed everything. Plus, insights from CIO Andy Stout on how tax-efficient investing strategies like tax loss harvesting and direct indexing can add real after-tax returns, and practical advice on gifting strategies, insurance gaps, and why not having a power of attorney could create major problems for your family.

Does Your Financial Plan Depend on a “Good” Market Decade?

On this episode of Simply Money presented by Allworth Financial, Bob and Brian tackle a critical question for investors: what happens if the next decade of market returns doesn’t cooperate—and does your financial plan rely on strong returns just to survive? They break down how to properly stress test your retirement plan using real-world scenarios, Monte Carlo analysis, and the importance of separating must-have expenses from discretionary spending to weather any environment.
Plus, they dive into the hidden complexities of restricted stock units (RSUs), including how they’re taxed, vesting schedules, and why they should be treated as a concentrated position in your portfolio.
You’ll also hear strategies for protecting your retirement timing from market downturns, how to think through pension lump sum versus income decisions, and smart ways to gift money for major life events without triggering unnecessary taxes.

Market Noise, Portfolio Strategy, and Smarter Investing Moves

On this episode of Simply Money, Bob and Brian break down three conflicting market predictions making headlines right now—and why reacting to any of them could derail your long-term plan—while also diving into the dangers of turning your 401(k) into a betting platform, whether a “too balanced” portfolio could actually hurt your growth, how appraisal gaps can impact what you really pay for a home, and smart strategies for high-net-worth investors including direct indexing, managing large IRA balances, and planning for long-term care without over-insuring.

Diversification Matters: What the Latest Market Rally Is Really Telling Investors

On this episode of Simply Money, Bob and Brian explain why the market rebounded sharply despite global conflict, highlighting how one company—Micron Technology—is driving a surprising share of earnings growth expectations and what that means for diversification and long-term investors. They also discuss the risks of relying on headline-making company CEOs, answer listener questions on direct indexing, tax planning in retirement, and concentrated stock positions, and wrap up with smart, flexible strategies for funding grandchildren’s education using tools like 529 plans.

The Biggest Stock Market Mistakes Investors Still Make

On this episode of Simply Money, Bob and Brian break down the biggest stock market mistakes investors still make—even as more Americans than ever are participating in the market. They discuss the shift from pensions to 401(k)s, why younger investors may be taking too little risk, and how to properly align your portfolio with your financial plan instead of your age.
Plus, a deep dive into the Rule of 55 and how it can help unlock early retirement, smart strategies for handling required minimum distributions if you don’t need the income, and how life insurance can evolve from basic protection into a powerful estate and legacy planning tool for high-net-worth families.

What Two Trading Days Exposed About Investor Behavior

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how just two trading days over the past year could have dramatically impacted your portfolio—and why trying to time the market based on fear can cost you millions over time. They also cover the risks of having multiple old 401(k)s, smart strategies for Roth conversions and tax-efficient charitable giving, how to approach estate planning conversations with aging parents, the importance of pre-planning end-of-life decisions, and when advanced strategies like direct indexing actually make sense for higher-net-worth investors.

What Smart Investors Are Doing With Their Portfolios Right Now

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why investors aren’t panicking despite rising geopolitical tensions, what that means for your portfolio, and how to prepare for volatility with smart planning, liquidity, and tax strategies—plus insights on life insurance decisions, concentrated stock risk, selling a business, Roth conversions, and why having proactive family conversations about long-term care matters more than ever.

The Hidden Gap Between Building Wealth and Feeling Secure

On this episode of Simply Money, Bob and Brian break down why so many people who have done everything right—saved, invested, and built significant wealth—still don’t feel confident about their financial future. They explore the difference between passive decision-making and intentional planning, the two factors that truly move the needle, and why “hoping it all works out” can quietly derail even strong portfolios. Plus, why a financial windfall can be a risky moment if you act too quickly, how AI is starting to influence financial decisions (for better and worse), and answers to listener questions on managing concentrated stock positions, coordinating income across accounts, planning for market downturns, and making sure your financial life is prepared for the unexpected.

Why Your Portfolio Doesn’t Match the Headlines (And the Hidden Cost of Lifestyle Creep)

On this episode of Simply Money, Bob and Brian break down why your portfolio may not be falling—even when scary headlines suggest markets are in turmoil. They explain the disconnect between media narratives and real investor experience, including why the Dow’s dramatic point swings don’t tell the full story and how proper diversification—especially with international stocks and small cap value—has quietly supported portfolios in 2026.
Plus, a surprising (and alarming) trend: high-income households earning $300K–$500K are more likely to feel “paycheck to paycheck” than those earning far less. Bob and Brian unpack the real culprit—lifestyle creep—and how even multi-million-dollar portfolios can be undermined by unchecked spending habits.

The Hidden Risks That Can Derail Your Financial Plan

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the first five years of retirement can make or break even a $5 million portfolio. They break down sequence of returns risk, walk through real-world examples of how early market drops can permanently impact your plan, and share strategies like liquidity buckets and disciplined rebalancing to protect your future.
Plus, common 401(k) mistakes successful investors make, how to prevent concentrated stock from quietly dominating your portfolio, what to do if your financial life is split across multiple advisors, and how to safeguard your finances if a spouse becomes cognitively impaired.