Advertise on podcast: Simply Money by Allworth Financial

On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal the surprising gap between thinking about retirement and actually planning for it, explain why paying taxes now could save you thousands later, and welcome Allworth estate planning expert Paul Schwartz to uncover common estate planning mistakes. Plus, smart strategies for selling a vacation home, making the most of tax losses, gifting appreciated stock to your kids, and the surprising role money plays in keeping relationships together.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal what decades of bull and bear markets can teach investors about building long-term wealth, explain why some new ETFs look more like gambling than investing, and discuss the executive dilemma of whether a bigger paycheck and title are worth the trade-offs. Plus, smart strategies for reducing capital gains taxes, donating appreciated stock to charity, knowing when you no longer need life insurance, and why bonds deserve another look.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why even great companies can become terrible investments, what earnings season could reveal about today's AI boom, and why some high earners are rethinking the advice to max out their 401(k)s. Plus, a financial makeover for empty nesters, smart ways to help adult children financially, what you should expect from a wealth advisor, and why planning for retirement means more than just managing your money.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal the costly financial mistakes even successful investors can make, from concentrated investments and poor tax planning to holding too much cash and lifestyle creep. Plus, they explore the life decisions that can shape your wealth, explain when it’s time to review old insurance policies, and answer retirement questions about Roth conversions, Social Security, and leaving an inheritance your heirs can handle.

On this episode of Simply Money, Bob and Brian crash-test a $3 million retirement plan against market drops, overspending, family gifts, and an early death. Plus, they lay out a five-year retirement countdown, explain how to help your kids without creating financial problems, and discuss smart tax moves that could open up once the paycheck stops.

On this episode of Simply Money, Bob and Brian count down the 10 decisions that can make or break your retirement plan. Plus, they reveal why some “set it and forget it” investment strategies may deserve a second look, tackle your questions about tax-smart investing and helping the next generation, and explain why slowing down could save you from a costly financial mistake.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why your net worth may not tell the full story of your financial health, how to identify your most valuable asset at every stage of life, and why forgotten 401(k)s deserve a closer look. Plus, they tackle retirement spending, helping your kids financially, concentrated stock positions, and when it’s time to rethink an old life insurance policy.

On this episode of Simply Money, Bob and Brian explain why the first five years of retirement can make or break your financial plan, how a rising market can quietly increase the risk in your portfolio, and why having enough money to buy something doesn’t necessarily mean you should. Plus, they tackle tax-loss harvesting pitfalls, managing concentrated company stock, and why today’s mortgage rates shouldn’t be the only factor driving your decision to buy a home.

On this episode of Simply Money, Bob and Brian explain why having more money doesn’t always mean feeling more financially secure, reveal the overlooked portfolio number that could trigger a major tax bill, and discuss why some retirees may be waiting too long to enjoy the wealth they’ve built. Plus, how to navigate wealth differences with friends, plan for valuable collectibles, and recognize three phrases that should immediately put you on alert for a scam.

On this episode of Simply Money, Bob and Brian count down the 10 decisions that can make or break your retirement plan. Plus, they reveal why some “set it and forget it” investment strategies may deserve a second look, tackle your questions about tax-smart investing and helping the next generation, and explain why slowing down could save you from a costly financial mistake.

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.

On this episode of Simply Money, Bob and Brian explain why today's market bubbles may be smaller—and less dangerous—than the ones investors remember from the dot-com era and the financial crisis. They also discuss when alternative investments like private equity actually make sense, sit down with Allworth Senior Estate Planning Specialist Paul Schwarz to share strategies for preparing the next generation for one of the largest wealth transfers in history, and answer listener questions on building a lasting family legacy and protecting generational wealth.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the key financial moves that matter most in every decade of your life—from building wealth in your 20s and 30s to protecting it in your 40s and preparing for retirement in your 50s and beyond. They also explain how hidden tax traps can develop inside brokerage accounts, answer listener questions on estate planning, retirement tax strategies, and umbrella insurance, and sit down with Allworth's insurance expert to discuss when long-term care insurance actually makes sense. Plus, Bob shares his perspective on whether homeownership is always the right financial move.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why this earnings season could be one of the biggest tests for the stock market in years—and what investors should really be watching beyond the headlines. They also discuss how much cash you actually need, why too much liquidity can quietly hurt your long-term wealth, practical ways to protect your finances from growing cybersecurity threats, and answer listener questions on helping adult children fairly, qualified charitable distributions, stock option taxes, and tax-smart investing strategies.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian challenge the traditional idea of retirement, exploring why having enough money isn’t the same as having a fulfilling plan for what comes next. Inspired by a powerful real-life story, they discuss “purpose risk,” the dangers of tying your identity solely to your career, and why true financial success is about creating optionality in your life—not just building wealth. They also break down how to turn your savings into a tax-efficient income stream, why rules like the 4% guideline can fall short, how to manage risk and cash flow in retirement, and why your “forever home” might not be as permanent as you think.