Not for Distribution

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. Get the new 14-page Portfolio Career Playbook on Etsy.

What paid gets you: one playbook a month — a specific problem solved the way I’d solve it for ...

AI is eliminating white-collar jobs faster than any technology in history. TheWorld Economic Forum projects 92 million jobs displaced by 2030. February’s jobs report just came in at -92,000 — 147,000 worse than expected.

So what do you do when the institution you built your career around decides you’re a line item to be optimized?

In this episode, Alex Randall Kittredge (ARK Strategy) and John Brewton (Operating by ...

Are knowledge workers the most at risk from AI disruption — not low-skilled workers?

In this episode of Build to Thrive, host Juan Salas-Romero is joined by Alex Randall-Kittredge (ARK Strategy) and Katie Barnes (Systems & Side Eyes) to break down why the old employment contract is broken, why mid-career corporate professionals are most vulnerable to AI displacement, and how to build a portfolio career before you’re...

ARK Strategy × Elite Leaders

Most career advice tells you to fix your mindset OR build a strategy. This conversation goes deeper: because neither one alone gets you out.

Alex Randall Kittredge (ARK Strategy) and Dennis Berry (Elite Leaders) break down the real reasons knowledge workers stay stuck: identity wrapped up in a job title, the collapse of the old corporate social contract, and the dopamine trap of social media that kills pr...

In this livestream, Alex Randall Kittredge speaks with John Brewton (Operating by John Brewton) to break down why the fractional executive model is replacing traditional consulting and corporate careers. They discuss AI-driven operational transformation, portfolio careers, pricing strategy, burnout, and the hard realities of building sovereign income streams.

Key topics:

* Fractional executive vs traditional consulting (embedded exec...

In this deep-dive conversation, European Entrepreneur Ilias Contreas joins Alex Randall Kittredge to unpack what it really takes to build, scale, exit, and restart a business across continents.

Ilias built a hospitality business from a single bar into a multi-million-dollar operation with 40+ employees in Italy, executed a strategic exit in 2024, and relocated to Costa Rica after a 4-year transition plan designed to test remote lead...

The Great Resignation Wasn’t the End — It Was the Beginning

In this Substack Live, Alex Randall Kittredge and John Bruton unpack the long tail of the Great Resignation — and why the real labor disruption may just be starting.

In 2021, nearly 4 million Americans per month quit their jobs. At the time, it felt like empowerment. Today, it looks more like a structural transition.

In this conversation, we cover:

* Why whit...

Hi everyone — Yesterday, I went live with economist John Brewton to unpack layoffs, job-loss headlines, and what the data actually measures (plus what to watch for inside your own company). Here are the key takeaways:

* Big layoff numbers often mix “newly laid off” with “still unemployed” (so the scary aggregate total isn’t the same thing as fresh cuts hitting this month).

* Challenger, Gray tracks...

This Labor Day, I spent some time with a small, brown ledger that my great-great-grandfather kept. It’s a working book (ports, ships, wages, weather) written in a neat, no-nonsense cursive hand. Gustav “William” Augusta Hanson was born January 23, 1867, in Karlshamn, Sweden. He didn’t cross the Atlantic in first class; he crossed it as crew, at the age of fifteen, two days after he was confirmed in the Luthe...

In 2017, I had the rare privilege of leading the Cambridge University sailing team to two victories that remain forever etched in my memory, and not just for the 32 pounds of silverware (more on that below).

Each instilled leadership lessons far beyond the racecourse. That year, I led our team to success against Oxford in the annual Varsity Match, and a few months later, led another crew to win the “ITUR” International ...

When people think about venture capital, they imagine pitch decks, panels, and parties. Few picture the silent hours behind a locked door, combing through compliance records, scraping registries in foreign jurisdictions, and chasing whispers of reputational risk.

Between 2019 and 2021, I served as a Senior Risk & Intelligence Analyst embedded in the venture arm of a multibillion-dollar family office. My job was simple, but not e...

Each June, LinkedIn turns into a patchwork of rainbow logos and well-meaning allyship. It’s Pride Month: a time to reflect, celebrate, and advocate. And yet, even after years of driving transformations and advising execs on how to lead with authenticity, I still found myself hesitating over one question:

Should I post about my husband this year?

The hesitation surprised me. I’ve been out for years. My identity isn’t...