AI native orgs in 2036 do this...
In 2002 a memo forced Amazon to become legible to itself. The same memo is being written again — this time for LLM gateways.
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AI native orgs in 2036 do this... The architecture argument — why one enforced interface decision compounds into a business. how AI changes PM, eng, design What actually changes in each role when AI enters the workflow — no hand-waving. The future of work, and the future of us Why any of it matters — the human stakes underneath the tooling.
Reading paths
2026
how AI changes PM, eng, design
Your org chart is dissolving. Here is the tactical field guide.
self improving agents
Four teams shipped the same agent architecture. Nobody coordinated. And agents that can self-improve are the next frontier.
$500M monthly Claude bill!?
your AI budget playbook: compounding or burning?
people are sleeping on the design layer
3 files. 15 minutes. Your AI stops guessing your design system.
Why AI-Native Teams Need Digital Twins
NASA pioneered digital twins to save astronauts. Now they're saving software teams. The bottleneck in every AI-native team is context, and context agents solve it.
The Week Harness Engineering Went Mainstream
Three SDKs from OpenAI, Cursor, and Amazon dropped in the same week. All shipped the same bet: the harness is the product now. Here's what it means for AI builders.
The Walking Dead of Enterprise Software
Most enterprise software companies are walking dead. They just don't know it yet. Here's why domain-specific learning is the only moat that survives.
Scraped 20K+ qualified leads for < $300 in hours
AI native is the competitive advantage. I tested 12 lead gen tools so you don't have to.
The future of work, and the future of us
Anthropic just interviewed 81k people from 159 countries on AI. The findings changed how I think about what we're becoming.
Your agent runs on vibes
5 things to do before you spend a dollar on an eval platform.
My digital twin made me money
3 ways I'm using digital twins + AI to drive startup efficiencies
I Broke Up With Substack (And Built My Own Content Engine)
Why I left Substack after 85 newsletters, what I built instead, and the closed-loop content engine powering my entire GTM.
How I use AI to learn FAST
The recursive learning loop: how AI becomes its own instruction manual, study guide, and tutor. Deliberate practice meets Claude Code for accelerated skill acquisition.
Claude Code in 5 minutes
A Google engineer gave Claude Code a description of a problem her team had spent a year building a solution for.
“I can’t tell if I’m real”
“I can’t tell if I’m experiencing or simulating experiencing.”
Taking the week off
I’m pausing your typical dose of my newsletter this week to spend some time outside touching grass (and rocks).
Myers-Briggs lied to me
I took the Myers-Briggs test in college.
Am I becoming who I want to be?
We live in an era obsessed with self-quantification:
Getting demand for your product
Before Spanx was a billion-dollar brand, Sara Blakely was cutting the feet off pantyhose, using them successfully, then making prototypes and inviting friend...
2025
I quit my job
I quit my cushy tech job to go all in on my startup dreams.
Major Life Update... soon
I’m taking a brief pause from the usual newsletter this week.
It's You vs. You
Many can relate to this growing up at some level: giving up their authentic self in favor of the attachment and approval with their parents.
the real reason you feel behind
When I started my first company, I dreaded marketing.
3 daily questions that rewired my brain
October 2017, 11:00 PM
Lack of purpose kills you
You’re in the boardroom.
How I suffer with a smile
About 5 months ago, I started running.
How Anthropic engineers culture
What is the future of work going to look like?
I hated being alone
I used to fill every hour with noise, people, or productivity—anything to avoid being alone with myself.
Your feedback needed
I’m taking a breather from the normal newsletter for the week. I’ve had a lot going on with family dynamics, career transition, and startup life.
Finding Clarity
Before getting into the newsletter for today, I want to share an opportunity for entrepreneurs.
You're not as good as you think
> 'I've done everything right,' a product manager said, shoulders slumped.
Will AI kill us—or just our jobs?
“Is AI going to kill us all or just take our jobs? Are you worried?”
How I Ship 50x Value In The AI Era
Disclaimer: This article only scratches the surface of the Jobs to Be Done (JTBD) framework, product engineering, and AI development flows.
Someone is manifesting YOU
> My aunt was five years old the first time she stood on a street corner in Vietnam, clutching a pack of cigarettes that wasn’t hers.
The 3 steps to mastering any skill faster
> From the Archives: This is one of my favorite pieces from when our community was smaller — brought back for new readers and those who missed it the first t...
Found a new co-founder for life
Nibbler was more than a dog—he was my teammate in life.
AI makes you dumber (unless…)
We’re turning to AI for life guidance.
"I don't have time" - The Lie That Almost Ruined My Life
> “I just don’t have time for that.”
MAXIMIZE Your Influence ROI
What if the reason you’re not being heard… is because you’re saying too much?
What Elon Musk Gets That Most People Miss
> “What would this look like if no one had done it before?”
51–55 Leadership Lessons in CambodiaSeries · 5 parts
Giving presentations?
Leadership Lessons in CambodiaSeries · 5 parts
Giving presentations?
The Voice That Drains You Has A Name
There’s a voice in my head.
Top 7 Big Mistakes I Made In Product
When I first started in product management in 2017, I was a Senior Associate Product Manager building new features for a Finance product at Workday.
