The James Altucher Show

He admits he was so bad at firing people at Carlyle that he sometimes promoted them instead by mistake...

A Note from James:

On this show, I’m usually the one asking the questions.

But near the end of this conversation, David Rubenstein turned it around on me.

He asked why I care whether the Mets win.

And I didn’t really have an answer.

I said, “I guess when I was a kid, it felt like I was winning when they won.”

And David said, basically, yeah. That’s the whole thing.

David owns the Baltimore Orioles now. And he explained that Baltimore has spent roughly 200 years living in the shadow of cities like New York, Boston, Philadelphia, and Washington. If the Orioles win, somebody in Baltimore who will never make a dollar from the team still gets to feel like they won too.

His new book is Inside the Owner’s Box: Conversations on Power and Leadership in Sports.

And there were two things David told me that I can’t shake.

One: he was so bad at firing people at Carlyle that employees would come into his office to get fired and somehow convince him to promote them instead.

So Carlyle took firing away from him.

He didn’t become better at it.

He just stopped doing it.

And two: since he bought the Orioles, they’ve more than doubled what they pay their players.

The team did not become twice as good.

I’ve spent a lot of money in my life trying to fix things that were never money problems.

And, honestly, I’ve spent a lot of my life feeling like a winner because of things I didn’t even own.

So I wanted to ask someone who actually owns the team what ownership teaches you that being a fan never can.

Here’s David Rubenstein.

Episode Description:

David Rubenstein has spent decades buying companies, building The Carlyle Group, negotiating major deals, interviewing world leaders—and now he owns the Baltimore Orioles.

That last job has taught him a few things the others didn’t.

His new book, Inside the Owner’s Box: Conversations on Power and Leadership in Sports, grew out of conversations with owners including Robert Kraft, Ted Leonsis, Tom Ricketts, Jeffrey Lurie, and others. James asks David what he learned from them now that he has crossed from businessman and sports fan into ownership himself.

The first surprise is that sports ownership isn’t primarily about maximizing profit. David says most owners obsess over something much more emotionally dangerous: winning.

And winning is difficult to buy.

Since David’s group took over the Orioles, player payroll has more than doubled without producing a corresponding improvement on the field. That leads James and David into a larger discussion about luck, accountability, talent evaluation, coaching, and how much credit any leader should take when things go well.

David is unusually comfortable admitting what he doesn’t know. He doesn’t pick every player. He doesn’t choose managers by himself. He relies on people who know far more about baseball than he does.

That same philosophy helped him at Carlyle: understand your limitations, then surround yourself with people whose expertise exceeds your own.

The conversation also turns into a masterclass on negotiation.

David tells the story of nearly walking away from the Orioles deal after an exchange with the seller’s investment banker. The important lesson wasn’t the disagreement itself. It was that even when the deal involved his hometown team—a team he genuinely wanted—he had to be willing to leave.

If the other side knows you will pay any price to get something, David says, you have already weakened your negotiating position.

James and David also discuss hiring, firing, job interviews, sports analytics, AI, betting, media rights, franchise valuations, and why elite athletes don’t necessarily make elite coaches or owners.

But the most interesting lesson comes near the end.

David asks why ordinary people care so intensely about teams in which they have no financial stake.

His answer is that sports allow people to participate emotionally in success. When the hometown team wins, the city wins. And for a few hours, millions of people get to feel that victory personally.

That, David says, is something he never encountered in private equity.

What You’ll Learn:

• Why owning a sports team is fundamentally different from owning a traditional business.
• Why spending more money can improve your odds without guaranteeing success.
• How David separates leadership decisions from luck and outcomes.
• Why knowing your limitations—and hiring people smarter than you—is a competitive advantage.
• What David looks for when interviewing and hiring people.
• Why the ability to walk away is essential in any serious negotiation.
• How analytics, AI, betting, and media rights are changing professional sports.
• Why fans feel genuine personal success when their hometown team wins.

Timestamped Chapters:

[02:00] Firing People and Walking Away From Deals

David previews two themes that recur throughout the conversation: why he was terrible at firing people and why a negotiator must always be prepared to leave.

