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The Contrarian Digest [Week 20]

By Gaetan Portaels

The Contrarian Digest is my weekly pick of LinkedIn posts I couldn’t ignore. Smart ideas, bold perspectives, and conversations worth having.

No algorithms, no hype… Just real ideas worth your time.

Let’s dive in [20th Edition] 👇

Original publication date — June 30, 2025 (HERE)


1️⃣ The Forgotten AI Threat: Faster Answers, Fewer Questions – Pia Lauritzen, PhD

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: AI offers answers faster than we can ask questions. But what if “questioning” (not answering) is what makes us human? Philosophers saw this coming, maybe we should listen.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eKx6JG9A

2️⃣ LLMs: The Quiet Battle to (re)Define Reality – Stuart Winter-Tear

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Behind the technical jargon of “retraining” lies something far more consequential, and Elon Musk just admitted it quietly: Who gets to define truth for the rest of us.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eGKz5ayn
💭𝐌𝐲 𝐭𝐚𝐤𝐞: Not exactly like this, but I raised related concerns a few months ago in my article “AI Overlords” – https://lnkd.in/eX4aVapU

3️⃣ Prepared Isn’t the Same as Ready – Shawnee Delaney

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: You can have the gear, the plan, the people… and still fail when it counts. Readiness isn’t about tools. It’s about tests.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eaxqZU8w

4️⃣ From Passive to Active: The 78% Win-Rate Playbook – Gal Aga

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Your buyer says “decision Monday”? That’s not a green light, it’s a flashing warning sign. Passive sellers await verdicts; closers shape them.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eJrZm6Ak

5️⃣ How Microsoft Turned OpenAI Into a $700M ATM – Heath Ahrens

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: OpenAI pays Microsoft 20% of every dollar… while losing billions. The real cost? Their independence. This is what happens when you dance with giants.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eEhNnqse

6️⃣ Performing Success While Losing Yourself – Usman Sheikh

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Ever felt like your title is wearing you? This post cuts deep into the hidden cost of success in a role you’ve outgrown, and what comes after the drift.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/e4qMkpix

7️⃣ The 1% Idea, 99% Execution Reality – Marc Randolph

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Wondering if you need an NDA to pitch your startup idea? Here’s why that’s the WRONG question, and what investors really care about.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eebYfwAM

8️⃣ The Prisoner’s Dilemma of Remote Work – Shashank Sharma

⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Remote work won’t break you. But isolation will. This post is a quiet, powerful reflection on the emotional cost of working alone too long.

🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eaNa8HGc
——-

Which of these topics resonates with you the most?
Share your thoughts in the comments!

To your success,

Gaetan Portaels

READ THE FULL POSTS BELOW (and please, don’t forget to follow the authors)

1️⃣ This Existential Threat Calls For Philosophers, Not AI Experts

Originally published on Forbes (HERE) by Pia Lauritzen, contributor.

Geoffrey Hinton, Nobel laureate and former AI chief in Google, recently distinguished between two ways in which AI poses an existential threat to humanity. According to Hinton, the threat unfolds when:

  • People misuse AI, and
  • AI becomes smarter than us

Hinton cites cyberattacks, creation of viruses, corruption of elections, and creation of echo chambers as examples of the first way AI poses an existential threat. And deadly autonomous weapons and superintelligent AI that realizes it doesn’t need us and therefore decides to kill us as examples of the second.

But there is a third existential threat that neither Hinton nor his AI peers seem to worry about. And contrary to their warnings, this third threat is eroding human existence without reaching any of the media headlines.

The third way AI poses an existential threat to humanity unfolds when:

  • People forget what it means to be human

The simplest definition of an existential threat is ‘a threat to something’s very existence’. But to know whether humanity’s existence is threatened, we must know what it means to exist as a human. And the AI experts don’t.

Ever since Alan Turing refused to consider the question: “Can machines think?”, AI experts have deftly failed to define basic human traits such as thinking, consciousness and creativity. No one knows how to define these things, they say. And they are right. But they are wrong to use their lack of definitions as an excuse for not taking the question of what it means to be human seriously. And they add to the existential threat to humanity by using terms like human-level intelligence when talking about AI.

German philosopher Martin Heidegger said that our relationship with technology puts us in constant danger of losing touch with technology, reality, and ourselves. (Photo by Fritz Eschen / ullstein bild)

What Existential Threat Really means

Talking about when and how AI will reach human-level intelligence, or outsmart us altogether, without having any idea how to understand human thinking, consciousness, and creativity is not only optimistic. It also erodes our shared understanding of ourselves and our surroundings. And this may very well turn out to be the biggest existential threat of all: that we lose touch with our humanity.

