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Ask The Compound

News

Ask The Compound

The Compound

Is $1 Million Still Considered Rich?

July 01, 2026 1:42pm 38 min

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...

Can You Retire on $1.5 Million?

June 24, 2026 11:50am 32 min

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....

Will Retiring Baby Boomers Crash the Stock Market?

June 17, 2026 4:54pm 48 min

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...

How Do You Sell Your Stocks Without a Big Tax Hit?

June 10, 2026 1:51pm 42 min

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 cas...

Is an AI Bubble Inevitable?

June 03, 2026 1:28pm 32 min

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 m...

Should the Bottom 50% Pay Taxes?

May 27, 2026 1:21pm 41 min

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 ...

Is It Time to Sell Some Stocks?

May 20, 2026 1:22pm 31 min

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 ...

Why Is the Stock Market Going Up?

May 13, 2026 12:55pm 38 min

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...

U.S. Debt Is Near $40T. Should Investors Be Worried?

May 06, 2026 1:30pm 38 min

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. S...

Do Valuations Still Matter?

April 29, 2026 1:28pm 33 min

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 ...

What Does It Take to Retire at 55?

April 22, 2026 1:14pm 38 min

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 ...

How Do You Protect Against a Bear Market?

April 15, 2026 1:40pm 34 min

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 ...

Will Social Security Be Around in 2060?

April 08, 2026 2:01pm 41 min

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 Associat...

Which Beaten Down Stocks Are Worth a Closer Look?

April 01, 2026 11:40am 36 min

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 yo...

How Much Do You Need to Retire?

March 25, 2026 2:20pm 37 min

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 ...

What’s the Worst Asset Class for the Next 5 Years?

March 18, 2026 2:19pm 34 min

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...

Why Won’t the Stock Market Go Down?

March 11, 2026 11:55am 25 min

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 rece...

How Do You Prepare for Market Uncertainty?

March 04, 2026 1:01pm 33 min

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 C...

Can You Retire in Your 40s and Live Off the Dividends?

February 25, 2026 1:38pm 38 min

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 y...

Should You Pay Off Your Mortgage Early or Invest in Stocks?

February 18, 2026 12:55pm 21 min

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 Compou...

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