Investing June 7, 2026 0 Comments

Why Top Tech CEOs Are Quietly Warning: AI Could Wreck Your Career Sooner Than You Think

Ever found yourself mid-queue for a Tiong Bahru pau, only to stumble upon a deep dive into the cutthroat world of tech layoffs? That’s exactly how I got hooked watching Michael Paulson—aka ThePrimeTime—break down the jaw-dropping tactics companies like Meta, Click Up, and WebFlow are using to slim down their workforce. Spoiler alert: some of these moves make you wonder if “employee” is just the new buzzword for “beta tester” before the AI takeover. Between monitoring software disguised as “strategic secrecy” and layoffs delivered via email accounts employees no longer can access, the tech world’s employment circus is both baffling and brutal. And let’s not forget the intriguing financial chess moves—Cloudflare’s empathetic but costly severance plans, interns filling in for seasoned pros, and what all this means for higher-paid Singapore employees grappling with job security in an AI-driven landscape. So, how do you stay afloat when the very companies you’ve given your blood, sweat, and code to might just be training your replacement? Buckle up as we unravel the mess, the money, and the haunting question: Are these tech giants already seeing something we mere mortals aren’t? LEARN MORE

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I was on my way to buy Tiong Bahru Pau after work and saw this interesting YouTube video by tech scene commentator Michael Paulson aka ThePrimeTime about the way some of these tech companies laid off their staff. He got financial commentator and former Nvidia, Twitch engineer Big A who usually talk about the money staff to have a financial sounding board.

I think Michael is usually damn hilarious about how jialat some of these software development things. As someone who was in computing but not in the industry, his content is so fascinating.

I definitely don’t belong to that tech scene so it is quite eye opening some of the employment practices.

I will briefly list them out if you are not interested to watch the video:

Meta Platforms install monitoring stuff on their employee’s computer. Mark Zuckerberg explained to his employees why management cannot tell their employees why they are monitoring what they do because it is not strategic in case it gets leaked (which it did get leaked). 1 day later, Meta fired 8,000 people.
Both of them also discussed how well known that Meta has a very corrosive work, power grabbing culture and tech employees demand a compensation “premium” just to work there, as oppose to Apple which have a compensation “discount” because of how much better it is.
According to how both they discussed, the job employment market isn’t that great. In another time period, people would look at Meta as stupid to let these “good” employees leave but this is not that environment because it may be damn challenging to find something just as good as the work in Meta.
Productivity company Click Up decide to fire 22% of their workforce. You can see the CEO Tweet here. In it, he says that business have never been better, and what they want to do is restructure the company to be a “100x” organization.
By that, Michael has a pretty big bone to pick: How the fxxk do you make your company 100x more productive? Do you mean Kyith can do in 3.65 days what Kyith used to be able to do in 365 days? The most critical part is can we shrink the decision making timeline from 1 year to 3 days lol?
Big A has a good sort of counterpoint or point: Do we know WHAT we are 100x-ing? Is it like now I can get my engineers to build what Service Now, Mongo DB, Docusign, Veeva in 1 year? Is everything like a factory that you can always increase output? Michael thinks that good decisions takes time to make and just because you have AI help, you can’t hasten them always. If you hasten some decisions, you crash and burn faster!
One week before firing the people, the CEO of Click-up made a ridiculous TikTok video destroying their employees at the expense of AI.
WebFlow laid off their employees but their employees didn’t know their fired because all their access to computers were revoked. The most idiotic thing is the email about their firing was sent to their work computer which now they have no access to. And the retrenchment was not announced to the public at all. So this left those without access wondering: Am I fired?? Turns out, this is not the first time this happens.
Cloudflare announced that they will be laying off 1100 employees (letter here). But what they are doing differently to their employees is this: We believe acting with empathy isn’t about avoiding hard decisions but rather about how you treat people when those decisions are made. If we are asking our team to be world-class, we have a reciprocal obligation to be world-class in how we treat them. We are pairing the directness of these measures with severance packages that lead the industry. The packages for departing employees will include the equivalent of their full base pay through the end of 2026. Healthcare coverage is different across the globe, and if you’re in the United States, we’ll continue to provide support through the end of the year. We are also vesting equity for departing team members through August 15th, so they receive stock beyond their departure date. And, if departing team members haven’t hit their one-year cliffs, we are going to waive those and vest their pro-rated equity through August as well.
The two discussed that Cloudflare is hiring a bunch of interns and wonder whether it is cheaper to redeploy these staff, instead of paying these hefty severance packages.

I think all of these is damn interesting for me.

Recently, what’s on my mind is about how companies treat their people and seeing these thing will make you recalibrate how you look at job security, how the company treats you. Some of these companies don’t have a choice because companies that provide no-code solutions such as Webflow are the companies that most likely will get killed by this wave of AI.

But if you treat employees like this, then I wonder how motivated will the rest be since if they finish training the AI, they might be next on the chopping block? But if you decide to leave, could you get enough compensation to pay for your hefty condo mortgage and your higher grade family spending?

Perhaps for the first time, those folks in Singapore with higher compensation jobs are at risks. More so those middle managers because for software firms, their capex, and expenses are mainly employees. Saving on this will make your financial statements look much better. It will reduce the stock-based compensation because you don’t have to pay AI stock-based compensation.

This is why in the recent quarter, we seem to see a lot of listed company’s stock-based compensation rising more slowly or even reducing. This improves the fre cash flow.

Is this going to be a problem for Singapore?

I am not sure.

The Singapore government would do something surely. They already have in that they are providing incentives to companies to use AI. I am not sure that is enough.

But I am not sure if mass layoffs of those earning S$100,000 and above is soon.

You can now understand better why people chase Financial Independence. My CEO Chris would say You only lived once (YOLO) is bad. FIRE is bad. Balance is good. But the perspectives from employees who have more doors shut off and not so many doors in the future is very different.

The more shit you see this happening the more it means you got to watch out for yourself because the company would not watch out for you, compare to when they squeeze you dry.

These Big Companies May have Seen “Something” in AI

I think I agree with Michael and Big A that Cloudflare might be doing it the right way. What they are saying is that “it is not a simple decision and we are firing because we want to optimize but we also don’t want to be fxxkers”

This is purely from that statement. Don’t come and hound me if you tell me Cloudflare actually has a shit culture.

I find that be it marketing, research and development, finance, there is a “this is the usual way” culture for many things and Cloudflare has a way to do it in a similar manner (which is not too good) but they chose to self-evaluate and say “No. We will treat them this way.”

It makes people sit up and think these people do it differently. At the very least they think independently and it make sense.

As investors we hope that more in the company can make good decisions and if they can get some of these little things right, it gives us greater confidence that they can get the strategic decisions even more right.

I think the companies that uses AI more may seen something that lead to them experimenting with less people. Google and Meta’s latest capital raising may indicate that.

Like the amount they spend is not enough! Have to raise some more! But why!

I infer they might have seen something but don’t ask me what that is.

I think is the same feeling as the more I use Claude the more potentially unanswered questions suddenly looks answerable.

I seen my friends talk about AI and I can tell you beyond the normal chat sophistication, you can tell they are not seeing it. And I would say if you talk to me, you may feel like I am only scratching just the surface.

That means that they are seeing something that Kyith is not seeing.

That sounds damn bullish for semi-conductors and the AI complex. Perhaps so bullish for medical science. Looks very bearish on our jobs.

I think there is something at the end that Michael and BIg A discuss that I resonate with a lot and would put it out in a separate post.

I sure hope we have less of these kind of retrenchments in the future here in Singapore

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