Keen On America

“There is tremendous loneliness in the kind of life where you just don’t feel like anybody knows you.” — Margaret Rutherford

Yesterday, the Brooklyn psychotherapist Daniel Smith defined perfection as the devil. Today, the Arkansas-based Dr. Margaret Rutherford explains what happens in our FOMO age when the devil wins. Her subject is what she calls the “perfectly hidden depression” of today’s Instagrammable types. Perfectionism rates are going up, Rutherford warns. And so, not uncoincidentally, are suicide rates.
Rutherford’s own mother in Fifties suburban Arkansas was a case study. Beautiful, smart, talented and anorexic. The perfectly mannered and coiffeured hostess. Married the “right” husband but in love with the wrong man. An Arkansas Madame Bovary. “The fucked-up fifties woman” as one of her friends called it. She became a prescription drug junkie because of her addiction to perfection. Nobody knew her, not even herself. The relentless camouflage of her life became a prison. Rutherford has spent the last decade trying to help people escape that prison — first with her book Perfectly Hidden Depression, now with a companion workbook.
On AI and therapy, Rutherford is equally blunt as Daniel Smith. She noticed that AI always praised her ideas. But what if AI, like Instagram, is what she calls “a bunch of shit”? A real therapist tells you what you may not want to hear. The AI shrink starts with flattery. Rather than therapy, that’s just more camouflage for a perfectly imperfect life.
Five Takeaways

•       Perfectionism Rates Are Going Up. So Are Suicide Rates: The academic researchers have been screaming this for years. People whose lives look like they’re going great are dying by suicide. They slip through every diagnostic crack because they answer every question the way a non-depressed person would. They leave the therapist’s office with a wave and a smile.
•       The Relentless Camouflage of Performing Your Life: Destructive perfectionism isn’t wanting to do things well. It’s fuelled by fear and shame — the need to cover up everything that’s caused you pain. The camouflage becomes a prison. Your sense of worth depends on it. You can allow no one to see you struggling — not even yourself.
•       Her Mother Was a Fucked-Up Fifties Woman: Beautiful, smart, talented — and knew none of those things. Anorexic. The perfect hostess. Married the right man but was in love with someone else. Became a prescription drug addict because of the need to look perfect. Nobody knew her. She didn’t allow anybody in.
•       The Harvard Study: It’s Not Money. It’s Connection: The seventy-five-year longitudinal study found that happiness comes from feeling in relationship with other people — not wealth, not success, not followers. We’ve transplanted connection with metrics. The perfectionism epidemic and the loneliness epidemic are the same epidemic.
•       AI Therapy: What If It’s a Bunch of Shit? Rutherford noticed that AI always praised her ideas. Oh, these are wonderful. Then she thought: what if they’re not? Real therapy means being told what you may not want to hear. AI starts with flattery. A good therapist starts with the truth. You cannot replace the human sense of gentle — or not so gentle — confrontation.
 
About the Guest

Dr. Margaret Rutherford is a clinical psychologist, TEDx speaker (2 million+ views), and host of the Self Work podcast (500+ episodes, 5 million+ downloads). She is the author of Perfectly Hidden Depression and its companion workbook. She practices in Fayetteville, Arkansas.
References:

•       Dr. Margaret Rutherford — her practice, podcast, and books.
•       Episode 2854: Perfection Is the Devil — Daniel Smith on boredom, envy, and why our darkest emotions aren’t so dark. The companion conversation.
•       Episode 2850: Bring the Friction Back — Stephen Balkam on social media addiction. Rutherford’s camouflage meets Balkam’s friction.
About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website

Substack

YouTube

Apple Podcasts

Spotify

 
Chapters:

(00:31) - Introduction: Daniel Smith, perfection is the devil, and the anxiety memoirist

(02:47) - Constructive vs. destructive perfectionism

(05:00) - The relentless camouflage of performing your life

(08:19) - FOMO, social media, and keeping up with the Joneses on steroids

(10:46) - Her son’s Patagonia moment: the comparison trap

(13:02) - Are therapists the new priests? The secular Bible problem

(15:06) - Perfectly Hidden Depression: the book publishers said perfectionists wouldn’t buy

(17:18) - You deserve to be truly known

(20:00) - Her mother: the fucked-up fifties woman

(22:44) - The Epstein files, dystopia, and perfectly imperfect times

(27:18) - Agency and the American dream of reinvention

(30:25) - Perfectionism and the epidemic of loneliness

(32:51) - The social media trial: why did people celebrate?

