Episoder
-
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 wasnât â and thatâs the whole point.
So we got on Substack Live to talk about the through-line you can only see in hindsightâŠ
The phrase I keep coming back to is the German idiom she used for Rocket Internet: âthey also just cook with waterâ. No secret ingredient. The people building hundred-million-dollar companies were working with the same chaos, and the same 24 hours, as everyone else. Once youâve seen that up close, the ladder stops looking like the only way up.
We also get into why the first move off that ladder is smaller than you think (she moonlighted, she didnât leap), why waiting for permission has quietly become a tax you canât afford to pay, and her closing advice (by way of Rick Rubin) to stop chasing a grand plan and start following the clues.
If youâre an operator staring at the next rung and feeling nothing, watch this one.
â ARK
Timestamp:
00:00 Four careers in the time most get two promotions
00:45 Meet Raffaela Rein â The AI Leadership Edge & BoardLens
01:41 The résumé: BlackRock, Rocket Internet, CareerFoundry, Porsche
02:24 The through-line you only see at 40: having no single passion
03:46 Master plan or organic? The drive to be self-employed
04:55 Why BlackRockâs ladder didnât fit
06:36 Intuition and frustration as career signals
08:44 âThey also just cook with waterâ â the German idiom
11:49 Rocketâs China bet: 0â126 cities in 6 months, then shutdown
13:28 Australia and The Iconic: same playbook, opposite result
13:54 The portfolio career as a series of bets
15:56 What the boardroom reveals (Porsche, Mutares, IU)
18:05 BoardLens + the newsletter: tooling gap meets thinking gap
20:12 Substack vs. LinkedIn: building the funnel
20:43 When does waiting for permission become a fatal tax?
23:16 Stuck mid-ladder? Start by moonlighting
25:18 Founders after 40: the Ray Kroc story
26:22 One sentence to your 25-year-old self
26:59 Look for clues, not grand plans (the Rick Rubin method)
28:15 Closing
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
AI is eliminating white-collar jobs faster than any technology in history. The World Economic Forum projects 92 million jobs displaced by 2030. Februaryâs jobs report just came in at -92,000 â 147,000 worse than expected.
So what do you do when the institution you built your career around decides youâre a line item to be optimized?
In this episode, Alex Randall Kittredge (ARK Strategy) and John Brewton (Operating by John Brewton) unpack Johnâs latest piece: The Last Employee. The First Founder â 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 â 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 â not skills â 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 youâre a Chief of Staff, a Director of Strategy, a consultant, or a knowledge worker trying to understand what comes next â this conversation is for you.
đ ARK Strategy: https://alexrandallkittredge.substack.com/subscribe
đ Operating by John Brewton:
Timestamp:
00:00 â Cold open and introductions â Alex Randall Kittredge (ARK Strategy) and John Brewton (Operating by John Brewton)
01:00 â The old playbook: grades â school â corporate â safety. Why a generation believed it.
02:30 â The death of the employment contract â and why itâs structural, not cyclical
04:45 â What a portfolio career actually looks like: W-2, fractional, consulting, Substack paid
07:00 â The compressed Industrial Revolution: Engelsâ Pause in a single decade
08:30 â Schumpeterâs creative destruction â weâre in the destruction phase, but creativity is already happening
10:00 â The WEF number: 92M displaced, 78M new roles â and why the new jobs arenât visible yet
11:00 â Honest skills audit: what AI has already made worthless (Excel macros, PowerPoint craft)
11:45 â Alexâs story from an AI demo night: the agent that vibe-coded a website instead of a deck
14:00 â Breaking down Johnâs piece â the fictitious director who lost everything and built something better
15:00 â The infrastructure flip: tools built to cut corporate costs now let one person replace a department
16:00 â Why human judgment is still the moat â the AI webinar nobody could log into
17:20 â Alexâs real-life version: solo consulting LLC, S-Corp election, active job search, straddling both worlds
19:00 â Distribution as the true differentiator when everyone has the same tools
20:30 â SEO is dead, AEO is the play: why repetition of your core terms matters for AI indexing
22:00 â The identity barrier: from âIâll never post a selfie videoâ to posting without thinking twice
24:00 â What owning your distribution actually requires â consistency, platform risk, and why you canât stop
27:30 â The NDA insight: your audience list is your customer list
29:00 â Breaking news: February jobs report â economy loses 92K jobs vs. +55K expected
30:30 â The gate is open. The question is who walks through it.
