Episodes
Dec. 10, 2025
How Much Longer Will the Bull Market Last?
On episode 201 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Jurrien Timmer to discuss: where we are in this bull market’s cycle, how the AI bubble compares to past bubbles, the right level of inflation, reth...
Dec. 3, 2025
Will Housing Prices Fall In 2026?
On episode 200 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO and ATC legend Bill Sweet to discuss: housing prices in 2026, retirement tax strategies, Gen Z loves Roth, renting during retirement, ...
Nov. 26, 2025
How Does the 4 Year Rule Work?
On episode 199 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Corey Hoffstein, co-founder, CEO and CIO at Newfound Research to discuss: what return stacking is, how the 4 year rule works, leveraging BNPL, maki...
Nov. 19, 2025
How to Recover From a 50% Loss
On episode 198 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO Bill Sweet to discuss: 50% losses in your portfolio, stock concentration, 401k optimization, HELOC, Roth, and more. Submit your Ask Th...
Nov. 12, 2025
How Do You Fix the Housing Market?
On episode 197 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Sr. Advisor Jonathan Novy to discuss: portfolio allocation, insurance products, structuring withdrawals, the 50-year mortgage, career advi...
Nov. 5, 2025
Should You Pay Off Your Mortgage Early?
On episode 196 of Ask The Compound, Ben Carlson and Duncan Hill discuss: the AI bubble, tech allocation, good debt, paying down a mortgage early, buyside vs sellside, cash on the sidelines, and more. Submit your Ask The Compo...
Oct. 29, 2025
How to Time the AI Bubble
On episode 195 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CFO Bill Sweet to discuss: trading a bubble, Roth strategy, buying your parents' house, capital losses, saving for a new child, buying a v...
Oct. 22, 2025
What is the Dave Ramsey Portfolio?
On episode 194 of Ask The Compound, Ben Carlson and Duncan Hill discuss outperformance, dying with zero, beating the market, Dave Ramsey’s investment strategy, saving for college and more. Submit your Ask The Compound questio...
Oct. 15, 2025
Is It Time to Take Some Profits?
On episode 193 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Josh Brown to discuss taking profits, rebalancing FOMO, what to do with your inheritance, asset allocation, advisor career advice, and more. Submit...
Oct. 8, 2025
Why Is Gold Outperforming the Stock Market?
On episode 192 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Jurrien Timmer, Director of Global Macro at Fidelity Investments to discuss the new normal of market concentration, the slowing labor market, inter...
Oct. 1, 2025
How Do You Invest in a Bubble?
On episode 191 of Ask The Compound, Ben Carlson and Duncan Hill discuss the 4% rule, dying with zero $$$, investing in a bubble, what is upper middle class, and more! Submit your Ask The Compound questions to askthecompoundsh...
Sept. 24, 2025
Where Should I Put Cash After the Fed Rate Cut?
On episode 190 of Ask The Compound, Ben Carlson and Duncan Hill discuss the best place to keep cash, career advice for young CFAs, where to invest $100k right now, and much more! Submit your Ask The Compound questions to askt...
Sept. 17, 2025
Is It Time to Buy Bonds?
On episode 189 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Chief Financial Officer Bill Sweet to discuss when investing in bonds makes sense, how to choose the right mortgage, the right bala...
Sept. 10, 2025
How Will the $84 Trillion Wealth Transfer Play Out?
On episode 188 of Ask The Compound, Ben Carlson and Duncan Hill discuss: diversifying a real estate empire, when it makes sense to splurge, RSUs with Joey Fishman, emergency funds, and more! Submit your Ask The Compound ques...
Sept. 3, 2025
Is This a Bubble?
On episode 187 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Financial Officer Bill Sweet to discuss fundamentals, the Roth limit conspiracy, spending income vs principal, and much more! Submit your Ask...
Aug. 27, 2025
How to Buy a Porsche on a Honda Budget
On episode 186 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Investment Strategist Barry Ritholtz to discuss pre-70s S&P data, buying used cars, private investment opportunities, evaluating your financi...
Aug. 20, 2025
How to Triple Your Net Worth in 5 Years
On episode 185 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Chief Market Strategist Callie Cox to discuss asset allocation advice, navigating a financialized economy, what if we don’t get a recession in the ...
Aug. 13, 2025
Millionaire Financial Goals
On episode 184 of Ask The Compound, Ben Carlson and Duncan Hill discuss the best emergency funds, impulse purchases, preparing for a future home purchase, and much more! Submit your Ask The Compound questions to askthecompoun...
Aug. 6, 2025
Markets Are Crazy. Is This the New Normal?
On episode 183 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO Bill Sweet to discuss tax-optimized investment management and withdrawal strategies, what makes a client annoying, buying vs renting, and m...
July 30, 2025
How To Be Rich
On episode 182 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM COO and Author Nick Maggiulli to discuss The Wealth Ladder, accounting for inflation in your plans, high net worth planning, career implication...
July 23, 2025
What’s the Best Time to Invest?
On episode 181 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM Senior Advisor Joey Fishman to discuss purchasing employee stock options, investing during a lost decade, asset allocation and crypto, optimizi...
July 16, 2025
What’s the Perfect Level of Wealth?
On episode 180 of Ask The Compound, Ben Carlson and Duncan Hill discuss planning for a home purchase, what to do if you failed a CFA test, optimizing 401k contributions, forgoing a real estate agent, and much more! Submit you...
July 9, 2025
How Does the Big Beautiful Bill Impact Your Taxes?
On episode 179 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and tax specialist Bill Sweet to discuss putting cash to work, thoughts on the new tax bill, how Trump accounts affect 529’s, creating a sa...
July 2, 2025
Should You Invest in Stocks at All-Time Highs?
On episode 178 of Ask The Compound, Ben Carlson and Duncan Hill discuss dating vs DCAing, if high college expenses will affect the economy, investing at all-time highs, and much more! Submit your Ask The Compound questions to...