“If You Can Build a Business in Italy, You Can Build One Anywhere”

Getting Laid Off Might Be the Best Thing That Happens to You in 2026

AI is eliminating white-collar jobs faster than any technology in history. The [https://www.weforum.org/press/2025/01/future-of-jobs-report-2025-78-million-new-job-opportunities-by-2030-but-urgent-upskilling-needed-to-prepare-workforces/] https://www.weforum.org/press/2025/01/future-of-jobs-report-2025-78-million-new-job-opportunities-by-2030-but-urgent-upskilling-needed-to-prepare-workforces/World Economic Forum [https://www.weforum.org/press/2025/01/future-of-jobs-report-2025-78-million-new-job-opportunities-by-2030-but-urgent-upskilling-needed-to-prepare-workforces/] 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 [https://www.linkedin.com/in/alexrandallkittredge/] (ARK Strategy) and John Brewton [https://www.linkedin.com/in/john-brewton-the-helper-strategy/] (Operating by John Brewton) unpack John’s latest piece: The Last Employee. The First Founder [https://www.operatingbyjohnbrewton.com/p/operating-storytelling-the-last-employee?triedRedirect=true] — a story about the director of strategic operations who followed every rule, got restructured anyway, and ended up building something better. What they cover: * Why the traditional employment contract is broken — not bending, broken * The portfolio career as a hedge against structural displacement * How the same tools eliminating corporate jobs are empowering solo operators * Why distribution — not skills — is the new career moat * SEO vs. AEO: how to get found as AI replaces Google search * What the February jobs report (-92,000 jobs vs. +55,000 expected) means for knowledge workers right now in February 2026. Whether you’re a Chief of Staff, a Director of Strategy, a consultant, or a knowledge worker trying to understand what comes next — this conversation is for you. 🔗 ARK Strategy: https://alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe] 🔗 Operating by John Brewton: Timestamp: 00:00 — Cold open and introductions — Alex Randall Kittredge (ARK Strategy) and John Brewton (Operating by John Brewton) 01:00 — The old playbook: grades → school → corporate → safety. Why a generation believed it. 02:30 — The death of the employment contract — and why it’s structural, not cyclical 04:45 — What a portfolio career actually looks like: W-2, fractional, consulting, Substack paid 07:00 — The compressed Industrial Revolution: Engels’ Pause in a single decade 08:30 — Schumpeter’s creative destruction — we’re in the destruction phase, but creativity is already happening 10:00 — The WEF number: 92M displaced, 78M new roles — and why the new jobs aren’t visible yet 11:00 — Honest skills audit: what AI has already made worthless (Excel macros, PowerPoint craft) 11:45 — Alex’s story from an AI demo night: the agent that vibe-coded a website instead of a deck 14:00 — Breaking down John’s piece — the fictitious director who lost everything and built something better 15:00 — The infrastructure flip: tools built to cut corporate costs now let one person replace a department 16:00 — Why human judgment is still the moat — the AI webinar nobody could log into 17:20 — Alex’s real-life version: solo consulting LLC, S-Corp election, active job search, straddling both worlds 19:00 — Distribution as the true differentiator when everyone has the same tools 20:30 — SEO is dead, AEO is the play: why repetition of your core terms matters for AI indexing 22:00 — The identity barrier: from “I’ll never post a selfie video” to posting without thinking twice 24:00 — What owning your distribution actually requires — consistency, platform risk, and why you can’t stop 27:30 — The NDA insight: your audience list is your customer list 29:00 — Breaking news: February jobs report — economy loses 92K jobs vs. +55K expected 30:30 — The gate is open. The question is who walks through it. 32:00 — Why now may be the right moment to start — capital is flowing even as employment contracts 33:00 — Close and next episode ARK Strategy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Alex Randall Kittredge [https://www.linkedin.com/in/alexrandallkittredge/] helps technical CEOs translate complex organizational challenges into strategic clarity, grounded in data, history, and human insight. With 9+ years leading transformation initiatives across Fortune 100s, PE-backed ventures, and high-growth startups, he specializes in operationalizing strategy, integrating M&A acquisitions, and designing change programs that stick. He is the founder and Managing Director of APR Strategic Consultin [https://www.linkedin.com/company/apr-strategic-consulting/]g, a strategic advisory firm for technical founders and CEOs. He mentors entrepreneurs through Oxford Entrepreneurs Network, [https://oxfordentrepreneurs.net/]CamEntrepreneurs [https://www.camentrepreneurs.com/], and Plug and Play Tech Center [https://www.plugandplaytechcenter.com/]. Kittredge holds degrees from Columbia University and the University of Cambridge, along with executive education in strategy execution and organizational leadership from Harvard Business School. He is the author of the forthcoming book, How Your Side Hustles Will Save You: Creating a Durable Career that Transcends the Corporate Ladder. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

AI Is Coming for Your Job. Your Coworkers Are Already Building the Exit.