32:00 â Why now may be the right moment to start â capital is flowing even as employment contracts
33:00 â 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 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 Consulting, a strategic advisory firm for technical founders and CEOs. He mentors entrepreneurs through Oxford Entrepreneurs Network, CamEntrepreneurs, and Plug and Play Tech Center.
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.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
Manglende episoder?
-
Are knowledge workers the most at risk from AI disruption â 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 youâre 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 âidentity lagâ may be the real reason professionals struggle to make the leap.
Whether youâre a corporate employee, founder, or operator considering going fractional, this conversation will help you understand what your experience is actually worth â and how to package it.
What youâll learn:
* Why AI is eliminating full-time roles faster than most expect
* The âidentity lagâ problem holding professionals back
* Fractional vs. freelance vs. portfolio careers â key differences
* How to price and manage multiple fractional clients
* Why building in public before you need to is the real career moat
* The âentrepreneur of the selfâ 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 Whoâs most at risk from AI? Mid-career knowledge workers
08:14 The identity problem: when your whole self is one employer
09:13 âIdentity lagâ â when your self-story canât keep pace with AI
09:45 Katieâs 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 youâre a parent
20:59 AI lowers the floor to execution â and commodifies generic expertise
22:28 What AI still canât do: judgment, persuasion, human trust
23:38 AI replacing entire corporate departments (legal, finance, ops)
26:44 The âRent a Humanâ trend: AI hiring people
27:38 SHRM AI + Human Intelligence conference takeaways
29:08 Why founders resist fractional workers â and why they shouldnât
30:00 How fractional ops workers set up systems and hand off to full-timers
33:07 Fractional vs. freelance vs. portfolio careers â 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 Foucaultâs âentrepreneur of the selfâ â 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
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
ARK Strategy Ă 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 â and what to replace it with
* The âvision planâ framework Dennis uses with everyone from early-stage entrepreneurs to Fortune 500 CEOs
* Mindset vs. strategy: which comes first, and why itâs the wrong question
* How AI is forcing even non-entrepreneurs to think like entrepreneurs
* The human skills AI still canât replicate â and how to double down on them
* Why the old âschool â job â pension â retireâ path is gone and what actually replaces it
* Practical tactics: phone grayscale mode, killing notifications, the 1% daily progress rule
Whether youâre climbing inside a system or building your own, the answer starts with knowing where youâre going.
Subscribe to ARK Strategy on Substack: 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 â through layoff, burnout, or AI displacement â thereâs nothing left to stand on. The fix isnât just mindset work; itâs building an independent identity through purpose-driven action.
2. Mindset vs. Strategy: Chicken or Egg?: Dennis argues you start with a vision plan â 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 canât wait to feel ready. You build, and clarity follows.
3. The Death of the Old Social Contract: The âschool â corporate job â 30 years â pension â gold watchâ path is functionally gone. Companies lay off quarterly. AI is accelerating displacement. Dennisâs 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. Dennisâs surgeon client can be surpassed by AI in the OR â but not in the pre-op room with a terrified patient. Thatâs the moat worth building.
