Episodes

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...
What if the Stock Market Falls 30%?
Dec. 24, 2025

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, ...
10 Things Every Stock Market Investor Needs to Know
Dec. 17, 2025

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 askthecompoundsh...
How Much Longer Will the Bull Market Last?
Dec. 10, 2025

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, reth...
Will Housing Prices Fall In 2026?
Dec. 3, 2025

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, ...
How Does the 4 Year Rule Work?
Nov. 26, 2025

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, maki...
How to Recover From a 50% Loss
Nov. 19, 2025

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 Th...
How Do You Fix the Housing Market?
Nov. 12, 2025

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 advi...
Should You Pay Off Your Mortgage Early?
Nov. 5, 2025

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 Compo...
How to Time the AI Bubble
Oct. 29, 2025

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 v...
What is the Dave Ramsey Portfolio?
Oct. 22, 2025

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 questio...
Is It Time to Take Some Profits?
Oct. 15, 2025

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...
Why Is Gold Outperforming the Stock Market?
Oct. 8, 2025

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, inter...
How Do You Invest in a Bubble?
Oct. 1, 2025

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 askthecompoundsh...