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.

Can You Live Off Dividends Without Selling Your Stocks?
Ask The Compound
Can You Live Off Dividends Without Selling Your Stocks?

Recent Episodes

Nov. 4, 2026

Can You Live Off Dividends Without Selling Your Stocks?

On episode 247 of Ask The Compound, Ben Carlson and Duncan Hill discuss: at what age would you start adding bonds to your portfolio, how to view the trade-off between simple and complex portfolios, how much should you put down for a down payment on your dream home, whether it’s possible to live off dividends without selling your stocks, how to save for a future down payment, and more! Compound Merch: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://idontshop.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Submit your Ask The Compound questions to ⁠
Oct. 28, 2026

How to Put Cash to Work In Any Market Environment

On episode 246 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Downtown Josh Brown to answer five listener questions on investing, financial planning, and the housing market. They discuss whether direct indexing is worth the extra fees, how to put excess cash to work instead of waiting for the perfect investment opportunity, and why luxury stocks like LVMH, Hermès, and Kering are struggling despite consumers' willingness to spend big on premium experiences. Plus, why energy stocks
Oct. 21, 2026

Why Won’t the Housing Market Crash?

On episode 245 of Ask The Compound, Ben Carlson and Duncan Hill answer five listener questions on investing, bonds, housing, and personal finance. They discuss why Ben finally bought bonds for the first time in his career, whether paying down a high-interest mortgage beats buying bonds, and why home prices haven't crashed despite higher mortgage rates. Plus, how to think about home country bias when investing internationally, the risks of currency fluctuations, and Ben's best money advice for a
Oct. 14, 2026

How Do You Hedge a Concentrated Stock Market?

On episode 244 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Bill Sweet to answer six listener questions on investing, retirement planning, taxes, and real estate. They discuss how to diversify away from the concentrated AI trade without going to cash, retirement strategies for high-income business owners, and the best ways for individual investors to buy bonds. Plus, which investments belong in a Roth IRA, how to manage an inherited IRA under the 10-year withdrawal rule, and wh
Oct. 7, 2026

What’s the Safe Withdrawal Rate for Retirement?

On episode 243 of Ask The Compound, Ben Carlson and Duncan Hill answer six listener questions on bonds, retirement, financial planning, and the psychology of spending. They discuss when it makes sense for long-term investors to own bonds, how to think about safe withdrawal rates and aggressive retirement portfolios, and what adult children should ask when meeting with their parents’ financial advisor. Plus, whether high yields could ever justify going 100% into bonds, how higher interest rates c
Sept. 30, 2026

When Will the Next Bear Market Hit?

On episode 242 of Ask The Compound, Ben Carlson and Duncan Hill discuss: when the next bear market and recession could hit, why rising Treasury yields haven’t rattled the stock market, and whether the AI boom could ultimately become the catalyst for the next major sell-off. Plus, insurance expert Jonathan Novy joins the show to explain when permanent life insurance actually makes sense, how to think about long-term care insurance versus self-insuring, and whether annuities can help cover future
Sept. 23, 2026

Why Do We Need Inflation?

On episode 241 of Ask The Compound, Ben Carlson and Duncan Hill answer listener questions on whether private markets are capturing more of the economy’s biggest gains before companies go public, what that could mean for index funds and ETFs, whether paying off a 2.875% mortgage can ever make sense, and how AI could reshape careers in equity research. They also discuss how to diversify an all-stock portfolio as a growth-heavy account gets larger, the role of defensive stocks, and why economies ne
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

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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