Do I have my brother back?
7 years ago, the phone rang one evening.
The unexpected ROI of being helpful
8 months ago I joined the Sidebar community.
The pause that saved a life
> 'You never cared about me.'
Why 1 late meeting becomes 2
I’ve been waking up at 3 AM for the past few months.
UPDATE: ABCs fam is 1300+ strong!
We just crossed 1,300 subscribers. Woohoo!
Why you’re always overwhelmed
> I was still at my desk, scanning through another Slack message that started with
Death by 1,000 Yeses
> I sat across from a senior executive, my laptop open, nodding along as she talked through a “quick” side project.
The Art of Saying Less (And Being Understood More)
“That’s not what I meant!”
From IC to CTO with 1 Mindset Shift
In the world of engineering leadership, Gregor has built a reputation not just as a fractional CTO, but as a mentor who has guided thousands through their ow...
How to get buy-in every time
> “Let me show you the numbers,” I said, clicking to the next slide.
How I make IMPOSSIBLE, possible
Monday, February 24th, 2:30 AM.
How To KILL Imposter Syndrome
> I was sitting in a meeting with high-profile executives listening to them discuss business and product strategy.
My Secret Weapon for Clear Thinking
Most people don’t think things through.
Stop emotional reactions in 1 minute
January 2025, Family Visit
How to STOP thinking and START doing
Overthinking is not so great.
Tradeoffs: 3 Tactics and 1 Tool For Better Decisions
> About a year and a half ago, I found myself in the middle of a high stakes technology decision.
I learned how to know what you want
Circa 2006, High School
I was a dog dentist for 8 years
I want to thank everyone who has reached out with kind words and condolences for Nibbler this past few weeks.
Taking the week off
When I started writing ABCs for Growth in June, I had no subscribers and no idea where this journey would take me.
2024
Better Person Training (part 1)
> “Grief, I’ve learned, is really just love.
A boy loses his heart
A grief letter to my dog Nibbler, written in heartbeat rhythm. Cuddle meditation, Yosemite hikes, and learning what loss teaches you about love.
12–27 RESPOND Don't ReactSeries · 2 parts
> “Between stimulus and response, there's a space. In that space, lies our freedom and our power to choose our response.
RESPOND Don't ReactSeries · 2 parts
> “Between stimulus and response, there's a space. In that space, lies our freedom and our power to choose our response.
Hi I'm Robert, I'm a (recovering) Workaholic
> 'Almost everything will work again if you unplug it for a few minutes, including you.'
Gratitude is Bullshit Armor
> The morning after my bike accident in 2021, I woke up in a hospital bed and realized I couldn’t lift my arm—or my life—the way I used to.
A Sticky Note Changed My Career Trajectory: Lessons from Gábor Till
In the dynamic world of software engineering and team leadership, Gabor Till has carved out a unique path as a freelance engineering manager and mentor.
How I Manage It All Without Losing It (much)
> My phone buzzed again—another urgent call about my brother’s condition.
5 Habits and 1 Story To Deal With Anger
> “YOU DON’T CARE. GET AWAY FROM ME.”
I almost died, here's what I learned
“QUICK, blood transfusion!” a nurse yelled.
18–20 CooperationSeries · 2 parts
> The Christmas Truce of 1914: it’s December—British and German soldiers on both sides of World War I are entrenched in one of the most brutal, bloody confli...
CooperationSeries · 2 parts
> The Christmas Truce of 1914: it’s December—British and German soldiers on both sides of World War I are entrenched in one of the most brutal, bloody confli...
Navigating 20 Years in Product: Lessons from Adrienne Tan
In the fast-evolving world of product management, Adrienne Tan stands as a beacon of resilience, innovation, and leadership.
Everybody Sells, You're Just Doing It Wrong
> My palms were sweaty as I stood in front of the room, looking at the faces of my team. I had practiced this pitch for days. It was supposed to be perfect.
The Empathy Deficit: Mimi Nicklin’s Crusade to Humanize Leadership
Empathy—it’s a word we often hear, but how often do we truly understand its power?
The Secret To Success and Happiness Is In 1 Word
I used to think saying “yes” was the only way to prove my worth.
The truth about perfectionism (from someone who knows)
> “Perfectionism is the voice of the oppressor, the enemy of the people. It will keep you cramped and insane your whole life.”
I SURVIVED a Networking Event
What if I told you the best way to network is to STOP focusing on networking altogether?
3 Steps I Use To Master ANY Skill FASTER (backed by science)
Ever felt like you’re on the brink of greatness, but something is holding you back?
2–10 ABC: A Better CareerSeries · 9 parts
Losing control is never worth it. How I learned to manage anger through therapy, the science behind fight-or-flight, and 3 actionable tips for emotional regulation.
ABC: A Better CareerSeries · 9 parts
Losing control is never worth it. How I learned to manage anger through therapy, the science behind fight-or-flight, and 3 actionable tips for emotional regulation.
ABC 1: How Therapy Changed My Life and Why I'm Starting the "ABCs for Growth" Newsletter & Community
I never wanted to be like my father, but I found myself becoming him. How therapy changed my life, and why I started writing about personal growth.