Ask The Compound
Welcome to Ask The Compound, the show where Ben Carlson, Duncan Hill, and a rotating cast of financial experts answer your questions about investing and personal finance.
Recent Episodes
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 ...
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...
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...
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...
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...
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...
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...
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 ...
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...
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