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
15 snips
Nov 11, 2026 • 45min
What Would You Do With a Guaranteed $50,000 a Year?
Bill Sweet, a Ritholtz Wealth Management financial planner, joins a lively discussion on enduring bear markets and the emotional toll of prolonged losses. They explore smart ways to use a $50,000 inheritance, why wealthy families still need written financial plans, how much emergency cash is enough, whether Trump accounts belong in the priority list, and when to dial back portfolio risk before retirement.
Nov 4, 2026 • 37min
Can You Live Off Dividends Without Selling Your Stocks?
How should investors choose bonds, manage risk, and balance simplicity with diversification? This conversation also explores dream-home down payments, safer ways to invest housing savings, covered calls, and the realities of relying on dividends for income. Plus, a cautionary tale about investment clubs and the importance of tracking performance accurately.
9 snips
Oct 28, 2026 • 48min
How to Put Cash to Work In Any Market Environment
Josh Brown, CEO of Ritholtz Wealth Management and prominent market commentator, joins a lively discussion on putting cash to work, direct indexing, and avoiding risky private deals. They explore why luxury stocks are struggling as spending shifts toward experiences, energy’s post-COVID resurgence, and whether buying a home makes sense when mortgage and ownership costs remain high.
Oct 21, 2026 • 35min
Why Won’t the Housing Market Crash?
Bonds are back in the conversation as rising yields reshape portfolios and mortgage paydown decisions. The discussion explores why home prices have held up despite high rates, how supply and mortgage lock-in affect buyers, and why international investing can reduce home-country and currency concentration. It closes with practical ideas for building strong financial habits and taking thoughtful risks early in life.
Oct 14, 2026 • 44min
How Do You Hedge a Concentrated Stock Market?
Bill Sweet, a financial planner and tax professional, joins the conversation on concentrated AI exposure, diversification, and whether bonds belong in ETFs or individual Treasuries. They also explore backdoor Roth contributions, Roth conversions after big stock gains, inherited IRA rules, retirement-home decisions, and the risks of chasing Airbnb tax deductions.
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.
7 snips
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.
