Episodes

  • When Should You Turn Bearish on the Stock Market?

    When Should You Turn Bearish on the Stock Market?
    Jul 29 2026
    On episode 233 of Ask The Compound, Ben Carlson, Duncan Hill, and Josh Brown tackle your investing and financial planning questions, including whether Shake Shack's recent collapse is a buying opportunity, how active management fits alongside indexing, what would actually make a long-term bull turn bearish, how to promote disciplined investing in a speculative market, and whether an expected inheritance should influence your financial plan. They discuss: Is Shake Shack a value opportunity after its earnings collapse? Why active management and indexing aren't mutually exclusive What would make a long-term investor turn bearish? Teaching long-term investing in a market driven by speculation How to think about a future inheritance without letting it change your financial decisions today This episode is sponsored by Betterment Advisor Solutions. Learn more at: https://betterment.com/advisors Compound Merch: ⁠⁠https://idontshop.com/⁠⁠ Submit your Ask The Compound questions to ⁠⁠askthecompoundshow@gmail.com⁠⁠! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    50 mins
  • What Are the Two Main Risks Right Now?

    What Are the Two Main Risks Right Now?
    Jul 22 2026
    On episode 232 of Ask The Compound, Ben Carlson is joined by Jurrien Timmer to discuss: whether the Magnificent 7's recent underperformance is a healthy sign of broader market leadership, why concentration risk and higher interest rates remain key risks for investors, how long the current earnings boom can continue, where speculative capital could flow next after Bitcoin, gold, and semiconductor stocks, and how to stay invested during a bull market while protecting against the risk of an eventual bubble. Plus, Jurrien shares insights from his Weekly Asset Allocation Review and explains why a barbell approach to AI and value investing could make sense in today's market. This episode is sponsored by Fidelity Investments and the all-new Fidelity Trader+, Fidelity’s most powerful trading platform yet. Learn more at http://www.fidelity.com/TraderPlus Compound Merch: ⁠https://idontshop.com/⁠ Submit your Ask The Compound questions to ⁠askthecompoundshow@gmail.com⁠! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    39 mins
  • Can Your Portfolio Survive Market Timing?

    Can Your Portfolio Survive Market Timing?
    Jul 15 2026
    On episode 231 of Ask The Compound, Ben Carlson, Taylor Hollis, and Duncan Hill answer your investing and financial planning questions, including whether the world's worst market timer could still build wealth, how to tackle $90,000 in credit card debt, and why estate planning should be part of every financial plan. They also discuss how to navigate difficult family conversations about wills and succession planning, whether financial advisors should hire advisors of their own, and the best ways to set your children up for long-term financial success through investing. This episode is sponsored by Public. Learn more at https://public.com/ATC Compound Merch: https://idontshop.com/ Submit your Ask The Compound questions to askthecompoundshow@gmail.com! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    32 mins
  • The 3 Best Inflation Hedges

    The 3 Best Inflation Hedges
    Jul 8 2026
    On episode 230 of Ask The Compound, Ben Carlson, Duncan Hill, and Bill Sweet discuss whether retirees and wealthy investors own too many bonds, the best way to sell stocks before buying a vacation home, if housing is still a long-term wealth builder, how much to put down on your first home, and the smartest financial gift for a 16-year-old. Compound Merch: https://idontshop.com/ Submit your Ask The Compound questions to askthecompoundshow@gmail.com! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    41 mins
  • Is $1 Million Still Considered Rich?

    Is $1 Million Still Considered Rich?
    Jul 1 2026
    On episode 229 of Ask The Compound, Ben Carlson, Duncan Hill and Bill Sweet discuss: whether $1 million still makes you rich, how to prioritize saving with a baby on the way, whether to aggressively pay down an 8.24% SBA loan or enjoy the rewards of your success, how rental properties fit into your asset allocation, and whether it's ever worth selling stocks to buy a house. Plus, they share practical insights on balancing wealth-building with real-life financial decisions. This episode is sponsored by Public. Learn more at https://public.com/ATC Submit your Ask The Compound questions to askthecompoundshow@gmail.com! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    38 mins
  • Can You Retire on $1.5 Million?

    Can You Retire on $1.5 Million?
    Jun 24 2026
    On episode 228 of Ask The Compound, Ben Carlson and Duncan Hill discuss: whether an AI bubble crash or market correction would be a buying opportunity for U.S. stocks, how to invest $150,000 in cash today, giving up a 2.9% mortgage to buy a larger home, whether $1.5 million is enough to retire, staying 100% invested in stocks with $5 million+ and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com⁠! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    33 mins
  • Will Retiring Baby Boomers Crash the Stock Market?

    Will Retiring Baby Boomers Crash the Stock Market?
    Jun 17 2026
    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 pausing investing to start a business is a smart move, how aging demographics could impact stock market returns, retirement planning with no property taxes and low-cost healthcare on tribal land, whether investors should pay attention to Ray Dalio's latest views and more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com! This episode is sponsored by Public. Learn more at https://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    49 mins
  • How Do You Sell Your Stocks Without a Big Tax Hit?

    How Do You Sell Your Stocks Without a Big Tax Hit?
    Jun 10 2026
    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 replace bonds, helping investors avoid panic-selling during market turmoil, and the most important investing advice for a 16-year-old. Submit your Ask The Compound questions to askthecompoundshow@gmail.com! Order your copy of Ben's book, 'Risk and Reward' here: ⁠https://lnk.to/riskandrewardbook⁠ This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🎥 Watch this episode on YouTube:...
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    42 mins