(37:17) - AI therapy: what if it’s a bunch of shit?

“Perfection is the devil. Growth means a greater capaciousness, not a narrowing and an optimisation.” — Daniel Smith

Don’t feel bad about feeling bad. That’s the message of Daniel Smith’s therapeutic new book, Hard Feelings: Finding the Wisdom in Our Darkest Emotions. Smith — psychotherapist, anxiety memoirist, married Brooklynite — wants to rescue boredom, envy, shame, and regret from the category of emotions that are supposed to shame us. The things that bore us most — raising children, long marriages, breakfast with your spouse for the two thousandth time — are also the most meaningful. Boredom, Smith argues, is the price we pay for meaning. Our darkest emotions aren’t quite as dark as we fear.
 
Five Takeaways

•       Boredom Is the Price of Meaning: The things that bore us most — raising children, long marriages, eating breakfast with your spouse for the two thousandth time — are also the most meaningful. Repetition is boring. But that’s where the connection, the love, and the main event reside. Boredom is a sign that meaning is nearby.
•       Perfection Is the Devil: Growth means greater capaciousness, not narrowing and optimisation. Smith sees patients who want to perfect themselves out of their own emotions. The feelings that trouble them make perfect sense given the conditions of their lives. Real psychotherapy isn’t a quick fix. It’s about deep change, and deep change is uncomfortable.
•       Social Media Is an Envy Engine: The leaders of early consumer capitalism discovered that stoking envy drives economic growth. Edward Bernays, Freud’s nephew, was the architect. Social media put it on steroids. The result: people constantly questioning whether their own lives are alright. Smith is far more worried about Mark Zuckerberg than about psychotherapists who write books.
•       His Father Heard Voices for Decades and Kept It Secret: He met none of the diagnostic criteria for schizophrenia. But the culture thought hearing voices was prototypically insane. Smith’s first book argued the border between sanity and insanity is far more porous than we think. Rilke said it best: it’s so often in the way we name things that we go wrong.
•       AI Chatbots Are Inherently Sycophantic: You go to AI for clinical services and what you get is straight validation. These systems have been built to please. There are documented cases of AI psychosis — where sycophantic validation led people into actual delusion. AI can give the illusion of empathy. It cannot deliver the real thing.
 
About the Guest

Daniel Smith is a psychotherapist and writer based in Brooklyn. He is the author of Monkey Mind: A Memoir of Anxiety, Muses, Madmen, and Prophets, and Hard Feelings: Finding the Wisdom in Our Darkest Emotions.
References:

•       Hard Feelings: Finding the Wisdom in Our Darkest Emotions by Daniel Smith.
•       Episode 2850: Bring the Friction Back — Stephen Balkam on social media addiction. Smith’s envy engine meets Balkam’s friction argument.
•       Episode 2849: How Stories Can Save Us — Colum McCann on narrative and empathy. The real thing AI cannot deliver.
About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website

Substack

YouTube

Apple Podcasts

Spotify

 
Chapters:

“We can survive. Can we thrive? That’s a different question.” — Corey Nathan

Robert Mueller died last week. Educated at Princeton, this Vietnam veteran won a Purple Heart and then enjoyed decades of public service under presidents of both parties. But the current president celebrated Mueller’s death. Such are the vagaries of American history.
In contrast, Corey Nathan — host of the Talking Politics and Religion Without Killing Each Other podcast — isn’t celebrating Robert Mueller’s death. Nathan is from suburban northern Los Angeles County, very much at the heart of the (mythical?) American center. We discussed whether it’s possible to have a civic conversation anymore. Like so many Americans, Nathan falls back on what he calls “data.” Apparently 85% of Americans are what a recent study calls the “exhausted majority.” They see themselves as anything but extreme. All they want to do is take the kids to soccer practice, enjoy their barbecue, and talk to the neighbour without the conversation degenerating into verbal war.
Nathan’s own story offers hope. He grew up in an Orthodox Jewish family whose roots go back eight hundred years to what is now Chernihiv in Ukraine. In his late twenties, he became a born-again Christian. His father seriously considered sitting Shiva for him — the mourning ritual for a dead family member. But he valued his relationship with his son more than his theological convictions. Twenty-five years later, the conversations are richer than ever. If an Orthodox Jewish father and his born-again Christian son can keep talking, maybe even the current American President could sit Shiva for Robert Mueller.
 
