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“[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 :

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.

Meta is acquiring Manus for $2.5 billion.¹² Alongside the announcement, Manus disclosed $100 million in ARR achieved in eight months, 147 trillion tokens processed since launch.³

Can we use those figures to explain the acquisition price?

Publicly traded software companies have gross margins of 71-72%. AI companies run lower. Gross profit per token may be a better indicator of earnings potential. Some AI companies already use gross profit as a quota metric rather than revenue.

This year I traveled through systems, human & machine, from the mathematics of complexity to industrial espionage.

1. The Complex World: An Introduction to the Foundations of Complexity Science: Donella Meadows’ Thinking in Systems introduced me to feedback loops a decade ago. This book goes deeper, surveying where complexity science stands today.
2. Math Without Numbers by Milo Beckman: A vivid & accessible tour of abstract mathematics. Beckman covers topology, infinities larger than infinity, & other mind-bending concepts, all without a single digit & with proofs to explain it all.
3. On Democracy by E. B. White: White, New Yorker editor, Charlotte’s Web author, Elements of Style co-creator, is among my favorite writers. These essays provide a time capsule to help us understand where we are today. Written as fascism spread across Europe & America debated isolationism, White’s defense of America provided a window into another era of rapid political change.
4. Breakneck: China’s Quest to Engineer the Future by Dan Wang: Wang argues that the US & China each have a dominant form of government problem-solving : through laws in the US, or through engineering in China.
5. God Save Texas by Lawrence Wright: Wright’s Pulitzer Prize-winning exploration of the Lone Star State. Both California & Texas value independence & innovation. As a Californian, it was fascinating to see Texas through Wright’s eyes.
6. The NVIDIA Way: Jensen Huang believes Nvidia’s worst enemy isn’t competition but complacency. Kim’s portrait reveals a CEO who spends late nights alongside his team, torturing them into greatness.
7. The Unaccountability Machine by Dan Davies: Davies argues that modern organizations function like runaway AIs, making decisions no human intends. A hotel executive cuts staff to improve the balance sheet. Later, you can’t check into your room & the clerk can only offer a voucher. There’s no one to call, no way to communicate back. That’s an unaccountability machine.
8. Karla’s Choice by Nick Harkaway: I’ve read every le Carré. His son Harkaway picks up where his father left off, adding a bracing entry to the canon.
9. Titanium Noir by Nick Harkaway: Before spy novels, Harkaway spent fifteen years writing science fiction. Curious about his earlier work, I was not disappointed. Titanium Noir explores a world in which the wealthy have access to drugs that double their lifespan & double their size. The novel examines what happens when health becomes a function of wealth.
10. Boom: Bubbles & the End of Stagnation by Byrne Hobart & Tobias Huber: Why does transformative progress require financial bubbles? This builds on Carlota Perez’s work on technology innovation cycles. Hobart & Huber argue that bubbles’ poor accountability shelters the world’s most important breakthroughs.

What should I read in 2026?

Motive, the AI-powered fleet management company formerly known as KeepTruckin, filed their S-1.

Founded in 2013 by Shoaib Makani, Ryan Johns, & Obaid Khan, the company has grown from an electronic logging device (ELD)¹ compliance tool into a comprehensive physical operations platform serving nearly 100,000 customers across trucking, construction, oil & gas, & manufacturing.

Motive’s platform has since expanded beyond compliance to combine AI-powered dashcams for driver safety, GPS tracking for real-time visibility, & spend management cards to control costs. This suite acts as a central operating system for physical economy businesses, unifying data from vehicles, drivers, & equipment into a single interface.

Every year I make a list of predictions & score the previous year’s. You can find my 10 Predictions for 2026 here. 2025 was a good year : I scored 7.85 out of 10.

1. The IPO market rips.

Score : 0.6.