PODCAST · business
Ask The Compound
by 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
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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...
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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...
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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...
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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…
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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...
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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...
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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...
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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…
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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...
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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…
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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...
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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…
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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…
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Can Your Portfolio Survive Market Timing?
On episode 231 of Ask The Compound, Ben Carlson, Taylor Hollis, and Duncan Hill answer your investing and financial planning questions, including whether the world's worst market timer could still build wealth, how to tackle $90,000 in credit card debt, and why estate planning should be part of...
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The 3 Best Inflation Hedges
On episode 230 of Ask The Compound, Ben Carlson, Duncan Hill, and Bill Sweet discuss whether retirees and wealthy investors own too many bonds, the best way to sell stocks before buying a vacation home, if housing is still a long-term wealth builder, how much to put down on your first home, and…
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Is $1 Million Still Considered Rich?
On episode 229 of Ask The Compound, Ben Carlson, Duncan Hill and Bill Sweet discuss: whether $1 million still makes you rich, how to prioritize saving with a baby on the way, whether to aggressively pay down an 8.24% SBA loan or enjoy the rewards of your success, how rental properties fit into…
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Can You Retire on $1.5 Million?
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,...
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Will Retiring Baby Boomers Crash the Stock Market?
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…
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How Do You Sell Your Stocks Without a Big Tax Hit?
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...
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Is an AI Bubble Inevitable?
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...
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Should the Bottom 50% Pay Taxes?
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%…
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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,...
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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...
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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 [email protected]!…
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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 [email protected]! Today’s show is sponsored by Teucrium. Find...
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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 [email protected]! Today’s show is...
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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…
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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...
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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 [email protected]! This…
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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 [email protected]! This episode is...
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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 [email protected]! This episode is...
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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...
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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 [email protected] This episode is…
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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 [email protected] This episode...
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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 [email protected] This episode is sponsored by...
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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 [email protected]! This episode is sponsored by Teucrium. Find out more…
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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 [email protected]! This...
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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 [email protected]! This episode is sponsored by Betterment...
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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...
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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…
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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...
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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...
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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 [email protected]! This episode is sponsored by Rocket Money. Cancel your...
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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...
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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...
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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...
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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 [email protected]! Visit:...
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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...
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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 [email protected]! This episode is sponsored...
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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...
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ABOUT THIS SHOW
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/
HOSTED BY
The Compound
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Frequently Asked Questions
How many episodes does Ask The Compound have?
Ask The Compound currently has 370 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Ask The Compound about?
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....
How often does Ask The Compound release new episodes?
Ask The Compound publishes regularly with 370 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Ask The Compound?
You can listen to Ask The Compound on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Ask The Compound?
Ask The Compound is created and hosted by The Compound.
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