20 November 2023
This week's additions focus on strategy, leadership, and mindset, with new digests from Cameron Herold, GaryVee, and TK Kader. Highlights include Most COOs hit a ceiling after two company doubles LinkedIn organic reach is as underpriced as Facebook was in 2013
Showing 26 digests for 20 November 2023.
Business operating systems
YouTube
How CEOs balance entrepreneurial energy with vision, family, and business structure
Cameron Herold
November 22, 2023
Business operating systems
9
Management
8
Resilience & grit
7
Bipolar traits and ADD are entrepreneur superpowers — if you manage the downside
Separate business units with their own vision or you'll lie to yourself about performance
Write a vivid vision for your marriage before scaling kills it
AI strategy & adoption
YouTube
Why banning ChatGPT from your company is a mistake
Dylan Davis
November 22, 2023
AI strategy & adoption
9
Automation & tools
6
LLM data leakage odds are roughly one in a million
Blocking AI tools costs 14–34% productivity per employee per hour
RAG architectures carry a genuinely higher leakage risk than base LLMs
Tom Murphy and Capital Cities: how a rowboat beat the QE2
Founders
November 22, 2023
Business models
10
Long-term planning
9
Capital allocation
8
A rowboat outran the QE2: focus beats scale over 30 years
Buying ABC at 100% of enterprise value — and doubling margins in two years
Why Murphy treated every new hire as a $3 million lifetime decision
Social media marketing, attention arbitrage, and building business conviction
GaryVee
November 22, 2023
Social media
9
Content marketing
8
Paid ads
7
Social moved from follower lists to interest graphs — content beats audience size.
Turn viral organic posts into conversion ads — brand meets performance.
Stop convincing the unconvincible; find the small group that already agrees.
Iteration & feedback loops
Podcast
How small product tweaks create massive social change
Masters of Scale
November 21, 2023
Iteration & feedback loops
9
Customer discovery
7
Founder interviews
6
One rule — women message first — cut harassment and rewrote dating norms.
Users hijacked Bumble for friendship and networking, spawning two new products.
Ship the tweak, then watch: Bumble's 24-hour asymmetry bug was caught and fixed fast.
On-page SEO: the three Cs framework for SERP visibility
Semrush
November 21, 2023
SEO
10
Automation & tools
6
Weak on-page SEO undermines every other SEO investment you make.
Three Cs framework: content clarity, code cleanliness, connection capital.
Internal link distribution is as important as backlink authority.
How Boot.dev grew from $6k to $110k monthly revenue in 15 months
Startups For the Rest of Us
November 21, 2023
Case studies
9
Niche selection
8
Unit economics
6
Back-end learning was ignored — that gap became Boot.dev's entire moat.
Zero growth for a year until rebranding, niching, and ditching a non-developer marketer.
Net revenue and MRR diverge sharply — why LTV is the only metric that matters here.
How a scalable online business runs without you during maternity leave
Sunny Lenarduzzi
November 21, 2023
Business models
9
Processes & SOPs
7
Work-life balance
6
Business generated multiple seven figures while founder was completely offline.
Packaging expertise into a program detaches income from your time.
The mother-or-career binary is a narrative — entrepreneurship breaks it.
Hiring & recruitment
YouTube
Hiring the right COO for each stage of company growth
Cameron Herold
November 20, 2023
Hiring & recruitment
9
Long-term planning
5
The COO who scales you to $100M can't take you to $450M.
Match the COO to your stage, not just their resume.
Two early-stage COO types: the partner and the confidant.
How to set and achieve transformative goals using reverse goal setting
Deep Questions with Cal Newport
November 20, 2023
Goal setting
10
Productivity & habits
7
Long-term planning
6
Work backwards from your goal — every link must be evidence-based
Hidden choke points and random-outcome steps derail most ambitious plans
Passion is cultivated through discipline and curiosity, not pre-discovered
How to operate and scale a business: lessons from building Carta
GaryVee
November 20, 2023
Case studies
10
Management
9
Processes & SOPs
7
Why pausing all sales for three months saved the company
Never surprise your board — make them bored instead
Middle managers are the oppressed middle class of growing organizations