
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.
Episodes

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: http

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
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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 AI-driven future, the risks of investing with margin, and whether it's possible to retire early by livi

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 inher

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 s

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 every financial plan.
They also discuss how to navigate difficult family conversations about wills an

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 the smartest financial gift for a 16-year-old.
Compound Merch: https://idontshop.com/
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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 your asset allocation, and whether it's ever worth selling stocks to buy a house. Plus, they share practi

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, staying 100% invested in stocks with $5 million+ and much more! Submit your Ask The Compound questions t

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 demographics could impact stock market returns, retirement planning with no property taxes and low-cost healthcare

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 turmoil, and the most important investing advice for a 16-year-old. Submit your Ask The Compound questions

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 askthecompoundshow@gmail.com!
Order your copy of Ben's book, 'Risk and Reward' here: https://lnk.to/riskandrewardbook
This

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%, how taxes impact the 4% retirement rule, the best way to access Roth money for early retirement, and the

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 smar

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' her

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 paper

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
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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 askthecompoundshow@gmail.com!
Today’s show is sponsored by Teucrium. Find out more at https://teucrium.com/agricultural-commodity-etfs
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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 finance lessons and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This epi

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 T

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
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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 askthecompoundshow@gmail.com!
This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors
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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 askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more at https://public.com/ATC
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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 askthecompoundshow@gmail.com
This episode is sponsored by Betterment for Advisors. Learn more at https://better

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
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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 askthecompoundshow@gmail.com
This episode is sponsored by Betterment Advisor Solutions. Learn more at: https://betterment.com/advisors

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.c

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
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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 askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more at https://public.com/ATC
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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 askthecompoundshow@gmail.com!
This episode is sponsored by Betterment Advisor Solutions. Learn more at http://Betterment.com/advisors
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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 askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more at https://public.com/ATC
Rea

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!
Th

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
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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 maximize tax-advantaged retirement savings and more. Submit your Ask The Compound questions to askthecomp

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://rocketmon

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.

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 Co

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 f

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!
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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 askthecompoundshow@gmail.com!
This episode is sponsored by Public. Fund your account in five minutes or less by visi

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 Rock

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 le

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
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Is It Time to Take Some Profits?
On episode 193 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Josh Brown to discuss taking profits, rebalancing FOMO, what to do with your inheritance, asset allocation, advisor career advice, and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
COMPOUND X CRAMER: https://compoundcramer.eventbrite.com/
This episode is sponsored by Public. Fund yo

Why Is Gold Outperforming the Stock Market?
On episode 192 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Jurrien Timmer, Director of Global Macro at Fidelity Investments to discuss the new normal of market concentration, the slowing labor market, international stocks, the deal with gold, defining a bubble and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Rocke

How Do You Invest in a Bubble?
On episode 191 of Ask The Compound, Ben Carlson and Duncan Hill discuss the 4% rule, dying with zero $$$, investing in a bubble, what is upper middle class, 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
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Where Should I Put Cash After the Fed Rate Cut?
On episode 190 of Ask The Compound, Ben Carlson and Duncan Hill discuss the best place to keep cash, career advice for young CFAs, where to invest $100k right now, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Check out Exhibit A here: https://exhibitaforadvice.com/
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Is It Time to Buy Bonds?
On episode 189 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Chief Financial Officer Bill Sweet to discuss when investing in bonds makes sense, how to choose the right mortgage, the right balance of Roth vs Traditional, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more at: ht

How Will the $84 Trillion Wealth Transfer Play Out?
On episode 188 of Ask The Compound, Ben Carlson and Duncan Hill discuss: diversifying a real estate empire, when it makes sense to splurge, RSUs with Joey Fishman, emergency funds, 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

Is This a Bubble?
On episode 187 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Financial Officer Bill Sweet to discuss fundamentals, the Roth limit conspiracy, spending income vs principal, and much 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: https://public.com/ATC

How to Buy a Porsche on a Honda Budget
On episode 186 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Investment Strategist Barry Ritholtz to discuss pre-70s S&P data, buying used cars, private investment opportunities, evaluating your financial advisor, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Rocket Money. Cancel your unwanted subscript

How to Triple Your Net Worth in 5 Years
On episode 185 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Market Strategist Callie Cox to discuss asset allocation advice, navigating a financialized economy, what if we don’t get a recession in the foreseeable future, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more at: https://pu

Millionaire Financial Goals
On episode 184 of Ask The Compound, Ben Carlson and Duncan Hill discuss the best emergency funds, impulse purchases, preparing for a future home purchase, and much 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://rocket

Markets Are Crazy. Is This the New Normal?
On episode 183 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO Bill Sweet to discuss tax-optimized investment management and withdrawal strategies, what makes a client annoying, buying vs renting, 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
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How To Be Rich
On episode 182 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM COO and Author Nick Maggiulli to discuss The Wealth Ladder, accounting for inflation in your plans, high net worth planning, career implications around moving, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Betterment Advisor Solutions. Grow your

What’s the Best Time to Invest?
On episode 181 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Senior Advisor Joey Fishman to discuss purchasing employee stock options, investing during a lost decade, asset allocation and crypto, optimizing your physical health, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more at: http

What’s the Perfect Level of Wealth?
On episode 180 of Ask The Compound, Ben Carlson and Duncan Hill discuss planning for a home purchase, what to do if you failed a CFA test, optimizing 401k contributions, forgoing a real estate agent, and much 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 f

How Does the Big Beautiful Bill Impact Your Taxes?
On episode 179 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and tax specialist Bill Sweet to discuss putting cash to work, thoughts on the new tax bill, how Trump accounts affect 529’s, creating a savings target, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Fund your account in five minutes

