February 2026 – CGW's Blog

Mind the difference between what you know, and what you think you know

More of us should familiar with Bayesian probability, in which you acknowledge your priors and update frequently.

In predictions and finance, the average is more often close to the best than to the worst. So figure if you really want to be average. Poker, chess, earthquakes and economics are either so varied or still missing some underlying sense for predictions to be especially good; in contrast to other weather and the emergence of collective wisdom.

All that’s from the 2015 book “The Signal and the Noise: Why So Many Predictions Fail–but Some Don’t,” by pollster, odds-maker and very-online-person Nate Silver. This book was before Trump’s first election, and when Silver began his combative persona online. Back then, poker and gambling was a world of mathematical insights, presaging other books like one in 2018 by Annie Duke. It injected a kind of numeracy among the professional class, which was good, though we’ve been fighting against the numbers ever since.

As Silver, who was 37 when this book came out, wrote then: “This book is less about what we know then about the difference between what we know and what we think we know.”

Below I share my notes for future reference.

Lessons on entrepreneurial ecosystem building

The entrepreneur-boosters of Boulder were always adept at packaging their story.

Over my years organizing while reporting on startup communities in the U.S. mid-Atlantic via the news org I founded Technical.ly, I understood a cohort of entrepreneurs and investors told a compelling story for their swath of Colorado. They packaged processes (an ever-evolving accelerator program called Techstars) and developed an outsized stream of software companies, alongside that state’s evolving economy.

Among the messages coming from their work that I personally believe in: “Quantity based approaches operate on the assumption that averages, not outliers, drive system value. That is incorrect.”

A “more of everything approach doesn’t work. Instead, an economy that is more accessible and dynamic requires a complex system of overlapping networks that rewards emergence and expects low probability events that have outsized reruns. The trouble is that economies and local policies are typically run by people motivated by linear progress.

That message is neatly described and navigated in The Startup Community Way, a 2020 revision with researcher Ian Hathaway of a 2012 book initially written by Brad Feld, an investor-organizer most associated with that Boulder, Colorado startup community and Techstars. Feld’s initial book became a common starting place for “entrepreneur ecosystem builders,” and he is a prolific writer and speaker, introducing and crediting himself with concepts, including the phrase “startup communities.”

This edition is the right place to start, and I enjoyed it. Given Colorado’s statewide economic story in the Mountain West, and Feld’s position, this book has particular authority and insight. Keeping with his “give back” mentality, working with many hands, the book includes a dozen or so page-length essays from contributors and longtime collaborators across the United States. Hathaway injects the growing research on the importance of entrepreneurship.

Their success lifts a tide that helps many boats, including places and subjects important to my work. I thank them for it. As per usual, outside my own journalism and organizing, here on my personal blog, below I share my notes for future reference from a book I enjoyed.

Our progress can disappear what we once were

One of the stranger feelings in adult life is realizing that “progress” can narrow a person as much as it elevates him.

A family climbs and suddenly whole kinds of work, whole ways of speaking, even whole categories of suffering start to feel farther away — not because they disappeared, but because success encourages the fantasy that you have outgrown them. That distance can look like refinement or achievement. It can also look like emotional cowardice, class vanity and a failure to say what really happened to you.

That’s an idea I took from Flesh, David Szalay’s 2025 novel that won the prestigious Booker Prize.

I adored this, pored over it and found it beautiful and visually-insightful and memorable. Below I have a few notes I took for future reference.

Summer of Our Discontent

The United States has slid into an “age of certainty” where institutions and individuals increasingly traded liberal norms (open inquiry, pluralism, persuasion) for moralized tribal narratives—and that this shift accelerated dramatically around COVID-19 and the summer of 2020.

That big idea comes from Thomas Chatterton Williams’s 2025 book Summer of Our Discontent: The Age of Certainty and the Demise of Discourse, which argues that this new moral certainty—amplified by social media—helped corrode discourse across politics, media, education and culture.

The title is an allusion to William Shakespeare’s Richard III, specifically the opening line of the play: “Now is the winter of our discontent / Made glorious summer by this sun of York” Below I have my notes for future reference.

Guerrilla war follows long-standing principles that powers often overlook

Insurgencies are usually won or lost less by battlefield tactics than by political legitimacy. Once a population comes to see the dominant power as foreign (or foreign-backed), the occupier’s position becomes structurally fragile.

That’s the central idea of William R. Polk’s 2007 book Violent Politics: A History of Insurgency, Terrorism, and Guerrilla War, from the American Revolution to Iraq. Polk argues (across 11 case studies, which I summarized below) that insurgencies follow recurring social and political patterns, and that “hearts and minds” is ultimately a legitimacy contest that outsiders rarely can win on durable terms. Polk (1929-2020) was a long-established political scientist, foreign policy analyst and former Dept. of State official.

It is common in history for guerrilla movements to succeed enough that some leader thinks it’s time to go more traditional in their war. But this is missing the lesson altogether: Conventional war is for defense but offense benefits from guerrilla. Below I share my notes for future reference.

Great men are rarely good; good men are rarely great.

This perspective has long influenced my thinking, and it comes to mind again in the context of the longstanding rivalry between the late Apple cofounder Steve Jobs and Bill Gates.

I was always uncomfortable with people valorizing Jobs, because the track record seemed clear: he treated people very badly. Meanwhile, Bill Gates has done objective good with his wealth since. And yes, rehabilitating a reputation by investing in meaningful global health projects… that is a good.

But, though we don’t know the final word on the Epstein files, Gates’s relationship there does not look good, especially in light of a noncommittal interview done by his ex-wife Melinda.

Blue Man Group founder Chris Wink (that’s not me) appears in the Epstein Files

Well, my name is in the Epstein files. Not me though.

There’s another Chris Wink. He’s the founder of Blue Man Group, the eclectic artistic troupe that got its start in New York and maintains a longstanding residency in Las Vegas.

That Chris Wink (Blue Man Group founder and artist) is 25 years older than the Chris Wink (journalist) who is writing this. Once a friend pointed out that name appeared in this heinous file and document release, I wanted to ensure somewhere on the internet this clarification was made: there are (at least) two very different Chris Winks. When I was getting my journalism started in 2008, I first learned of the name competition.

A History of the Eleven Rival Regional Cultures of North America

There was not just one American war for independence, and there are whole nations inside the United States that do not conform to state boundaries. Linguists in accents, anthropologists on material culture and political scientists on voting patterns recognize this.

That’s from American Nations: A History of the Eleven Rival Regional Cultures of North America, the influential 2011 book by writer-researcher Colin Woodward. It sparked much follow-on research, and the Nationhood Lab, which continues developing the book’s premise today.

Below my notes for future reference.