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Will designers design first in a world where AI can code software immediately, or just describe the design? Will large enterprises pay for premium observability when AI can migrate & monitor open source competitors?

As Michael Mauboussin writes, there’s information in price. These questions are priced in. It’s too early to see revenue erosion, but the market is pricing in the risk.

The median SaaS stock is down 14-17% year to date. 64% of software companies are down. Adobe has fallen 32%, HubSpot 57%, Atlassian 54%.

After a decade of success, the modern data stack has entered consolidation. What comes next?

The postmodern data stack is AI.

The modern data stack created more than $100 billion in market cap with a simple promise : move the data via ETL, transform it inside a cloud data warehouse, put a semantic layer on top of it to unify metric definitions, & analyze it through BI.

This worked brilliantly for structured data, numerical data found within tables. But AI & businesses thrive on unstructured data, such as call transcripts, status reports, web searches, & PDFs.

This week I chatted with an acquaintance who mentioned a board game. I caught half the title & looked for the full title & Amazon link using my AI in Asana.

The system tried with Gemini & failed. The failover to Claude also failed. Rather than continuously iterating with the AI until it worked, I created a Ralph Wiggum loop.

AI is NVIDIA’s third climb up a steep slope.

First came gaming in the late 2010s.

Then cryptocurrency.

Now artificial intelligence.

Each wave pushed revenue growth above 50% & with it, P/E¹ ratios surged. P/E ratios rose before the revenue growth materialized.

There’s a four-quarter offset between P/E ratio & TTM² revenue growth. When you shift revenue growth forward by a year, the correlation with P/E jumps to 0.80.

“[Silicon Valley] is the biggest, most volatile petri dish of raw capitalism on the planet.” So what lessons does a successful short-seller living here have? As founder of Crown Capital Management, Scott Fearon has shorted the stocks of over 200 companies.

In his book Dead Companies Walking, Fearon distills three decades of meetings with executives into six failure modes :

Despite their differences, they all failed because their leaders made one or more of six common mistakes that I look for :

1. They learned from only the recent past.
2. They relied too heavily on a formula for success.
3. They misread or alienated their customers.
4. They fell victim to a mania.
5. They failed to adapt to tectonic shifts in their industries.
6. They were physically or emotionally removed from their companies’ operations.

I asked Claude Cowork to read my tools folder. Eleven steps later, it understood how I work.

Over the past year, I built a personal operating system inside Claude Code : scripts to send email, update our CRM, research startups, draft replies. Dozens of small tools wired together. All of it lived in a folder on my laptop, accessible only through the terminal.

Salesforce, Datadog & Epic are building walls. After two decades of flourishing through open APIs & data portability, the software industry’s largest incumbents are locking down.

Salesforce restricted Slack’s API¹ in May 2025, limiting third-party apps to one API call per minute & fifteen messages per request. Datadog deactivated accounts² for Deductive AI, a competing observability startup. Epic faces a Texas lawsuit³ accusing it of turning patient records into a “gatekeeping tool.”

In 2012, we cared that we used software. Today we care how we use it.

The difference is trajectory.

In the last decade, adopting software was the priority. Moving from on-premise to the cloud or digitizing a manual workflow promised productivity gains. Adoption was the finish line.

Today software is ubiquitous. Every salesperson uses a CRM & every engineer uses an IDE. The edge no longer comes from having the tool but from the specific path & manner in which that tool is used to achieve an outcome : a trajectory through software.

The PC era began with a black screen & a blinking cursor. This stark prompt was the only gateway, beckoning a user to test the computer’s power.

Today, the interface to AI looks identical : an empty text box & a blinking cursor.

1980s Command Line	2020s AI Interface
Image credit: Newton Freehostia

We’ve spent decades moving away from the command line, first to Windows & then to websites. Now we’re arriving right back where we started, albeit with a much smarter partner behind the box.

For decades, the to-do list has been a catalog of debt, a deceptively thin list of items to do, with icebergs of work hidden beneath the surface.

AI transforms tasks to work that has already been done.

Vibe Kanban, Gastown, & Conductor are the first instantiations of this for software developers. They have jargon-laden descriptions like “multi-agent orchestrator” or “visualizer,” but they are, at heart, simple & beautiful Kanban boards of done & dusted work.