[02:53] A Note from James

James introduces David, the Orioles, Inside the Owner’s Box, and the strange emotional relationship fans have with teams they don’t own.

[04:13] Will There Be Baseball Next Year?

James opens with the uncertainty surrounding Major League Baseball’s next labor agreement.

[04:58] Why David Bought the Orioles

David explains why sports ownership is less financially motivated than traditional investing and why he sees the Orioles partly as a way to give back to Baltimore.

[06:06] Spending More Doesn’t Guarantee Winning

The Orioles have significantly increased payroll, but David says the results demonstrate why money alone cannot manufacture success.

[06:26] When Do You Fire the Manager?

James asks whether a struggling team’s manager deserves the blame when so many factors determine performance.

[07:34] How Much of Winning Is Luck?

Tom Brady becomes the example for separating brilliant decision-making from the enormous role of uncertainty.

[08:39] When One Decision Changes Everything

James and David discuss whether owners can identify specific decisions that truly altered the trajectory of a franchise.

[10:08] The People Who Make the Baseball Decisions

David explains why he trusts the Orioles’ baseball executives rather than attempting to make decisions outside his expertise.

[10:34] David Rubenstein Was Terrible at Firing People

David admits employees sometimes talked him out of firing them—and even into promotions—so Carlyle eventually gave the job to somebody else.

[11:29] How Do You Evaluate Someone Smarter Than You?

James asks how a leader can judge an expert whose technical knowledge exceeds his own.

[13:19] David’s Rules for a Job Interview

Always have questions. Be prepared. Show curiosity. And don’t make compensation the first thing you ask about.

[15:17] What Sports Owners Have in Common

After interviewing owners across major leagues, David identifies the trait they share most consistently: an obsession with winning.

[16:13] Losing in Public

Unlike many business failures, sports losses happen in front of everyone—and are analyzed every day.

[17:02] Becoming a Public Figure in Baltimore

David describes how owning the Orioles changed the way people recognize and interact with him.

[18:00] Buying a Team Is Personal

James compares Ted Leonsis’s approach to buying teams with David’s much longer negotiation for the Orioles.

[19:04] The Zoom Call That Nearly Killed the Deal

David explains why a condescending explanation of debt irritated him enough to walk away from the negotiation.

[20:19] The Most Important Negotiating Rule

Even when you desperately want the deal, David says you have to establish red lines and genuinely be prepared to leave.

[21:36] Preparation, Advisors, and Hidden Liabilities

David breaks negotiation down to preparation, financial sophistication, good advice, and understanding exactly what you’re buying.

[22:46] Starting Carlyle Was Riskier Than Buying the Orioles

David remembers creating Carlyle with no real business background and far less certainty than he has today.

[23:26] Money Is Not the Solution to Every Problem

Ownership reinforces a lesson David already knew from investing: capital helps, but it cannot compensate for every organizational weakness.

[24:00] Why Baseball Prospects Are So Hard to Predict

David compares baseball’s long development path with the greater predictability of early draft picks in basketball and football.

[25:20] Tom Brady, Johnny Unitas, and Hidden Talent

James and David discuss the stars nobody recognized early enough and the limits of forecasting human potential.

[28:05] Do Great Players Make Great Leaders?

David explains why playing brilliance does not automatically translate into coaching, management, or ownership ability.

[29:17] Know What You Don’t Know

James identifies one of David’s recurring strengths: recognizing his limitations and surrounding himself with people who possess the expertise he lacks.

[31:20] How Do You Actually Turn a Team Around?

David runs through the variables an organization has to examine after a disappointing season, from coaching and player development to health and team chemistry.

[32:00] Surviving Criticism as an Owner

David’s strategy for social media criticism is simple: he doesn’t read it.

[34:16] Why Sports Rights Keep Getting More Valuable

David talks about streaming, global audiences, television economics, and live sports’ unusual ability to keep attracting mass audiences.

[36:20] Finding the Next Great Sport

Investors pitch David everything from pickleball and padel to cricket and women’s hockey—but he admits he can’t reliably predict which will break through.

[36:47] Why Baltimore Matters More Than Baseball

David returns to his real motivation for buying the Orioles: his connection to his hometown.

