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Ask The Compound

Ask The Compound

The Compound 353 Episodes Sep 17, 2026

Got money questions? We’ve got answers. Join Ben Carlson, Duncan Hill, and a rotating lineup of financial pros as they break down your biggest questions about investing, markets, and personal finance. Ben is a leading financial writer and the Director of Institutional Asset Management at Ritholtz. Duncan is a podcast producer and the Director of Creative Media at The Compound.

Episodes

Should You Pick Stocks or Buy Index Funds?
Should You Pick Stocks or Buy Index Funds? Sep 17, 2026 1927 On 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 traded portfolio. They discuss what a 5%+ bond yield really means, how inflation affects fixed-income investments, and where TIPS can fit into a portfolio. Plus, wh
How Does the Mega Backdoor Roth Conversion Work?
How Does the Mega Backdoor Roth Conversion Work? Sep 9, 2026 2488 On 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 mega-backdoor Roth 401(k) conversions work, what to do with down payment savings when buying a home is still years away, and whether a pension can serve as the bond alloc
Best Investment Right Now: Stocks, Bonds or Cash?
Best Investment Right Now: Stocks, Bonds or Cash? Sep 2, 2026 2050 On 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 short-term savings, dealing with bigger portfolio swings as your wealth compounds, and how lifelong savers can learn to spend and enjoy their money in retirement.
When Should You Sell Your Stocks?
When Should You Sell Your Stocks? Aug 26, 2026 2555 On 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 variable income. Plus, they cover the financial planning basics every family should have in place, how much risk to take in college savings accounts, and more. T
When Will the Stock Market Crash Again?
When Will the Stock Market Crash Again? Aug 19, 2026 2150 On 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 sustainable spending rates. This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors Compound Merch: ⁠⁠⁠⁠⁠http
How Do You Invest Without Paying Taxes?
How Do You Invest Without Paying Taxes? Aug 12, 2026 2547 On 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, how Roth 401(k)s work, and more! This episode is sponsored by Betterment Advisor Solutions. Learn more at https://betterment.com/advisors Compound Merch: ⁠⁠⁠
Is Buying a Home Still a Good Investment?
Is Buying a Home Still a Good Investment? Aug 5, 2026 1936 On episode 234 of Ask The Compound, Ben Carlson, Duncan Hill, and Jack Raines tackle your investing and financial planning questions, including the financial advice they'd give their younger selves, whether buying a home still makes sense in today's market, how young people should prepare for an AI-driven future, the risks of investing with margin, and whether it's possible to retire early by livi
When Should You Turn Bearish on the Stock Market?
When Should You Turn Bearish on the Stock Market? Jul 29, 2026 2972 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 inher
What Are the Two Main Risks Right Now?
What Are the Two Main Risks Right Now? Jul 22, 2026 2313 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 s
Can Your Portfolio Survive Market Timing?
Can Your Portfolio Survive Market Timing? Jul 15, 2026 1901 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 an
The 3 Best Inflation Hedges
The 3 Best Inflation Hedges Jul 8, 2026 2440 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
Is $1 Million Still Considered Rich?
Is $1 Million Still Considered Rich? Jul 1, 2026 2296 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 practi

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