CGW's Blog – Page 2 – Journalist-entrepreneur Christopher Wink has shared his reading, writing and learning here since 2006.

The risk-taking that connects Wall Street, Las Vegas and Silicon Valley

A certain approach to risk and decision-making spans Wall Street, Las Vegas, Silicon Valley and, yes, even cryptocurrency libertarianism. Not all of it’s good, but some is.

It’s important to understand this community and worldview. That’s from On the Edge: The Art of Risking Everything, a 2025 book by popular statistician Nate Silver.

The book is at least 150 pages too long, and needed a more disciplined edit. The author says he had three book proposals: gambling, AI and game theory. As far as I can tell, he combined them all. The bloated book has detailed poker gossip, historical passages about Las Vegas and biography of Steve Wynn. Lengthy passages detail how LLMs work and the personalities behind game theory. It’s all moderately interesting but bizarrely off focus of his book, in my read.

I happen to like the stuff, but I kept finding myself circling passages that could have been edited away. Regardless, I took away plenty of charming little details.

Below I share my notes for future reference.

AI a Performance-Enhancing Drug: my interview on WYPR

Host Jason Michael Perry sits down with Chris Wink, cofounder and CEO of Technical.ly, to explore whether AI is becoming a performance-enhancing drug for founders and what that means for workers, entrepreneurs, and the cities trying to build ecosystems around both.

Recorded in Philadelphia during Philly Tech Week at the WHYY studios, the conversation digs into Chris’s framework for cutting through the AI noise, the gap between what AI could do at work and what people are actually using it for, why the most exposed workers may not be who you expect, and what the bar is now to be taken seriously as a founder in 2026.

LISTEN HERE

How a poem’s 1417 rediscovery shaped the Enlightenment

The concept hooked me: Lucretius’s On the Nature of Things, a materialist Roman poem, gets rediscovered in 1417 by book-hunter Poggio Bracciolini, and its ideas — atoms, a universe without divine design, pleasure as a worthy pursuit — help crack open the modern world.

That’s the setup of The Swerve: How the World Became Modern, a 2011 book by historian Stephen Greenblatt that won both the Pulitzer Prize and National Book Award. I just read it.

What I actually wanted was the origins story: how could anyone in the centuries BCE arrive at “atomism” at all, with no microscopes and no evidence? The book gave me less of that than I hoped, so I went digging on my own — and that turned out to be the more rewarding part. The answer: ancient atomism wasn’t a discovery. It was a logical deduction. Parmenides had argued that nothing can come from nothing and therefore change is impossible; Democritus’s answer was tiny, eternal, uncuttable bits (atomos) rearranging in a void. It only looks like modern science because the word survived. The concept was independently rebuilt on real evidence 2,000 years later.

Which reframed the whole book for me. The Swerve isn’t really a book of ideas — it’s a beautifully written, story-forward narrative built on a single irresistible image: a lone bibliophile pulling a lost masterpiece off a monastery shelf at exactly the right moment to change everything. That’s why it won: gorgeous prose, a great yarn, and a secular-humanist thesis that landed perfectly in the science-vs-religion mood of 2011.

The insight I want to keep: Greenblatt’s book is itself an example of its own thesis. It’s a work that met its moment — the right idea, well-told, arriving when the culture was primed to reward it. Drop it into today and I’m not sure it wins anything. Books, like the texts they’re about, get lucky in their timing.

Below I share my notes from the book for future reference.

Who are entrepreneurs enemies? My 2026 Technical.ly Builders Conference keynote

Below is my Friday speech, inspired by this bet, and following this live podcast recording.

I want to tell you about a bet I have with Brian Brackeen.

I’ve known for Brian for more than 10 years, back when he founded a facial recognition startup in Miami. He’s built in machine learning longer still. He and his wife and partner, Candice, cofounded Ohio-based VC firm Lightship Capital, investments around AI. He organizes Black Tech Week. He’s got opinions.

Last year we debated whether AI would imminently replace software developers. Brian said yes—developer jobs would fall. I disagreed. We bet a cheesesteak, or more properly having to wait in line for one, deadline May 2026.

