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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.
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You're already following all of this. Kalshi pays you.
Governor races. Senate runoffs. Billboard charts. Celebrity news. Rotten Tomatoes scores. Kalshi has real-money markets on all of it. Every price reflects what the crowd actually thinks will happen next. If you're already following politics and culture closely, you're already doing the work. Kalshi lets you act on 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,
