How Do You Sell Your Stocks Without a Big Tax Hit?
Speakers
Bill Sweet
— Partner & CFP, Ritholtz Wealth Management
Ben Carlson
— Director of Institutional Asset Management, Ritholtz Wealth Management
Summary
The Compound's Ben Carlson, Duncan Hill, and Bill Sweet answer listener questions on managing concentrated stock positions with large tax liabilities, determining retirement readiness, lessons from aging parents, whether cash can replace bonds, preventing panic selling, and investing advice for a 16-year-old.
- They advise paying taxes to rebalance stock-heavy portfolios in high-tax states, as ignoring risk can be costlier.
- Ben Carlson suggests the S&P 500 is likely to end the year higher, based on historical averages.
- Long-duration bonds like TLT are called too volatile and not worth the risk; cash or short-term instruments are preferred.
- Cash provides behavioral comfort but may underperform bonds over long horizons, depending on the rate environment.
- For panicked clients, a written plan and a trend-following circuit-breaker strategy can help more than verbal reassurance.
- A 16-year-old investor should focus on simplicity, automation, and letting compounding work without unnecessary tinkering.
Ideas
Pay taxes to de-risk stock-heavy portfolios.
For retired investors in high-tax states sitting on large unrealized stock gains, it's better to incur capital gains taxes and sell to rebalance to a less risky allocation, because the market could correct and eliminate the gains; don't let tax consequences drive portfolio decisions, you've won the game and should pay taxes to secure your retirement.
Avoid long-duration Treasury bonds (TLT).
Long-duration Treasury bonds (like TLT) are too volatile and do not compensate investors for that risk; better to avoid them and use cash or short-term instruments, while taking risk in equities where you are paid for volatility.
Up Next
This The Compound News video, published June 10, 2026, features Bill Sweet, Ben Carlson discussing SPY, VTI, TLT. 2 trade ideas extracted by AI with direction and confidence scoring.
Speakers: Bill Sweet, Ben Carlson · Tickers: SPY, VTI, TLT