
Lessons for building lasting businesses and systems: On technology (AI and software), people (high-performing teams), and growth (accelerated learning) - developed at 7 startups and 4 exits.
| Platform | Pricing | Only free issues | Publishes | Weekly | |
|---|---|---|---|---|---|
| Issues | 34 | Founded | 2 years ago | Last Issue | a month ago |
| Active | |||||

I’ve been managing people for over a decade and have been coaching managers and leaders for several years. Recent conversations with managers I’m coaching made me think about the kinds of managers we have and I put it on a “ladder” scale. T...
What do you do when your biggest customer asks for a new feature?
A customer asks for a dashboard. Default behavior is to build so you keep the customer happy. After fifteen years of designing B2B systems, I’ve learned to ask two questions...
More emails. More messages. More meeting follow-ups. Product decisions. Engineering work. Testing. Reviews.
Some of these are simple and clear enough that can be delegated with little explanation. Some aren’t....
This past week, I talked to probably the tenth founder building an AI tutoring application. Because I work at the intersection of education and technology and mentor in a few startup programs, I see many founders in this space. And I see a...
Like most other developers, when I first pointed AI at my codebase, I gave it the whole repo. Every file. Maximum context. Figure it out.
It hallucinated field names that didn’t exist. It confidently edited a salary field without knowing t...
Subscribers, engagement, traffic and sponsorship for Wisdom of Systems.
| Subscribers | Engagement | 60 | Monthly Web Visits | ||
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| Accepts Sponsors | Estimated Cost per Ad | ||||
The writers behind this newsletter.
Building AI platform for founders with Harvard Business School Foundry and teaching Applied AI and software engineering at the Department of CS at the U of Toronto. (Opinions are mine). Formerly founding/Leadership/Tech in 7 startups (4 acquired).
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