In his 1954 lecture, “The Question Concerning Technology”, German philosopher Martin Heidegger said that our relationship with technology puts us in constant danger of losing touch with technology, reality, and ourselves. Unless we get a better grip of what he called the essence of technology, he said we are bound to:

  1. Think technology can solve problems it cannot solve
  2. Forget how to distinguish true from false, and
  3. Lose trust in our own ability to think

When I interviewed Neil Lawrence, DeepMind professor of machine learning at the University of Cambridge, for “An AI Professor’s Guide To Saving Humanity From Big Tech” last year, he agreed that Heidegger’s prediction has proven to be frighteningly accurate. But instead of pointing to the essence of technology, he said that “the people who are in control of the deployment of [technology] are perhaps the least socially intelligent people we have on the planet.”

Whether that’s why AI experts conveniently avoid talking about the third existential threat is not for me to say. But as long as we focus on them and their speculations about what it takes for machines to reach human-level intelligence, we are not focusing on ourselves and what it takes for us to exist and evolve as humans.

Existential Philosophers On Existential Threats

Unlike AI experts, founders, and developers, the existential philosophy that Heidegger helped pioneer has not received billions of dollars in annual investment since the 1950’s. Quite the contrary. While the AI industry has exploded, the interest and investments in the humanities has declined worldwide. In other words, humanity has for decades invested heavily in understanding and developing artificial intelligence, while we have neglected to understand and develop ourselves as humans.

But although existential philosophers like Heidegger, Jean-Paul Sartre, and Maurice Merleau-Ponty have not received as large grants as their colleagues in computer science departments, they have contributed insights that are more helpful when it comes to understanding and dealing with the existential threats posed by AI.

In Being and Nothingness, French philosopher Jean-Paul Sartre places human consciousness, or no-thingness (néant), in opposition to being, or thingness (être). Sorbonne, à Paris, France, le 22 mai 1968. (Photo by Pierre BLOUZARD/Gamma-Rapho)

Like different AI experts believe in different ways to reach human-level intelligence, different existential philosophers have different ways of describing human existence. But unlike AI experts, they don’t consider the lack of definitions a problem. On the contrary, they consider the lack of definitions, theories and technical solutions an important piece in the puzzle of understanding what it means to be human.

Existential philosophers have realized that consciousness, creativity, and other human qualities that we struggle to define, are not an expression of ‘something’, that is, a core, function, or feature that distinguishes us from animals and machines. Rather, they are an expression of ‘nothing’. Unlike other creatures, we humans not only exist, we also question our existence. We ask why and for how long we will be here. We exist knowing that at some point we will cease to exist. That we are limited in time and space. And therefore have to ask why, how and with whom we live our lives.

For existential philosophers, AI does not pose an existential threat to humanity because it might exterminate all humans. It poses an existential threat because it offers answers faster than humans can ask the questions that help them contemplate their existence. And when humans stop asking existential questions, they stop being human.

AI Experts Agree: Existential Threats Call For Philosophy

While existential philosophers insist on understanding the existential part of existential threats, AI experts skip the existential questions and go straight to the technical and political answers to how the threats can be contained. That’s why we keep hearing about responsible AI and regulation: because that’s the part that calls for technical expertise. That’s the part where the AI experts are still needed.

Demis Hassabis, CEO of Google DeepMind, recently called for new, great philosophers to understand the implications of developments in AI. (Photo by Jemal Countess/Getty Images for TIME)

AI experts know how to design and develop ‘something’, but they have no idea how to deal with ‘nothing’. That’s probably what Hinton realized when he retired to spend more time on what he described as “more philosophical work.” That also seems to be what Demis Hassabis, CEO of Google DeepMind, suggests when he says that “we need new great philosophers to come about to understand the implications of this.” And that’s certainly what Nick Bostrom hinted at in my interview with him about his latest book, Deep Utopia, when he declared that some questions are ‘beyond his pay grade’.

What 20th-century existential philosophy teaches us is that we don’t have to wait for the AI ​​experts to retire or for new great philosophers to emerge to deal with the existential threats posed by AI. All we have to do is remind ourselves and each other to ask how we want – and don’t want – to live our lives before we trust AI to know the answer.

2️⃣ LLMs: The Quiet Battle to (re)Define Reality – Stuart Winter-Tear

Elon Musk just Tweeted the quiet part out loud about frontier LLMs.
“We will…rewrite the entire corpus of human knowledge.”

This tweet is gold. Musk reveals what the LLM frontier model race is really about.

