Uncrowded Strategies #011: I told my team — learn to manage AI or lose your job

Welcome to this week's edition of Uncrowded Strategies.

Here are my private notes on what I'm building, how I'm growing my family, and the weird things I'm doing to optimize my health this week.

(Sonny Update + The Identity Crisis No One Talks About)

I posted a new video breaking down where Sonny is at. If you want to see the AI agent I've been building... watch it here.

But this week, I don't want to talk about the tech. I want to talk about what happens to you when 80% of your work gets done by machines.

Because here's the uncomfortable truth: when you remove the doing... you have to face who you are without it.

I built my identity around being the guy who grinds. Who works harder. Who stays longer. Who knows more. And now I'm building a system that makes all of that... irrelevant.

That's terrifying. And liberating. At the same time.

Here's what I told my team this week — and I wasn't sugarcoating it:

"Anyone who cannot manage a team of AI agents will have no job."

Harsh? Maybe. But the flip side is the real story.

If you can orchestrate agents? You get your life back. AI handles the day-to-day. The repetitive grunt work. The things that drain you. And you? You handle strategy. Direction. The stuff that actually requires a human soul.

The Uncrowded Take: Everyone's asking "Will AI take my job?" Wrong question. The right question is: "Can I be the one with taste and judgment?"

Because here's what AI can't do. It can't tell you if something is good. It can execute. It can produce. It can move fast. But it can't look at the output and say: "This doesn't feel right. Scrap it. Try again."

That's taste. That's judgment. That's the one thing that stays human.

The future job isn't "doer." It's not even just "orchestrator." It's curator. You're the one who sets the standard. You're the one who says "this is excellent" or "this is garbage." AI builds. You judge.

Think about it like a film director. The director doesn't operate the camera, mix the sound, or edit the footage. But without the director's taste... you just have expensive noise.

That's the role. Taste. Judgment. Vision. Everything else gets delegated to agents who never sleep.

If you want to be updated with the latest AI news, you can checkout the sponsor of this week’s post at the end.

Zoey and I are healing. Together. And not from anything the other person did.

A few editions ago, I shared that I started somatic therapy to heal childhood trauma embedded in my nervous system. The kind of stuff your body carries long after your mind has "moved on."

What I didn't expect? Zoey started seeing patterns in her own childhood too.

Not because I pushed her. Not because a therapist told her to. She just started recognizing things. Moments from her past that shaped how she responds today. Reactions that don't match the situation. Triggers that come from nowhere.

So now we talk about it. Together.

And here's the thing that surprised me most: we don't need to fix anything in those conversations. No solutions. No action plans. No "here's what you should do."

We just talk. We listen. We help each other process what we never got to process as kids.

Because when you grow up in dysfunction... no one gives you space to feel things. You just survive. You adapt. You push it down and keep going.

The "Uncrowded" Move: Most couples wait until something breaks before they start digging into the hard stuff. We're choosing to dig before the cracks show. Not because we're broken. But because we refuse to pass unhealed wounds to our kids.

This is what breaking a generational curse actually looks like. It's not dramatic. It's not a movie scene. It's two people sitting on the couch after the kids go to bed... saying the things they were never allowed to say out loud when they were small.

I told you I'd share this story. So here it is.

I took no active income for nearly a year.

Not because the business failed. Not because I got fired. I chose to stop.

Here's why: I had an offer that was making good money. But after scaling the company, the offer was no longer up to my standard. It wasn't what I would want to buy if I were the customer. And I couldn't keep taking people's money for something I wasn't proud of.

So I stopped selling it. Cold.

No pivot. No "lite" version. No "let's just ride it out while we build something better." I shut the revenue off and went back into R&D. Full rebuild mode. Creating offers I could actually stand behind.

Most people would call that insane.

And honestly... some weeks it felt insane. Watching zero come in while expenses keep going out. That does something to your head.

But here's what saved me: during the good years, I didn't just save. I invested. Mostly into AI stocks. And those investments grew — to the point where our portfolio now covers 10-15 years of current expenses.

That sounds comfortable. But here's the pain...

Every dollar I withdraw to live on comes from our long-term financial freedom portfolio. The thing we built for our future. For the kids. For the "never have to work again" number. Every month of burn eats into that.

And that's a real tension. Every time I check the balance, there's a voice that says: "You should be earning. You're shrinking the thing you spent years building."

The Reframe: But then I realized... this one year of burn? It's also an investment.

If I had been stressed and chasing revenue, I never would have had the time to explore AI the way I did. I never would have built Sonny. I never would have discovered Claude Code, or started building a digital factory.

All of those things happened because I gave myself permission to stop earning and start learning. The portfolio shrinks a little on paper. But what I'm building with that time could be worth 10x what I withdrew.

I sleep on an Eight Sleep mattress in Singapore. Temperature set low. All the right conditions. And most days? I wake up yellow on my Whoop. Not red. But yellow. Mediocre recovery. Even when I sleep 7-8 hours. Night after night, the same... just okay.

Then I went to Hakuba, Japan. I snowboarded all day. 6-7 hours of sleep. Same Eight Sleep temperature control.

I woke up green. Full recovery. Every single morning.

Same mattress tech. Same temperature. Fewer hours of sleep. More physical output. And my body recovered better.

The only variable that changed? I completely disconnected from work.

The Data: HRV — the number that drives your Whoop recovery score — responds more to chronic psychological stress than sleep duration or physical output. Let that sink in. I can snowboard for 8 hours, sleep less, and still recover better than a quiet day in Singapore... because my nervous system finally let go.

Building AI agents. Running a digital factory. Debugging Sonny at midnight. Checking Slack in bed. That keeps your sympathetic nervous system in a low-grade fight-or-flight state. 24/7. Even when you think you're "relaxing."

The moment I removed the work input — even when I added heavy physical stress — my body downregulated. Recovery spiked.

The Experiment: I'm engineering a hard "Operator Off" cutoff in Singapore. A specific time each night where I fully disconnect. No Slack. No agent debugging. No "quick check." I'm treating my evening like I'm on a mountain with no cell signal.

The Hypothesis: If I can simulate the Hakuba disconnect every night, my HRV baseline should shift within 2-3 weeks.

The Honest Part: This is the hardest protocol I've ever tried. Harder than mouth taping. Harder than the walking pad. Because this one requires me to trust that the agents can run without me. That the business doesn't need me for those hours. That I'm not falling behind by switching off.

And that... ties right back to the nervous system work I'm doing in therapy. The hyper-vigilance. The fear that stillness is dangerous. Turns out, my Whoop data is just confirming what my therapist already told me.

The battlefield isn't my sleep schedule. It's my inability to let go.

See you next week,

Gabriel

P.S. If you want to become an AI expert with just 5 minutes a day, check out the deep view below.

If you’re a decision maker at your company, you need to be on the bleeding edge of, well, everything. But before you go signing up for seminars, conferences, lunch ‘n learns, and all that jazz, just know there’s a far better (and simpler) way: Subscribing to The Deep View.

This daily newsletter condenses everything you need to know about the latest and greatest AI developments into a 5-minute read. Squeeze it into your morning coffee break and before you know it, you’ll be an expert too.

Subscribe right here. It’s totally free, wildly informative, and trusted by 600,000+ readers at Google, Meta, Microsoft, and beyond.