Are knowledge workers the most at risk from AI disruption — not low-skilled workers? In this episode of Build to Thrive [https://www.buildtothrive.co/], host Juan Salas-Romero is joined by Alex Randall-Kittredge (ARK Strategy [http://alexrandallkittredge.substack.com/subscribe]) and Katie Barnes (Systems & Side Eyes [https://riseandoptimize.substack.com/?utm_campaign=profile_chips]) 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 forced to. We cover the rise of fractional work, how to unbundle your professional identity from your employer, the difference between freelance vs. fractional vs. portfolio careers, and why “identity lag” may be the real reason professionals struggle to make the leap. Whether you’re a corporate employee, founder, or operator considering going fractional, this conversation will help you understand what your experience is actually worth — and how to package it. What you’ll learn: * Why AI is eliminating full-time roles faster than most expect * The “identity lag” problem holding professionals back * Fractional vs. freelance vs. portfolio careers — key differences * How to price and manage multiple fractional clients * Why building in public before you need to is the real career moat * The “entrepreneur of the self” framework for career resilience ARK Strategy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Timestamp: 00:00 Intro & welcome 00:36 Alex introduces ARK Strategy & the post-AI career landscape 01:22 Katie Barnes introduces Systems & Side Eyes 01:50 The AI agent mishap: what went wrong with the webinar 05:08 Why the social contract of employment is broken 07:28 Who’s most at risk from AI? Mid-career knowledge workers 08:14 The identity problem: when your whole self is one employer 09:13 “Identity lag” — when your self-story can’t keep pace with AI 09:45 Katie’s fractional journey: knowing what you do vs. selling it 11:33 How to validate market demand before building your offer 13:02 The 60-second value test: no brand names allowed 16:39 Thinking in five-year career sprints & the 100-year life 18:01 Building outside your job when you’re a parent 20:59 AI lowers the floor to execution — and commodifies generic expertise 22:28 What AI still can’t do: judgment, persuasion, human trust 23:38 AI replacing entire corporate departments (legal, finance, ops) 26:44 The “Rent a Human” trend: AI hiring people 27:38 SHRM AI + Human Intelligence conference takeaways 29:08 Why founders resist fractional workers — and why they shouldn’t 30:00 How fractional ops workers set up systems and hand off to full-timers 33:07 Fractional vs. freelance vs. portfolio careers — key differences 35:11 Treating your career like an investment portfolio 37:20 How to price yourself when demand exceeds your hours 38:23 Building visibility & overcoming the identity barrier 41:14 Foucault’s “entrepreneur of the self” — now just called Tuesday 42:27 Solo founders building $5M agentized businesses 43:18 LLC vs. S-Corp: the practical path to going independent 44:54 Closing thoughts & where to find all three newsletters This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

