As some of you know, Jeremiah is looking for a day job (since he’s currently bootstrapping his EdTech startup, Playbook). Gots to pay those bills!
There’s a really interesting opportunity on the Azure Portal team, to improve how people onboard onto and use Azure. Since Jeremiah has been using the Portal on the daily for a while, he has … opinions.
Because it’s us, he thought he’d see if being an “AI Power User” would help here. He gave himself 1 hour (before his interview) to see how far he could get. Wish him luck!
Here’s what he did – to the Chat GPTs, batman!!!
PROMPT: You are an expert PM leader, who’s been asked to improve the Azure Portal. Looking back at my previous sessions and history, please write a short blogpost of how I’ve been building Playbook and Agent Tod over the past few months. Write down what I’ve been trying to do, and focus especially on the times when I’ve struggled to understand and use the Azure Portal. Map out my user journey so far, and call out the pain points I’ve experienced.
Jeremiah got an answer back from ChatGPT, but wanted to add in a few more points:
PROMPT: this is a great start. please add the following challenges I encountered: <with a few examples here>
Le voila!! We got back a good draft! Since Jeremiah was under (self-imposed) time pressure, he made very light edits and published as Part 1!
Title: Learning in Public: My Azure Portal Struggles (and Why It Matters)
Over the last few months, I’ve been building two scrappy, high-conviction projects: Playbook, a career discovery app for high school students, and Agent Tod, a minimal AI agent for testing Responsible AI principles. Both lean into a simple tech stack—Node.js, Express, local LLMs—and both have pushed me deep into Azure land.
And while I’ve managed to get things working, it’s been… a journey.
🧠 The Projects
Playbook is designed to help students figure out who they are and what they want to do—guiding them from self-discovery to interviews and job prep. Agent Tod is my experimentation ground: a small, local-first AI agent using text prompts and open-source models like phi4-mini and tinyllama.
At the beginning, it was all local. Then came the Azure lift.
🛣️ My Azure User Journey
Here’s what that path has looked like—and where I’ve repeatedly stumbled.
1. Pay to Play
When I was ready to get Playbook live, Azure wouldn’t let me do much without entering a credit card. At the time, we hadn’t incorporated yet—no EIN, no bank account—so I had to use a personal card. Not ideal, but fine.
Except: when I started Prima Dona Studios years ago, I used that same card and home address. This time around, trying to do the same under a new company name? I was blocked from receiving “new user” credits and startup benefits.
I ended up just accepting the limitations so I could start building.
Pain Point #1: The payment system assumes one credit card = one user journey. It doesn’t account for people founding multiple startups, especially early-stage.
2. The Naming Trap
I spun up a free-tier app and database to get started quickly, but didn’t name things with “prod” in mind. Later, when I tried to set up separate test and production environments, I realized I’d have to rename or rebuild parts of the system. But deleting a resource just to rename it? That’s risky when you’re not sure of the downstream effects.
Pain Point #2: There’s no safe, guided way to refactor cloud architecture mid-build. Renaming feels like breaking.
3. The “Where’s the Error?” Game
When something went wrong during a deploy or test migration, I found myself stuck in a guessing game:
- Was it a bad connection string?
- Did my password have a special character like ! or @ that needed encoding?
- Was the app service actually running?
- Did the database exist? Was it using the latest schema?
- Could the frontend, backend, and DB even see each other?
The portal gave me no single view to track this—no quick trace of system health.
Pain Point #3: Debugging a dev/test/prod setup is a scatter hunt. There’s no unified view across layers.
4. Too Many Tools, Not Enough Glue
I primarily use VS Code to write HTML, CSS, and Node.js. Sometimes I pull in GitHub Copilot or switch to Cursor for help. Since I’m not a designer, I occasionally use V0 or Bolt for UI. But getting all of these changes integrated, pushed to GitHub, and successfully deployed through GitHub Actions to dev/test environments? It wasn’t trivial—especially when deployment failures gave vague or no feedback.
Pain Point #4: The dev-to-cloud flow is fragile when working across multiple tools. One misstep and you’re left wondering which layer broke.
5. Visual Thinker, Text-Based Portal
I’m a visual learner, and Azure’s portal layout didn’t help. It presents resource groups, app service plans, app services, and databases as if they’re all on the same level—but they’re not. Relationships between them aren’t always intuitive. And making even simple changes (like renaming something) often meant deleting and recreating, with unclear implications for cost or functionality. Could you put any of this into a visual hierarchy? (Maybe with those cute little pictures of web servers & databases & API calls)?
Pain Point #5: Azure’s interface doesn’t guide mental models. It assumes you already know how it all fits together.
🔍 What I’d Do Differently as PM of Azure Portal
If I were on the Azure Portal team, I’d focus on first-time founder experience and multi-tool dev flow. Some quick wins:
- Offer a “Startup Setup Wizard” that understands when a user is starting fresh under a new company name.
- Let users tag and reclassify environments (dev/test/prod) without rebuilding infrastructure.
- Visualize system health across all connected resources (frontend/backend/DB).
- Add better error tracing and commit linkage for GitHub Actions in the portal.
- Reorganize the UI to reflect dependency chains—not just flat lists.
👣 Still Building
I’ve learned a ton: how to separate environments, how to structure GitHub workflows, how to run local models and build responsibly. But I’ve also burned hours clicking through Azure tabs, wondering why a resource won’t connect—or even show up.
The Azure Portal has the bones of a great system. But right now, for indie devs and startup builders trying to learn on the fly?
It still feels like a boss battle without a map.
If you’ve been in the same boat—or if you’re on the Azure PM team and want real user feedback—I’m happy to chat. This is what learning in public looks like.
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