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Ask 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/
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Episodes

Is It Time to Sell Some Stocks?

On episode 223 of Ask The Compound, Ben Carlson and Duncan Hill discuss: energy stocks vs. the S&P 500, building the perfect portfolio, overcoming the fear of investing aggressively when you’re young, whether it’s worth sacrificing passion for higher pay, when retirees should finally add bonds, target-date funds vs. index funds in marriage, and whether today’s AI-driven market feels more like smart investing or dot-com bubble euphoria. Submit your Ask The Compound questions to askthecompound...

May 20, 202631 min

Why Is the Stock Market Going Up?

On episode 222 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO Bill Sweet to discuss: if this market makes sense, S&P 500 returns, value added tax, foreign tax credits, how to save for college, small bussiness retirement accounts and more! Submit your Ask The Compound questions to ⁠⁠askthecompoundshow@gmail.com⁠⁠ ! Order your copy of Ben's book, 'Risk and Reward' here: https://lnk.to/riskandrewardbook Today’s show is sponsored by The Compound Insider. For all the ...

May 13, 202639 min

U.S. Debt Is Near $40T. Should Investors Be Worried?

On episode 221 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CIO Barry Ritholtz to discuss: debt, finding money happiness, how to invest $100k cash, when to sell intel, single stocks and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! Today’s show is sponsored by Public. Find out more at https://public.com/ATC Barry’s book out in paperback: https://ritholtz.com/2026/05/how-not-to-invest-paperback-arrives/ Subscribe to The Compound Newslett...

May 06, 202638 min

Do Valuations Still Matter?

On episode 220 of Ask The Compound, Ben Carlson and Duncan Hill discuss: how much diversification is necessary, does the CAPE ration still exist, how do bond ladders work and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! Today’s show is sponsored by Teucrium. Find out more at https://teucrium.com/agricultural-commodity-etfs Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get ...

Apr 29, 202634 min

What Does It Take to Retire at 55?

On episode 219 of Ask The Compound, Ben Carlson, Duncan Hill and Jonathan Novy discuss: helping your kids save money, life insurance, how to retire in 10 years, withdrawing funds to pay for college and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! Today’s show is sponsored by Teucrium. Find out more at https://teucrium.com/agricultural-commodity-etfs Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who t...

Apr 22, 202639 min

How Do You Protect Against a Bear Market?

On episode 218 of Ask The Compound, Ben Carlson and Duncan Hill discuss: how to protect against drawdowns in retirement portfolios, why markets move if most investors buy and hold, the current state of the consumer, how advisors should think about diversification and alternatives, personal finance lessons and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newslet...

Apr 15, 202634 min

Will Social Security Be Around in 2060?

On episode 217 of Ask The Compound, Guest Host Bill Sweet and Duncan Hill are joined by Ritholtz Wealth Director of Tax Services Bill Artzerounian, Ritholtz Wealth Investment Analyst Sean Russo and Data Research Associate and founder of Exhibit A Matt Cerminaro to discuss Trump accounts vs 529 plans, government bonds, social security, moving to NYC in 2026, AI and taxes and more. Submit your Ask The Compound questions to ⁠⁠⁠ askthecompoundshow@gmail.com ! This episode is sponsored by Betterment ...

Apr 08, 202642 min

Which Beaten Down Stocks Are Worth a Closer Look?

On episode 216 of Ask The Compound, Ben Carlson, Duncan Hill discuss opportunities in beaten-down stocks, what happens when Mag 7 stocks get slammed, the issues with a stock market that’s always open, and more. Submit your Ask The Compound questions to ⁠⁠⁠ askthecompoundshow@gmail.com ! This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is...

Apr 01, 202637 min

How Much Do You Need to Retire?

On episode 215 of Ask The Compound, Ben Carlson, Duncan Hill discuss saving for retirement, what is middle class, why you should own bonds, how should veterans save for retirement during school and more. Submit your Ask The Compound questions to ⁠⁠⁠ askthecompoundshow@gmail.com ! This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who t...