5. AI as Efficiency, Not Apocalypse: Dennis reframes AI through a historical lens: washing machines didnât destroy labor, they freed time for new creation. AI is the same pattern. Panic is the wrong response. Adaptation â learning what AI enables rather than what it replaces â 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: Dennisâs universal starting framework, used with every client regardless of level: write down your vision. Not because itâs 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:
* âThe goal is to never retire. The goal is just to not have to work.â â Dennis Berry
* âShort-form video is the death of all productivity.â â Dennis Berry
* âThe magic formula: action, consistency, persistence, resilience, patience.â â Dennis Berry
* âI donât fundamentally believe in the values of the thing Iâm doing day in and day out â thatâs the most dangerous type of burnout.â â Alex Randall Kittredge
* âEvery notification is off on my phone. Itâll keep you stuck exactly where you are.â â Dennis Berry
Actionable Takeaways:
* Write a vision plan â 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. Thatâs it.
* Audit your current activities: does what youâre doing right now actually move you toward your vision? If not, stop.
* Use corporate employment strategically â to learn skills â but donât build your identity around it.
Timestamp:
00:00 Introductions â 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 â knowing the difference
03:35 Mindset vs. strategy: which comes first?
04:13 The death of the "school â job â pension" path
05:28 The vision plan: Dennis's universal starting framework
06:16 Purpose alignment â 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 â values misalignment
08:58 Billions are trapped in a system that no longer exists
11:42 Why you should work in corporate â 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 â it's efficiency (the washing machine analogy)
17:59 Every technology shift follows the same arc: resistance â adoption â 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 â 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 â 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 â 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
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
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 âgold watchâ 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
* 4â6 year timeline to real autonomy
If youâre 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 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 Consulting, a strategic advisory firm for technical founders and CEOs. He mentors entrepreneurs through Oxford Entrepreneurs Network, CamEntrepreneurs, and Plug and Play Tech Center.
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 â what changed
01:36 Mass layoffs, managed attrition, and the contractorization of work
02:02 Johnâs path into fractional work: what the transition actually looks like
03:22 Fractional vs. consulting: whatâs the real difference?
05:08 Freelance vs. fractional: tasks vs. outcomes, commodity vs. scarce expertise
06:19 Large corporates vs. small business â 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 â whatâs next
10:36 Alexâs 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 â or the past? The nonlinear career path
15:01 Johnâs âGeneralist Problemâ piece and the case for multi-specialization
16:49 Polymaths: the next evolution beyond generalism?
17:06 The psychological shift required â 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 Johnâs 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 Johnâs four years of no vacation â 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 â and why this work is all heâs 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
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
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 leadership, delegation systems, and operational resilience.
This livestream covers:
* The hostile regulatory and cultural environment for entrepreneurs in Italy and the EU
* Why âif you can succeed in Italy, you can succeed anywhereâ
* The 3 business growth levers most founders ignore
* Why raising prices is the most powerful scaling strategy
* The mathematics of delegation: â3 people at 60% = 180% outputâ
* The psychology of entrepreneurial happiness
* The âCosta Rica illusionâ vs. reality
* Why âwherever you go, there you areâ 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 youâre building a portfolio career or designing location-independent income, this discussion directly aligns with the philosophy behind ARK Strategy.
___
Alex Randall Kittredge 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, a strategic advisory firm for technical founders and CEOs. He mentors entrepreneurs and startup founders through Oxford Entrepreneurs Network, CamEntrepreneurs, and Plug and Play Tech Center. 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 Iliasâs origin story: from bartender to multi-million dollar business
03:56 Opening his first bar â 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 â bureaucracy, stigma, and the social contract
09:47 âIf you can make it in Italy, you can make it anywhereâ
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 â 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 â Pricing: why raising prices filters out wrong clients and improves results
18:51 Lever 2 â Frequency: growing revenue without adding new customers
19:36 Lever 3 â Volume: why new clients compound on top of better pricing and frequency
20:35 Why 10% + 10% + 10% is not 30% â 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 â what the âsurferpreneurâ brand leaves out
22:08 Why Ilias moved to Costa Rica (hint: he wasnât escaping anything)
24:22 The right way to test a life change: do it incrementally, not impulsively
25:56 âWherever you go, there you areâ â problems that follow you across borders
28:50 Money, happiness, and founder psychology: redefining what âenoughâ 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 â 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 canât 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
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
The Great Resignation Wasnât the End â It Was the Beginning
In this Substack Live, Alex Randall Kittredge and John Bruton unpack the long tail of the Great Resignation â 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 white-collar corporate jobs are down nearly 3% since 2023
* How payroll revisions suggest employment growth effectively stalled in 2025
* Why healthcare is carrying the job market
* How AI is collapsing 8 roles into 1
* Why Excel, PowerPoint, and analyst-level work are rapidly commoditizing
* The rise of the one- or two-person $80kâ$200k business
* Why the âstable jobâ is becoming a myth
* How to think about portfolio careers in the post-AI economy
John shares a real example of using Claude Opus to replace what once required an entire departmentâs worth of analytical labor.
