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What this publication is about (and why you might want to stay)
What is technology actually costing us?
Not in dollars but in judgment, in craft, in the quiet erosion of what makes work meaningful. This newsletter explores the human side of building with technology.
I’m Diamantino. I’ve spent 20 years in tech leadership, engineering, product, and everything in between. This is where I write about what I’ve learned, what I got wrong, and why the industry keeps repeating the same mistakes.
And somewhere in there, I stopped believing that the answer was moving faster or being smarter.
Now I am asking a different question. What is technology actually costing us? And what becomes possible when leaders stop pretending they have the answer and start asking the real questions together?
That is what this publication is about.
Not frameworks for how to lead better. Not templates for running meetings. Not the comfortable ideas about shared leadership that sound nice in a talk but crumble under pressure.
Instead: what does it mean to be a leader who thinks systemically about power, economics, and human stakes in an age of AI?
Who This Is For
You are a tech leader, CTO, founder, or engineer somewhere on the path to leadership.
You probably moved fast once. Built things. Got rewarded for it. And somewhere along the way, you started asking harder questions privately that you cannot ask publicly.
Questions like:
What is the business model of AI actually optimising for, and who pays the cost?
Why does tech keep replicating the same broken patterns of power and control?
What are we building into systems that Gen Z will inherit?
Is the speed worth what we are trading away?
You are not looking for someone who has all the answers. You are looking for a thinking partner who is asking the same questions you are.
That is what you will find here.
The Three Threads You Will Follow
This publication has three connected threads. You might follow one deeply, or drift between them. Either way, you are following something coherent.
1 - AI and Human Stakes
What is AI actually doing to the world? Not the hype. The real impact.
Posts about algorithms optimising for engagement in teenage feeds. The electricity and water crisis nobody is talking about. Data being stolen as a business model. The loneliness crisis growing inside AI-assisted teams. What motivation and meaning at work look like when AI does the junior work that used to develop people.
Follow this if you are using AI in your work and starting to wonder about the costs.
2 - Tech Culture and Economics
Why does tech keep breaking the same way?
Posts about how technology companies structure power. Why move fast and break things is a broken business model masquerading as innovation. How centralised leadership in tech created centralised leadership in teams. The real cost of disruption and who pays it.
3 - Intergenerational Responsibility
What world are you building your children into?
Posts about what tech leaders are responsible for beyond the quarter. The stakes of today’s choices. What Gen Z will inherit from the decisions being made right now. Why stewardship matters more than growth.
What You Will Actually Find Here
Honest thinking, not frameworks. Every post asks a question more than it answers one. You will finish reading with more to sit with, not less.
Specific moments, not abstractions. There is always one real story. A conversation I had. A decision I watched happen. A thing I realised about myself. Never generic advice. Always grounded.
Systemic analysis, not tips. I am interested in why things break the way they do. The economics underneath. The power structures. The choices that led us here. Not how to run a better meeting. Why meetings are the shape they are, and what that actually costs.
No resolution required. Some posts end with I still do not know. That is honest. That is the point.
The Paid Tier: What It Actually Is
The free newsletter gives you the full essays. Paid is for people who want to go deeper extended analysis, frameworks I use in my own work, and a community of people thinking critically about tech.
Deep-dive essays and case studies
Decision-making templates and frameworks
Community discussions and Q&A threads
How to Find Your Way In
If you are brand new. Pick whichever thread matches what you are thinking about right now. Read two or three posts from that thread. Get a feel for the voice. See if it lands. You do not need to start anywhere specific. Start where your curiosity is.
If you have been reading a while and want to go deeper. The paid tier is where to come. Not for templates. For thinking together about the hard stuff.
If you have a specific situation you are navigating. Bring it to the Meet the Author session. This is where the real work happens.
If you are already a paid subscriber. Everything you have access to lives in The Room.
If you just want to think and read. You are welcome to stay here as long as you need. No sales. No guilt. Just the thinking.
One Thing About Me
Figuring out what the next chapter looks like while building this publication at the same time.
I tell you that not for sympathy.
I tell you because this publication is about asking hard questions honestly. And that starts with me being honest about where I am.
I have sat in rooms with CTOs who said things privately they would never say on stage. I have watched engineers become leaders. I have watched leaders remember they were human.
I have also watched technology make choices that harmed people. And I have watched leaders look away.
This publication is for people who are tired of looking away.
What Happens Now
You have four choices.
Pick a thread and start reading. Follow whichever one matches what you are thinking about. See if the voice lands.
Sign up for the free letters. A post every Tuesday about one of the three threads. Sometimes longer essays. Sometimes shorter reflections. Always honest.
Join the paid tier. If you are ready to think about this together, not alone.
Step into The Room. If you are already a paid subscriber and want to know what you have access to, the live sessions, the chat, the editorial influence, it is all there.
Or you can just close this and move on. That is fine too.
But if you are still here, reading this, it is probably because somewhere you recognised yourself. You asked a hard question privately that you cannot ask publicly. You wondered if someone else was asking it too.
Someone is.
I am.
And I would be glad to have you thinking about it alongside.
To get started, read these posts:
— Diamantino
Leadership as a Verb · newsletter.diamantinoalmeida.com
If you're a founder, consultant, or incorporated owner in the US, UK, or Canada — your subscription here likely qualifies as a business expense. I've put together a reimbursement template for you.
P.S. — I also offer one-to-one mentoring sessions for leaders who want to think through a specific situation. If that is you, book a Clarity Session here. The publication is enough. The mentoring is for when you want to go further.