Mar 25, 202638 min

What’s the Worst Asset Class for the Next 5 Years?

On episode 214 of Ask The Compound, Ben Carlson, Duncan Hill and Nick Maggiulli discuss private markets vs real estate, is a guaranteed return worth it, 401k vs brokerage account, saving for college and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get ...

Mar 18, 202634 min

Why Won’t the Stock Market Go Down?

On episode 213 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Barry Ritholtz and Blair duQuesnay to discuss: the current market environment, the importance of the market to the Trump admin, odds of a recession, and more! Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com⁠⁠⁠ This episode is sponsored by Betterment for Advisors. Learn more at https://betterment.com/advisors 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF:...

Mar 11, 202625 min

How Do You Prepare for Market Uncertainty?

On episode 212 of Ask The Compound, Ben Carlson and Bill Sweet discuss managing risk in an uncertain environment, how much is too much Roth, how the BOXX ETF works, 529 accounts for adults and more. Submit your Ask The Compound questions to ⁠⁠askthecompoundshow@gmail.com⁠⁠ This episode is sponsored by Public. Find out more at https://public.com/ATC 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thecompoundnews.com/show/TCAF/ Animal Spirits...

Mar 04, 202634 min

Can You Retire in Your 40s and Live Off the Dividends?

On episode 211 of Ask The Compound, Ben Carlson and Bill Sweet discuss how box spread loans work, taxes vs asset location, small business retirement plan options, how to coast FIRE, living on dividends and more. Submit your Ask The Compound questions to ⁠askthecompoundshow@gmail.com⁠ This episode is sponsored by Betterment Advisor Solutions. Learn more at: https://betterment.com/advisors 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.theco...

Feb 25, 202638 min

Should You Pay Off Your Mortgage Early or Invest in Stocks?

On episode 210 of Ask The Compound, Ben Carlson discusses buying a house for 5-10 years, paying down your mortgage vs investing, when to pause your DCA, house wealth, investing abroad and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com This episode is sponsored by Public. Find out more at https://public.com/ATC 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thecompoundnews.com/show/TCAF/ Animal Spirits: https:/...

Feb 18, 202622 min

Is It Time to Buy Software Stocks?

On episode 209 of Ask The Compound, Ben Carlson, Josh Brown and Duncan Hill discuss falling knives, the tech re-rating, the housing market, finance career advice and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Teucrium. Find out more at https://teucrium.com/agricultural-commodity-etfs Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates o...

Feb 11, 202648 min

How Do You Invest a Lump Sum of Cash In This Market?

On episode 208 of Ask The Compound, Ben Carlson, Bill Sweet and Duncan Hill discuss how much is too much to manage alone, Roth TSPs, Trump accounts, health insurance in retirement, budgeting for retirement and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest i...

Feb 04, 202637 min

Does the 4% Rule Still Work?

On episode 207 of Ask The Compound, Ben Carlson and Duncan Hill discuss the 4% rule, emerging markets, tax-advantaged accounts, diversification, selling a home with a low rate and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Betterment Advisor Solutions. Learn more at http://Betterment.com/advisors Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, ...

Jan 28, 202628 min

How Do You Hedge With Options?

On episode 206 of Ask The Compound, Ben Carlson and Duncan Hill discuss equity hedging strategies and buffered ETFs with Brian Jacobs (PM at Aptus), the outlook for international stocks, the benefits of a stay-at-home spouse, and much more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Find out more at https://public.com/ATC Read more from Brian Jacobs at: https://aptuscapitaladvisors.com/blog/ Subscribe to The Compound Newsletter f...

Jan 21, 202640 min

Is the Stock Market Overvalued?

On episode 205 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Barry Ritholtz to discuss how to value today's stock market, the problem with credit card interest rate caps, the best financial news sources, if employer 401(k) contributions are enough, buy now or wait to save a bigger down payment and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Exhibit A. Visit: https://exhibitaforadvice.com/ to learn more. Subscribe to...

Jan 14, 202645 min

Should You Buy a House Right Now?

