Ask The Compound
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Latest episodes
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How to Put Cash to Work In Any Market Environment
October 28, 2026 · 48 minOn episode 246 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Downtown Josh Brown to answer five listener questions on investing, financial planning, and the housing market. They discuss whether direct indexing is worth the…
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Why Won’t the Housing Market Crash?
October 21, 2026 · 35 minOn episode 245 of Ask The Compound, Ben Carlson and Duncan Hill answer five listener questions on investing, bonds, housing, and personal finance. They discuss why Ben finally bought bonds for the first time in his career, whether paying…
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How Do You Hedge a Concentrated Stock Market?
October 14, 2026 · 44 minOn episode 244 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Bill Sweet to answer six listener questions on investing, retirement planning, taxes, and real estate. They discuss how to diversify away from the concentrated…
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What’s the Safe Withdrawal Rate for Retirement?
October 7, 2026 · 33 minOn episode 243 of Ask The Compound, Ben Carlson and Duncan Hill answer six listener questions on bonds, retirement, financial planning, and the psychology of spending. They discuss when it makes sense for long-term investors to own bonds…
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When Will the Next Bear Market Hit?
September 30, 2026 · 40 minOn episode 242 of Ask The Compound, Ben Carlson and Duncan Hill discuss: when the next bear market and recession could hit, why rising Treasury yields haven’t rattled the stock market, and whether the AI boom could ultimately become the…
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Why Do We Need Inflation?
September 23, 2026 · 32 minOn episode 241 of Ask The Compound, Ben Carlson and Duncan Hill answer listener questions on whether private markets are capturing more of the economy’s biggest gains before companies go public, what that could mean for index funds and…
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Should You Pick Stocks or Buy Index Funds?
September 17, 2026 · 32 minOn this live episode of Ask The Compound from Future Proof in Huntington Beach, Ben Carlson, Alex Morris, Bill Sweet, and Barry Ritholtz tackle listener questions on bonds, luxury spending, generational wealth, and managing an actively…
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How Does the Mega Backdoor Roth Conversion Work?
September 9, 2026 · 41 minOn episode 239 of Ask The Compound, Ben Carlson, Bill Sweet, and Duncan Hill tackle six listener questions on investing, retirement, and managing risk. They discuss the research behind trend-following and momentum strategies, how…
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Best Investment Right Now: Stocks, Bonds or Cash?
September 2, 2026 · 34 minOn episode 238 of Ask The Compound, Ben Carlson and Duncan Hill discuss how to prepare for a potential government debt crisis, choosing between stocks, bonds and cash, how much to allocate to international stocks, the best places to park…
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When Should You Sell Your Stocks?
August 26, 2026 · 43 minOn episode 237 of Ask The Compound, Ben Carlson, Bill Sweet and Duncan Hill discuss the most important things investors should know before buying stocks, how to transfer retirement accounts tax-efficiently, and managing large chunks of…
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When Will the Stock Market Crash Again?
August 19, 2026 · 36 minOn 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…
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How Do You Invest Without Paying Taxes?
August 12, 2026 · 42 minOn 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…

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