It’s May 2026. This morning we’re going to learn the answer together, and what it means either way.

Moravec’s Paradox

This was original a social video post

I want AI to do my dishes and laundry so that I can do art and writing, not for AI to do my art and writing so I can do more dishes and laundry.

That 2024 tweet went viral. And there’s a name for this: Moravec’s Paradox, and it dates back to 1988, from a machine learning researcher.

Immigration creates a “lake society,” rather than a stagnant swamp

Immigrants are neither villains, nor victims.

The through put in any economy is where dynamism comes from to get a “lake society”, rather than a stagnant swamp.

More to the point, foreign workers tend to not be the same as native workers, and when that’s the case everyone benefits. So that should be the focus, less displacement and more a core component of how an economy thrives.

That’s from The Truth About Immigration: Why Successful Societies Welcome Newcomers, a 2024 book written by Wharton School professor Zeke Hernandez.

In truth this pro-immigration stance is something of a straw man. Overall, even amid partisan American culture war, as I frequently report, high-skilled immigration is bipartisan— regardless of campaign rhetoric. It’s among the few things we agree on.

Instead, in many societies the question is what is the right level of immigration.

Below are my notes for future reference.

Statistics aren’t reversible

This was originally a social video.

You might have seen Robert F. Kennedy Jr. make a statistics mistake today.

Rather than clown on it, I wanted to explain the simple and interesting concept behind the gaff.

RFK: “And I said, well, if the drug was $100 and it raised the price to $600, that would be a 600% rise. If it drops from 600 to 100, that’s a 600% savings.”

I’m not one to judge because I’ve made lots of numeracy mistakes in my day, including in my journalism. And statistics actually are complicated, but they’re
cool. So, it’s worth looking at what’s happening here.

“If Anyone Builds It, Everyone Dies”

The alchemist who takes on the king’s trial to attempt to turn lead into gold. If he does so he gets fabulous wealth for all around him. If he doesn’t, everyone dies.

Believing it impractical to stop everyone else’s from trying, he decides that he is the best shot because he has the most discipline. His sister begs him not to, but he goes anyway.

That fable opens the 11th chapter of the comfortingly named “If Anyone Builds It, Everyone Dies,” the fall 2025 book by Eliezer Yudkowsky (“the prophet of AI doom”) and Nate Soares.

To their credit, the book is more reasoned than the title might suggest (I actually think it’s a great book title). They say again and again that they do not know the timeline: AI research, then, they say is a ladder on which each rung is billions of dollars but if anyone reaches the top everything explodes — and no one knows how long the ladder is.

Their argument is competition between China and the United States is silly Nobody “has” ASI (or AGI ), only it has itself, is their argument

Their argument, and this book in particular, helped refine my own framework for interpreting the moment, and my own AI philosophy, distilled in the chart below as a two-by-two axis depending on what your best guess is on the technology.

Below I have my notes for future reference.

Let Them

Commercially successful self-help authors have a story that a book-buying audience wants to hear. That message lands simply and clearly for those who need it, and may not seem like much to anyone else.

So it is with The Let Them Theory, the 2024 book by Mel Robbins, a former CNN legal analyst and self-help star, that has sold 10 million copies. I got the book to better understand this category, which frequently spawns coursework and speaking careers from tidy packages and simple ideas.

Technical.ly journalists leading an AI discussion

I was proud to see three journalists and current and former Technical.ly newsroom staffers are leading an upcoming AI conversation a conference hosted at Philadelphia’s NPR affiliate.

My current colleague Danya Henninger, who oversees our newsroom, will be alongside two treasured former teammates: Julie Zeglen, who is now at the Philadelphia Inquirer, and Paige Gross, who has joined the B2B publisher Industry Dive. It felt reaffirming that when organizers curated a list of thinkers on the topic of artificial intelligence and media, all three have Technical.ly ties.

They’re smart and delightful. Check out the Philadelphia Student Press Association‘s inaugural summit April 24.