Ask The Compound

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/

Episodes

Can You Retire on $1.5 Million?

June 24, 2026 • 32 mins
On episode 228 of Ask The Compound, Ben Carlson and Duncan Hill discuss: whether an AI bubble crash or market correction would be a buying opportunity for U.S. stocks, how to invest $150,000 in cash today, giving up a 2.9% mortgage to buy a larger home, whether $1.5 million is enough to retire, staying 100% invested in stocks with $5 million+ and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com⁠! ...
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Will Retiring Baby Boomers Crash the Stock Market?

June 17, 2026 • 48 mins
On episode 227 of Ask The Compound, Ben Carlson, Duncan Hill and Bill Sweet discuss: staying in shape while raising young kids and balancing family life, using Married Filing Separately to maximize PSLF benefits, whether pausing investing to start a business is a smart move, how aging demographics could impact stock market returns, retirement planning with no property taxes and low-cost healthcare on tribal land, whether investors ...
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How Do You Sell Your Stocks Without a Big Tax Hit?

June 10, 2026 • 42 mins
On episode 226 of Ask The Compound, Ben Carlson, Duncan Hill and Bill Sweet answer questions about selling highly appreciated stocks, figuring out your retirement number, financial lessons from aging parents, whether cash can replace bonds, helping investors avoid panic-selling during market turmoil, and the most important investing advice for a 16-year-old. Submit your Ask The Compound questions to askthecompoundshow@gmail.com! ...
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Is an AI Bubble Inevitable?

June 3, 2026 • 32 mins
On episode 225 of Ask The Compound, Ben Carlson discusses: the SpaceX IPO and whether it's a threat to index fund investors, the potential market impact of AI-driven job losses, balancing savings goals in your 20s, and much 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 This episode is sponsored by Public. Le...
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Should the Bottom 50% Pay Taxes?

May 27, 2026 • 41 mins
On episode 224 of Ask The Compound, Ben Carlson, Ritholtz Wealth CFO Bill Sweet and Duncan Hill discuss: whether it’s time to sell energy stocks before the next oil crash, the smartest way to rebalance risk heading into retirement, Jeff Bezos’s idea to eliminate income taxes for the bottom 50%, how taxes impact the 4% retirement rule, the best way to access Roth money for early retirement, and the tradeoff between maxim...
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Is It Time to Sell Some Stocks?

May 20, 2026 • 31 mins
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 o...
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Why Is the Stock Market Going Up?

May 13, 2026 • 38 mins
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/riskandr...
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U.S. Debt Is Near $40T. Should Investors Be Worried?

May 6, 2026 • 38 mins
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://rith...
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Do Valuations Still Matter?

April 29, 2026 • 33 mins
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 Com...
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What Does It Take to Retire at 55?

April 22, 2026 • 38 mins
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 Newsle...
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How Do You Protect Against a Bear Market?

April 15, 2026 • 34 mins
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 o...
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Will Social Security Be Around in 2060?

April 8, 2026 • 41 mins
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 ⁠⁠⁠askthec...
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Which Beaten Down Stocks Are Worth a Closer Look?

April 1, 2026 • 36 mins
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 Comp...
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How Much Do You Need to Retire?

March 25, 2026 • 37 mins
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 fo...
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What’s the Worst Asset Class for the Next 5 Years?

March 18, 2026 • 34 mins
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 conten...
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Why Won’t the Stock Market Go Down?

March 11, 2026 • 25 mins
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...
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How Do You Prepare for Market Uncertainty?

March 4, 2026 • 33 mins
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 o...
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Can You Retire in Your 40s and Live Off the Dividends?

February 25, 2026 • 38 mins
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 sh...
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Should You Pay Off Your Mortgage Early or Invest in Stocks?

February 18, 2026 • 21 mins
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...
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Is It Time to Buy Software Stocks?

February 11, 2026 • 48 mins
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 e...
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