In partnership with
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.
GM to the Top 1% ☕
A founder told me last month he was about to replace half his SDR team with an AI stack. He had the deck built. He had the savings modeled. He just wanted a gut check before he pulled the trigger.
I asked him one question. Have you seen the per-seat pipeline numbers on fully automated pods.
He had not. He pulled them that night. He did not send the layoff email.
💡 THE NUMBER THAT KILLED THE LAYOFF EMAIL
Here is what the comparative data on 2026 sales pods actually shows, and it is the opposite of the pitch every vendor is running. Teams were measured in three configurations. Human only pods produced about 187,000 dollars in pipeline per seat per month. Pure AI pods produced about 94,000. And hybrid pods, a human with AI leverage, produced about 278,000.
Sit with the order of that. The fully automated pod, the one the whole market is racing toward, was the worst performer in the building. It made roughly a third of what the hybrid did and barely half of what unaided humans did.
This lines up with two other findings from the same year. Sellers who effectively partner with AI are 3.7 times more likely to hit quota than those who merely have access to the same tools. And AI equipped teams posted 77% attainment against a 69% miss rate for teams with no tooling at all.
The pattern is not subtle. AI is a lever, and a lever does nothing without a human pushing on it. Remove the human and you do not get efficiency. You get the cheapest, worst pipeline in the company.
🔧 THE LEVERAGE STACK
Build the hybrid pod that wins instead of the automated one that does not.
1. Put the human on judgment, the AI on volume: Let the model do research, drafting, list building, and summarizing. Reserve every judgment call, qualification, multithreading, message strategy, for the person. That split is the 278,000 dollar configuration.
2. Make AI brief you, not replace you: Before every account, have AI produce a one page intelligence brief. You walk in informed in two minutes instead of twenty. You still walk in.
3. Audit one automated touch a day: Read one message your stack sent on its own. If you would not have signed your name to it, your AI is producing the 94,000 dollar pipeline. Fix the prompt, not the headcount.
4. Protect the relationship layer: The expensive, high-converting work is human to human. Guard it. Never let a tool own a champion relationship or a closing conversation.
🎯 THIS WEEK'S HOMEWORK
Map your own motion into the three pod types. Which stages are pure AI, which are human only, and which are true hybrid. Wherever you find a pure AI stage feeding a revenue moment, put a human judgment checkpoint back in this week and watch what it does to quality.
❓ QUESTION OF THE DAY
Where in your funnel have you quietly let AI run without a human checkpoint, and what is it costing you?
Hit reply with the stage. I read every one.
See you tomorrow.
Edward
Founder, Morning Sales
P.S. Building the hybrid pod that produces 278,000 a seat is a skill, not a software purchase, and it is exactly what I teach in the AI-Native Sales Leader course on Maven. We cover the human-AI split, the brief system, and the leverage stack stage by stage. If you lead a team and want them on the winning side of these numbers, the course is here: https://maven.com/edward-gorbis/the-ai-native-sales-leader