Episodes

On 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 AI trade without going to cash, retirement strategies for high-income business owners, and the best ways for individual investors to buy bonds. Plus, which investments belong in a Roth IRA, how to manage an inherited IRA under the 10-year withdrawal rule, and wh...

On 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, how to think about safe withdrawal rates and aggressive retirement portfolios, and what adult children should ask when meeting with their parents’ financial advisor. Plus, whether high yields could ever justify going 100% into bonds, how higher interest rates c...

On 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 catalyst for the next major sell-off. Plus, insurance expert Jonathan Novy joins the show to explain when permanent life insurance actually makes sense, how to think about long-term care insurance versus self-insuring, and whether annuities can help cover future ...

On 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 ETFs, whether paying off a 2.875% mortgage can ever make sense, and how AI could reshape careers in equity research. They also discuss how to diversify an all-stock portfolio as a growth-heavy account gets larger, the role of defensive stocks, and why economies ne...

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, when it makes sense to spend on luxury purchases like watches, whether baby boomers are really a threa...

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 allocation in your portfolio. Plus, Roth vs. traditional 401(k) contributions for high earners, borrowing...

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. This episode is sponsored by Fitnexa. For $10 off SomniPods 3, visit: http://go.fitnexa.com/qQ0AbS...

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. This episode is sponsored by Fitnexa. For $10 off, visit: http://go.fitnexa.com/qQ0AbS Compound Merch:...

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: ⁠⁠⁠⁠⁠https://idontshop.com/⁠⁠⁠⁠⁠ Submit your Ask The Compound questions to ⁠⁠⁠⁠⁠askthecompoundshow@gmail.com⁠⁠⁠⁠...

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: ⁠⁠⁠⁠https://idontshop.com/⁠⁠⁠⁠ Submit your Ask The Compound questions to ⁠⁠⁠⁠askthecompoundshow@gmail.com⁠...

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 living an ultra-frugal lifestyle. They discuss: - The financial lessons they'd share with their younge...

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 afte...

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 eventua...

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...

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 al...

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 spons...

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 c...

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...

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://ln...

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 more! 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 Public. Learn more at: https://public.com/ATC Subscribe to The Compound Newsle...

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 retirement, Jeff Bezos’s idea to eliminate income taxes for the bottom 50%, how taxes impact the 4% retirement rule, the best way to access Roth money for early retirement, and the tradeoff between maximizing 529 plans and making memories with your kids today. Submit your Ask The...

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 sacrificing passion for higher pay, when retirees should finally add bonds, target-date funds vs. index funds in marriage, and whether today’s AI-driven market feels more like smart investing or dot-com bubble euphoria. Submit your Ask The Compound questions to askthecompoundshow...

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, small bussiness retirement accounts and more! Submit your Ask The Compound questions to ⁠⁠askthecompoundshow@gmail.com⁠⁠! Today’s show is sponsored by The Compound Insider. For all the latest info, subscribe at ⁠https://www.thecompoundnews.com/subscribe Subscribe to The Compo...

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 your Ask The Compound questions to askthecompoundshow@gmail.com! Today’s show is sponsored by Public. Find out more at https://public.com/ATC Barry’s book out in paperback: https://ritholtz.com/2026/05/how-not-to-invest-paperback-arrives/ Subscribe to The Compound Newsle...