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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.
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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.
GM to the Top 1% ☕
I sat in on a deal review where a rep proudly said his account was "fully AI enabled." I asked him to show me one thing the AI did on the deal that he could not have done himself.
Long pause. He pulled up a tool. He clicked around. He landed on a summary of a call he had already been on.
That was it. That was the whole transformation. A login and a summary of a meeting he attended.
💡 EXPERIMENTATION THEATER
Here is the gap nobody wants to name. As of early 2026, 89% of organizations report AI adoption. But only 24% have actually deployed agentic AI in any real workflow. 81% say they are experimenting or implementing, yet only about half of those are truly live. The distance between "we have it" and "we run on it" is enormous, and most of the market is standing in that gap calling it progress.
Buying a license is not deploying. Adding a copilot tab is not transformation. A huge share of what gets reported as AI adoption is one rep who opened a tool twice and a slide in a board deck that says the word agentic.
This matters for you because your buyer lives on the same spectrum, and they can feel where you are on it. When you actually run on AI, your prep is sharper, your questions are more specific, and your follow up references things a generic rep would never surface. When you are performing AI, you sound exactly like the 89% who adopted and the 76% who never deployed. Polished, current on the buzzwords, and indistinguishable from everyone else.
The edge in 2026 is not having AI. Almost everyone has it. The edge is being one of the 24% who actually changed how the work gets done.
🔧 THE DEPLOYMENT TEST
Find out which side of the gap you are really on.
1. The "what would break" test: If your AI tools vanished tomorrow, what in your workflow actually breaks. If the honest answer is nothing, you adopted but never deployed. Real deployment leaves a hole when you remove it.
2. Pick one workflow and go all the way: Stop sprinkling AI across ten things. Choose one, account research, deal prep, or follow up, and rebuild it entirely around AI until it genuinely runs differently. Depth beats breadth.
3. Make the output un-fakeable: Deployment shows up as specificity a generic rep cannot produce. If your AI work does not change what a buyer hears on the call, it is theater. Push until it does.
4. Measure the workflow, not the license: Track one before-and-after metric on the workflow you rebuilt. Prep time, reply rate, meeting conversion. A deployed workflow moves a number. A purchased tool moves a slide.
🎯 THIS WEEK'S HOMEWORK
Pick the one workflow you most want to run on AI. Rebuild it end to end this week so that removing the AI would actually break it. Then run it on three live accounts and compare the output to how you used to do it. If a buyer could not tell the difference, you are not done.
❓ QUESTION OF THE DAY
If your AI tools disappeared tonight, what part of your sales week would actually stop working?
Hit reply with the honest answer. I read every one.
See you tomorrow.
Edward
Founder, Morning Sales
P.S. The fastest way out of experimentation theater is a deep, repeatable system for one workflow, run by prompts you trust. I packaged the 500 prompts I use to actually deploy AI across research, prep, qualification, and follow up into one PDF. It is $27 and it turns a tool you own into a workflow you run. Grab it here: https://www.edwardgorbis.com/products/500-ai-powered-prompts-for-elite-sales-professionals