Newsletter Archive

AI has an agency problem

Companies ask employees to reinvent work with AI without a clear share in the gain. Leaders who want change must let people play for the upside.

Grok Bot is a glimpse of the future

When a product is truly great, the technology fades into the background. Grok Bot turns agents, tools, and routines into something familiar.

Walking my dog. My new favorite way to use AI.

His name is Mac, and the lab runs on a Mac. Which one is better trained depends on the day.

Your Margin Is My Opportunity

Anthropic may be on its way to $100 billion in revenue with gross margins approaching 80 percent on Claude’s API. Competing those margins away is someone else’s mission in life.

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AI Sovereignty

AI gets more useful every time we teach it how our business works. The question is whether we can take that learning with us.

The Finished Product

Companies are buying AI faster than they are learning to use it.

Context, Control, Cost & Choice

Enterprise AI is moving from access to deployment. The winners will be the companies that give AI the right context, keep control of the learning loop, manage cost, and preserve choice

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What a Diamond Mine in South Africa Taught Me About The Build Trap

When a new technology expands what can be done, leaders have to become much clearer about what is worth doing.

The Seven Primitives of an AI-Native PersonalOS

The future of knowledge work belongs to systems that know your context and improve themselves. These are the seven primitives behind an AI-native PersonalOS.

⚡ Electrons → 🧠 Tokens → 📈 Outcomes

Nvidia turns electrons into tokens. Model providers turn tokens into intelligence. Everyone else is racing to turn that intelligence into outcomes someone will trust.

I asked AI about a dead tree limb. The next morning, it was gone.

Stop treating AI like a better Google. Start treating it like something that can help you get shit done.

The new knowledge work

Last week, the transition tax. This week, what paying it looks like.

The Transition Tax

The future has arrived. The hard part is reorganizing around it.

Building AI-Native Products. Where’s the IP?

The model may be rented. The harness may be the product. The outcome may be the business.

The next killer app is AI computer use

AI computer use sounds reckless. It may also be the next step in moving AI from answering questions to actually getting work done.

How I use AI in my daily life

We are much earlier than it feels. Here’s what it looks like when AI moves from answering questions to helping run the day.

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Always-On Intelligence

The next great AI product may not be a chat app at all. It may be an always-on executive assistant that organizes your knowledge, preserves continuity, and returns finished work.

The Stall

Progress is jagged, systems keep you steady

Prompt to Harness: The Future of Software Development

Prompt, context, and harness engineering are best understood as cumulative ideas. They build on one another. Together, they are beginning to define the future of software development.

Trust is the rate limiter on risk transfer

AI compresses build cycles, but reliance still moves at human speed.

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Top 5 lessons learned vibe coding AmbitiousOS

Two weeks. A private beta. Appreciation for what AI accelerates, and what it doesn’t. The five lessons I learned going from vibe-coded demo to production software with Claude Code.

Building AmbitiousOS v2 + Total Recall & Memory + AI Agents w/ Claude Code

Today, we’re launching the next version of AmbitiousOS in private beta with plans to make it generally available to Reading Ambitiously subscribers soon.

You can just build things

Are you going to be the person who does?

Not all software is created equally

The market is trying to re-price roughly $3T of software as if it were.

Building AmbitiousOS & AI Agents w/ Claude Code

How AI agents built with Claude Code are becoming Reading Ambitiously’s editor-in-chief. Turning AI from a better version of Google into leverage.

Context is king, protect it at all costs

The context window is the scarce resource inside every LLM. Recent innovations are just different ways of spending that budget wisely.

It's a new world with Claude Code. My 2026 AI powered workspace.

Watch me build software by describing to AI what I want, not writing code, as I create a voice-powered PersonalCRM with Claude Code.

High Agency teams win AI era

In the AI era, the bottleneck is not intelligence. It is the willingness and the permission to act on it.

