Ask The Compound

Ask The Compound

Welcome to Ask The Compound, the show where Ben Carlson, Duncan Hill, and a rotating cast of financial experts answer your questions about investing and personal finance.

Recent Episodes

Sept. 17, 2026

Should You Pick Stocks or Buy Index Funds?

On this live episode of Ask The Compound from Future Proof in Huntington Beach, Ben Carlson, Alex Morris, Bill Sweet, and Barry Ritholtz tackle listener questions on bonds, luxury spending, generational wealth, and managing an actively traded portfolio. They discuss what a 5%+ bond yield really means, how inflation affects fixed-income investments, and where TIPS can fit into a portfolio. Plus, when it makes sense to spend on luxury purchases like watches, whether baby boomers are really a threa
Sept. 9, 2026

How Does the Mega Backdoor Roth Conversion Work?

On episode 239 of Ask The Compound, Ben Carlson, Bill Sweet, and Duncan Hill tackle six listener questions on investing, retirement, and managing risk. They discuss the research behind trend-following and momentum strategies, how mega-backdoor Roth 401(k) conversions work, what to do with down payment savings when buying a home is still years away, and whether a pension can serve as the bond allocation in your portfolio. Plus, Roth vs. traditional 401(k) contributions for high earners, borrowing
Sept. 2, 2026

Best Investment Right Now: Stocks, Bonds or Cash?

On episode 238 of Ask The Compound, Ben Carlson and Duncan Hill discuss how to prepare for a potential government debt crisis, choosing between stocks, bonds and cash, how much to allocate to international stocks, the best places to park short-term savings, dealing with bigger portfolio swings as your wealth compounds, and how lifelong savers can learn to spend and enjoy their money in retirement. This episode is sponsored by Fitnexa. For $10 off SomniPods 3, visit: http://go.fitnexa.com/qQ0AbS
Aug. 26, 2026

When Should You Sell Your Stocks?

On episode 237 of Ask The Compound, Ben Carlson, Bill Sweet and Duncan Hill discuss the most important things investors should know before buying stocks, how to transfer retirement accounts tax-efficiently, and managing large chunks of variable income. Plus, they cover the financial planning basics every family should have in place, how much risk to take in college savings accounts, and more. This episode is sponsored by Fitnexa. For $10 off, visit: http://go.fitnexa.com/qQ0AbS Compound Merch:
Aug. 19, 2026

When Will the Stock Market Crash Again?

On episode 236 of Ask The Compound, Ben Carlson and Duncan Hill discuss whether market crashes are a thing of the past, planning for longevity risk, stocks vs. real estate, talking finances with aging parents, and how inflation impacts sustainable spending rates. This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors Compound Merch: ⁠⁠⁠⁠⁠https://idontshop.com/⁠⁠⁠⁠⁠ Submit your Ask The Compound questions to ⁠⁠⁠⁠⁠askthecompoundshow@gmail.com⁠⁠⁠⁠
Aug. 12, 2026

How Do You Invest Without Paying Taxes?

On episode 235 of Ask The Compound, Ben Carlson, Duncan Hill, and Bill Sweet discuss where housing is most expensive, which investments to sell first, AI’s impact on homebuying, owning volatile investments, when HSAs may not make sense, how Roth 401(k)s work, and more! This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors Compound Merch: ⁠⁠⁠⁠https://idontshop.com/⁠⁠⁠⁠ Submit your Ask The Compound questions to ⁠⁠⁠⁠askthecompoundshow@gmail.com⁠
Aug. 5, 2026

Is Buying a Home Still a Good Investment?

On episode 234 of Ask The Compound, Ben Carlson, Duncan Hill, and Jack Raines tackle your investing and financial planning questions, including the financial advice they'd give their younger selves, whether buying a home still makes sense in today's market, how young people should prepare for an AI-driven future, the risks of investing with margin, and whether it's possible to retire early by living an ultra-frugal lifestyle. They discuss: - The financial lessons they'd share with their younge
July 29, 2026

When Should You Turn Bearish on the Stock Market?

On episode 233 of Ask The Compound, Ben Carlson, Duncan Hill, and Josh Brown tackle your investing and financial planning questions, including whether Shake Shack's recent collapse is a buying opportunity, how active management fits alongside indexing, what would actually make a long-term bull turn bearish, how to promote disciplined investing in a speculative market, and whether an expected inheritance should influence your financial plan. They discuss: Is Shake Shack a value opportunity afte
July 22, 2026

What Are the Two Main Risks Right Now?

On episode 232 of Ask The Compound, Ben Carlson is joined by Jurrien Timmer to discuss: whether the Magnificent 7's recent underperformance is a healthy sign of broader market leadership, why concentration risk and higher interest rates remain key risks for investors, how long the current earnings boom can continue, where speculative capital could flow next after Bitcoin, gold, and semiconductor stocks, and how to stay invested during a bull market while protecting against the risk of an eventua

About the Hosts

Ben Carlson Profile Photo
Ben Carlson

co-host

Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management. He is the co-host of Animal Spirits & Ask The Compound. He is the author of four books, a columnist for Fortune, and the creator of the blog A Wealth of Common Sense.

Duncan Hill Profile Photo
Duncan Hill

co-host

Duncan Hill is the Creative Director at Ritholtz Wealth Management and co-host of Ask The Compound.

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