[38:01] Moneyball Meets AI

James asks how artificial intelligence could push sports analytics beyond the statistical revolution popularized by Moneyball.

[39:35] Statistics Matter—But Athletes Still Have to Perform

David argues that increasingly sophisticated analytics remain secondary to skill, motivation, health, and execution.

[41:10] Lies, Damn Lies, and Sports Statistics

They discuss the limits of metrics like WAR and the danger of mistaking measurement for complete understanding.

[42:00] Prop Betting and the Integrity Problem

David explains why bets on individual player actions can create risks that traditional winner-and-loser betting does not.

[42:55] The One Thing Carlyle Couldn’t Teach Him

Sports ownership reveals an emotional relationship between a business and a community unlike anything David encountered in private equity.

[43:49] Why Fans Feel Like They Won

David turns interviewer and asks James why a Mets victory matters to him personally.

[46:03] Population, Media, and the Future Value of Sports

James and David consider what demographics, immigration, AI, and productivity could mean for the future sports economy.

[47:30] Nobody Knows

The serious conversation ends on uncertainty before David pivots to perhaps the episode’s hardest question: what exactly is happening with James’s hair?

[48:55] Closing Thoughts

James recommends Inside the Owner’s Box and wishes David luck on the rest of his ownership journey.

Additional Resources:

• Inside the Owner’s Box — Simon & Schuster
• David Rubenstein — The Carlyle Group
• Baltimore Orioles Ownership Group
• How David Rubenstein Became Owner of the Orioles — MLB.com
• The David Rubenstein Show: Peer-to-Peer Conversations — Bloomberg
• History with David Rubenstein — PBS
• MLB’s 2026 Collective Bargaining Negotiations

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Description:

Before Cal Fussman interviewed Muhammad Ali, Mikhail Gorbachev, Kobe Bryant, Serena Williams, Al Pacino, Robert De Niro, and hundreds of other extraordinary people, he spent nearly a decade traveling the world without much of a plan.

He would get on buses without knowing where they were going. He had little money, so he often needed to strike up a conversation with a stranger and build enough trust to be invited home.

That became his training.

Cal learned to read people, listen closely, follow curiosity, and ask the question that could turn a stranger into a friend. Those same skills eventually became the foundation of his celebrated What I’ve Learned interviews for Esquire.

In this first conversation between James and Cal, they explore why questioning is becoming more valuable in a world overflowing with answers. Google can give you information almost instantly. What it cannot necessarily give you is the question that changes how someone sees their own life.

Cal explains why television interviews often fail to create real connection, why canned questions produce canned answers, and why he eventually stopped bringing a written list of questions into interviews.

Preparation still matters. But once the conversation begins, the interviewer has to listen.

James and Cal also talk about curiosity as a skill that gets suppressed over time. Children ask questions constantly. Adults often stop because asking reveals that they do not know something. Cal argues that the process can be reversed: curiosity can be deliberately rebuilt.

They break down some of Cal’s most memorable interviews, including the question that opened up Mikhail Gorbachev, what he learned from Larry King and Oprah Winfrey, and why a seemingly strange question to Dr. Dre can reveal far more about passion than asking someone directly whether they work hard.

The conversation eventually turns back on James. Cal becomes fascinated by James’s ability to simplify ideas into repeatable formats, and the two start brainstorming how questions themselves could become tools for hiring, parenting, relationships, education, and business.

Underneath all of it is a simple idea:

A better question can lead somewhere you never expected to go.

Editorial Note:

This is a From the Archive episode and the first interview between James Altucher and Cal Fussman. The original episode, #324: “The Art of a Great Question,” was published March 5, 2018.

References to Cal being new to podcasting, Big Questions just getting started, his role at Esquire, the state of magazines and terrestrial radio, and podcasting being in its “second inning” reflect the original recording period.

Several people discussed in the episode have since died, including Kobe Bryant, Larry King, and Mikhail Gorbachev. Their interviews are discussed here in the context of Cal’s career and his experiences with them.

