Reading Ambitiously 12.19.25 - 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

Enjoy this week’s Big Idea vibe coded by me:

The big idea: There is no going back. A year in vibes.

Reading time: 5 minutes

This is the final Reading Ambitiously of 2025, and it closes our first full year of writing to you every week.

Every technology era has a clean line you only recognize once you’ve crossed it. This past twelve months, I believe we’ve crossed it with AI. I believe we’ll look back at 2025 and say this year was the clear before and after. I encourage you to watch our video edition this week to understand why I hold that view.

Starting Reading Ambitiously had its own before and after in my life. Writing every week sounds simple enough until you try to do it. What I’ve learned is that the work is not the writing itself. It is defending a block of time, every week, long enough to actually think.

And in an ever-busy world where we are all in a hurry, that thinking time feels like one of the scarcest resources for us all. Writing is how I personally get it back.

When you give someone words for an idea they already felt but could not articulate, you give them power. Reading Ambitiously is a weekly endeavor to foster language and community for what we are all experiencing, to empower you to utilize it and lead with it.

In pursuit of that mission, we wrote a lot this year. A few numbers tell the story better than I can.

Today is our 48th edition of 2025. In total, that added up to 100k+ words. The word counter has its own sense of humor. “ai” was the most common word, with 1,020 whole-word mentions, and “openai” and “software” weren’t far behind.

The themes reveal where the gravity was: AI & Models dominated, followed by Enterprise Software & SaaS, Markets & Investing, and Infrastructure & Semiconductors, with a notable strand of Leadership & Culture.

Over the past year, we have reached more than 1.7 million eyeballs on LinkedIn, Substack, and X.

Most importantly, at our first full year since launch, we have 905 readers who read very closely, share thoughtfully, rarely miss a week, and want this work to continue. These are the folks who will text me at ten minutes past the hour on Friday morning, asking if I’m “OK” because we haven’t published yet.

Kevin Kelly talks about your first 1,000 true fans. This newsletter is not designed for the widest possible audience. It’s designed for the most ambitiously dense. If that is you in the “905”, thank you for being here. You are why we do this every week.

Your notes and testimonials fire me up. They also keep me humble and remind me to keep innovating every week.

If Reading Ambitiously earned a slot in your weekly routine, I have one ask: help me improve it, help me share it, and help me reach our first 1,000 true fans by forwarding this to one person as ambitious as you.

Thank you, truly. Happy Holidays and Happy New Year. We look forward to being back with you on January 9, 2026.

Best of the rest:

💸 Amazon reportedly in talks to invest $10B in OpenAI as circular deals stay popular – If this lands, it signals OpenAI is moving from a Microsoft-centric compute stack to a multi-cloud, multi-chip world where capital, chips, and cloud credits blur into one giant strategic bargain. – TechCrunch

🧠 Portable Memory & Behavioral Signatures: the missing layer for AI personalisation – The real leap in personalization is not better in-model memory tricks, it is making your “behavioral signature” portable across apps so “sign in” becomes “import how you work,” killing onboarding and turning identity providers into memory providers. – Venture Bystander

⚙️ TPU Mania – A sharp tour of Google’s TPU resurgence that frames the real fight as ecosystem and software moat versus NVIDIA’s CUDA, and asks if this is the CISC vs RISC moment for modern AI accelerators. – The Chip Letter

🚀 SpaceX Targets $1.5 trillion IPO – Reports say SpaceX is lining up a 2026 public debut, and the deeper “why” is Starlink plus Starship turning space into scalable infrastructure for orbital compute, with an IPO-sized war chest to accelerate the plan. – Ars Technica

🧾 Clouded Judgement 12.12.25 - Long Live Systems of Record – A needed corrective to “agents replace systems of record” hype, arguing automation makes canonical truth more valuable, not less, and that the winners will be the platforms that turn warehouses plus semantic layers into an explicit “truth registry” agents can safely read and write. – Clouded Judgement

Charts that caught my eye:

→ Why does it matter? A new cohort of AI-native companies is hitting $100M in annual recurring revenue faster than any software generation before it. The real test is quality. Is this durable, expanding revenue, or a surge of buyers sampling a shiny new tool before moving on?

→ Why does it matter? CEO’s are embracing AI and suggesting it’s going to change the shape of your workforce.

→ Why does it matter? Strong list to watch in 2026. I’m paying closest attention to #27, Vercel. I’ve also enjoyed testing a few others here, including Cursor, ElevenLabs, and Wispr.

→ Why does it matter? Valuations circa 1999 vs. today.

Tweets that stopped my scroll:

→ Why does it matter? Incredible execution by the team at Notion in growing to their $10B valuation. After the 2021 froth, the reset did not come from financial engineering, it came from revenue catching up, plus smart packaging like bundling AI into Business and Enterprise tiers.

→ Why does it matter? We used Opus 4.5 in today’s vibe coding demonstration!

→ Why does it matter? Google is on the offensive with Gemini. As it gets woven deeper into Google Workspace, formerly G Suite, the in-app integrations across Gmail, Docs, Sheets, and Slides are starting to feel like a real workflow shift. Exciting example here.

Worth a watch or listen at 1x:

→ Why does it matter? No podcast has stayed in my rotation longer than Tim Ferriss, one of the originals of the format. Bill Gurley is a strong guest, and they cover a lot of ground. This is an easy one to add next time you’re multitasking to catch up on multiple topics.

→ Why does it matter? I wouldn’t multi-task through this one. Henry Ellenbogen, founder and managing partner of Durable Capital Partners, and formerly the lead manager of T. Rowe Price’s New Horizons Fund, is thoughtful in a way that rewards attention. The episode, “Man Versus Machine,” is a long-form tour through how he thinks about people, change, and the small handful of companies that drive most long-term returns, worth hearing on 1x.

→ Why does it matter? Twice a year, Benedict Evans produces a big presentation exploring macro and strategic trends in the tech industry. New in November 2025, AI Eats the World. Here he is on The a16z Show with Erik Torenberg to break the deck down, and to connect it to the broader shift some people call “Software 2.0,” where more capability moves from hand-written code into models trained on data.

Quotes & eyewash:

→ Why does it matter? New Toy Story 5 is coming next summer. Guess who the villain is? An iPad. Perhaps this will be the turning point to fight back against too much screen time. I seriously hope so.

The mission:

The Wall Street Journal once used “Read Ambitiously” as a slogan, but I took it as a personal challenge. Our mission is to give you a point of view in a noisy, changing world. To unpack big ideas that sharpen your edge and show why they matter. To fit ambition-sized insight into your busy life and channel the zeitgeist into the stories and signals that fuel your next move. Above all, we aim to give you power, the kind that comes from having the words, insight, and legitimacy to lead with confidence. Together, we read to grow, keep learning, and refine our lens to spot the best opportunities. As Jamie Dimon says, “Great leaders are readers.”

Disclaimer: This content is for informational purposes only and does not constitute financial, investment, or legal advice. Readers should do their own research and consult with a qualified professional before making any decisions.