When Will the Stock Market Crash Again?

Watch on YouTube ↗  |  August 19, 2026 at 17:47  |  35:55  |  The Compound News
Speakers
Ben Carlson — Director of Institutional Asset Management, Ritholtz Wealth Management
Duncan Hill — Co-Host, The Compound

Summary

Ben Carlson and Duncan Hill answer listener questions on whether fewer recessions mean fewer stock market crashes, planning for a parent's retirement housing gap, real estate versus levered stocks, discussing finances with aging parents, and sustainable withdrawal rates under inflation. Ben argues that stock market crashes will still occur despite fewer recessions, that real estate has structural advantages and lower volatility, and that retirement withdrawals benefit from balanced portfolios and cash buffers.

  • Fewer recessions have not eliminated bear markets; crashes remain a recurring risk.
  • A short-term bond/CD ladder can cover near-term retirement spending gaps while longer-dated target-date funds grow.
  • Real estate offers leverage, tax benefits, rental income, and lower price volatility compared with stocks.
  • Retirement withdrawal portfolios may be safer with 60/40 to 70/30 allocations and cash buffers rather than all stocks.
  • Conversations with aging parents about finances are difficult but important, with fraud and cognitive decline risks rising.
  • Inflation affects sustainable withdrawal rates, but historical impact is less dramatic than often assumed.
Ideas
Ben Carlson Director of Institutional Asset Management, Ritholtz Wealth Management 6:02
Stock market crashes will still occur.
Fewer recessions do not mean fewer stock market crashes. Historical data shows bear markets have occurred just as frequently across 20-year periods despite recessions becoming rarer, because markets are more emotional than the economy and human nature is constant. Faster information and regular money flows may shorten drawdowns, but they will not eliminate crashes.
SPY HIGH
Ben Carlson Director of Institutional Asset Management, Ritholtz Wealth Management 12:46
Bond/CD ladder plus growth fund works.
For a retiree needing to cover a specific annual spending gap, a short-term bond/CD ladder for the first several years while allowing a longer-dated target-date fund to grow is sound. It could be improved by extending the ladder to seven years and shifting from a 2020 target-date fund toward a 2035 fund for a little more equity exposure because the growth money will not be touched for six or seven years.
VTTVX MED
Ben Carlson Director of Institutional Asset Management, Ritholtz Wealth Management 18:00
Real estate offers durable leveraged appreciation.
Real estate remains attractive despite stocks' recent outperformance. It provides tangible value, local market inefficiencies, tax efficiencies, rental income, equity build-up, and bank-available leverage that stock portfolios do not get. House prices are far less volatile and rarely fall, so during the next stock market downturn housing values and rental income will probably hold up, making real estate appealing.
XLRE HIGH
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This The Compound News video, published August 19, 2026, features Ben Carlson discussing SPY, VTTVX, XLRE. 3 trade ideas extracted by AI with direction and confidence scoring.

Speakers: Ben Carlson  · Tickers: SPY, VTTVX, XLRE