Not for Distribution

Last week I wrote about Raffaela Rein : BlackRock analyst, Rocket Internet operator across three Asian markets, the founder who sold CareerFoundry to private equity, Porsche board director, and now building BoardLens. From the outside it looks like a master plan. It wasn’t — and that’s the whole point. So we got on Substack Live to talk about the through-line you can only see in hindsight… The phr...

AI is eliminating white-collar jobs faster than any technology in history. The World 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 Br...

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 portfo...

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 dopami...

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 v...

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 transiti...

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,...

A deep dive into the 2026 job market slowdown, the rise of contractors, and portfolio careers—why companies are cutting headcount and what workers must do next, grounded in Peter Cappelli’s research on financialized labor. Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe

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 trac...

You don’t often get to tell a CEO, “I can save you $10.5 million,” and mean it. This story starts in a way you’ll recognize: a mid-sized company with roughly 2,000 employees, a healthy revenue line, and a quiet hemorrhage nobody wanted to look at too closely. Annual voluntary attrition: ~22%. On paper, that was “in line with market.” Maybe…. ARK Strategy is a reader-supported publication. To recei...

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 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 t...

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 offi...

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...