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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.
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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 few years into selling, I had the best activity quarter of my life. I had wired up automation across my whole motion. My outbound volume went up roughly six times. I was sending more in a week than I used to send in two months.
My manager loved the dashboard. Green everywhere. I loved it too.
Then the quarter closed and my number was down. Not flat. Down. I sat in my car in the parking garage and could not explain to myself how I worked that much harder and finished behind.
💡 THE NUMBER I STOPPED LOOKING AT
There is a benchmark making the rounds this year that put words to what happened to me. Across sales teams, per-rep outbound volume climbed from around 1,150 touches to 7,400 once AI got involved. In the same shift, raw reply rates fell from 4.7% to 2.9%. And here is the seductive part. Cost per qualified opportunity dropped from $487 to $224.
Read that last number again, because it is the trap. On a spreadsheet, my quarter looked like a win. Cost per opp was down. Efficiency was up. Every metric a finance team loves was pointing the right direction.
But I do not get paid on cost per opp. I get paid on closed revenue. And while my efficiency metrics glowed, the actual humans on the other end were replying less, trusting less, and remembering me less. I had optimized the cheap part of the funnel and starved the expensive part, the relationships that actually close.
The machine made each touch cheaper. It also made each touch worth less. I only watched the first half of that sentence.
🔧 THE PAY-ME METRIC FRAMEWORK
Pick the metric that matches your comp plan, not your dashboard.
1. Find your pay-me metric: It is the last number before commission. For most reps that is closed-won revenue per qualified opportunity, not activity, not cost per opp, not sends. Write it on a sticky note where you can see it.
2. Demote the vanity metrics: Activity, sends, and cost per touch are inputs. They are allowed to inform you. They are not allowed to congratulate you. Move them off your primary dashboard.
3. Audit the expensive half: Spend one hour reviewing only your live deals in the back half of the funnel. Reply quality, champion strength, decision-maker access. That is where the money actually moves, and it is the half automation cannot do for you.
4. Trade ten touches for one conversation: Every week, cut ten automated touches and reinvest that time into one real human interaction on a deal that matters. Track which one moves your pay-me metric.
🎯 THIS WEEK'S HOMEWORK
Write down the single metric your commission is actually calculated from. Then look at your dashboard and count how many of the numbers on it have nothing to do with that one. If your screen is full of vanity, rebuild it this week around the number that pays you.
❓ QUESTION OF THE DAY
What is the one metric your comp is actually based on, and is it the number you look at first every morning?
Hit reply and tell me. I read every one.
See you tomorrow.
Edward
Founder, Morning Sales
P.S. The quarter I described cost me a number I cannot get back, and the fix was not a tool. It was someone forcing me to look at the right metric. If you want that lens on your own pipeline, I run a small number of 1:1 AI sales coaching sessions where we rebuild your week around the number that pays you. It is $500 and we work on your real deals. Reply to this email if you want one of the slots.