Newsletter Archive

95 editions of Reading Ambitiously. Each one feeds the AI knowledge graph powering AmbitiousOS.

The case for a more decentralized AI future

The case for a more decentralized AI future

Mainframes centralized computing, PCs spread it out, and the cloud pulled it back together. Could AI swing the pendulum again, giving people and businesses more control over the intelligence they use?
Keep your bathrooms clean

Keep your bathrooms clean

A lot of talk about AI eroding traditional software moats. A weekend at Disney World reminded me that some of the most enduring advantages are built on paying attention to the little things
Everyone wants a business like Windows

Everyone wants a business like Windows

But as enterprises teach AI how they work, they may demand a different bargain over who owns the intelligence.
Agent Swarms & Machine Speed

Agent Swarms & Machine Speed

AI already works at machine speed. Now imagine 10,000 AI agents working together. 🤯
Run the business, change the business.

Run the business, change the business.

"You can't be getting there, you have to already be there." Five bets for 2026 on data, security, and redesigning the work with AI. 👋 from Base Camp 2026!
Meat proxy and AI slop

Meat proxy and AI slop

A meat proxy: someone who passes along AI-generated text without reading, understanding, or validating it.

The Last S in SaaS

AI can build the software you’ve always wanted in an afternoon. Before your business depends on it, ask one question: Who carries the iceberg?

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.

The window was the way out

The human truth in anything you make rarely appears at the beginning. You have to go through the work to find it.

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

America turns 250. It almost ended in Brooklyn.

Sometimes, the wind holds just long enough for the courageous ones to act.

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.

What I am teaching my kids about AI

My first-grader can turn ideas into software faster than I ever thought possible. That has me thinking less about which careers will matter, and more about the street smarts kids will need to thrive.

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.

AI Product Strategy for Model Consumers

If you are not training the model, you are renting it. Where durable moats actually live for AI product teams.

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

Reading Ambitiously 10-10-25

Paradox of Skill, OAI $500B, Apple's next CEO, The Bitter Lesson, OAI Dev Day, Always be Creating, Orlando Bravo on bubbles, Power Demand, AI 8-hour workday

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

Reading Ambitiously 8-1-25

AI slop, catching a wave, Figma's IPO, AI capex = private stimulus, $1B comp packages, the "dark art" of pricing & the similarities in art & venture

Reading Ambitiously 7-25-25

Target date funds add private credit, BlackRock says bring a burner, Oracle's $30B whale is OpenAI, WarrenBuffettGPT, Stripe on API design, GameStop, Acquired interviews Jamie Dimon

Reading Ambitiously 7-18-25

Pressing Buttons, Claude for FinServ, Service as Software, Reflexive AI, AI-Native Web Browsers, Founders Fund, Robots Folding Laundry & Scott Scheffler on Winning

Reading Ambitiously 7-11-25

Forward deployed engineers, oracle signs $30B deal, safe choices, excel hooked up to LLMs, AI prices down 85% in 2-years, context engineering, meta $200M comp packages, future of SFDC

Reading Ambitiously 6-27-25

Software 3.0, Infrastructure > Apps > Infrastructure, LLMs as OS, Agentforce 3.0, OpenAI drama, Andy Jassy on GenAI, Coatue EMW, Going the Extra Mile & Hustle

Reading Ambitiously 6-20-25

AI, Trust & Level 5 Leadership, OpenAI v. Microsoft, Constraints > Goals, Coatue's Fantastic 40, The "ole" Build v. Buy Iceberg, This is Water, Sam Altman & Marc Andreessen on Jack Altman's pod

Reading Ambitiously 6-13-25

memory and context, idea resistance, forward deployed engineers, openai at $10b, US IPO return, mag 7 dislocation, meta talent wars, khosla on pitches, king’s mindset, apple glass.

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

Reading Ambitiously 5-30-25

Software managing software, do hard things, Midas List 2025, Salesforce acquires Informatica for $8B, power laws, systems of record & action, Google processing 50x more tokens, play for the upside

Reading Ambitiously 5-23-25

You can think faster than you can type, OpenAI buying Jony Ive's design firm for $6.4B, Google I/O & Microsoft Build, JP Morgans 1799 founding, AI reading x-rays, Shopify 10-year since IPO

Reading Ambitiously 5-16-25

AI as an operating system, Klarna is hiring again, software buying software, the $1T opportunity, ServiceNow & systems of engagement, Sequoia’s AI ascent & Fred Wilson on the future of crypto

Reading Ambitiously 5-9-25

Shift Left, RSA, JP Morgan CISOs open letter, Agent costs, pre-money startup valuations, Palantir 93.4x ARR, Buffet buying Apple in 2016, Ken Griffin, Marc Benioff, all new cells every 7 years

Reading Ambitiously 5-2-25

Workflow gets a brain, Thrive builds a holdco, Altman & Nadella drift, the Experience Era dawns, Jack Altman’s career gems, LVMH’s timeless wisdom, Vatican > UK treasury in Bloomberg Terminals

Reading Ambitiously 4-25-25

Enterprise AI won't run on vibes, OpenAI in talks to buy Windsurf for $3B, Cascading Agency in Medicine, AI Agent pricing, Jane Street made $20B trading & EPIC Systems