The implications are profound: lower costs, higher productivity â and fewer traditional roles.
John and Alex also discuss:
* Underemployment after the 2008 financial crisis
* Burnout among remaining corporate employees
* The psychological aftershock of pandemic isolation
* Creative destruction and what historically follows technological revolutions
* Whether the next five years produce mass displacement⊠or mass entrepreneurship
The core question:
If the corporate ladder isnât coming back, what replaces it?
If youâve been laid off, are stuck in a burnoutâinducing corporate role, or simply sense that the old 35âyearsâatâoneâcompany path is gone for good, this episode offers both realism and a roadmap. Youâll hear concrete examples of how to leverage AI as leverage (not a threat), why âcreatorâ is becoming a serious economic category, and how to start building a durable, postâAI career with online platforms today.
Subscribe to ARK Strategy for weekly analysis on work, power, and durable careers in the post-AI economy.
Timestamp:
00:00 Intro: Unpacking the Great Resignation and what it means today
00:41 The numbers: 3.9M quits per month, 4.5M all-time high in November 2021
01:29 Did the Great Resignation hit John's company? His firsthand experience
02:41 The 2008 financial crisis connection: underemployment and the "lost generation"
03:44 How your first job out of college sets your pay trajectory for a decade
04:12 Graduating in 2020: pandemic commencements, zoom offices, and wanting out
04:50 The soul-searching effect of lockdown isolation â what it changed for people
05:24 The Great Resignation wasn't retirement â it was industry-switching and identity searching
06:44 The technology stack that made self-employment possible: Gmail, Zoom, Substack, and more
07:40 The anxiety is real â but so is the opportunity
08:22 Great Resignation vs. today: from quitting by choice to layoffs by force
09:15 Why lives and in-person conversation matter more as AI deepfakes multiply
10:00 How to prove your expertise when everyone's using AI: do lives about your writing
10:20 A chief of staff recruiter is now filling roles where one person replaces eight
11:00 Goldman Sachs IPO teams: from 11-12 people to AI + one expert
12:02 John's Claude story: 40-minute conversation, 20 minutes of output, better Excel than ever built
13:04 The gut punch realization: entire departments reduced to one manager overseeing agents
13:47 The competitive trap â if your competitor automates first, you have to follow or lose
14:27 "Much of what I've done in my career is completely obsolete now"
15:19 The diminishing marginal returns on Excel, PowerPoint, and technical skills
15:46 Real example: executive board reports that took 10 hours now done in 30 minutes
16:19 White-collar corporate jobs down 2.9% from 2023 to 2026
16:44 The 2025 jobs data: 168,000 total jobs added â and most weren't corporate
17:07 Strip out healthcare, and job growth was basically negative
17:20 The portfolio career as the only logical response
17:34 Forced entrepreneurship: when everyone has to become an entrepreneur of the self
18:09 What does it look like in five years? 1-2 person businesses doing $80Kâ$200K
18:52 The shift from "grow followers" to "build a business and signal availability"
19:56 Alex's book: How Your Side Hustles Will Save You
20:16 The fluid line between work and non-work â and why side hustles become main hustles
22:53 Hypothetical: if AI tools existed in 2021, would people have gone back to work at all?
