Episodes

Will Retiring Baby Boomers Crash the Stock Market?
June 17, 2026

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 paus...
How Do You Sell Your Stocks Without a Big Tax Hit?
June 10, 2026

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...
Is an AI Bubble Inevitable?
June 3, 2026

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 m...
Should the Bottom 50% Pay Taxes?
May 27, 2026

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 retir...
Is It Time to Sell Some Stocks?
May 20, 2026

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 sacri...
Why Is the Stock Market Going Up?
May 13, 2026

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, sma...
U.S. Debt Is Near $40T. Should Investors Be Worried?
May 6, 2026

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...
Do Valuations Still Matter?
April 29, 2026

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 as...
What Does It Take to Retire at 55?
April 22, 2026

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 T...
How Do You Protect Against a Bear Market?
April 15, 2026

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 advis...
Will Social Security Be Around in 2060?
April 8, 2026

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...
Which Beaten Down Stocks Are Worth a Closer Look?
April 1, 2026

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 As...
How Much Money Should You Save?
March 25, 2026

How Much Money Should You Save?

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 C...
What’s the Worst Asset Class for the Next 5 Years?
March 18, 2026

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 ...
Why Won’t the Stock Market Go Down?
March 11, 2026

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...
How Do You Prepare for Market Uncertainty?
March 4, 2026

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 Compou...
Can You Retire in Your 40s and Live Off the Dividends?
Feb. 25, 2026

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 A...
Should You Pay Off Your Mortgage Early or Invest in Stocks?
Feb. 18, 2026

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 qu...
Is It Time to Buy Software Stocks?
Feb. 11, 2026

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 askthecompo...
How Do You Invest a Lump Sum of Cash In This Market?
Feb. 4, 2026

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 yo...
Does the 4% Rule Still Work?
Jan. 28, 2026

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 ...
How Do You Hedge With Options?
Jan. 21, 2026

How Do You Hedge With Options?

On episode 206 of Ask The Compound, Ben Carlson and Duncan Hill discuss equity hedging strategies, buffered ETFs, international stocks, benefits of a stay at home spouse and more. Submit your Ask The Compound questions to ask...
Is the Stock Market Overvalued?
Jan. 14, 2026

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 e...
Should You Buy a House Right Now?
Jan. 7, 2026

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 Rot...