Episodes

Why Is Market Timing a Bad Idea?
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...
What Happens in a Recession?
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...
Is There a Passive Investing Bubble?
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...
Should You Pay Off Your Mortgage Before Early Retirement?
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...
Are Tariffs a Tax on Consumers?
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...
Is It Time to Buy the Dip?
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...
Is It Time to Lock In 5% Yields?
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...
Is It Time to Take Money off the Table?
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...
When Should I Sell Tesla?
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...
How Do You Compound Your Money for 50 Years?
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...
How Do I Invest in Stocks at All-Time Highs?
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...
Am I on Track for Retirement?
Dec. 4, 2024

Am I on Track for Retirement?

On episode 152 of Ask The Compound, Ben Carlson and Duncan Hill are joined by RWM CFO and Tax Specialist Bill Sweet to discuss parameters to follow when using a brokerage account, optimizing taxable and non-taxable assets, se...
Is It Too Late to Buy Bitcoin?
Nov. 27, 2024

Is It Too Late to Buy Bitcoin?

On episode 151 of Ask The Compound, Ben Carlson and Duncan Hill discuss the importance of diversification as a young investor, if younger generations are getting left behind, if it's too late to buy Bitcoin, financial plannin...
Investing a Pile of Cash in a Bull Market
Nov. 20, 2024

Investing a Pile of Cash in a Bull Market

On episode 150 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management CIO and Masters In Business Host Barry Ritholtz to discuss politics and investing, timing the sale of a house, dollar co...
Is the U.S. Government Going Broke?
Nov. 12, 2024

Is the U.S. Government Going Broke?

On episode 149 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Cullen Roche, Founder and CIO of Discipline Funds to discuss how worried we should be about government debt, how to slow down government debt movin...
How Will the Election Impact Your Taxes?
Nov. 6, 2024

How Will the Election Impact Your Taxes?

On episode 148 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Bill Artzerounian, a CFP, CPA, and Director of Tax Services at Ritholtz Wealth Management to discuss which candidate is more likely to cause econom...
How to Retire at Age 36
Oct. 30, 2024

How to Retire at Age 36

On episode 147 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Jill Schlesinger, CFP of Jill on Money to discuss reducing concentrated holdings, gold as an investment, utilizing Roth conversions, the argument f...
How to Write with Morgan Housel
Oct. 23, 2024

How to Write with Morgan Housel

On episode 146 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Morgan Housel, Partner at The Collaborative Fund and author of The Psychology of Money and Same as Ever to discuss how to produce engaging content ...
How Overvalued Is the Stock Market?
Oct. 16, 2024

How Overvalued Is the Stock Market?

On episode 145 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Callie Cox, Chief Market Strategist at RWM and author of OptimistiCallie to discuss when diversification goes too far, timing the housing market, o...
When to Sell Your Big Winners
Oct. 9, 2024

When to Sell Your Big Winners

On episode 144 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Nick Maggiulli, RWM COO and author of Just Keep Buying and Of Dollars and Data to discuss bull and bear market definitions, if small cap exposure e...
How to Spend Your Money
Oct. 2, 2024

How to Spend Your Money

On episode 143 of Ask The Compound, Ben Carlson and Duncan Hill do a speed round to discuss pursuing a CFA, shifting to long-term bonds near retirement, utilizing home equity lines of credit, what it means to be over or under...
How to Manage Your Money When Retiring Early
Sept. 25, 2024

How to Manage Your Money When Retiring Early

On episode 142 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management CFO and Head of the Tax team Bill Sweet to discuss retirement income planning, tax considerations when getting married, ...
What the Fed Rate Cut Means for Your Finances
Sept. 19, 2024

What the Fed Rate Cut Means for Your Finances

On episode 141 of Ask The Compound, Ben Carlson and Duncan Hill discuss how bond math works, the best time to refinance your mortgage, what rate cuts mean for the economy, making a career change to wealth management, and much...
Can Cash on the Sidelines Save the Stock Market?
Sept. 12, 2024

Can Cash on the Sidelines Save the Stock Market?

On episode 140 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz Wealth Management advisor, investment committee member, and estate specialist Taylor Hollis to discuss if we are in a buy-the-dip market d...