23:44 Can AI help us get more accurate economic data? What the Fed economists are hoping for
24:55 The BLS revised employment down by ~1M in 2024 and ~900K in 2025
25:21 The "good jobs" are disappearing â healthcare and hospitality are all that's left
25:36 Why building on Substack right now is the smart career hedge
25:48 Is "content creator" a cringe term? Alex vs. John debate
26:43 Viewing the current moment with empathy â this disruption is real and painful
27:01 Historical perspective: creative destruction eventually creates new jobs and sectors
28:04 The generation that gets caught in the middle â and what they face
28:25 Closing: where to find ARK Strategy and Operating by John Bruton
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
A deep dive into the 2026 job market slowdown, the rise of contractors, and portfolio careersâwhy companies are cutting headcount and what workers must do next, grounded in Peter Cappelliâs research on financialized labor.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
Hi everyone â 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 ânewly laid offâ with âstill unemployedâ (so the scary aggregate total isnât the same thing as fresh cuts hitting this month).
* Challenger, Gray tracks layoff announcements, not confirmed separations â and announcements can be timed around earnings/stock signaling rather than immediate headcount reduction.
* Public-company layoffs dominate the news cycle, but theyâre not the whole labor market; the private/small-business economy drives a lot of job creation.
* A major share of job losses can come from one unusual source (we discussed the outsized impact of federal-related cuts in the current numbers).
* Small businesses âstopping hiringâ matters more than most people realize because itâs where a lot of net new jobs typically come from.
* Layoffs have been normalized beyond finance â what used to feel sector-specific now shows up as standard operating procedure across more industries.
* Post-COVID taught companies they could run leaner (and some of todayâs âefficiencyâ push is downstream of those lessons).
* AI is compressing the value of certain production skills (e.g., âdeck-makingâ), while raising expectations for output and breadth.
* The career moat is shifting toward human + cross-functional skill: influence, change management, synthesis, and the ability to operate across domains.
* Early internal warning signs: hiring freezes, blocked backfills, leadership language shifting to ârunway/efficiency,â and the classic vibe shiftâmore closed-door meetings, less transparency, quieter leadership rooms.
If youâre employed and uneasy, this video is a practical lens for separating headlines from signals â and if youâre job searching, it reframes where the real opportunities and risks may be into the future.
If you want us to do more of these, reply with topics youâd like us to cover next.
And thank you Farida Khalaf, Anna Levitt, and many others for tuning into the live video with John Brewton! Join me for my next live video in the Substack app.
ARK Strategy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
You donât often get to tell a CEO, âI can save you $10.5 million,â and mean it.
This story starts in a way youâll 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 âin line with market.â MaybeâŠ.
ARK Strategy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
This Labor Day, I spent some time with a small, brown ledger that my great-great-grandfather kept. Itâs a working book (ports, ships, wages, weather) written in a neat, no-nonsense cursive hand. Gustav âWilliamâ Augusta Hanson was born January 23, 1867, in Karlshamn, Sweden. He didnât cross the Atlantic in first class; he crossed it as crew, at the age of fifteen, two days after he was confirmed in the Lutheran church. And heâs the last person in my family who immigrated to the United States. A different era, different rules; but the habitsârecord-keeping, discipline, serviceâstill ring true.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
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 âITURâ International Top Universities Regatta in Qingdao, China, against over a dozen highly skilled teams from across the world.
Sailing is a strange sport. Itâs at once brutally physical and intensely cerebral.
Many of my closest sailing friends are literally physicists, which makes sense, I supposeâŠ
Youâre navigating wind shifts, team dynamics, and your own physical and emotional limits, all in real time, often on little sleep. At times you are, quite literally, steering in the dark.
Hereâs what I learned while I was strategizing at the stern:
1. Leadership is about clarity, not control.
As the captain, I wasnât the best sailor on the team. I didnât need to be. My job was to set the tone, communicate our goals, and make sure every crew member understood their role and felt supported in it.
