When Should You Sell Your Stocks?

Watch on YouTube ↗  |  August 26, 2026 at 19:38  |  42:37  |  The Compound News
Speakers
Ben Carlson — Director of Institutional Asset Management, Ritholtz Wealth Management
Bill Sweet — Partner & CFP, Ritholtz Wealth Management
Duncan Hill — Co-Host, The Compound

Summary

The hosts answer financial planning questions: Ben Carlson runs through ten things investors should know about stock market history and risk, Bill Sweet covers retirement account rollovers and backdoor Roth rules, and the group discusses investing lumpy variable income, family financial planning checklists, and de-risking college funds. They close by debating whether the economy is shifting from software to hardware and physical assets.

  • Ben reviews ten equity market lessons, including drawdown frequency, lumpy returns, volatility, and long-term optimism.
  • Bill advises on tax-efficient retirement rollovers and backdoor Roth IRA mechanics.
  • For variable income, Ben favors immediate lump-sum investing while Bill suggests short-term Treasury/money-market buckets for near-term needs.
  • They outline family financial planning basics such as insurance, estate documents, guardians, beneficiaries, emergency funds, budgeting, and tax planning.
  • For college savings with a five-year horizon, they recommend reducing S&P 500 risk and matching liabilities with short-term bonds.
  • The final discussion frames a possible structural shift from software to hardware, semiconductors, energy, and physical assets.
Ideas
Ben Carlson Director of Institutional Asset Management, Ritholtz Wealth Management 4:56
Stocks favor long-term optimists.
Ben argues that for someone receiving large recurring annual commission windfalls, waiting and dollar-cost averaging from cash creates mental games and cash risk; he prefers putting the entire lump sum to work immediately because repeated lump sums average out and time in the market matters more.
SPY HIGH
Bill Sweet Partner & CFP, Ritholtz Wealth Management 25:35
Use short-term Treasuries for near-term cash.
Bill argues that for lumpy variable income, the money should be divided into buckets, with near-term living and tax reserves parked in short-term Treasuries or money market funds; this creates defined monthly coupons and a self-made paycheck.
Money market fund SHY MED
Bill Sweet Partner & CFP, Ritholtz Wealth Management 33:02
Don't risk near-term college savings in stocks.
Bill argues that with only about five years until Angela's college-fund withdrawals, S&P 500 equity risk is too high because historical drawdowns have taken many years to recover; he would not keep the remaining tuition money heavily invested in stocks.
Vanguard S&P 500 HIGH
Bill Sweet Partner & CFP, Ritholtz Wealth Management 39:48
Hardware buildout favors semiconductors.
Bill argues the economy is undergoing a phase shift from the 2010s software/social cycle toward physical hardware buildout: compute requires chips, chips require power and water, and this structural infrastructure shift favors semiconductors and physical assets.
SMH MED
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This The Compound News video, published August 26, 2026, features Ben Carlson, Bill Sweet discussing SPY, Money market fund, SHY, Vanguard S&P 500, SMH. 4 trade ideas extracted by AI with direction and confidence scoring.

Speakers: Ben Carlson, Bill Sweet  · Tickers: SPY, Money market fund, SHY, Vanguard S&P 500, SMH