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I help people build a portfolio career in the post-AI economy. Written by a 3x chief of staff whose career spans a $20B family office, a fintech startup, intel work & now my own firm.

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Substack
PricingFreemiumPublishesTwice weekly
Issues123Foundeda year agoLast Issue5 days ago
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Latest Issues

An AI Agent Ran My Book Ads. The First Buyer Was Shopping for the Pope.

$5 a day, two weeks, nine campaigns. What an AI agent did with my Amazon book ads, and the price cut it told me to make.

Alex Randall Kittredge writes ARK Strategy, a Substack about portfolio careers at the end of the corporate ladder that...

5 days ago
2
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Nobody Holds a Town Hall to Announce They Didn't Renew My Invoice

The sentence I have heard most often from clients since I founded my company in 2021 is some version of this: “I can’t get a req approved until Q2. I can probably get a PO approved by Friday.”

A “req” is a requisition, the form that create...

12 days ago
20
6

Own the Judgment, Rent the Expertise: The T-Shaped Portfolio, Operationalized

A four-test audit for whether your skills are judgment or tasks, a script for renting expertise you don’t own, and a 90-day plan for a T-shaped career.

In August I published my conversation with Neha Kabra, and one line out of four thousan...

13 days ago
12
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Nobody Has 20 Years of AI Experience. That's the Opening.

Seven minutes into Saturday’s live, was describing the system that records every conversation he has, when he stopped mid-sentence. He had forgotten to turn on his own recording. I told him I’d send him the file.

Which is about where ever...

a month ago
33
16

A McKinsey Partner Says Cutting Junior Hires Is a 5-Year Mistake

Neha Kabra came back to test her August thesis against a September of rate hikes, jobs beats and GPT-6. It held.

Six weeks after naming the three things AI reprices inside organizations (judgment, translation and orchestration), McKinsey p...

a month ago
22
4
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  • Alex Randall Kittredge

    Your employer is not a career plan. I help millennials & gen z build portfolio careers that survive layoffs & AI. Speaker and 3x Chief of Staff: ex-$20B family office, fintech, intel, and now my own firm. Writing How Your Side Hustles Will Save You.

  • Raffaela Rein

    Board Director, Entrepreneur, Forbes Woman in Tech

  • Neha Kabra

    Business is changing faster than organisations can adapt. HumAnIzing is for enterprise leaders who care about decisions that shape complex choices across AI, technology, leadership & execution - and want to think more clearly about what comes next.

  • Cory Blumenfeld

    On a mission to help 1M founders take back their time. | 5x Founder (2 exits) | Founder of BlueMoso.com. We connect businesses with the right virtual assistants.

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