Why High Performers Stay Stuck in Careers They've Already Outgrown

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 productivity before you even start. In this conversation: * Why tying your identity to a company is a career liability — and what to replace it with * The “vision plan” framework Dennis uses with everyone from early-stage entrepreneurs to Fortune 500 CEOs * Mindset vs. strategy: which comes first, and why it’s the wrong question * How AI is forcing even non-entrepreneurs to think like entrepreneurs * The human skills AI still can’t replicate — and how to double down on them * Why the old “school → job → pension → retire” path is gone and what actually replaces it * Practical tactics: phone grayscale mode, killing notifications, the 1% daily progress rule Whether you’re climbing inside a system or building your own, the answer starts with knowing where you’re going. Subscribe to ARK Strategy on Substack: alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe] Subscribe to Elite Leaders on Substack: Tags: career strategy, portfolio career, post-AI economy, career reinvention, knowledge worker, entrepreneur mindset, productivity, focus, Dennis Berry, Elite Leaders, ARK Strategy, Substack, how to leave corporate, career independence, AI and jobs, burnout, career pivot, vision planning, solopreneur Core Themes: 1. The Identity Trap: Both Alex and Dennis opened on the same diagnosis: too many people build their entire sense of self around a job title or company. When that job disappears — through layoff, burnout, or AI displacement — there’s nothing left to stand on. The fix isn’t just mindset work; it’s building an independent identity through purpose-driven action. 2. Mindset vs. Strategy: Chicken or Egg?: Dennis argues you start with a vision plan — a written North Star that gives you direction before you have confidence. Alex frames it as building the structural conditions (multiple revenue streams, portfolio career) that generate confidence as a byproduct. Both agree: you can’t wait to feel ready. You build, and clarity follows. 3. The Death of the Old Social Contract: The “school → corporate job → 30 years → pension → gold watch” path is functionally gone. Companies lay off quarterly. AI is accelerating displacement. Dennis’s point: not everyone is built to be an entrepreneur, but the economic environment is increasingly forcing entrepreneurial thinking on everyone regardless. 4. The Human Advantage in an AI World: Technical skills are being commoditized by AI. What remains irreplaceable: emotional intelligence, presence, persuasion, and human connection. Dennis’s surgeon client can be surpassed by AI in the OR — but not in the pre-op room with a terrified patient. That’s the moat worth building. 5. AI as Efficiency, Not Apocalypse: Dennis reframes AI through a historical lens: washing machines didn’t destroy labor, they freed time for new creation. AI is the same pattern. Panic is the wrong response. Adaptation — learning what AI enables rather than what it replaces — is the only viable strategy. 6. The Dopamine Trap: Social media platforms are engineered to hijack attention via dopamine hits (notifications, red dots, short-form video). Dennis has had all phone notifications off for 4+ years. Alex runs his devices in grayscale. Both advocate for radical focus: one task, no interruptions, consistent 1% daily progress. 7. The Vision Plan: Dennis’s universal starting framework, used with every client regardless of level: write down your vision. Not because it’s permanent, but because without a North Star, your subconscious defaults to comfort and distraction. The vision can evolve. Not having one guarantees drift. Key Quotes: * “The goal is to never retire. The goal is just to not have to work.” — Dennis Berry * “Short-form video is the death of all productivity.” — Dennis Berry * “The magic formula: action, consistency, persistence, resilience, patience.” — Dennis Berry * “I don’t fundamentally believe in the values of the thing I’m doing day in and day out — that’s the most dangerous type of burnout.” — Alex Randall Kittredge * “Every notification is off on my phone. It’ll keep you stuck exactly where you are.” — Dennis Berry Actionable Takeaways: * Write a vision plan — even a rough one. It gives your subconscious a direction to move toward instead of defaulting to distraction. * Turn off all phone notifications. * Try grayscale mode on your devices to reduce the dopamine pull of screens. * Do 1% per day on the thing that moves you toward your goal. That’s it. * Audit your current activities: does what you’re doing right now actually move you toward your vision? If not, stop. * Use corporate employment strategically — to learn skills — but don’t build your identity around it. Timestamp: 00:00 Introductions — ARK Strategy meets Elite Leaders 00:44 Why tying your identity to a job title is a career liability 01:58 Focus, productivity, and following a path not designed for you 02:42 Not everyone is wrong for corporate — knowing the difference 03:35 Mindset vs. strategy: which comes first? 04:13 The death of the "school → job → pension" path 05:28 The vision plan: Dennis's universal starting framework 06:16 Purpose alignment — the surgeon who knew at 17 vs. the ski bum who didn't 07:54 If your job doesn't align with your goal, you have to change 08:04 The most dangerous type of burnout — values misalignment 08:58 Billions are trapped in a system that no longer exists 11:42 Why you should work in corporate — just don't build your identity around it 12:15 AI is forcing entrepreneurial thinking on everyone 13:30 The human advantage AI can't replicate: EQ, presence, persuasion 14:18 Why robots won't replace surgeons in the room with terrified patients 15:27 AI isn't apocalypse — it's efficiency (the washing machine analogy) 17:59 Every technology shift follows the same arc: resistance → adoption → normal 18:40 Amazon laid off 60,000 people. Panic isn't a strategy. What's next? 19:35 The success formula: action, consistency, persistence, resilience, patience 20:34 Short-form video is the death of all productivity 21:08 How Instagram turns a 5-minute search into 4 hours of giraffe videos 22:05 Many valid paths — the only filter is: does this move me toward my vision? 23:56 Alex's 5-year career plan is obsolete because of AI 25:26 The attention economy is engineered to keep you stuck 26:07 Why most people quit at Level 2 (and what to do instead) 27:44 Your subconscious runs 90% of your behavior — and it's working against you 28:04 Dennis spent months learning Substack. He wanted to quit. He didn't. 29:03 Bezos started with a wooden door on four legs 29:41 James Clear's 1% rule — and why it actually works 30:03 Practical steps: grayscale mode, kill notifications, start the vision plan 31:02 Dennis hasn't had a phone notification in 4 years 32:05 Wrap-up and where to find both newsletters This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