On episode 204 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Bill Sweet to discuss the worst time to buy a house, going full Roth, is margin a good idea, when are Roth conversions worth it, traditional vs Roth 401(k) and more. Submit your Ask The Compound questions to ⁠askthecompoundshow@gmail.com⁠ ! This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find...

Jan 07, 202640 min

What if the Stock Market Falls 30%?

On episode 203 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Eric Balchunas to discuss owning Bitcoin ETF vs Bitcoin Itself, can Crypto crashes hurt the stock market, are cheap gas prices a recession signal, is a 20–30% market drop actually an opportunity, how high earners can maximize tax-advantaged retirement savings and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Rocket Money. Cancel your unwanted subscriptions a...

Dec 24, 202530 min

10 Things Every Stock Market Investor Needs to Know

On episode 202 of Ask The Compound, Ben Carlson and Duncan Hill discuss: top 10 stock market indicators, what "secular" means in markets, 15-year mortgages, and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Rocket Money. Cancel your unwanted subscriptions and reach your financial goals faster with Rocket Money. Go to https://rocketmoney.com/atc today. Pick up a copy of "Everything You Need to Know About Saving for Retirement" at: http...

Dec 17, 202534 min

How Much Longer Will the Bull Market Last?

On episode 201 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Jurrien Timmer to discuss: where we are in this bull market’s cycle, how the AI bubble compares to past bubbles, the right level of inflation, rethinking traditional allocations, financial markets and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Grayscale. Find out more about Grayscale by visiting: ⁠⁠ https://www.grayscale.com/ Learn more about Fidelity Tra...

Dec 10, 202540 min

Will Housing Prices Fall In 2026?

On episode 200 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO and ATC legend Bill Sweet to discuss: housing prices in 2026, retirement tax strategies, Gen Z loves Roth, renting during retirement, trading in the military and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Compound Insider. Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next...

Dec 03, 202543 min

How Does the 4 Year Rule Work?

On episode 199 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Corey Hoffstein, co-founder, CEO and CIO at Newfound Research to discuss: what return stacking is, how the 4 year rule works, leveraging BNPL, making up for lost investing time, and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Fund your account in five minutes or less by visiting http://public.com/ATC Subscribe to The Compound Newsletter for all the...

Nov 26, 202534 min

How to Recover From a 50% Loss

On episode 198 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO Bill Sweet to discuss: 50% losses in your portfolio, stock concentration, 401k optimization, HELOC, Roth, and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! Visit: https://exhibitaforadvice.com/ for all your charting needs! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on t...

Nov 19, 202541 min

How Do You Fix the Housing Market?

On episode 197 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Sr. Advisor Jonathan Novy to discuss: portfolio allocation, insurance products, structuring withdrawals, the 50-year mortgage, career advice, and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Fund your account in five minutes or less by visiting http://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, l...

Nov 12, 202536 min

Should You Pay Off Your Mortgage Early?

On episode 196 of Ask The Compound, Ben Carlson and Duncan Hill discuss: the AI bubble, tech allocation, good debt, paying down a mortgage early, buyside vs sellside, cash on the sidelines, and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Rocket Money. Cancel your unwanted subscriptions and reach your financial goals faster with Rocket Money. Go to https://rocketmoney.com/atc today. Subscribe to The Compound Newsletter for all the la...

Nov 05, 202528 min

How to Time the AI Bubble

On episode 195 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO Bill Sweet to discuss: trading a bubble, Roth strategy, buying your parents' house, capital losses, saving for a new child, buying a vacation home and more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Fund your account in five minutes or less by visiting http://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound c...

Oct 29, 202543 min

What is the Dave Ramsey Portfolio?

On episode 194 of Ask The Compound, Ben Carlson and Duncan Hill discuss outperformance, dying with zero, beating the market, Dave Ramsey’s investment strategy, saving for college and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com ! This episode is sponsored by Public. Fund your account in five minutes or less by visiting http://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCA...

Oct 22, 202527 min
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