Cal’s Big Questions podcast remains active, and his work today continues to center on questioning, human connection, leadership, and increasingly the future of work in the age of AI.

What You’ll Learn:

• How a decade of unplanned travel taught Cal to connect with almost anyone.
• Why Cal believes great questions have become more valuable in a world overflowing with answers.
• How asking questions helped turn a young sportswriter into one of the world’s best-known interviewers.
• Why Cal prepares extensively but throws away his written questions once the interview starts.
• How curiosity gets suppressed as we grow older—and how to deliberately rebuild it.
• Why asking the heart before the head can produce a completely different conversation.
• What Cal learned about interviewing from Mikhail Gorbachev, Larry King, Oprah Winfrey, and Dr. Dre.
• How changing a single question can alter hiring, parenting, education, business, and even the direction of a life.
• Why simple formats can sometimes create more impact than complicated ones.
• How podcasting gave Cal a new way to pursue the uncertainty and discovery he once found traveling the world.

Timestamped Chapters:

[03:20] Meet Cal Fussman

James introduces Cal, his Esquire career, Big Questions, and the hundreds of iconic people he has interviewed.

[05:00] Leaving a Life That Felt Too Predictable

Cal remembers leaving St. Louis because he could already see the rest of his career unfolding in front of him.

[07:30] Inside Sports and the Writers Who Raised the Bar

Cal describes entering a remarkable New York writing culture alongside people like Hunter S. Thompson and David Halberstam.

[11:00] When a Passion Disappears Overnight

Inside Sports collapses, leaving Cal to decide whether to find another job or build a completely different life.

[14:00] A Decade of Not Knowing What Happens Next

Cal leaves for Europe and becomes addicted to waking up without knowing where he will go, who he will meet, or where he will sleep.

[20:30] Learning to Connect With Strangers

Bus rides become Cal’s laboratory for reading people, starting conversations, and creating trust across language and cultural barriers.

[24:00] Are We Losing the Ability to Connect?

James and Cal discuss smartphones, earbuds, scripted media, and how modern communication can reduce opportunities for spontaneous conversation.

[26:00] Why Television Interviews Aren’t Conversations

Cal contrasts genuine interviewing with short, confrontational television segments built around talking points and “gotcha” moments.

[29:00] When Clicks Replace Interesting Stories

Cal describes how measurable popularity changed which people and stories media organizations choose to pursue.

[31:00] Questions as a Superpower

James argues that Cal’s ability to ask the right question has generated experiences, friendships, opportunities, and an entire career.

[33:00] The Question That Made Cal a Reporter

As a college freshman, Cal sneaks into a football locker room and asks a question that makes the veteran reporters around him start taking notes.

[36:00] We Have Plenty of Answers

Cal explains why Google changed the value equation: answers are abundant, while great questions remain scarce.

[38:30] Why Cal Throws Away His Questions

Cal remembers interviewing attorney F. Lee Bailey and learning that notes could interfere with confidence, equality, eye contact, and genuine conversation.

[45:00] The Woman Standing in the Bus Aisle

James finally circles back to the question he has wanted answered from the start: how did Cal meet his wife while traveling through Brazil?

[50:00] “Would You Like My Seat?”

Cal tells the story of meeting the woman he immediately believed he would marry—and the decidedly unimpressive first question he asked her.

[53:00] Cal’s Hidden 10,000 Hours

James realizes that Cal’s years traveling the world were effectively his apprenticeship in reading people, listening, and asking questions.

[55:00] Rebooting Curiosity

Cal explains why children ask hundreds of questions while adults learn to suppress curiosity out of fear of appearing ignorant.

[59:00] Change the Question, Change the Relationship

Cal demonstrates how questions like “Why is your best friend your best friend?” reveal far more than standard job-interview questions.

[01:00:00] The Question That Opened Mikhail Gorbachev

Instead of beginning with politics or nuclear weapons, Cal asks about Gorbachev’s father—and gets a deeply personal story connected to war and peace.

[01:03:00] What Cal Learned From Larry King

Cal explains how interviewing Larry eventually turned into daily breakfasts and a lasting friendship.

