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ARK Strategy

Careers aren't ladders anymore — they're portfolios. I've built mine across a $20B family office, a fintech startup, intelligence work, and my own consulting firm. ARK Strategy is one essay a week on designing a durable career in the post-AI economy.

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A McKinsey Partner told me what AI actually makes valuable

Neha Kabra sees more AI deployments in a quarter than most operators see in a career. Here's what's actually scarce.

The Recruiter Hadn’t Read My Resume. They Told Me So — Twice.

A call about a “chief of staff on steroids” role, a masterclass in candidate experience, and a genuine question for you at the end because I know something the recruiter doesn't...

Your Job Already Moved Overseas — They Just Haven't Told You Yet

AI won't take your job — global talent might. Alex Randall Kittredge and Cory Blumenfeld on offshoring, remote work, and how to become irreplaceable.

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Three people said they read my Substack. I nearly apologized.

Three people told me in person that they read my newsletter — and I was embarrassed. Why being read feels like debt — and why that instinct belongs to a dead economy.

Your job already moved to India. They just haven't told you yet.

How the same corporate offshoring playbook that emptied American factories in 1994 is now emptying American cubicles, one JPMorgan and Microsoft campus at a time.

[From the Archive] Laid Off Twice: How I Built a Portfolio Career Instead

Kintsugi, the Japanese art of mending pottery with gold.

The One Email My Boss Sent That Changed How I Think About Work Forever

There are only two times all your favourite people gather in one place: your wedding and your funeral. Here's why you should always show up — no matter the cost.

She Left BlackRock With No Plan. Four Careers Later, Here's What She Learned.

Raffaela Rein on building a portfolio career across BlackRock, Rocket Internet, CareerFoundry and BoardLens — and why the first move off the ladder is smaller than you think.

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So Who Reads "ARK Strategy" Anyway?

I analyzed 2,100 Substack subscribers and 3,379 LinkedIn followers to find where readers come from, who actually engages, and which platform drives growth.

Why a Side Hustle Is Your Best Protection Against Layoffs

The loyalty-for-security deal is dead. Here's why a side hustle is career insurance — and how a portfolio career hands you leverage before a layoff ever hits.

BlackRock → Porsche Board → AI Founder. None of It Was Planned.

From BlackRock analyst to Porsche board director to AI founder — Raffaela Rein on what actually compounds across a non-linear career, why calculated risk beats the ladder, and the first move if you're feeling the pull.

20 Million Tokens Later, I Built an App

I used Claude Code, 20 million tokens, SQLite, and Streamlit to build a working database and web app in a weekend—and learned why human judgment still matters.

The Cost of Competence: Why the Floor Is Shrinking Under White-Collar Work, and What to Stand On Instead

The AI job panic is missing the point. A three-part strategy memo on shrinking competence, the wrong shoes, and why a humanities degree may be the most undervalued asset in your career — by Alex Randall Kittredge.

Did A Humanities Degree Just Become More Valuable?

AI can summarize Foucault, imitate Woolf, and explain Kant in seconds. But the real question is whether humanistic judgment, taste, and interpretation are becoming more valuable, not less.

What I Wish Someone Had Told Me About S-Corps

I asked Claude how to start an S-Corp. It gave me the wrong New York tax address. The recovery taught me more about portfolio-career infrastructure than the tax savings ever could.

The AI Job Panic Is Missing the Point

Apollo economist Torsten Slok argues AI could expand employment through the Jevons paradox. Here’s what that means for knowledge workers, careers, and the future of professional work.

The AI Bubble: Startups Funded Before Product-Market Fit

A conversation with a funded AI startup founder revealed the clearest sign of market froth: companies raising capital before they know which urgent customer problem they're solving.

The Wrong Shoes: How a Non-Linear Career Path Got Built

A three-act story of building a non-linear, portfolio career — from hedge fund analyst to startup Chief of Staff to founder — and the framework that emerged.

I Spent an Afternoon With Founders Building the Next American Century. Here's What They Told Me.

Deep Tech NYC 2026: Materials Science, Drone Infrastructure, and the Future of American Manufacturing

Space Lasers, Tissue Samples, and the Pitch That Taught Me Where My Edge Ends

I pitched two deep-tech startups through Plug and Play — a space laser company and a biomedical tissue testing firm. I lost both. Here's what failing taught me about the real limits of portfolio careers, why transferable skills aren't the same as transferable credibility, and the diversification discount no one talks about.