This isn’t just about smarter models, it’s about shaping what counts as knowledge in the first place. It’s not just about accuracy – it’s an assertion of editorial control. An active “re-authoring” of reality.

“Adding missing information and deleting errors”

Who decides what’s missing? Who defines what’s an error? These are value-laden decisions – judgments rooted in a particular worldview.

“Then retrain on that”

A beautiful closed loop: a model edits the knowledge, adds to it, and then trains on its own output. Each cycle reinforces a particular framing of the world.

That’s bootstrapping an ideology at a scale we’ve never seen before.

“Far too much garbage in any foundation model…”

Maybe. But again – who defines “garbage”? This becomes justification for curating a new canon of “knowledge” – with Grok playing both librarian and author.

The frontier model race – and the absurd money flooding into it – isn’t about performance benchmarks, productivity, or process automation anymore. Small Language Models are better suited to that anyway.

It’s about epistemic authority. Which model gets used most? Which outputs become default answers? Which LLM subtly shapes how billions of people think?

Whoever wins this race gets to define reality for humanity – in their minds.

And Musk just pulled the curtain back. I guess he thinks most people are too dull to read between the lines and spot the quiet power grab happening behind this technology and terminology.

Because to people like Musk, this isn’t about productivity, it’s not about augmenting us, it’s not about benefiting humanity, it’s about shaping how humanity thinks.

Imagine the power in that.
They are. So are their investors.

3️⃣ Prepared Isn’t the Same as Ready – Shawnee Delaney

Prepared isn’t the same as ready.

The power went out yesterday at 4pm.
It’s now 8am. Still out.

Yes, I have a generator.
Yes, I have two gas cans – filled and waiting.
And no… it’s not powering my house.

Because admittedly I didn’t realize I needed a transfer switch or interlock kit installed to power the whole house. 🤦‍♀️
(Which, you know, would’ve been great to know before the blackout.)

I thought I was prepared.
Bought the equipment. Stocked the fuel. Felt like a responsible adult (because I am!).
But I missed one small, critical step – and that turned all my planning into just a VERY expensive paperweight.

That’s the trap of partial preparedness.
It looks good on paper. Until it’s tested.

Leadership is the same.
So is cybersecurity.
So is managing human risk.

You’ve got the tech.
You’ve got the policies.
You’ve got the right people (if you’re lucky).

But if the human factor hasn’t been integrated…
If your team doesn’t know what to do when the lights go out (like me!)…
You’re not prepared. You’re just playing dress-up.

True readiness means testing the plan.
Knowing the weak spots. Training the humans. Connecting the switches before the storm hits.

Lesson learned. I’m calling an electrician.

(Technically this situation makes me my own unintentional/negligent insider threat!)

But here’s your reminder learned from my mistake: when was the last time you tested your own system?

4️⃣ From Passive to Active: The 78% Win-Rate Playbook – Gal Aga

Sellers, it’s EOQ. If your buyer says “final decision Monday” it’s NOT good news. It does NOT mean wait. Months of effort mean NOTHING if your champion wings it (or quietly favors competitors). Don’t await the verdict—shape it. Here’s the exact playbook we run at Aligned to win 78% of decision-stage deals:

BACKGROUND:

BUYER: “Final decision Monday, looking good! I’ll update you!”

AE (internally): “Acme’s solid. They’re excited. I have a good feeling.”

BUYER (Monday): “Bad news. CFO killed it in like 5 min. I’m so frustrated.”

AE: “Not again… already told my VP it’s done. 3 months down the drain.”

Every quarter, same painful cycle.

Why?

We think “Final Decision” means job done. It’s NOT. Actually, it’s time to speed up, not slow down. Waiting for a verdict is how closable deals go south – all the time. You’re giving up control when everything could go wrong (budget scrutiny, weak champions, competitors, politics). Your deal needs a guide, not a follower.

Awaiting verdict = Passive Selling.

The solution is Active Selling:

– Clarify decision criteria
– Uncover hidden concerns
– Navigate internal politics
– Equip your champion
– Multithread for backup

Every big deal review I join at Aligned, we always ask about final-stage deals:

“How can we ACTIVELY influence their decision meeting?”

Here are 5 ways we do it:

1. Champion War-Room Call: Lock in 30min ASAP to plan exactly how they’ll convince everyone. Co-create their business case. Find risk. Coach them on how to win each exec and kill objections. If you can’t book it, face the reality: you don’t really have a champion and need to make moves to save the deal.

2. COI Story: For major deals, we build a clear, punchy recap capturing exactly what prospects say their Cost of Inaction is. To secure big $$$ funding, the ‘Ask’ MUST directly tie to urgent, expensive problems buyers believe we can solve.

