Episodes
June 18, 2025
What Is the Expected Return for the Stock Market?
On episode 176 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Market Strategist Callie Cox to discuss Ben's typical work day, expected returns, understanding risk tolerance, if a savings rate is too high...
June 11, 2025
How to Live Tax-Free in Retirement
On episode 175 of Ask The Compound, Ben Carlson and Duncan Hill are joined by CFO and Tax Specialist Bill Sweet to discuss downsides to 100% of assets in a Roth, making a career shift towards finance, the best savings options...
June 4, 2025
What’s the Biggest Risk Right Now?
On episode 174 of Ask The Compound, Ben Carlson and Duncan Hill discuss AI and deflation, private equity in 401(k)s, ETFs for the long run, and much more! Submit your Ask The Compound questions to askthecompoundshow@gmail.com...
May 28, 2025
When Should I Sell My Stocks?
On episode 173 of Ask The Compound, Ben Carlson and Duncan Hill discuss using stocks as an emergency fund, optimizing RMDs, factoring in pensions as income, fictional book recommendations and much more! Submit your Ask The Co...
May 21, 2025
Is Retail the Smart Money Now?
On episode 172 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Steve Quirk, Chief Brokerage Officer at Robinhood to discuss when buy the dip will stop working, the future of retail trading, AI as an advisor, an...
May 14, 2025
I Timed the Market. Now What?
On episode 171 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Bill Sweet, tax specialist and RWM CFO to discuss tax-optimizing a portfolio rebalance, 60/40 portfolio drawdowns, moving or finding a new remote j...
May 7, 2025
Does Private Equity Belong in 401k Plans?
On episode 170 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Michael Sidgmore, Co-Founder and Partner at Broadhaven Ventures to discuss diversification using private markets, how tariffs affect private credit, at what net worth private assets make sense, and much more! Submit your …
April 30, 2025
The Stock Market Rallied. Now What?
On episode 169 of Ask The Compound, Ben Carlson and Duncan Hill discuss the meaning behind U.S. dollar strength or weakness, investing in bonds vs using high yield savings accounts, the optimal amount of emergency savings, bu...
April 23, 2025
What’s the Best Case Trade War Scenario?
On episode 168 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Chief Investment Officer and Masters in Business host Barry Ritholtz to discuss staying invested amidst bearishness, the best case scenario aro...
April 16, 2025
How to Invest in an Uncertain Market
On episode 167 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Chief Market Strategist Callie Cox to discuss dealing with policy uncertainty, the bull case for tariffs, politics affecting portfolios, planni...
April 2, 2025
Are Portfolios Becoming Partisan?
On episode 166 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and tax expert Bill Sweet to discuss consumer sentiment and politics, how TIPS are taxed, parking money after a home sale, getting an inter...
March 26, 2025
When Will Housing Prices Fall?
On episode 165 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CEO and Halftime Report star Josh Brown to discuss what’s going on with real estate, going through job loss, when to hire a financial advisor, ...
March 19, 2025
Will Tariffs Tank the Economy?
On episode 164 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Advisor Blair duQuesnay, CFP, CFA to discuss inaccurate Wall Street price targets, possible outcomes from tariffs, approaching difficult conver...
March 12, 2025
Why Is Market Timing a Bad Idea?
On episode 163 of Ask The Compound, Ben Carlson and Duncan Hill discuss why market timing is a bad idea, letting winners ride, keeping or selling rental property, preparing for a regional recession, and much more! Submit your...
March 5, 2025
What Happens in a Recession?
On episode 162 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and Tax Specialist Bill Sweet to discuss narratives around recessions, dealing with market uncertainty, financial planning for a private go...
Feb. 26, 2025
Is There a Passive Investing Bubble?
On episode 161 of Ask The Compound, Ben Carlson and Duncan Hill discuss if ETFs can bring down the market, what to focus on as an investment committee member, reducing risk due to a government-induced market collapse, using s...
Feb. 12, 2025
Should You Pay Off Your Mortgage Before Early Retirement?
On episode 160 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management Chief Investment Officer and Masters in Business host Barry Ritholtz to discuss buying the dip, portfolio management nea...
Feb. 5, 2025
Are Tariffs a Tax on Consumers?
On episode 159 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management Chief Financial Officer and Tax Specialist Bill Sweet to discuss unaffordable housing around the world, utilizing a rent...
Jan. 29, 2025
Is It Time to Buy the Dip?
On episode 158 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management Chief Investment Strategist Callie Cox to discuss if now is the time to sell NVDA, timing the market with rebalancing, t...
Jan. 22, 2025
Is It Time to Lock In 5% Yields?
On episode 157 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Advisors Taylor Hollis and Nick Sapienza to discuss advice for overconfident investors, reducing the cost of insurance, how many ye...
Jan. 15, 2025
Is It Time to Take Money off the Table?
On episode 156 of Ask The Compound, Ben Carlson and Duncan Hill discuss concentrating within sectors of the S&P 500, how economies outside the US affect US markets, taking chips off the table vs timing the market, financial p...
Jan. 8, 2025
When Should I Sell Tesla?
On episode 155 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and Tax Specialist Bill Sweet to discuss tax planning for trading accounts, thoughts on custom indexing, using margin to stay invested, and...
Dec. 17, 2024
How Do You Compound Your Money for 50 Years?
On episode 154 of Ask The Compound, Ben Carlson and Duncan Hill discuss the most optimal savings rate, if buffered ETFs should be considered fixed income, timing the housing market, investing as a teenager, and much more! Sub...
Dec. 11, 2024
How Do I Invest in Stocks at All-Time Highs?
On episode 153 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CEO and CNBC Halftime star Josh Brown to discuss if AI will solve the financial advisor shortage, buying the election and selling the inaugurat...