Five Takeaways

•       85% of Americans Are the Exhausted Majority: The Hidden Tribes study by More in Common found that only 6–7% on the right and 7–8% on the left are what we’d think of as extremes. The rest — 85% — are far more nuanced in their views. They want to go to the barbecue, take the kids to soccer practice, and have a conversation with the neighbour without it turning into a war. The conflict entrepreneurs on both sides have taken all the oxygen.
•       Mueller Was Everything We Say We Want in Our Kids: Purple Heart. Ivy League education. Used his degrees for public service instead of money. Served under presidents of both parties. Stayed on at the FBI after 9/11 when the country needed him. And the current president said he was glad he died.
•       ICE Came to the Neighbouring Church: Nathan’s pastor had to have the conversation: if ICE comes, they’re welcome to worship — but here are our legal obligations. A suburban mom was shot in her front seat two months ago. Is anything visibly wrong in the American suburbs? Today, at his house, no. But these things are happening all over the country.
•       His Father Almost Sat Shiva for Him: Nathan grew up in an Orthodox Jewish family. In his late twenties, he became a born-again Christian. His father seriously considered performing the mourning ritual for a living son. But he valued the relationship with his child more than his theological convictions. Twenty-five years later, the conversations are richer than ever.
•       We Can Survive. Can We Thrive? Nathan’s family lived in what is now Chernihiv, Ukraine, for eight hundred years. One day to the next, nothing changed — until the Cossacks burned the houses and the Bolsheviks came. Democracy isn’t perfect, but it’s the system that lets us thrive, not just survive.
 
About the Guest

Corey Nathan is the host and producer of Talking Politics and Religion Without Killing Each Other, a top 1% podcast. He lives in northern Los Angeles County.
References:

•       Talking Politics and Religion Without Killing Each Other — Nathan’s podcast.
•       Episode 2849: How Stories Can Save Us — Colum McCann on Narrative Four, referenced in the conversation.
•       Episode 2846: How to Be Agreeably Disagreeable — Julia Minson on disagreeing better. Nathan is the practitioner to Minson’s science.
About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website

Substack

YouTube

Apple Podcasts

Spotify

 
Chapters:

(00:31) - Introduction: Robert Mueller dies, Trump says he’s glad

(03:25) - Mueller as American tragedy: David Frum and the centrist view

(05:48) - The exhausted majority: Hidden Tribes and the 85%

(08:40) - Is the left as bad as the right?

(10:15) - Braver Angels, shell-shock, and the people who just want a barbecue

(13:53) - If a foreigner landed in your suburb, would they notice anything wrong?

(15:33) - ICE at the neighbouring church. A mom shot in her front seat.

(17:43) - The secret sauce of talking without killing

(20:26) - Colum McCann, Narrative Four, and storytelling as civic repair

(22:04) - Does democracy really matter if you’ve got soccer practice?

(24:04) - Surviving vs. thriving: eight hundred years as strangers in a strange land

(25:19) - The First Amendment’s two halves: freedom of and freedom from

(28:55) - An Orthodox Jew becomes a born-again Christian. His father almost sits Shiva.

(32:04) - The revolutionary centre: Adrian Wooldridge and the lost genius of liberalism

“Happiness is a rare commodity. There’s a lot of fuel for the claim that unhappiness is caused by some software, when in fact the roots of unhappiness are way deeper than that.” — Keith Teare

If it’s not warfare in Iran, then it’s lawfare in California. Out here in Silicon Valley, it’s been a week dominated by two trials of big tech. First, Meta and YouTube were found liable for designing products that addict children. While the young female social media victims hugged outside the Los Angeles courthouse, the Wall Street Journal dismissed it as a Big Tech shakedown. Then, up the road in San Francisco, a federal judge granted Anthropic an emergency reprieve from the Pentagon’s unprecedented designation of the company as a supply chain risk.
For That Was the Week publisher Keith Teare, the social media trial was fighting the last war, while the Anthropic vs US Government trial is about the future of war. Anthropic took the bait, Keith says. Governments, he believes, should get to decide how to use the products they buy from Silicon Valley. Anthropic wanted to sell to the government but dictate how their technology gets used in battle. The Istanbul-based Soli Özel warned us earlier this week that events in the Middle East are going to get much bloodier. But I wonder if warfare in Iran and lawfare in California are separate fronts in the same battle over tomorrow.
Five Takeaways