Before we left for China, we had barely trained together as a full team. Half of us came from different countries, with different styles and strengths. I quickly realized that micromanagement would sink us. Instead, I built the race plan, created shared language, and let each sailor bring their own excellence to the deck.
And guess what⊠It worked.
In both Portsmouth and Qingdao, it wasnât the most technically proficient crew who won âalthough all teams were very technically adeptâ it was the most cohesive.
2. Pressure reveals the truth.
The Varsity Match between Oxford and Cambridge is less a regatta than a rite of passage. The rivalry is fierce, the wind and current is shifty in the Solent, and each tack is scrutinized. Needless to say, the nerves run high.
At ITUR, the pressure was different: we were halfway across the world, jet-lagged, adjusting to strange currents and unfamiliar boats weâd never sailed before. We were racing teams from Melbourne, Moscow, Amsterdam, California and China, and each with something to prove. (I mean, who wants to travel 20+ hours, and lose?).
What I found out is that pressure has a funny way of stripping away everything thatâs not essential to success. You canât fake preparation, or discipline, or trust in your team. You either have it, or you donât. And if you donât, the wind, water, and waves will show you right away.
3. Victory isnât always loud
Iâve won and lost races by less than a few seconds. There are no stadium crowds in sailing, no replay cameras, no roaring applause. And sometimes, you finish the race not even knowing whether youâve won.
Some say thereâs no worse spectator sport than sailingâŠ
The victory in Qingdao was announced over a crackling loudspeaker after deliberations in the protest room. Just a quiet nod and a tired smile from my teammates, before being rushed by a Chinese TV crew with many, many questionsâŠ
The Varsity win was similar: a handshake, a few pints at the pub with the teams, and back to the library the next day. Oh and a thirty-two pound silver chalice:
What I learned from all this is that real wins donât need to be loud. The best ones are internal. You feel them deep down in your chest: the satisfaction of having done something hard, together as a team, and having done it well.
4. Legacy isnât what you winâitâs who you meet along the way.
Looking back, what Iâm proudest of isnât the trophies or the rankings. If leadership is about anything, itâs about forging strong relationships and leaving people better than you found them. The ocean will forget your name, but the people wonât:
Epilogue: Revisiting Qingdao
Sometimes I think back to Qingdao: the neon skyline, the dark-brown âYellow Seaâ, the intense industrial smog just before a heavy August rainstorm, and the salt spray in the air just after. We were nearly all strangers who became a team in just four days. We didnât all speak the same native language, but yet we understood each other. Time together on the water, however brief, has a way of doing that to youâŠ
And every now and then, when Iâm in a corporate boardroom or a job interview or just navigating life in New York City, I think back to those races. How calm can look like chaos. And what looks like chaos externally can be exacting, intentional and entirely deliberate.
And how, if youâre lucky, you realize that leadership isnât always about being out in front, but rather learning to trust the team thatâs standing right beside you, all while never losing touch with the feeling of the wind at your back:
If you liked this post, consider sharing it with your favorite British sailor, or subscribing for even more on leadership development, coaching high-performing teams, modern careers, and the future of work. And the odd sea shanty every now and thenâŠ
This Substack is reader-supported. If you found this helpful and to receive new posts and support my work, consider becoming a paid subscriber.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
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 easy: quietly and surgically vet early- to growth-stage companies across Series A through E. Over the course of two years, I supported diligence on over 15+ venture capital investments across AI, manufacturing, climate tech, and media.
These werenât consumer fluff plays or copycat apps. They were frontier tech companies: climate modeling platforms, linear generators for distributed energy, on-demand digital manufacturing systems, batteryless sensors, and industrial IoT security. The kind of businesses where a mistake isnât just costly, itâs existential:
The Truth About Diligence
Most diligence decks are performance theater. Theyâre packed with models, charts, and five-year plans that no founder believes will unfold as written. My work was different. I was tasked with answering three uncomfortable questions:
* Can this founder be trusted?