[01:05:00] Larry King, Oprah, and Olympic-Level Interviewing

Cal breaks down the different forms of intelligence and connection required by great interviewers.

[01:08:00] What 72 Hours Awake Tells You About Dr. Dre

A seemingly unusual question becomes a way to uncover passion, persistence, and how someone approaches their work.

[01:10:00] Entrepreneurs Discover the Value of Better Questions

After speaking at Summit, Cal realizes business leaders are hungry for better ways to interview and hire people.

[01:13:00] Cal Fussman’s 100 Questions

James spontaneously pitches Cal a book concept based on the questions he has used with extraordinary people.

[01:15:00] Change the Question, Change a Life

James and Cal compare stories about parents who asked their children better questions—including “What good question did you ask today?” and “What did you fail at today?”

[01:18:00] Picasso, Simplicity, and Removing What You Don’t Need

Cal uses Guernica to explain how great work often becomes more powerful as it becomes simpler.

[01:20:00] James’s Superpower: Simplification

The roles reverse as Cal questions James about how he turns complicated ideas into simple, repeatable formats.

[01:23:00] Writing vs. Podcasting

Cal reflects on how much faster a podcast allows him to capture conversations compared with the painstaking process of producing magazine pieces.

[01:27:00] Why Podcasting Changes Dead Time

James explains why audio can transform commuting, exercise, and other periods when people would never traditionally sit down to read.

[01:29:00] The Fear That Kept Cal From Podcasting

Cal admits that fear of recording technology—not interviewing—was what delayed him from starting Big Questions.

[01:32:00] From Journalist to Entrepreneur

Cal begins thinking differently about distribution, media, business, and how to get more impact from the work he already knows how to do.

[01:34:00] How Much Preparation Is Too Much?

James and Cal compare approaches to research and discuss the balance between preparation and arriving genuinely curious.

[01:36:00] Do You Always Need a New Story?

Gary Vaynerchuk and Jerry Seinfeld become examples of why repetition can be more useful than constantly creating something new.

[01:41:00] Podcasting as the New Unknown

Cal realizes that listening to unfamiliar conversations may recreate some of the discovery he once found by getting on buses without knowing the destination.

[01:43:00] Big Questions and Cal’s Next Act

Cal talks about committing to podcasting and asks James for recommendations as he enters a new medium.

[01:48:00] Stop Reinventing the Wheel

Cal reflects on how much of his career has been built around chasing the next story and why repeatable systems might let him accomplish more.

[01:51:00] 80% of the Value for 20% of the Work

James and Cal discuss simplicity, production quality, and finding the format that creates the most value without unnecessary complexity.

[01:53:00] The Beginning of Act Three

At 61, Cal says he feels capable of accomplishing more in the next chapter of his life than he did in the previous six decades.

Additional Resources:

• Cal Fussman — Official Website
• Big Questions with Cal Fussman
• The Tim Ferriss Show
• Tools of Titans by Tim Ferriss
• Don’t Sweat the Small Stuff by Richard Carlson
• The 4-Hour Workweek by Tim Ferriss

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Two weeks after one phone call, four hostages walked free from Gaza...

A Note from James:

After the election, before Trump was sworn in for his second term, Biden’s national security team needed to reach the president-elect about the hostages in Gaza.

According to Bill O’Reilly, they couldn’t get through.

So who did they call?

Bill O’Reilly.

Bill says he set up the conversation, moderated it, and didn’t offer a single opinion. About two weeks later, four hostages were released.

That story is a good example of his new book, Confronting America: What Has to Change.

Bill has spent more than 50 years around the people who make the news. Presidents. Political leaders. Media executives. Celebrities. He’s interviewed five presidents. He’s traveled around the world. And in this book, he names names. No anonymous sources.

It’s Trump. It’s Mamdani. It’s Soros. It’s Paul McCartney. It’s David Letterman.

In 1996, Bill launched The O’Reilly Factor. It was an opinion show that openly said it was an opinion show, and it became one of the biggest programs in cable news.

Now he runs his own media operations outside the traditional networks.

Fair warning: I was more opinionated in this interview than I usually am.

