Software Lead Weekly
Issue #707, 12th June 2026
This Week's Favorite
Of Termites & Tokens: Notes on the Company as Colony
7 minutes read.
Bingo, this is the mindset we have to adopt to find new leverage versus deploy faster automations: "Making an existing process more efficient is a margin play: same output, cheaper. But a lot (most?) of businesses I’ve been involved with would far rather keep margin consistent and drive top line growth. I think workflow automation is a margin trap: AI makes cost reduction so legible that we miss the weirder growth move. We ask how to do the existing workflow with fewer people, fewer steps and less time. The better question might be: what happens when this workflow is no longer scarce?"
Read it later via Instapaper.
Share it via Twitter or email.
7 minutes read.
Bingo, this is the mindset we have to adopt to find new leverage versus deploy faster automations: "Making an existing process more efficient is a margin play: same output, cheaper. But a lot (most?) of businesses I’ve been involved with would far rather keep margin consistent and drive top line growth. I think workflow automation is a margin trap: AI makes cost reduction so legible that we miss the weirder growth move. We ask how to do the existing workflow with fewer people, fewer steps and less time. The better question might be: what happens when this workflow is no longer scarce?"
Read it later via Instapaper.
Share it via Twitter or email.
Culture
AI Startup CFO, CEO, CMO, and CTO
1 minutes read.
My humble effort to help you start the weekend with a smile. Great photo and a great (NBA) game!
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1 minutes read.
My humble effort to help you start the weekend with a smile. Great photo and a great (NBA) game!
Read it later via Instapaper.
Share it via Twitter or email.
After Automation: AI Progress Creates More Work for Humans, Not Less
17 minutes read.
This observation really got me thinking of where humans will have an edge over AI and why we see Jevons paradox in play, again: "This is why “agent” is such an easily misunderstood word. The models have more and more ability to act autonomously. But agency, in the human sense, is not just action. It is wanting for oneself. It is play for the sake of it. Model compliance and helpfulness are fundamentally at odds with this kind of agency, so even as the models improve, the gap between models and humans will remain."
Read it later via Instapaper.
Share it via Twitter or email.
17 minutes read.
This observation really got me thinking of where humans will have an edge over AI and why we see Jevons paradox in play, again: "This is why “agent” is such an easily misunderstood word. The models have more and more ability to act autonomously. But agency, in the human sense, is not just action. It is wanting for oneself. It is play for the sake of it. Model compliance and helpfulness are fundamentally at odds with this kind of agency, so even as the models improve, the gap between models and humans will remain."
Read it later via Instapaper.
Share it via Twitter or email.
Why High Performers Stall on the Path to Principal - And What They’re All Missing
7 minutes read.
The three stories by Anyell Cano provide a great way to consider where you find yourself failing, so you can unlock another step in your career growth. If you're unsure about your blind spots, share the post with a teammate and ask for honest feedback.
Read it later via Instapaper.
Share it via Twitter or email.
7 minutes read.
The three stories by Anyell Cano provide a great way to consider where you find yourself failing, so you can unlock another step in your career growth. If you're unsure about your blind spots, share the post with a teammate and ask for honest feedback.
Read it later via Instapaper.
Share it via Twitter or email.
From “System of Record” to “System of Intelligence”
6 minutes read.
Capturing the value of the workflows and continuous research, insights, and actions on top of the system of record is where we'll see companies create new types of value. What does it mean for your product? "The customer data continues to live where it has always lived, for the reasons it has always lived there. But the locus of value is migrating upward, into the layer that reads and writes to the database and does the actual thinking. The pie is getting larger in the process, not smaller. Just as the feed increased the TAM of social media to “everything of interest”, the agent revolution expands what software can plausibly charge for, and does it without gutting the labor budget that funds most GTM work today."
Read it later via Instapaper.
Share it via Twitter or email.
6 minutes read.
Capturing the value of the workflows and continuous research, insights, and actions on top of the system of record is where we'll see companies create new types of value. What does it mean for your product? "The customer data continues to live where it has always lived, for the reasons it has always lived there. But the locus of value is migrating upward, into the layer that reads and writes to the database and does the actual thinking. The pie is getting larger in the process, not smaller. Just as the feed increased the TAM of social media to “everything of interest”, the agent revolution expands what software can plausibly charge for, and does it without gutting the labor budget that funds most GTM work today."
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
How to Interview the Company While They Think They're Interviewing You
5 minutes read.
When you're interviewing for a position, they'll go deeper to understand your fit for the role, and you should use the questions by Louise Deason to better understand the company's fit to your career aspirations. Asking a few interviewers in the process, "Where do you see a technical or organiational vacuum that you'd hope someone like me can fill?" can help identify immediate opportunities.
Read it later via Instapaper.
Share it via Twitter or email.
5 minutes read.
When you're interviewing for a position, they'll go deeper to understand your fit for the role, and you should use the questions by Louise Deason to better understand the company's fit to your career aspirations. Asking a few interviewers in the process, "Where do you see a technical or organiational vacuum that you'd hope someone like me can fill?" can help identify immediate opportunities.
Read it later via Instapaper.
Share it via Twitter or email.
How to Remember Everything You Read (Video)
18 minutes read.
Reading books and learning memory retrieval skills are becoming more and more important in the day of "I'll just ask AI", as you compete for the ability to create insights and understand nuances to apply better judgment and innovate where LLMs were trained on mediocre ideas (or none at all). There are very few people you should listen to and copy from, such as Ryan Holiday.
Read it later via Instapaper.
Share it via Twitter or email.
18 minutes read.
Reading books and learning memory retrieval skills are becoming more and more important in the day of "I'll just ask AI", as you compete for the ability to create insights and understand nuances to apply better judgment and innovate where LLMs were trained on mediocre ideas (or none at all). There are very few people you should listen to and copy from, such as Ryan Holiday.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@PeterDiamandis: People ask me how I stay so optimistic. The honest answer: I read the data, not the headlines.
@sam_stoffel: “in the 1,526 singles matches I played in my career, I won almost 80% of those matches … what percentage of points do you think I won in those matches? only 54%.” -- Roger Federer
- Oren
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.