97 entries since June 2024.
New? Three that hold up:
Anthropic deleted 80% of Claude Code's system prompt and nothing broke. All 6 new rules of context engineering in plain English, the prompt that audits your repo for you, and the one asset that survives the next model release.
In 2002 a memo forced Amazon to become legible to itself. The same memo is being written again — this time for LLM gateways.
Your org chart is dissolving. Here is the tactical field guide.
Four teams shipped the same agent architecture. Nobody coordinated. And agents that can self-improve are the next frontier.
your AI budget playbook: compounding or burning?
3 files. 15 minutes. Your AI stops guessing your design system.
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.
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.
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.
AI native is the competitive advantage. I tested 12 lead gen tools so you don't have to.
Anthropic just interviewed 81k people from 159 countries on AI. The findings changed how I think about what we're becoming.
5 things to do before you spend a dollar on an eval platform.
3 ways I'm using digital twins + AI to drive startup efficiencies
Why I left Substack after 85 newsletters, what I built instead, and the closed-loop content engine powering my entire GTM.
The recursive learning loop: how AI becomes its own instruction manual, study guide, and tutor. Deliberate practice meets Claude Code for accelerated skill acquisition.
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 experiencing or simulating experiencing.”
I’m pausing your typical dose of my newsletter this week to spend some time outside touching grass (and rocks).
I took the Myers-Briggs test in college.
We live in an era obsessed with self-quantification:
Before Spanx was a billion-dollar brand, Sara Blakely was cutting the feet off pantyhose, using them successfully, then making prototypes and inviting friend...
I quit my cushy tech job to go all in on my startup dreams.
I’m taking a brief pause from the usual newsletter this week.
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.
When I started my first company, I dreaded marketing.
October 2017, 11:00 PM
You’re in the boardroom.
About 5 months ago, I started running.
What is the future of work going to look like?
I used to fill every hour with noise, people, or productivity—anything to avoid being alone with myself.
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.
Before getting into the newsletter for today, I want to share an opportunity for entrepreneurs.
> 'I've done everything right,' a product manager said, shoulders slumped.
“Is AI going to kill us all or just take our jobs? Are you worried?”
Disclaimer: This article only scratches the surface of the Jobs to Be Done (JTBD) framework, product engineering, and AI development flows.
> 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.
> 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...
Nibbler was more than a dog—he was my teammate in life.
We’re turning to AI for life guidance.
> “I just don’t have time for that.”
What if the reason you’re not being heard… is because you’re saying too much?
> “What would this look like if no one had done it before?”
Giving presentations?
There’s a voice in my head.
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.
7 years ago, the phone rang one evening.
8 months ago I joined the Sidebar community.
> 'You never cared about me.'
I’ve been waking up at 3 AM for the past few months.
We just crossed 1,300 subscribers. Woohoo!
> I was still at my desk, scanning through another Slack message that started with
> I sat across from a senior executive, my laptop open, nodding along as she talked through a “quick” side project.
“That’s not what I meant!”
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...
> “Let me show you the numbers,” I said, clicking to the next slide.
Monday, February 24th, 2:30 AM.
> I was sitting in a meeting with high-profile executives listening to them discuss business and product strategy.
Most people don’t think things through.
January 2025, Family Visit
Overthinking is not so great.
> About a year and a half ago, I found myself in the middle of a high stakes technology decision.
Circa 2006, High School
I want to thank everyone who has reached out with kind words and condolences for Nibbler this past few weeks.
When I started writing ABCs for Growth in June, I had no subscribers and no idea where this journey would take me.
> “Grief, I’ve learned, is really just love.
A grief letter to my dog Nibbler, written in heartbeat rhythm. Cuddle meditation, Yosemite hikes, and learning what loss teaches you about love.
> “Between stimulus and response, there's a space. In that space, lies our freedom and our power to choose our response.
> 'Almost everything will work again if you unplug it for a few minutes, including you.'
> 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.
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.
> My phone buzzed again—another urgent call about my brother’s condition.
> “YOU DON’T CARE. GET AWAY FROM ME.”
“QUICK, blood transfusion!” a nurse yelled.
> 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...
In the fast-evolving world of product management, Adrienne Tan stands as a beacon of resilience, innovation, and leadership.
> 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.
Empathy—it’s a word we often hear, but how often do we truly understand its power?
I used to think saying “yes” was the only way to prove my worth.
> “Perfectionism is the voice of the oppressor, the enemy of the people. It will keep you cramped and insane your whole life.”
What if I told you the best way to network is to STOP focusing on networking altogether?
Ever felt like you’re on the brink of greatness, but something is holding you back?
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.
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.