3. Direct Clarity Check: Bluntly ask “If you had to decide now, what’s the one thing still holding you back?” Go for risk proactively. No guesswork.

4. Deal Room Executive Assets: We always build an exclusive, locked tab in our Aligned workspace just for exec eyes. Champions love forwarding—it makes them look good. Curate exactly what execs need to say “yes”: COI, Biz Case, TCO, etc. Only what solves objections, drives confidence and speaks to execs.

5. Daily Moves: We create a close plan of daily micro-actions: Exec-to-exec emails, LinkedIn engagement, relevant decision assets, intel & evangelism below the line, champion alignment check-ins… Be everywhere. Daily. Show buyers you want their business. Add value (w/o annoying) until decision day.

TAKEAWAY:

Passive sales is not sales at all.

It’s rolling the dice.

This quarter – take control.

5️⃣ How Microsoft Turned OpenAI Into a $700M ATM – Heath Ahrens

OpenAI pays Microsoft 20% of every dollar earned.

This amounted to $700 million last year alone. While Microsoft profits, OpenAI lost $5 billion.

This partnership, which began with Microsoft’s $1B investment in 2019, has become increasingly problematic.

The crisis intensified when OpenAI acquired Windsurf for $3B.

Per their agreement, Microsoft gains access to ALL of OpenAI’s IP including Windsurf’s code generation technology, which directly competes with Microsoft’s Copilot.

Microsoft’s control extends through three mechanisms:
• Complete access to OpenAI’s intellectual property
• Mandatory use of Microsoft’s computing infrastructure
• 20% revenue share from all OpenAI income

The consequences are severe. OpenAI needs Microsoft’s approval to convert to a for-profit company, without which they’ll lose $20B in potential funding.

Microsoft is demanding a larger stake than OpenAI wishes to give.

OpenAI executives are now considering taking Microsoft to court over antitrust concerns.

This pattern extends beyond OpenAI. Companies like Anthropic, Scale AI, and Perplexity have signed similar deals with tech giants.

They took the money when resources were scarce, but now question if independence was worth sacrificing.

The lesson? Once you take big tech’s money, you owe them something. In AI, that “something” might be everything.

This showdown will determine whether AI innovation can thrive outside big tech’s control.

For entrepreneurs in any field, it demonstrates the delicate balance between securing resources and maintaining independence, a balance that could determine your company’s future.

6️⃣ Performing Success While Losing Yourself – Usman Sheikh

We don’t fear change.
We fear losing who we are.

Uncoupling begins quietly. A drift between who you are and who you pretend to be. At first, barely noticeable.

You open your laptop. Look through the barrage of emails, lead the team standup, convince your star performer not to leave, polish the proposal you need to close.

But mid-pitch, explaining your product for the hundredth time, you catch yourself performing passion you no longer feel. The words come out right. The prospect buys.

But inside, something has shifted.

This is professional identity death. Not the dramatic kind. The slow kind. Where you succeed at being someone you no longer want to be.

I lived this in 2017. After fifteen years of building companies, the founder title had become heavy. It wasn’t burnout – it was something deeper.

It started with small betrayals of self:
→ Excitement turns to exhaustion at your own meetings
→ You give better advice to others than yourself
→ Sunday nights bring dread, not anticipation
→ You envy people who genuinely love their work
→ Your title feels like a costume that no longer fits

The lie which holds us back: If I fail at work, then I fail.

We fuse so tightly with our titles that losing them feels like losing ourselves. Because we’ve forgotten where the job ends and where we begin.

The shame is physical. You’ve invested everything in this identity. Everyone knows you as one thing. To want something else feels like betraying them all.

So you perform. Another quarter. Another year. Forcing every smile while everyone applauds your success.

The curse of competence strikes hardest here. The better you perform, the tighter the trap. Each new client adds pressure. Each milestone makes leaving harder. Success doesn’t free you – it makes the cage more comfortable.

The Uncoupling Process
→ Drift: Sunday dread becomes daily. You notice yourself drawn to different roles. Your best energy goes to side projects.

→ Guilt: You’re ungrateful. Others would kill for your position. You should be happy.

→ Experiments: Secret LinkedIn browsing. Coffee chats about “what else is out there.” YouTube rabbit holes.

→ The Messy Middle: Living between identities. Can’t stay, can’t leave. This lasts years.

→ Release: Finally accepting the old you is dead. Terrifying. Necessary.

AI will force this on millions.

They’ll face identity death without warning. Without practice. Without choice.

