Risk, Reward, & Record Highs

Risk, Reward, & Record Highs

From Money On Tap by Ben Brayshaw & Seth Krussman

June 11, 2026 · 56 min · Season 11 · Episode 402

About this episode

The episode discusses the implications of record high market indices and what it means for investors.

Nearly every major index is at a record high — and everyone’s asking the same question: is this the beginning of something great, or the end of something that’s gone too far?This week on Money On Tap, Ben Brayshaw and Dan Michelon take that question apart with 75 years of market history, a few statistics that genuinely surprised them, and a clear look at what a record high means for you — whether you’re decades from retirement or already drawing income.What you’ll learn: The Fidelity data showing investing at an all-time high beats investing on a random day Why a record high is usually a signal of a healthy economy, not a top A walk through 1982, 1987, 1995–1999, 2000, 2009, and 2020 Why today’s AI market looks more like 1995 than the 2000 dot-com bubble Why timing the market is a loser’s game — and why taking profits isn’t fear Sequence-of-returns risk — why the first years of retirement decide everything Buffered ETFs — staying in the market with downside guardrails Annuities with lifetime income and long-term-care riders Plus Money In The News: American financial literacy hits a 10-year low — U.S. adults answered just 47% of the TIAA Institute’s 2026 questions correctly (Yahoo…

People in this episode

Host: Ben Brayshaw

Guest: Dan Michelon

Topics covered

  • market history
  • record highs
  • investing strategies
  • financial literacy
  • AI market

Keywords

  • record highs
  • market history
  • investing
  • financial literacy
  • AI market

Mentioned in this episode

Organizations: Fidelity, Yahoo Finance, WSJ, Fox Business

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