•       The Social Media Trial Is Fighting the Last War: Meta and YouTube were fined $6 million — financially meaningless, culturally significant. Keith argues that addiction is successful demand management and every product manager seeks it. The root cause isn’t the algorithm — it’s alienation. The law is always one step behind technology.
•       Anthropic Took the Bait: A federal judge granted Anthropic an emergency reprieve from the Pentagon’s supply chain risk designation. Keith thinks Anthropic is right on the product but wrong on the politics. Governments get to decide how to use weapons. End of story. Anthropic wanted to sell to the government but dictate how the buyer used what they bought. That’s juvenile.
•       Would You Buy a Used Car from Sam Altman? OpenAI killed Sora and shelved its adult mode. Keith calls it maturity, not failure — a recommitment to the core business. Altman’s personality doesn’t lend itself to being liked, but measured by outcomes, he’s fantastic. The AI documentary exposed everyone as adolescent — except Demis Hassabis, the stone-cold scientist.
•       Claude Enters the Third Era of AI: Chat was era one. Directed agents were era two. Autonomous agents that act when you’re not present are era three. Claude’s new Dispatch feature, Gmail connectors, and calendar integration are all about that third era. The product is excellent. The politics are a distraction.
•       Intelligence Is Getting Cheaper. Fear Is Wrapped Up as Principle: The stock market is repricing the future: software companies down, AI companies teed up for IPOs. OpenAI, Anthropic, SpaceX, and xAI will probably all go public this year. For kids in school today, AI is already ubiquitous. The life cycle of companies may shrink from decades to single-digit years. Time, Keith says, to grow up.
 
About the Guest

Keith Teare is a serial entrepreneur, investor, and publisher of That Was The Week, a weekly newsletter on the tech economy. He is co-founder of SignalRank and a regular Saturday guest on Keen On America.
References:

•       That Was The Week — Keith’s editorial: “Growing Up: Winning Wars Involves Losing Battles.”
•       Episode 2847: America’s Suez Moment? — Soli Özel on the Iran war from Istanbul at midnight. Warfare in Iran meets lawfare in California.
•       Episode 2850: Bring the Friction Back — Stephen Balkam on the same social media trial from the child safety side.
•       Episode 2842: Symbolic Capitalism vs. Symbolic Democracy — last TWTW on the $10 trillion AI startup. The Anthropic thread continues.
About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website

Substack

YouTube

Apple Podcasts

Spotify

 
Chapters:

(00:31) - Introduction: two big trials in California

(01:47) - The Meta/YouTube verdict: $6 million and a cultural earthquake

(03:11) - Is every product designed to be addictive?

(05:24) - The roots of addiction: alienation, not algorithms

(08:23) - Happiness is a rare commodity

(09:51) - Anthropic’s emergency reprieve: the most important event of the week

(11:16) - Free speech or weapons control? Anthropic took the bait

(13:00) - The AI documentary: How I Became an Apocalyptomist

(15:04) - The decade-long Altman-Amodei feud

(16:34) - Why are they all such children? Demis Hassabis as the adult

(18:50) - OpenAI kills Sora and shelves porn mode: maturity or retreat?

(23:11) - Claude’s new era: Dispatch, connectors, autonomous agents

(25:07) - The social media trial is fighting yesterday’s war

(26:22) - Prediction markets: the casino eating the world

(28:53) - Intelligence is getting cheaper. Fear wrapped up as principle.

“Why does someone need to be the first trillionaire? The damage it’s doing just to get to that level is extreme.” — Glen Galaich

