Ask The Compound
The Compound
Got money questions? We’ve got answers. Join Ben Carlson, Duncan Hill, and a rotating lineup of financial pros as they break down your biggest questions about investing, markets, and personal finance. Ben is a leading financial writer and the Director of Institutional Asset Management at Ritholtz. Duncan is a podcast producer and the Director of Creative Media at The Compound.
See our disclosures here - https://ritholtzwealth.com/podcast-youtube-disclosures/
See our disclosures here - https://ritholtzwealth.com/podcast-youtube-disclosures/
Episodes
Mentioned books
9 snips
Oct 7, 2026 • 33min
What’s the Safe Withdrawal Rate for Retirement?
A lively tour through retirement’s toughest questions: how bonds can cushion downturns, why withdrawal plans need flexibility, and what families should ask financial advisors. The conversation also explores whether high bond yields can replace stocks, how rising rates may strain AI infrastructure spending, and the psychology of finally upgrading your lifestyle without financial anxiety.
Sep 30, 2026 • 40min
When Will the Next Bear Market Hit?
Jonathan Novy, an insurance and financial planning professional, joins a lively discussion on bear markets, recession risks, rising Treasury yields, and whether AI spending could trigger a sell-off. He also explores when permanent life insurance fits, ways to prepare for long-term care costs, annuities, gloomy consumer sentiment, and the smart use of 0% financing.
21 snips
Sep 23, 2026 • 32min
Why Do We Need Inflation?
A lively tour through investing’s biggest questions: Are private markets capturing innovation before IPOs? Should anyone rush to pay off a cheap mortgage? How will AI transform equity research? The discussion also explores defensive stock allocations, portfolio diversification, and the economic dangers of deflation versus the stabilizing role of moderate inflation.
19 snips
Sep 17, 2026 • 32min
Should You Pick Stocks or Buy Index Funds?
Bill Sweet, a financial planner and Roth IRA specialist, joins Barry Ritholtz, a wealth manager and markets commentator, for a lively discussion on investing. They explore bond yields, inflation and TIPS, responsible luxury spending, and why baby boomers may not crash markets. Plus, they weigh index funds against stock picking, the role of a small speculative account, tax-smart retirement strategies, and choosing an advisor.
18 snips
Sep 9, 2026 • 41min
How Does the Mega Backdoor Roth Conversion Work?
Bill Sweet, a Ritholtz Wealth Management financial planner specializing in tax and retirement strategy, explores the mega backdoor Roth, employer-plan rules, and maximizing Roth savings. He also discusses Roth versus traditional 401(k) contributions, investing a future down payment, pensions as portfolio support, momentum strategies, and how career risk should shape investment choices.
18 snips
Sep 2, 2026 • 34min
Best Investment Right Now: Stocks, Bonds or Cash?
How should investors prepare for a government debt crisis? The discussion explores stocks, bonds, cash, gold, Bitcoin and other hedges, along with global portfolio diversification. It also covers smart places for short-term savings, handling larger dollar swings as wealth grows, and helping lifelong savers turn retirement money into meaningful experiences, family support and charitable giving.
22 snips
Aug 26, 2026 • 43min
When Should You Sell Your Stocks?
They cover essential stock-market lessons like volatility, lumpy returns, and long-term trends. They explain pension rollovers and Roth nuances. They debate whether checking balances helps or harms trading psychology. They give tips for handling large, variable pay and outline must-have non-investment financial basics. They discuss matching college savings risk to timing and shifts toward physical infrastructure investments.
4 snips
Aug 19, 2026 • 36min
When Will the Stock Market Crash Again?
They debate whether market crashes can still happen and why fewer recessions did not eliminate bear markets. They cover why individual stocks move faster today and how algos raise idiosyncratic volatility. They compare real estate and stocks, including leverage and tax differences. They discuss planning for aging parents, bridging senior housing costs, and how inflation alters withdrawal rules.
20 snips
Aug 12, 2026 • 42min
How Do You Invest Without Paying Taxes?
Bill Sweet, a tax-focused financial professional, explains tax-smart moves in plain terms. They cover which investments to sell first when buying a house. Conversations include how to handle volatile stocks in conservative portfolios. HSA priorities for single parents get practical attention. Roth 401(k) rules, mortgage points, and timing home purchases are also discussed.
9 snips
Aug 5, 2026 • 32min
Is Buying a Home Still a Good Investment?
Jack Raines, author of Young Money and advisor to young professionals, shares practical advice on careers, investing, and life choices. They debate renting versus buying in pricey cities. They cover simple custodial gifting and index ETFs. They discuss preparing for AI in the workplace, the risks of margin and leverage, and the tradeoffs of extreme frugality and financial independence.
