Episodes

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...

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 askthecompoundshow@gmail.com! Today’s show is sponsored by Teucrium. Find out more at https://teucrium.com/agricultural-commodity-etfs Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get...

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 The Compound questions to askthecompoundshow@gmail.com! Today’s show is sponsored by Teucrium. Find out more at https://teucrium.com/agricultural-commodity-etfs Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who ...

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 advisors should think about diversification and alternatives, personal finance lessons and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com! This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newsle...

On episode 217 of Ask The Compound, Guest Host Bill Sweet and Duncan Hill are joined by Ritholtz Wealth Director of Tax Services Bill Artzerounian, Ritholtz Wealth Investment Analyst Sean Russo and Data Research Associate and founder of Exhibit A Matt Cerminaro to discuss Trump accounts vs 529 plans, government bonds, social security, moving to NYC in 2026, AI and taxes and more. Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com! This episode is sponsored by Betterment A...

On episode 216 of Ask The Compound, Ben Carlson, Duncan Hill discuss opportunities in beaten-down stocks, what happens when Mag 7 stocks get slammed, the issues with a stock market that’s always open, and more. Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com! This episode is sponsored by Public. Find out 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...

On episode 215 of Ask The Compound, Ben Carlson, Duncan Hill discuss saving for retirement, what is middle class, why you should own bonds, how should veterans save for retirement during school and more. Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com! 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 t...

On episode 214 of Ask The Compound, Ben Carlson, Duncan Hill and Nick Maggiulli discuss private markets vs real estate, is a guaranteed return worth it, 401k vs brokerage account, saving for college and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com! This episode is sponsored by Public. Find out 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...

On episode 213 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Barry Ritholtz and Blair duQuesnay to discuss: the current market environment, the importance of the market to the Trump admin, odds of a recession, and more! Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com⁠⁠⁠ This episode is sponsored by Betterment for Advisors. Learn more at https://betterment.com/advisors 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF...

On episode 212 of Ask The Compound, Ben Carlson and Bill Sweet discuss managing risk in an uncertain environment, how much is too much Roth, how the BOXX ETF works, 529 accounts for adults and more. Submit your Ask The Compound questions to ⁠⁠askthecompoundshow@gmail.com⁠⁠ This episode is sponsored by Public. Find out more at https://public.com/ATC 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thecompoundnews.com/show/TCAF/ Animal Spirit...

On episode 211 of Ask The Compound, Ben Carlson and Bill Sweet discuss how box spread loans work, taxes vs asset location, small business retirement plan options, how to coast FIRE, living on dividends and more. Submit your Ask The Compound questions to ⁠askthecompoundshow@gmail.com⁠ This episode is sponsored by Betterment Advisor Solutions. Learn more at: https://betterment.com/advisors 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thec...

On episode 210 of Ask The Compound, Ben Carlson discusses buying a house for 5-10 years, paying down your mortgage vs investing, when to pause your DCA, house wealth, investing abroad and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com This episode is sponsored by Public. Find out more at https://public.com/ATC 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thecompoundnews.com/show/TCAF/ Animal Spirits: htt...