Should You Invest in Stocks at All-Time Highs?
On episode 178 of Ask The Compound, Ben Carlson and Duncan Hill discuss dating vs DCAing, if high college expenses will affect the economy, investing at all-time highs, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get

How Do Young People Get Rich?
On episode 177 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth CEO and TCAF Host Josh Brown to discuss how to get rich without crypto, how RWM invests, reaching retail investors, 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
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What Is the Expected Return for the Stock Market?
On episode 176 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Market Strategist Callie Cox to discuss Ben's typical work day, expected returns, understanding risk tolerance, if a savings rate is too high, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Rocket Money. Cancel your unwanted subscriptions and r

How to Live Tax-Free in Retirement
On episode 175 of Ask The Compound, Ben Carlson and Duncan Hill are joined by CFO and Tax Specialist Bill Sweet to discuss downsides to 100% of assets in a Roth, making a career shift towards finance, the best savings options for kids, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Fund your account in five minutes or

What’s the Biggest Risk Right Now?
On episode 174 of Ask The Compound, Ben Carlson and Duncan Hill discuss AI and deflation, private equity in 401(k)s, ETFs for the long run, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Rocket Money! Download the Rocket Money app and enter my show name Ask the Compound in the survey so they know I sent you!
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When Should I Sell My Stocks?
On episode 173 of Ask The Compound, Ben Carlson and Duncan Hill discuss using stocks as an emergency fund, optimizing RMDs, factoring in pensions as income, fictional book recommendations and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Find out more by visiting: http://public.com/ATC
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Is Retail the Smart Money Now?
On episode 172 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Steve Quirk, Chief Brokerage Officer at Robinhood to discuss when buy the dip will stop working, the future of retail trading, AI as an advisor, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
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I Timed the Market. Now What?
On episode 171 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Bill Sweet, tax specialist and RWM CFO to discuss tax-optimizing a portfolio rebalance, 60/40 portfolio drawdowns, moving or finding a new remote job, feeling stuck after selling too early, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. You c

Does Private Equity Belong in 401k Plans?
On episode 170 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Michael Sidgmore, Co-Founder and Partner at Broadhaven Ventures to discuss diversification using private markets, how tariffs affect private credit, at what net worth private assets make sense, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Bettermen

The Stock Market Rallied. Now What?
On episode 169 of Ask The Compound, Ben Carlson and Duncan Hill discuss the meaning behind U.S. dollar strength or weakness, investing in bonds vs using high yield savings accounts, the optimal amount of emergency savings, building a cash reserve vs paying down debt, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Fund

What’s the Best Case Trade War Scenario?
On episode 168 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Chief Investment Officer and Masters in Business host Barry Ritholtz to discuss staying invested amidst bearishness, the best case scenario around tariffs, preparing for a recession, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Rocket Money. Down

How to Invest in an Uncertain Market
On episode 167 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Chief Market Strategist Callie Cox to discuss dealing with policy uncertainty, the bull case for tariffs, politics affecting portfolios, planning for the future amidst chaos, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Fund your account

Are Portfolios Becoming Partisan?
On episode 166 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and tax expert Bill Sweet to discuss consumer sentiment and politics, how TIPS are taxed, parking money after a home sale, getting an interest-only mortgage, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
This episode is sponsored by Public. Fund your account in five minut

When Will Housing Prices Fall?
On episode 165 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CEO and Halftime Report star Josh Brown to discuss what’s going on with real estate, going through job loss, when to hire a financial advisor, getting out of illiquid investments, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Check out Exhibit A: https://exhibitaforadvice.com

Will Tariffs Tank the Economy?
On episode 164 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Advisor Blair duQuesnay, CFP, CFA to discuss inaccurate Wall Street price targets, possible outcomes from tariffs, approaching difficult conversations around diversification, taking a 401k loan, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Thanks to Public for sponsoring thi

Why Is Market Timing a Bad Idea?
On episode 163 of Ask The Compound, Ben Carlson and Duncan Hill discuss why market timing is a bad idea, letting winners ride, keeping or selling rental property, preparing for a regional recession, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
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What Happens in a Recession?
On episode 162 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and Tax Specialist Bill Sweet to discuss narratives around recessions, dealing with market uncertainty, financial planning for a private golf membership, tax planning with Roths and 401ks, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Thanks to Public for sponsoring this

Is There a Passive Investing Bubble?
On episode 161 of Ask The Compound, Ben Carlson and Duncan Hill discuss if ETFs can bring down the market, what to focus on as an investment committee member, reducing risk due to a government-induced market collapse, using savings to restore a car, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Thanks to Rocket Money for sponsoring this episode. Visit: htt

Should You Pay Off Your Mortgage Before Early Retirement?
On episode 160 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management Chief Investment Officer and Masters in Business host Barry Ritholtz to discuss buying the dip, portfolio management near retirement, retiring with a mortgage, buying a luxury vehicle, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Thanks to Rocket Money

Are Tariffs a Tax on Consumers?
On episode 159 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management Chief Financial Officer and Tax Specialist Bill Sweet to discuss unaffordable housing around the world, utilizing a rental to reduce taxes, tax optimizing an inherited IRA, if tariffs are a form of tax, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Than

Is It Time to Buy the Dip?
On episode 158 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management Chief Investment Strategist Callie Cox to discuss if now is the time to sell NVDA, timing the market with rebalancing, the strength of the U.S. Economy, getting out of highly concentrated positions, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Thanks t

Is It Time to Lock In 5% Yields?
On episode 157 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Advisors Taylor Hollis and Nick Sapienza to discuss advice for overconfident investors, reducing the cost of insurance, how many years of spending you should have saved, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com!
Thanks to Public for sponsoring this episode! Fu
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