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
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...
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...
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...
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...
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...
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...
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...
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...
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...
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