Episodes
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...
June 25, 2025
How Do Young People Get Rich?
On episode 177 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth CEO and TCAF Host Josh Brown to discuss how to get rich without crypto, how RWM invests, reaching retail investors, and much more! ...
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...