

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

Nov 5, 2025 • 28min
Should You Pay Off Your Mortgage Early?
Dive into the world of finance with intelligent insights! The hosts debate the potential AI bubble and its impact on young investors. They explore the risks of heavy tech allocations amidst volatility and weigh the merits of keeping low-rate mortgages versus paying them off early. Discover how paying off a mortgage fits into retirement goals and the differences between buy-side and sell-side investment strategies. Plus, learn whether cash in money markets is a wise choice for retirees!

7 snips
Oct 29, 2025 • 43min
How to Time the AI Bubble
Bill Sweet, CFO of Ritholtz Wealth Management, shares his insights on various financial strategies. He dives into the complexities of timing the AI bubble and the importance of trend-following to mitigate losses during market crashes. Sweet also explores the balance between financing a home purchase from parents versus renting and stresses prioritizing retirement contributions over educational savings. The discussion wraps up with tips for buying a vacation home, detailing tax implications and practical advice on rentals.

9 snips
Oct 22, 2025 • 26min
What is the Dave Ramsey Portfolio?
Ben Carlson and Duncan Hill dive into the intriguing world of investment strategies. They explore how many stocks outperformed the S&P over different periods and the challenges of active management. The discussion touches on the 4% withdrawal rule for retirement, providing insights on spending down assets. They also evaluate Dave Ramsey's four-fund portfolio and share practical advice on investing for college savings. Plus, they discuss the importance of behavioral finance when it comes to managing money.

7 snips
Oct 15, 2025 • 46min
Is It Time to Take Some Profits?
Josh Brown, an experienced equity investor and industry commentator, dives into the art of taking profits after big market rises. He explains how to differentiate between investments and trades, advising on when to hold or sell after rapid gains. The discussion also tackles the complexities of asset allocation for those receiving an inheritance and outlines strategies for middle-aged investors navigating their financial planning. With practical insights on trimming high-performing stocks, Josh shares valuable wisdom for all types of investors.

Oct 8, 2025 • 43min
Why Is Gold Outperforming the Stock Market?
Join Jurrien Timmer, Director of Global Macro at Fidelity Investments, as he dives into the intriguing world of market dynamics. He explains why top tech firms continue to thrive and how the labor market's changes are surprisingly overlooked by stocks. Timmer reveals why international stocks are gaining traction, while directly addressing the recent rally in gold despite the AI surge. He also discusses how to identify asset bubbles, contrasting today’s market with past tech manias. Tune in for a blend of insightful analysis and market trends!

27 snips
Oct 1, 2025 • 39min
How Do You Invest in a Bubble?
The hosts tackle the intriguing question of investing during a bubble, offering four strategic approaches. They also dive into the complexities of using home equity within the 4% rule, discussing options like downsizing and reverse mortgages. Balancing enjoyment of wealth with prudent planning is highlighted in the 'Die With Zero' debate. Additionally, they dissect what defines upper middle class in America and how perceptions shift across demographics. It's a thought-provoking discussion perfect for navigating today's financial landscape.

9 snips
Sep 24, 2025 • 31min
Where Should I Put Cash After the Fed Rate Cut?
The discussion kicks off with advice on where to keep cash after recent Fed rate cuts. Topics include whether parking cash in a Roth IRA is wise and how Social Security may act like bonds in your portfolio. The hosts dive into the impact of Fed cuts on mortgage rates and offer career tips for aspiring CFAs. They also provide strategies for deploying a $107k profit from a home sale, emphasizing the importance of risk management and financial planning.

9 snips
Sep 17, 2025 • 39min
Is It Time to Buy Bonds?
Bill Sweet, Chief Financial Officer at Ritholtz Wealth Management, shares his financial wisdom, particularly about bonds and mortgages. He explains why bonds have struggled recently and the importance of yields in predicting returns. Sweet offers tailored investing advice for service members, emphasizing automation and the use of TSP. He also discusses the nuances of switching from Roth to Traditional accounts, the merits of 30-year fixed mortgages versus ARMs, and smart practices for managing HSA distributions. An enlightening discussion for anyone looking to enhance their financial game!

Sep 10, 2025 • 32min
How Will the $84 Trillion Wealth Transfer Play Out?
The discussion dives into the massive wealth transfer from baby boomers to younger generations, questioning its true economic impact. Strategies for diversifying a real estate empire are explored, balancing investment risks with cash reserves. Gender differences in investment queries highlight unique perspectives, while the importance of enjoying the present amidst financial planning shines through. Personal anecdotes reveal the complexities of financial decisions, especially for young investors handling RSUs and retirement contributions.

25 snips
Sep 3, 2025 • 41min
Is This a Bubble?
Bill Sweet, a seasoned Chief Financial Officer, shares his savvy insights on navigating today's financial landscape. He discusses the potential bubble in the U.S. stock market and how historical PE ratios can guide investment strategies. Sweet dives into the quirks of Roth IRAs versus 401(k)s, revealing surprising trends in retirement participation. He also humorously explores the forgotten financial accounts of lottery winners, advocating for wiser investment choices over mere chance. Tune in for tips on balancing portfolios and uncovering the hidden costs of tariffs!


