
Weekly guidance on who decides your worth—and how to make sure it's you.
| Platform | Pricing | Only free issues | Publishes | Weekly | |
|---|---|---|---|---|---|
| Issues | 77 | Founded | a year ago | Last Issue | 5 days ago |
| Active | |||||

Last month I sat in on a mock negotiation with a client. President-level role. Eight-figure package over four years if the equity performs.
For forty minutes he was flawless. Commanded the business case. Handled the hard questions. Sounded...
The offer arrived at 4:52 PM on a Friday.
Warm subject line. Exclamation point. “We’re thrilled to extend...”
Then, three paragraphs down, almost apologetic: we’ll need your decision by Monday morning.
My client forwarded it to me with...
Last week I ended on a trap.
How do you know what you’re worth?
A few of you wrote in with variations on the same question: fine, but seriously—how do I know?
Here’s the harder answer.
You don’t.
And that is the point.
I noticed a YouTube comment on my appearance on Lenny’s podcast.
“You would think Jacob was this pushy shark to be a comp negotiator. But he’s so measured and balanced—a modern-life Dale Carnegie.”
I read it twice. Then a third time, and...
I was staring at an encrypted Signal thread a few days ago, facilitating a counter-scenario between an elite AI researcher and a leadership team I’m not at liberty to name.
The numbers already on the screen were deep into the eight figures...
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The writers behind this newsletter.
$1B+ in compensation lift across Fortune 500, tech, and entertainment. Most of what looks fixed usually isn't.
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