
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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GM to the Top 1% ☕
A CRO pulled me aside after a QBR last week and said the quiet part out loud. His team had more tools, more data, and more automation than any roster he had ever run. And his quota attainment was the lowest of his career.
He wanted to blame the market. Rates, budgets, longer cycles, the usual list.
Then he showed me the board. Every rep had a copilot. Every sequence was AI assisted. Activity was the highest it had ever been. And the number kept sliding anyway.
💡 THE QUOTA PARADOX
Here is the stat that should be on every sales leader's wall this quarter. General AI adoption across sales orgs hit 89%. In the same window, quota attainment fell to roughly 42%, down from 53% in 2022 and 46% just last year. 74% of B2B sales leaders now say closing deals has gotten harder.
The instinct is to read those two numbers as a contradiction. We bought all this AI, so why are we worse?
They are not a contradiction. They are cause and reveal.
For two decades, activity hid the real problem. If your pipeline was thin, you sent more. If your number was soft, you dialed more. Volume was the bandage that let weak judgment survive. AI just made volume free, infinite, and identical across every rep in your market. So the bandage stopped working, and the thing it was hiding got exposed for everyone to see.
AI did not lower your attainment. It removed your last excuse. The reps still hitting quota are not the ones who automated the most. They are the ones who were never relying on volume to begin with.
🔧 THE JUDGMENT AUDIT
Stop asking what your AI can automate. Start asking what it just exposed.
1. Separate effort from outcome: Pull your activity numbers and your win rate side by side for the last two quarters. If activity climbed and win rate did not, you do not have a volume problem. You have a targeting and qualification problem that volume was hiding.
2. Re-rank your pipeline by truth, not hope: Take every open deal and ask one question. Have they told me what happens if they do nothing. If you cannot answer that for a deal, it is not real pipeline. It is activity wearing a suit.
3. Reinvest the time AI gave you: Automation handed you hours back. Most reps spent them sending more. Spend them instead on the three accounts where a human judgment call moves the deal. Multithread one. Rebuild one champion. Kill one zombie.
4. Measure judgment, not motion: Track win rate per qualified opportunity this quarter, not touches per day. That single swap changes what your week optimizes for.
🎯 THIS WEEK'S HOMEWORK
Open your closed-lost from the last 90 days and find the three deals that hurt the most. For each one, write the single judgment call you got wrong. Wrong champion, wrong timing, wrong qualification, wrong room. Not the market. The call. If you cannot do that exercise honestly, that is the work this week.
❓ QUESTION OF THE DAY
If you stripped every automation out of your week, would your number go up or down?
Hit reply with your honest answer. I read every one.
☕ Share Morning Sales & Earn Rewards
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See you tomorrow.
Edward
Founder, Morning Sales
P.S. The reps who survived the attainment drop did it with better judgment at every stage, and judgment is a thing you can systematize. I packaged the 500 prompts I actually use to qualify harder, multithread faster, and pressure test every deal into one PDF. It is $27 and it pays for itself on the first zombie deal it kills. Grab it here: https://www.edwardgorbis.com/products/500-ai-powered-prompts-for-elite-sales-professionals