Why the Fractional Executive Is the New Safety Net for Corporate Refugees

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 execution vs advisory) * How fractional operators build real systems (inventory, receivables, HR, AI ops) * Why diversification beats the “gold watch” career model * AI transformation demand from CEOs and operators * Pricing strategy: undercharge, overdeliver, then scale * Burnout: exhaustion vs values misalignment * The psychological shift from employee to sovereign operator * 4–6 year timeline to real autonomy If you’re a founder, operator, executive, or corporate professional navigating layoffs, managed attrition, or AI disruption, this is a tactical discussion on how to reposition your career as a portfolio of assets, not a single paycheck. Subscribe to ARK Strategy for weekly essays on modern work, power, and career strategy. Alex Randall Kittredge [https://www.linkedin.com/in/alexrandallkittredge/] helps technical CEOs translate complex organizational challenges into strategic clarity, grounded in data, history, and human insight. With 9+ years leading transformation initiatives across Fortune 100s, PE-backed ventures, and high-growth startups, he specializes in operationalizing strategy, integrating M&A acquisitions, and designing change programs that stick. He is the founder and Managing Director of APR Strategic Consultin [https://www.linkedin.com/company/apr-strategic-consulting/]g, a strategic advisory firm for technical founders and CEOs. He mentors entrepreneurs through Oxford Entrepreneurs Network, [https://oxfordentrepreneurs.net/]CamEntrepreneurs [https://www.camentrepreneurs.com/], and Plug and Play Tech Center [https://www.plugandplaytechcenter.com/]. Kittredge holds degrees from Columbia University and the University of Cambridge, along with executive education in strategy execution and organizational leadership from Harvard Business School. He is the author of the forthcoming book, How Your Side Hustles Will Save You: Creating a Durable Career that Transcends the Corporate Ladder. Timestamp: 00:00 Intro: Why the fractional executive is the new safety net 01:00 The death of the 30-year career — what changed 01:36 Mass layoffs, managed attrition, and the contractorization of work 02:02 John’s path into fractional work: what the transition actually looks like 03:22 Fractional vs. consulting: what’s the real difference? 05:08 Freelance vs. fractional: tasks vs. outcomes, commodity vs. scarce expertise 06:19 Large corporates vs. small business — two different fractional markets 07:30 How the fractional CFO model expanded into COO, CMO, HR, and beyond 08:41 Why senior executives would be bored working full-time at a small company 10:10 Fractional roles are moving down the value chain — what’s next 10:36 Alex’s experience: when clients want to hire you full-time and you have to say no 11:40 The generalist vs. specialist debate in the AI era 13:19 Sovereignty through scarcity: the fractional executive as their own allocator 14:00 Is the generalist the future — or the past? The nonlinear career path 15:01 John’s “Generalist Problem” piece and the case for multi-specialization 16:49 Polymaths: the next evolution beyond generalism? 17:06 The psychological shift required — stop asking permission to have multiple identities 17:55 Treating your career like a portfolio: compounding assets vs. climbing a ladder 18:30 The pricing mistake most fractional executives make 19:03 John’s contrarian take: price low, get reps, build a reputation for over-delivering 20:37 When and how to raise your prices as demand grows 21:32 Two types of burnout: exhaustion vs. values misalignment 22:57 John’s four years of no vacation — what extreme work demands look like in practice 25:57 The economic case: single employer as concentration risk 26:28 Why fractional work makes you anti-fragile 27:10 Pricing power as a function of scarcity and demand 28:03 The hard truths: brand clarity, emotional resilience, and financial runway 29:44 John on growing up entrepreneurial — and why this work is all he’s ever known 30:47 What to actually expect when making the leap: hours, uncertainty, and grace 32:09 Closing: where to find ARK Strategy and Operating by John Bruton This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

“If You Can Build a Business in Italy, You Can Build One Anywhere”

