Sitemap - 2025 - Cautious Optimism

Crypto Rises, Agents Drop, Factories Hum

7 Thoughts About Substack's $100M Series C

Uber is getting back into the self-driving game

Dispatches from the earnings trenches

What's up with datacenters? And the Three Horse Race

All the AI circus you can fit in a single tent

Economic Calendar for the Week of July 13th

Who’s raising, IPO updates, and what company is buying Grok?

The "Kill Chrome Olympics" Has Started

We may have reached an early AI usage peak

Ambiq’s IPO is good fun, and 7 Q2 '25 VC data points

I thought we were broke

Economic Calendar for the Week of July 6th, 2025

High-cost AI is potentially bullish

Inside the guts of Figma's S-1 Filing

Internet Independence Day

Your local bodega owner is safe for now

Economic Calendar for the Week of June 29th

What did Meta buy? A person? A dataset? A capability?

Mamdani won. Now what?

How stablecoins could fail

Uber’s AWS era

Economic Calendar for the Week of June 22nd

Circle’s valuation is getting nutty

Microsoft’s big stick era

Are you a GENIUS?

PostHog vs. The Industry

The robotaxi wave is catching speed

Economic Calendar for the Week of June 15, 2025

The LLM paper wars continue

Ring the bell

All eyes on Cyera

Diverging AI bets detail two-lane future

The LLM wall, Chime's IPO and is it robotaxi week?

Economic Calendar for the Week of June 8, 2025

Yes, there are other things to talk about

Circle’s IPO Makes Tech IPOs 3 For 3 This Year

Ok, but what about the spying?

TechCrunch’s Ozempic era

Samsung-Perplexity and the Google Question

Economic Calendar for the Week of June 1st

Don’t call it a comeback loan

Hot damn, Nvidia

How to lose $7.5M a day for more than a year

Salesforce spending austerity has ended

What are we doing here?

The first company with no employees wins

Happy Birthday to Cautious Optimism

Klarna IPO Update: A Mix of Good and Hmm…

Economic Calendar for the Week of May 18, 2025

So that was a lie

Building a hyperscaler isn’t cheap

Chime’s Road to IPO: Growth Holds, Margins Improve, and Losses Slowly Fade

It all makes sense now

OpenAI wants to go public

Economic Calendar for the Week of May 11, 2025

Y Combinator wants full-stack AI Companies

Here’s a win of sorts for the tech-right

The M&A size premium is still falling

OpenAI solves its internal crisis, snaps up Windsurf

Can anyone slow Cursor?

Economic Calendar for the Week of May 4, 2025

Trump hits out at Harvard, might smack VCs instead

All that spend and Meta is still GPU poor?

GDP down, employment growth down, inflation up

Let’s eat our vegetables

Will the tech-right survive Trump 2.0 as a political unit?

Economic Calendar for the Week of April 27, 2025

Alphabet’s AI earnings bonanza

The global supercomputer race

AI in market niches can soar

Just @ me, bro

I thought we wanted this?

Economic Calendar for the Week of April 20, 2025

So much for global trade

Windsurf. Do the deal. But at $5B, not $3B. Sam can afford it.

This newsletter is now called "DEV MODE" 🤪

Can you secondary your way to top-decile DPI?

Everyone but Meta gets a breather

Economic Calendar for the Week of April 13, 2025

Why IPOs are over (for now)

All gas, no brakes in AI-land

In wake of tariffs, Europe backs its AI industry

Dead Cat Bounce

RIP the liquidity cycle: born Q1 2025, died Q1 2025

Economic Calendar for the Week of April 6, 2025

We just shot our own foot, reloaded, and shot the other

Blood in the Streets

Circle is going public!

CoreWeave comes pounding back

Is OpenAI worth $300B?

X + xAI = a16z, Fidelity, Kingdom Holdings, Sequoia Capital

Economic Calendar for the Week of March 30th

CoreWeave's IPO disappoints, inflation comes in hot

Just Go Public

Everyone wants a piece of the stablecoin boom

eToro is going public!

Thoughts on the TechCrunch sale

Economic Calendar for the Week of March 23, 2025

The CoreWeave-OpenAI-Microsoft drama explained

CoreWeave sets IPO price range at $47 to $55

The AI Factory model of the future

We underestimated how much corporate America hates paying developers

Rippling's suit against Deel is wild

Five takeaways from Klarna's IPO filing

Economic Calendar for the Week of March 16, 2025

Can I borrow your life's work? It's a matter of national security!

Do today’s best startups need venture capital?

Closed-source AI models are doing pretty darn well

Good exit news!

Crypto Cope and the Curve of Software Jobs

Economic Calender for the Week Of March 9, 2025

Yes to expensive AI agents 💰

For whom the Gong tolls

Everyone is eating

The vibes are bad

Coreweave is going public!

I scream, you scream, we all scream for exit liquidity!

Economic Calendar for the Week of March 2, 2025

Is Stripe expensive, or is Adyen cheap?

Nvidia makes gains on rising inference demand

Without AI, are startups crawling?

I was told there would be rate cuts

How does a 63% premium sound?

Economic Calendar for the Week of February 23rd

I thought we liked free markets

What happens if you pause growth, invest in AI, and relaunch?

Small startups, doing too much to stop too little, and Chinese tech waking up

Economic Calendar for the Week of February 16th, 2025

AI models’ fusion future

How soon until we can afford robot butlers?

Defense funding, Lyft earnings, inflation data, and the sad state of IPOs

Sailpoint’s lonely IPO accelerates

Bonjour, je suis un modèle IA français!

Economic Calendar for the Week of February 9, 2025

All Fear The Cloud and Twitter Financials

Do you want to pay startup prices for public companies?

How much capital can startups profitably eat?

Well, there goes the neighborhood

Let's just value OpenAI at infinite money and be done with it

Earnings, capex, and models, oh my!

Brief and to the point

I, too, am terrified of better, faster, and cheaper AI models and services

Chinese AI is crushing tech stocks

Economic Calendar for the Week of January 26, 2025

Industry over caution in new Crypto Executive Order

Why tokenize stocks?

What's a half-trillion between friends?

So, it begins

It’s going to be A Week

Economic Calendar for the Week of January 19, 2025

Rockets go up, learning Mandarin, and the good news for SaaS

At 25x ARR, why is Cursor so cheap?

All aboard the quantum rollercoaster, and reaching peak child under capitalism

The second era of fintech

The fight for global AI supremacy, and Steve Bannon versus the Tech Right

Thus ends my Twitter addiction

My most conservative beliefs: Price controls suck and Federal deficit matters

US AI investment is world crushing

Can anyone slow Nvidia down?

It’s good business, but knee-bending is gross

Economic Calendar for the Week of January 05, 2025

It's power laws all the way down

Answering our 2024 questions, and charting a bright path into the New Year