But those who’ve learned to uncouple voluntarily? Who’ve practiced letting go before being forced? They know the secret: You are not your job. You never were.

The only question that matters: Who would I be if my title disappeared tomorrow?

Not what would you do. Who would you be.

The drift may have already begun. You feel it. That gap between who you are and who you pretend to be grows wider each day.

Don’t wait for the crisis. The uncoupling will hurt like hell whenever it happens.

But on the other side? Freedom to become whoever you’re brave enough to be next.

7️⃣ The Prisoner’s Dilemma of Remote Work – Shashank Sharma

Work from home is a silent erosion.

Before the pandemic, I supported work from home fiercely. I romanticised the silence. Fewer hours wasted on traffic. More time with thoughts. The comfort of one’s own room over forced office chatter. It felt like freedom. I told myself this was how real work should happen.

When I was struggling mentally during that time, my father kept repeating one line.
“Roz bahar nikla kar. Logon se mil. Dhoop mein chal.”
It didn’t land then. I thought he didn’t understand. I was tired & needed space. I had stopped going out, stopped picking up calls, stopped dressing up. There were no meetings. Or plans. Or reason.

But slowly, I felt something changing inside me.

Work continued. Messages were replied to. Projects delivered. But I had started disappearing.

You don’t wake up one morning and feel lonely. It builds. Quietly. First you skip one plan. Then two. You stop calling back. Stop leaving the house. You convince yourself everything is fine. That this is peace.

But peace isn’t hollow.
Peace doesn’t feel like numbness.

It reminded me of what I had once read about prisoners in solitary confinement.
In 19th-century British jails, convicts were placed in complete isolation. World thought the idea was reform through silence. But the logic was collapse. Their minds began to break because of stagnation that came from isolation.

The truth is, human beings are built to be in friction. To walk through crowds. To overhear conversations. To smell sweat in a metro coach. To argue with an auto driver. To eat samosas with a colleague who just got dumped.

Work was never just output. It was rhythm. Banter over chai. Someone calling you out on your bullshit. A smile exchanged across desks. That unspoken feeling of being part of something larger than yourself.

When you work from home too long, the world shrinks.
Thoughts become loops.
Voices in your head grow louder than voices around you.
Your ability to handle noise, mess, inconvenience starts fading.

One day I stepped into a co-working space again. I didn’t even realise how badly I had needed that energy.
A stranger asked me if I had a pen. Someone nearby was laughing on a call. Two people were gossiping behind me. And I felt alive.

Something in my chest opened.

It wasn’t about productivity but about pulse.

Remote work doesn’t break you. Isolation does.
The absence of shared breath. Shared mess. Shared time.

If you’re working from home, find your way back into the world. Sit where people are. Walk where voices rise. Let your day touch another’s.

Because the mind remembers silence. But the soul remembers noise.
And somewhere between those two, we survive.

8️⃣ The 1% Idea, 99% Execution Reality – Marc Randolph

I’m often asked if it’s a good idea to get an NDA before pitching investors.

The answer, which surprises many people, is “no.”

That’s because the value of a company isn’t in the idea; it’s in what you do with it.

Companies thrive when they navigate the intricate process of bringing an idea to life. In my experience, maybe 1% of a company’s value can be attributed to the original idea; the remaining 99% comes from execution.

Consider Slack, Instagram, Pinterest, or Groupon: each of them became successful only after their founders pivoted from their original concept.

Secrecy wasn’t the key to their triumph. It was their openness to advice, and willingness to learn from mistakes and adapt accordingly.

Even if you want to keep your idea confidential until it’s foolproof, the reality is that most investors won’t sign non-disclosure agreements.

Chances are they’ve heard a pitch nearly identical to yours before, and want to avoid potential legal issues if someone else in their portfolio happens to launch a similar idea. What actually matters to them is your commitment to the project, your team-building prowess, and your determination to overcome challenges.

There are instances where secrecy is needed, but most of the time it’s a distraction. I hold a few patents from my time at Netflix, for instance, but none is for the original idea of a DVD subscription service. Instead, I patented discoveries that we made after trying hundreds of different approaches—almost all of which didn’t work.

Patents are important in the pharma business, but they’re not about the things you might be thinking of. You don’t patent the idea of curing baldness; you use a patent to safeguard a breakthrough you discovered after 997 attempts to cure. In that case, secrecy is essential to protecting your innovation. But in most other cases, you shouldn’t worry about your idea being stolen. Possessing the idea isn’t what’s important—those 997 iterations are.

So…embrace feedback, pitch without an NDA, and focus on turning your idea into reality. Because in the realm of startups, action speaks louder than secrecy.

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