In this deep-dive conversation, European Entrepreneur Ilias Contreas [https://substack.com/profile/242444637-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 leadership, delegation systems, and operational resilience. This livestream covers: * The hostile regulatory and cultural environment for entrepreneurs in Italy and the EU * Why “if you can succeed in Italy, you can succeed anywhere” * The 3 business growth levers most founders ignore * Why raising prices is the most powerful scaling strategy * The mathematics of delegation: “3 people at 60% = 180% output” * The psychology of entrepreneurial happiness * The “Costa Rica illusion” vs. reality * Why “wherever you go, there you are” applies to founders * How to build a business that supports your life, not consumes it We also examine the operational difference between strategic work and reactive work, and why many entrepreneurs stay trapped because they refuse to temporarily earn less in order to scale more. This conversation is for founders, operators, digital nomads, hospitality entrepreneurs, and anyone rethinking work in 2026. If you’re building a portfolio career or designing location-independent income, this discussion directly aligns with the philosophy behind ARK Strategy. ___ Alex Randall Kittredge [https://www.linkedin.com/in/alexrandallkittredge/] helps professionals building careers in a system not designed for them. He is a graduate of Columbia University and the University of Cambridge and began his career as an intelligence analyst before moving into Chief-of-Staff and leadership roles across hedge funds, private equity, and industrials. After leading business transformations and M&A integrations, he now helps founders, CEOs, and investors align people, performance, and culture. He is the founder of APR Strategic Consulting [https://www.linkedin.com/company/apr-strategic-consulting/?], a strategic advisory firm for technical founders and CEOs. He mentors entrepreneurs and startup founders through Oxford Entrepreneurs Network [https://oxfordentrepreneurs.net/], CamEntrepreneurs [https://www.camentrepreneurs.com/], and Plug and Play Tech Center [https://www.plugandplaytechcenter.com/]. He is the author of the forthcoming book, How Your Side Hustles Will Save You: Creating a Durable Career that Transcends the Corporate Ladder. Timestamp: 00:00 Intro: Startup-grade growth without losing your life 00:41 Ilias’s origin story: from bartender to multi-million dollar business 03:56 Opening his first bar — the accidental path into entrepreneurship 04:19 Scaling to 40+ employees and millions in revenue 04:31 Discovering Costa Rica and deciding to leave it all behind 05:44 The real risk of remote ownership: running a company from the other side of the world 06:30 How he did it: three to four years of testing before fully relocating 07:16 Selling his stake in 2024 and starting over from zero 07:51 Entrepreneurship in Italy vs. America — bureaucracy, stigma, and the social contract 09:47 “If you can make it in Italy, you can make it anywhere” 10:19 Did he sell the business when he moved to Costa Rica? The full answer 11:00 The 12 Strategic Moves framework: what works for solopreneurs vs. funded startups 11:32 Finding the bottleneck — and planning for the future bottleneck 14:21 Testing as honesty: tracking numbers instead of just doing what you like 15:10 The three levers that beat inflation: pricing, frequency, volume 16:19 Lever 1 — Pricing: why raising prices filters out wrong clients and improves results 18:51 Lever 2 — Frequency: growing revenue without adding new customers 19:36 Lever 3 — Volume: why new clients compound on top of better pricing and frequency 20:35 Why 10% + 10% + 10% is not 30% — the math of exponential growth 20:58 Alex on pricing his own advisory work and walking away from wrong-fit clients 21:38 The illusions of moving to paradise — what the “surferpreneur” brand leaves out 22:08 Why Ilias moved to Costa Rica (hint: he wasn’t escaping anything) 24:22 The right way to test a life change: do it incrementally, not impulsively 25:56 “Wherever you go, there you are” — problems that follow you across borders 28:50 Money, happiness, and founder psychology: redefining what “enough” looks like 29:27 Why chasing more money is probably the wrong goal 30:41 Making your first priority in the morning the thing you actually love 32:06 The psychology definition of happiness: the distance between ideal self and actual self 33:18 The dangerous belief about work Ilias held in his 20s — and what it cost him 34:30 Urgent vs. important: the time allocation shift that changed everything 35:57 Time is the only resource money can’t buy more of 36:27 The one uncomfortable decision to make in the next 30 days 37:55 Why delegating at 60% still beats doing it all yourself 39:48 Pura Vida as a management philosophy: letting go of perfection 41:26 Closing: where to find Ilias and ARK Strategy This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit alexrandallkittredge.substack.com/subscribe [https://alexrandallkittredge.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]