Bill has strong views on the media, Iran, New York City, the political parties, and where the country is headed. I pushed back in a few places, agreed with him in others, and the point is not that you have to agree with either of us.

Listen and decide for yourself.

At the end, I asked Bill about something he wrote in the book: his father’s final words were about never reaching his potential.

So I asked Bill whether he feels like he has reached his.

I expected him to say he was still chasing it.

He didn’t.

Episode Description:

Bill O’Reilly joins James to talk about Confronting America: What Has to Change, a book built from decades of firsthand encounters with presidents, political figures, media executives, and major events.

The conversation starts with O’Reilly’s account of helping establish communication between the outgoing Biden national-security team and President-elect Trump during negotiations over hostages in Gaza. From there, James asks what being close to power has taught him—and how much of what happens behind the scenes ever reaches the public.

They turn to the U.S.-Iran conflict, oil prices, the Strait of Hormuz, and the risks of making decisions when the consequences are difficult to predict. O’Reilly argues that the conflict became more complicated than initially expected, while James asks how media coverage shapes public perceptions of events like these.

That leads to a larger debate over political media. O’Reilly distinguishes the openly opinionated format of The O’Reilly Factor from what he sees as increasing ideological alignment inside news organizations. James pushes on whether opinion-driven cable news helped create that environment in the first place.

They also discuss the Trump administration’s fight with CNN, MS NOW, and Politico over White House access. Despite his criticism of those outlets, O’Reilly says he would have handled the dispute differently: keep them in the room, but don’t give them additional attention.

The conversation then moves to New York City politics, affordability, inequality, Mayor Zohran Mamdani’s agenda, municipal grocery stores, and the broader disagreement over how much government should intervene in markets. James is unusually explicit about his own views in this section, while O’Reilly explains how he sees the ideological divide reshaping both parties.

Near the end, James asks what changed when O’Reilly left corporate television and began running his own media operations. O’Reilly says independence gives him something he values more than reach: control over what he says and how he says it.

Finally, James asks about one of the most personal passages in the book. O’Reilly’s father died believing he had not fully realized his potential. Does Bill still feel the same pressure?

His answer is surprisingly settled. He wants to continue doing good work, but he no longer feels he has something left to prove.

What You’ll Learn:

• O’Reilly’s account of helping connect the Biden and Trump teams during Gaza hostage negotiations.
• Why he views the U.S.-Iran conflict as a major political and strategic risk.
• How James and O’Reilly think media bias, opinion programming, and White House press access have changed political journalism.
• Why O’Reilly says The O’Reilly Factor was designed to present strong opinions alongside competing viewpoints.
• How affordability, inequality, municipal grocery stores, and government intervention shape their debate over New York City politics.
• Why O’Reilly believes technology and partisan media environments are changing how voters understand politics.
• What running his own media companies taught O’Reilly about editorial independence and control.
• How his father’s final words shaped his thinking about ambition, achievement, and whether he has fulfilled his potential.

Timestamped Chapters:

[02:57] A Note from James

James introduces Confronting America, O’Reilly’s career, the political tone of the conversation, and the question he asks Bill about fulfilling his potential.

[04:21] Why This Book Is More Personal

James asks why Confronting America feels different from O’Reilly’s historical books and previous Confronting titles.

[04:55] Fifty Years Around Power

O’Reilly says his career gave him firsthand access to presidents, political figures, media executives, and major events he wanted to document.

[06:10] The Hostage Negotiation Story

James asks O’Reilly to explain his account of connecting the Biden foreign-policy team with President-elect Trump.

[07:44] Trump, Netanyahu, and the Transition of Power

James asks why Israeli Prime Minister Benjamin Netanyahu wanted Trump’s approval during the presidential transition.

[08:17] The Risk of the Iran Conflict

O’Reilly discusses Trump’s decision-making on Iran, the length of the conflict, and potential political consequences.

[09:37] Is Iran Near a Breaking Point?

James and O’Reilly discuss economic pressure on Iran, oil shipments, Hormuz, and the administration’s strategy.

[10:28] Why the Media Covers Bad News

James asks why negative stories often dominate political and economic coverage.

[11:50] Playing Devil’s Advocate

James challenges the idea that rising household assets necessarily constitute an exceptional news story.

