Newsletter Archive

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

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.

42426 how i use

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.

41026 always

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.

11626 its a new

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

4 18 25

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

4 4 25

3 28 25

3 21 25

3 14 25

3 7 25

2 28 25

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