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The Last Time Stocks Were This Expensive Was December 1999.
"Right now, it's good. But it was in '72, '86, 2000, and 2007." - Jamie Dimon, May 2026.
The Shiller CAPE ratio just hit 42.3. The only time in 140 years it's been higher? December 1999.
Stocks can stay expensive for a long time...
It’s one metric to consider, but when your portfolio is built around the most expensive equities in modern history, what else you diversify with could really matter.
Blue-chip contemporary and post war art has shown near-zero correlation with the S&P since 1995.* Prices are largely driven by private collectors competing for a fixed supply of artwork by artists like Banksy, Basquiat, and Picasso.
Masterworks lets you invest in shares of that market.
$1.3B deployed across 500+ artworks
29 exits to date
Net annualized returns like 16.5%, 17.6%, and 17.8%, not including those unsold
*According to Masterworks data. Investing involves risk. Past performance is not indicative of future returns. See important Reg A disclosures at masterworks.com/cd.
Wall Street’s New Shopping List
Big money is rotating into a select group of stocks for the second half of 2026.
MarketBeat’s analysts tracked the move and identified 10 companies attracting fresh capital right now.
The updated 10 Best Stocks to Own in 2026 report lays out the tickers, trends, and catalysts.
AI/Tech Angle A, June - Secondary
Claude vs Gemini. GPT-7 vs Llama 5. Which AI lab ships AGI first. These are live Kalshi markets with real money on both sides, updated in real time as releases land. The person who follows model cards and tracks evals has a genuine edge here. If that's you, trade it.
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*This newsletter is designed for business owners, entrepreneurs, marketers, and professionals to keep up with the daily trends, news, tools, and opportunities that can help them grow their business and stay ahead of the competition.
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Until next time,
