16 June 2025
This week's additions focus on mindset, leadership, and ai, with new digests from Rob Walling, EO, and TK Kader. Highlights include Consumer churn of 10–25% monthly makes scaling nearly impossible Seven years of near-failure ended with one viral tweet and $20M ARR in two months.
Showing 53 digests for 16 June 2025.
Hiring & recruitment
YouTube
How to hire the right COO for your business
Cameron Herold
June 16, 2025
Hiring & recruitment
10
Delegation
6
Your weaknesses define the COO role before anything else.
Good COOs aren't job-hunting — you have to poach them.
CEO and COO belong at the bottom of the org chart, not the top.
AI strategy & adoption
YouTube
How leaders can partner effectively with AI
Coaching for Leaders
June 16, 2025
AI strategy & adoption
8
Identity & self-belief
6
Management
5
Asking deeper, contextual questions is the core AI skill.
Beginner's mind unlocks more value than domain confidence alone.
Emotional intelligence now determines whether AI deployment builds or destroys trust.
Deep work & focus
Podcast
Cal Newport on Byung-Chul Han, AI reasoning hype, and digital depth
Deep Questions with Cal Newport
June 16, 2025
Deep work & focus
9
Productivity & habits
8
AI strategy & adoption
7
Digital visibility erodes respect by collapsing the distance strangers require
Pseudo-productivity, not capitalism, explains why knowledge workers are burning out
LLM 'genius-level math' collapses on unseen problems — pattern matching, not reasoning
Pass or Fail: What Good Brand Messaging Actually Looks Like
StoryBrand With Donald Miller
June 16, 2025
Self-hero messaging always fails; deliver value to others instead.
Provocative language earns attention when it fits the target audience.
User reviews beat company copy on trust; solicit both strategically.
Founder interviews
Podcast
How Dylan Field built Figma from dorm-room idea to $20B offer
How I Built This with Guy Raz
June 16, 2025
Founder interviews
10
Management
7
Resilience & grit
6
Four years of building before shipping — why slow starts can still win
Microsoft threatened to drop Figma unless it started charging for itself
Adobe's $20B acquisition was blocked; Figma filed for IPO instead
AI tools & automation
Podcast
Using AI voice mode as a thinking and practice partner
How I Work
June 16, 2025
AI tools & automation
9
Productivity & habits
6
Talking to AI beats typing for idea generation and workshopping
Role-play high-stakes conversations or presentations before they happen
AI voice mode is a coach — not a substitute for real professionals
Resilience & grit
Podcast
Stoic lessons on legacy, gratitude, and asking for help
The Daily Stoic
June 16, 2025
Resilience & grit
7
Identity & self-belief
6
Marcus wrote privately; his words now reach millions across millennia.
Asking for help is refusing to give up, not admitting defeat.
Fear of looking foolish is the unstoic move — Epictetus agreed.
How incumbents lose to startups during major technology shifts
The Science of Scaling
June 16, 2025
Pivoting
9
Business models
8
Resilience & grit
6
Knowing disruption is coming still won't save you from it
Agentic AI breaks SaaS architecture and pricing models simultaneously
Crashes are the best time to start a company — not avoid one