Year In Vibes

Amazon’s $10B OpenAI deal, TPU mania, SpaceX $1.5T IPO, Notion’s valuation, the $100M ARR speedrun, 1999 vs. today’s valuations, Opus 4.5, Google’s AI email assistant, Henry Ellenbogen, Software 2.0

Reading Ambitiously 12-12-25

Change management, Pantone color of year, IBM acquires Confluent, GPT 5.2, Sequoia, Gavin Baker on ILTB, perceived AI winners in SaaS, Meritech 2025 market update, AI Santa

Reading Ambitiously 12-5-25

Google Gemini 3, Netscape, Henry Ellenbogen, OpenAI "code red" 🚨, Ilya Sutskever "all of this is real", global economic clock, Google workspace studio, Michael Burry, AI led GTM, IBM electronic calc

Reading Ambitiously 11-21-25

AI regulation, Em-dashes, Bezos is back w/ $6B+, SaaS ARR per employee, Gemini 3, Google TPUs, Harada method, SaaS's fate, AI thoughts from Gavin Baker, Anti AI = live, Buffett's thanksgiving note

Reading Ambitiously 11-14-25

Tokenize everything, machine-readable economy, inside Cursor, Howard Marks on private credit, SoftBank Nvidia exit, YC’s Chad IDE, Kimi K2 vs GPT-5, Anthropic vs OpenAI spend, 1.3Q AI tokens at Google

Reading Ambitiously 11-7-25

Bubble vs. Abundance, Michael Burry, Big "AI" Short, US vs China open source, K-shaped economy, Robinhood, Palantir hiring high schoolers, Bitcoin updates, Satya & Sam, Google's productivity hacks

Reading Ambitiously 10-31-25 🎃

Knowledge work vs. Judgement work, Cursor's 300 meetings, Nvidia GTC, 2025-2050, OpenAI prepares $1T IPO, a16z's network effects, OAI's now a PBC, high agency, Halloween

Reading Ambitiously 10-24-25

AI Regulation, High Agency, Agents v. ChatBots, Coatue Fall update, LLMs are like ghosts not animals, Ramp AI index, AI traffic share, top 15 AI companies by value, state of crypto 2025, Vision Pro

Reading Ambitiously 10-17-25

AI Froth, Paradox of Skill, Techno Optimism, SaaS Multiples, JPMs $1.5T plan, AI Slop, Happiness, Thrive Capital, Robots, SFDC installs ChatGPT, Sorkin's 1929

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Reading Ambitiously 10-3-25

Nvidia at $4.5T+, SiriGPT, ThinkingMachines, OAI & Nvidia's 10GW, Microsoft Excel w/ AI, Meta Smart Glasses, D/E ratios, Sora 2, Picks & Shovels, LLMs cite Reddit

Reading Ambitiously 9-26-25

Base Camp, AI passes CFA exam, OpenAI signs iPhone supplier, Nvidia $100B OAI investment, Chinese open source LLMs, advisor shortage, a16z generated $25B for LPs, Blackstone's Jon Gray

Reading Ambitiously 9-19-25

Botfarms, Microsofts OAI investment = $170B, ChatGPT usage, infra spending, median IPO 14-years, developer headcount trends, Insights Jeff Horing on ILTB

Reading Ambitiously 9-12-25

Software predictions, Anthropic $1.5B judgement, AI infra spending, expense fraudsters, OAI’s LinkedIn competitor, Replit Agent 3, Ellison worlds richest, Palantirs AIP 2025, iPhone 17 choices

Reading Ambitiously 9-5-25

Systems of Intent, FinTech IPOs, Google antitrust, Software M&A ticking up, Google Finance beta, US v. China AI race, Ship it

Reading Ambitiously 8-29-25

Shiny objects, eating frogs, the status quo, end of software vs. good luck rebuilding SoRs, adding up AI revenues, P/E land update, RPU at Uber, $10T AI market opportunity, Marc Benioff on 20VC

Reading Ambitiously 8-22-25

Apple Intelligence, small language models, AI supernovas, enter the AI matrix, bitcoin $1M by 2030, the power of compounding, scooby dooby do, Dylan Patel on GPT 5 & semis, Oscar Health

Reading Ambitiously 8-15-25

Software is changing, GPT-5, vibes = legacy code, BVPs State of AI, CAPEX, is it maximally accelerated?

Reading Ambitiously 8-8-25

Technology ≠ Purpose, GPT-5, open "source" AI, Figma IPO, magic loop, SaaS IPO leaderboard, data centers vs. office space, asking the right questions

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Reading Ambitiously 6-6-25

AI FUD—bet on optimism, rally your people & dream big; Coatue May ’25 market update, Karpathy on which OpenAI model to use, Apollo’s Zito × Greenlight’s Einhorn spark, change vs. transition

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Reading Ambitiously 11-1-24

Can Klarna really ditch Salesforce and Workday for AI dominance? Dive into the boldest moves in tech, the future of AI agents, Nvidia’s rise, and lessons in storytelling that every leader should know.

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