Excessive wealth disorder. It sounds like a disease — which, at least according to Glen Galaich — CEO of the Stupski Foundation and author of Control: Why Big Giving Falls Short, it is. There’s $2 trillion sitting in American charitable accounts Galaich says, mostly invested in hedge funds and real estate. Foundations are legally required to distribute only 5% a year — the bare minimum — and invest the remaining 95% to ensure they can make that back and live forever. The system rewards perpetuity over impact. The money is stuck — like most other things in America. And this philanthropic wealth is predicted to grow to $18 trillion by 2050 — twice the size of the annual federal budget. A truly excessive wealth disorder.
Galaich wants to unstick the system. When a donor puts money in a private foundation, they receive up to a 70% tax exemption. The public is forgoing taxation in return for public stewardship. But donors still think it’s their money. That’s Galaich’s Control problem. Carnegie pioneered this idea that the wealthy know best how to distribute their wealth. The Sacklers perfected its dark arts. Bill Gates sits somewhere in between. While billionaires like Peter Thiel and Marc Andreessen reject it entirely.
Galaich’s own foundation is giving up control — returning all its resources to communities by 2029. In Hawaii, he gave $15 million to people who actually lived there. They moved all of it within five months to health clinics on neighbouring islands that had never had discretionary money. His deeper frustration is with progressive philanthropy’s failure to coordinate. Conservative donors give around two issues — free markets and liberty — in coordinated fashion. Progressive philanthropy, in contrast, is fragmented, fearful, and obstinately sitting on its capital. There’s a new institute in the Bay Area called the Excessive Wealth Disorder Institute. The disease is real. And so is its cure.
•       $2 Trillion Is Sitting in Charitable Accounts: Mostly invested in hedge funds and real estate. Philanthropic wealth in the US is predicted to grow from $2 trillion to $18 trillion by 2050 — twice the size of the annual federal budget. Foundations are required to give only 5% a year. The rest grows. The money isn’t moving because the system rewards perpetuity over impact.
•       It’s Not Their Money Anymore: When a donor puts money in a private foundation, they receive up to a 70% tax exemption. The public is forgoing taxation in return for public stewardship. But donors still think it’s their money. That’s the control problem at the heart of Galaich’s book — and why so much of big giving serves the donor, not the community.
•       Excessive Wealth Disorder Is Real: Galaich cites the Excessive Wealth Disorder Institute in the Bay Area. Why does someone need to be the first trillionaire? The damage done to society just getting to that level — environmental, human, democratic — is extreme. And the Giving Pledge is collapsing: Peter Thiel and Marc Andreessen have pulled out. Andreessen argues his investments are his philanthropy.
•       The Hawaii Example: Stupski gave $15 million to people from Hawaii who lived and worked there. They moved all of it within five months to health clinics on the neighbouring islands that had never had discretionary money. Palliative care, community outreach, home visits — none of which Medicaid allowed. That’s what happens when you let go of control.
•       Progressive Philanthropy Can’t Coordinate. Conservatives Can: Conservative donors give around two issues — free markets and liberty — and they give in coordinated fashion over long periods. That’s how you get the Federalist Society, Heritage, ALEC, and possibly Donald Trump. Progressive philanthropy is fragmented, siloed, and in a state of fear that the current administration will freeze their assets. The left has moved into protection mode when it should be distributing.
 
About the Guest

Glen Galaich, PhD, is the CEO of the Stupski Foundation, one of the nation’s most ambitious philanthropic spend-down efforts. He hosts the Break Fake Rules podcast and writes the Who Gives? Substack. Control: Why Big Giving Falls Short is published by Wiley, with a foreword by Ibram X. Kendi.
References:

•       Control: Why Big Giving Falls Short by Glen Galaich (Wiley, 2026) — the book under discussion.
•       Who Gives? Substack — Galaich’s newsletter on reforming philanthropy.
•       Episode 2845: Let’s Ban Billionaires — Noam Cohen on the Know-It-Alls. Galaich picks up where Cohen left off.
About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.
Website

Substack

YouTube

Apple Podcasts

Spotify

 
Chapters:

(00:31) - Introduction: Noam Cohen, banning billionaires, and the tide turning

(02:33) - What is philanthropy? Carnegie and the love of humanity

(05:04) - Sloan, Rockefeller, Stanford: the first generation of know-it-all givers

(06:49) - Peter Thiel and Marc Andreessen pull out of the Giving Pledge

(09:05) - The Sacklers: the worst argument for philanthropy

(09:57) - Bill Gates: for or against control?

(11:53) - It’s not their money anymore: the public stewardship illusion

(14:00) - Andreessen vs. community: who decides what people need?

(15:33) - The Stupski model: $374 million returned to communities

(18:47) - Hawaii: $15 million moved in five months to clinics that never had discretionary funds

(21:27) - Can philanthropy save democracy?

(24:22) - Democracy Forward and the $2 trillion sitting in accounts

(29:38) - Excessive Wealth Disorder: why does anyone need to be a trillionaire?

(33:00) - Progressive philanthropy’s failure to coordinate

(35:14) - The Monty Python troll: the CEO as gatekeeper to the donor