* Is this business what it claims to be?
* Is there any latent risk weâre going to wish we found sooner?
This meant deep background checks, political exposure screenings, and reputational analysis that went far beyond LinkedIn and Crunchbase. I reviewed litigation histories in the U.S. and abroad. I validated incorporation documents, traced IP ownership, and cross-referenced supplier relationships in regions with less-than-transparent governance standards, among other sources and methods.
Sometimes we found red flags. Other times, we found a smoking gunâŠ
Lessons from the Edge:
1. The best founders leave breadcrumbs.
The most trustworthy Founders and CEOs didnât just have clean records, they had reputational infrastructure. A track record of co-founders rejoining them, board members who vouched without prompting, vendors who spoke off the record with respect. Itâs hard to fake consistency across stakeholders. Trust, like credit, builds over time, and it compounds.
2. Markets move fast, but risk moves faster.
One company in the tech space was impressive on paper, but its co-founderâs prior startups had all declared bankruptcy and left investors holding the bag. It never made the mainstream news, but it changed our risk calculus completely. If youâre not reading between the lines, youâre already behind.
3. Due diligence is asymmetric warfare.
Founders pitch at full volume. Risk analysts work in silence. The job wasnât to âwinâ the meeting, it was to keep the fund from losing its credibility or making a bad venture bet. That required rigor, detachment, and often saying ânoâ when everyone else wanted to say âyes.â
4. Itâs not the risk you see. Itâs the risk you explain away.
The most dangerous investments werenât the ones with obvious problems, they were the ones with subtle issues investors talked themselves out of investigating. A disputed patent. A strategic partner with opaque ownership. A founderâs past role at a defunct entity with lingering liabilities. Each one is easy to dismiss. Until it isnât.
This Substack is reader-supported. To receive new posts and support my work, consider becoming a paid subscriber.
The Real Work of Venture
Today, the word âdiligenceâ gets thrown around like a formality. But in practice, itâs the last true lever of control investors have before the money leaves the building.
Good diligence isnât just about finding whatâs wrong. Itâs about articulating what might go wrong, and equipping the investment committee with eyes wide open. Itâs risk storytelling. Strategic paranoia. A final act of fiduciary fidelity in a world chasing exponential upside.
I walked away from those 15+ deals more cautious, but also more convinced: Venture is not a gamble when the diligence is honest, the work is thorough, and the team trusts its analysts to tell the truth, even when it stings. Especially when it sinks the deal.
Have a diligence war story of your own? Or want a playbook for startup red flag detection? Hit reply or leave a commentâIâm offering a venture diligence checklist for those interested in learning more.
This Substack is reader supported. Consider becoming a paid subscriber to support my continued work.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe -
Each June, LinkedIn turns into a patchwork of rainbow logos and well-meaning allyship. Itâs 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. Iâve been out for years. My identity isnât a secret⊠but LinkedIn is different. Itâs not a social network; itâs a professional broadcast channel. My audience includes private equity partners, startup founders, Fortune 100 execs. People who trust me with multi-million-dollar transformations. People who expect polish, control, discretion.
But hereâs the truth: If weâre going to talk about authenticity, leadership, and culture, then queerness belongs in that conversation too. If I can help a founder navigate their company through M&A chaos, I can also help them build a world where no one feels they have to hide their truth to succeed.
So yes, I posted about my husband this year. Not just because itâs Pride, but because visibility is leadership. And in rooms where silence is often the default, sometimes the most strategic move is to speak calmly and plainly.
I know some will see it as âtoo personalâ for LinkedIn. But I also know that someone else, maybe a rising star, or maybe a future CEO, is watching. And maybe theyâll feel a little more seen, a little more possible, because someone like them didnât edit himself out of his own professional narrative.
In the end, influence is not just what you say.
Itâs also what youâre willing to stand for.
Happy Pride folks.
This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.
Get full access to ARK Strategy at alexrandallkittredge.substack.com/subscribe