[13:16] Did Opinion Television Change News?

James asks whether programs like The O’Reilly Factor helped push television toward more subjective political coverage.

[13:51] The O’Reilly Factor as an Op-Ed Show

O’Reilly says the distinction was that his program explicitly identified itself as opinion.

[15:32] Trump vs. CNN, MS NOW, and Politico

James and O’Reilly discuss the administration’s attempt to remove several media organizations from White House access.

[16:13] Press Freedom and Media Bias

O’Reilly makes his case that political alignment has damaged trust in corporate media.

[17:03] Why O’Reilly Would Have Kept Them in the Room

Despite his criticism of the outlets, O’Reilly says he would not have removed them from the White House.

[18:11] New York City and Zohran Mamdani

James openly states his own disagreement with the mayor and asks O’Reilly why Mamdani’s message connected with voters.

[19:01] Inequality, Affordability, and Anti-Establishment Politics

O’Reilly gives his interpretation of the economic frustrations behind Mamdani’s support.

[20:13] Candidates or Movements?

O’Reilly argues that modern elections increasingly represent competing political movements rather than just individual personalities.

[22:17] History, Populism, and Authoritarianism

James asks about lessons from historical authoritarian movements and what voters understand about political ideology.

[23:28] Technology and the Political Information Bubble

O’Reilly argues that smartphones and personalized media make it easier for people to construct information environments that reinforce existing beliefs.

[24:17] The Affordability Debate

James and O’Reilly discuss cost of living and whether political rhetoric matches policy outcomes.

[25:26] Does Mamdani Believe His Own Policies?

James asks whether the mayor’s economic positions are strategic or sincerely held.

[26:05] The Municipal Grocery Store Debate

James and O’Reilly discuss grocery margins, city-backed stores, subsidies, bodegas, and government intervention in consumer markets.

[27:35] George Soros and Criminal-Justice Policy

James asks O’Reilly about his criticism of George Soros and organizations supporting progressive prosecutors.

[29:14] Life After Fox News

James asks what changed when O’Reilly went from hosting a corporate television program to running his own media businesses.

[30:33] Editorial Independence at The Factor

O’Reilly describes the autonomy he says he had during most of his years at Fox and how he wanted the program to attract viewers across political lines.

[31:27] When Cable News Became an Echo Chamber

O’Reilly criticizes the modern tendency to build panels and programming around people who largely agree with one another.

[32:08] Did Bill O’Reilly Fulfill His Potential?

James asks whether O’Reilly still feels driven by his father’s final words.

[32:24] “I Don’t Know What Else I Gotta Do”

O’Reilly says he no longer feels he has another major quest to complete, though he still wants to make good programs and grow his current work.

Additional Resources:

• Confronting America: What Has to Change
• Bill O’Reilly — Official Website
• NYC Municipal Grocery Store Program

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Description:

A good outcome does not necessarily mean you made a good decision.

And a bad outcome does not necessarily mean you made a bad one.

That distinction is at the heart of James’s conversation with Annie Duke, former professional poker player and author of Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts.

Poker gave Annie an unusually intense laboratory for studying uncertainty. You can make exactly the right decision and lose money. You can make a terrible decision and win. If you judge yourself only by the result, you may reinforce bad habits, discard good strategies, and learn the wrong lesson entirely.

James connects this immediately to business, investing, comedy, relationships, and his own experience selling a company during the dot-com boom. When things work out, people naturally want to take credit. When things go badly, they naturally want to blame luck.

Both reactions interfere with learning.

Annie argues that one of the most valuable skills is learning to separate what you controlled from what you did not. Instead of asking only, “Did I win?” ask whether the process that produced the result was sound.

The conversation then becomes an exploration of how to learn faster.

Annie says one of the best shortcuts is to “borrow other people’s 10,000 hours.” When she entered professional poker, her brother had already spent years around players like Erik Seidel and Dan Harrington. Instead of rediscovering everything through expensive trial and error, Annie entered a community that had already spent thousands of hours thinking about the game.

But being around experts is not enough.