Reading Ambitiously 4-18-25

Do more with AI, OpenAI building an X-like social network, Safe Superintelligence hits $32B, Buffett sits on enough cash to buy 476 S&P 500 companies, Rory's Masterpiece & more

Reading Ambitiously 4-11-25

The dollar gets a software upgrade, Microsoft turns 50, Llama 4, everything is sales, AI evals, Hollywood legend Michael Ovitz, Brex 3.0, and Jamie Dimon’s leadership commandments

Reading Ambitiously 4-4-25

Public & Private markets blur, OpenAI flirts with open source at new $300B valuation, SaaS spy flushes phone down toilet, McDermott enterprise sales G.O.A.T., High Agency & Be a ten

Reading Ambitiously 3-28-25

Disrupt Yourself w/ Blackstone’s former CTO Bill Murphy, Data 3.0, DeepSeek tops non-reasoning models, ChatGPT’s new image engine, a rare USV founders interview, and lessons from Lynch & Buffett

Reading Ambitiously 3-21-25

Model Context Protocols (MCP), SaaS Espionage, Google’s $32B Wiz Acquisition, Cursor’s $0 Marketing Strategy, and NVIDIA’s GTC Keynote — “The AI Super Bowl”

Reading Ambitiously 3-14-25

Anthropic CEO predicts AI will generate 90% of new code, Rotten Apple, OpenAI’s $9B burn for a $5B loss, Ridgeline’s new AI agents, parrots chatting with AI, and Lattice CEO on the evolving workforce

Reading Ambitiously 3-7-25

OpenAI's Deep Research, the "it" in AI is the dataset, Stripe's Annual Letter, own AI.com for $100M, Citi mistakenly sends a client $81T, Granola.ai, Ask for "NO" vs. "YES"

Reading Ambitiously 2-28-25

Anthropic Claude 3.7, Claude Code, OpenAI Releases GPT 4.5, Amazon Alexa Plus, High Agency, Bybit $1.45B Crypto Hack, SailPoint IPO, R2D2, Bill Gates & Patrick Collison, Andrej Karpathy on using LLMs

Reading Ambitiously 2-21-25

Meet Grok3 from xAI, ex-OpenAI CTO's new gig, Replit + Agents = we can all build software, Unbundling BPO & Service as Software from a16z, The Best Teams Win, Groq & Apple's $19 polishing cloth

Reading Ambitiously 2-14-25

AI Moats & Buffet, GPT 4.5 & 5, Workday Agents, OpenAI Chairman Brett Taylor, YC top 40 most valuable, Cursor 100M+ ARR fastest ever

Reading Ambitiously 2-7-25

Jevons Paradox, Zuck's 1B Digital Assistants, 2025 IPO Candidates, Palantir Earnings, AI Moats, Shopify CEO Tobi Lütke, Replit's AI App Builder and Thomas Watson's Wild Ducks

Reading Ambitiously 1-31-25

DeepSeek R1 w/ Special Guest Scott McNealy (Co-Founder & CEO, Sun Microsystems), What's in your stack?, SailPoint First IPO Of 2025, Zuck's Data Centers are the size of Midtown Manhattan

Reading Ambitiously 1-24-25

Project Stargate, reasoning models, startup land, S&P 500 concentration, DeepSeeks new LLM, Howard Marks on Bubbles, Netflix now more valuable than all US movie & TV studios combined, The Kobe Rules

Reading Ambitiously 1-17-25

Tesla Full Self-Driving, VCs buying accounting firms, Goldman says S-1's 95% written by AI, exponential thinking, Bezos's New Glenn, Benioff says digital labor is a trillion dollar TAM

Reading Ambitiously 1-10-25

Nvidia's 2025 CES keynote, AI Scaling, startups are taking longer to build, the DellEMC story, PLUS Jerry Jones takes Hollywood, 2025 tech predictions, and timeless wisdom from founders.

Reading Ambitiously 12-20-24

DataBricks $10B Series J, Private & Public Market Convergence, AI Revenues & 2024 Startup Valuations, AgentForce 2.0, Google Veo2, SantaGPT & It's A Wonderful Life

Reading Ambitiously 12-13-24

Google's Quantum Leap, Elon & Zucks AI Infrastructure Race, Venture Power Laws, ChatGPT Pro & More

Reading Ambitiously 12-6-24

Why are tech’s biggest founders back in the arena? Generative AI usage in the enterprise, the rise of vertical agents, and the art of capturing someone's attention in six seconds.

Reading Ambitiously 11-22-24

Google’s dominance tested under antitrust scrutiny? This week, uncover how AI is replacing traditional RPA, networking in Silicon Valley now involves saunas, private markets update with Apollo's CEO

Reading Ambitiously 11-15-24

Is AI hitting a plateau? This week, we dive into AI scaling laws, Salesforce’s AI hiring spree, and the latest on cloud markets poised for a $4 trillion Service as Software shakeup.

Reading Ambitiously 11-8-24

Exploring how AI-driven Service-as-Software is transforming enterprise tech and unlocking new market opportunities.

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.

Reading Ambitiously 10-25-24

Reading Ambitiously Vol. 38 is now available for your reading pleasure!

Never miss an edition

Free newsletter every Friday.