Simply Money by Allworth Financial

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.

What Oil Shocks Mean for Your Investment Portfolio

On this episode of Simply Money, Bob and Brian break down the stock market volatility tied to escalating tensions in the Middle East and the critical Strait of Hormuz, where roughly 20% of global oil flows, looking back at the 1973 OPEC oil embargo, stagflation, and how markets have historically responded to geopolitical shocks.
Plus, they answer listener questions on adjusting stock allocations amid global conflict, calculating emergency cash when income fluctuates, and whether to lock in gains early in retirement or simply rebalance and stay disciplined.

What Would You Actually Do in a 20% Market Drop?

On this episode of Simply Money, Bob and Brian tackle a question that hits differently when you’ve built real wealth: if the market dropped 20% tomorrow, what would you actually do? They walk through the emotional and mathematical realities of managing a $2–10 million portfolio, why risk tolerance and plan design don’t always align, and how shifting from accumulation to preservation changes everything. You’ll also hear strategies around sequence of returns risk, separating income streams from piles of money, and why diversification today may mean more than just a 60/40 portfolio. Plus, the guys explain why bonds weren’t the “safe haven” many expected in 2022, how to think strategically about 401(k) contributions across pre-tax, Roth, and after-tax buckets, and answer listener questions on retirement withdrawals, dividend income, and spending in early retirement.

The “We’re Fine” Trap: Withdrawal Rates, Wealth Gaps & Planning That Actually Works

On this episode of Simply Money, Bob and Brian break down the most expensive lies couples tell themselves about money—especially the dangerous comfort of saying “we’re fine” —and explain how a lack of communication around retirement timing, estate plans, and financial roles can cost families millions and fracture relationships. They also dig into why a single withdrawal rate like the traditional 4% rule isn’t enough, exploring sequence of returns risk, bucket strategies, flexible spending guardrails, and how small tweaks in Monte Carlo assumptions can dramatically change your plan’s success rate. Plus, Allworth’s in-house insurance expert, Jodee Deutsch, joins the show to discuss when life insurance shifts from simple protection to advanced estate and legacy planning, and how high-net-worth families can better align their wealth with their long-term goals.

Big Wealth, Small Mistakes: The Decisions That Matter Most

On this episode of Simply Money, Bob and Brian break down why the financial decisions that feel boring or easy to postpone often have the biggest impact on long-term success. From overlooked beneficiary designations and withdrawal strategies to missed tax-planning windows and life risks that don’t show up in market charts, they explain how successful families can do everything “right” and still run into avoidable problems.
The conversation highlights why planning for taxes, longevity, healthcare, control, and flexibility matters just as much as investment returns—especially as net worth grows—and how proactive, thoughtful decisions today can protect both your lifestyle and your legacy.

Does a Strong January Really Matter? Rethinking Bonds, Risk, and Retirement Planning

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down whether a strong January really sets the tone for the rest of the market. They explain why diversification is resurfacing as international stocks and small caps outperform, dig into why the world’s largest asset manager says bonds may no longer protect portfolios the way investors expect, and share smarter ways to manage risk and income in retirement, including shorter-duration bonds and buffered strategies.
The show also tackles real planning decisions around selling appreciated investments, evaluating active managers, estate planning for blended families, and why proactive conversations around aging parents can prevent financial and emotional chaos later on.