You have to know how to talk to them. You have to communicate the relevant details. You have to remove the outcome when asking for advice so it does not bias the conversation. And you have to find people willing to challenge you instead of simply confirming what you already believe.

Annie describes three essential commitments for a strong decision-making group: a commitment to accuracy, accountability for your beliefs, and openness to dissent.

James and Annie also explore the role of teaching. Annie says her own poker game changed dramatically once she had to explain her strategies to students. If you cannot clearly explain why you believe something, you may not understand it nearly as well as you think.

The second half of the episode turns toward practical decision-making.

Annie explains mental time travel: instead of allowing the emotion of the present moment to dominate a decision, imagine how your future self will view it. A $100 gambling win can feel terrible if you were previously up $2,000, while a $100 loss can feel great if you were previously down $2,000. But one year later, you would simply prefer the $100 win.

Perspective changes the decision.

James adds his own variation: “situation traveling.” If he cannot see a personal problem clearly, he asks what advice he would give his daughter or how he would handle the same situation in business.

They also discuss pre-mortems, negative visualization, planning for obstacles, parenting, “yes, and,” self-serving bias, echo chambers, and the value of saying “I’m not sure.”

For Annie, uncertainty is not weakness.

It is the beginning of curiosity.

And curiosity is what makes learning possible.

Editorial Note:

This is a From the Archive episode originally centered on the 2018 release of Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts. Annie has since published How to Decide and Quit: The Power of Knowing When to Walk Away.

The episode uses Nate Silver’s 2016 U.S. presidential-election forecast to illustrate probabilistic thinking. FiveThirtyEight’s final forecast gave Hillary Clinton roughly a 71% chance and Donald Trump roughly a 29% chance—meaning a Trump victory was less likely in the model, but far from a zero-probability event.

What You’ll Learn:

• Why a good outcome does not prove that you made a good decision.
• Why bad luck can follow a strong decision—and good luck can reward a bad one.
• Why winning can sometimes make learning harder than losing.
• How ego interferes with honest feedback.
• What temporal discounting does to decision-making.
• Why people prefer certainty even when certainty is impossible.
• How to “borrow” another person’s 10,000 hours.
• Why community can dramatically accelerate learning.
• How experts know which details actually matter.
• Why teaching something can expose weaknesses in your own understanding.
• How to separate signal from noise when evaluating feedback.
• Why you should often hide the outcome when asking someone to evaluate a decision.
• The difference between wanting to be right and wanting to be accurate.
• Why accountability improves decision quality.
• How disagreement can make a learning group stronger instead of weaker.
• Why peer groups can become dangerous echo chambers.
• How to plan for future obstacles before they appear.
• What Annie means by mental time travel.
• How James uses “situation traveling” to make emotionally difficult decisions.
• Why changing your definition of “winning” can change your behavior.
• Why Annie deliberately dropped down in stakes when learning a new poker game.
• How saying “I’m not sure” creates hunger for new information.
• Why experts tend to be more aware of the limits of their own knowledge.
• How “yes, and” can help someone reconsider a belief without triggering defensiveness.
• Why improving your learning process even slightly can compound into enormous gains.

Timestamped Chapters:

[03:03] Thinking in Bets

James introduces Annie and her framework for making decisions when you do not have all the facts.

[05:16] Luck, Skill, and the Stories We Tell Ourselves

James remembers selling a company during the dot-com boom and mistaking a fortunate outcome for evidence that he was a genius.

[07:36] Why It’s Hard to Learn From Winning

Annie and James discuss the tendency to stop examining your performance when the outcome was good.

[09:16] Ego and Temporal Discounting

Annie explains why humans naturally take credit for good outcomes, blame bad ones on luck, and favor immediate emotional rewards.

[11:18] Good Decisions Can Fail

The conversation shifts from learning to decision-making and the importance of accepting uncertain outcomes.

[13:01] Why We Pay to End Uncertainty

James and Annie discuss business deals, pensions, lotteries, and why people accept large discounts to get certainty now.

[14:24] Workshopping the Book in Front of Audiences

Annie explains how years of speaking helped her turn decision science into stories people could actually use.

[17:03] Can You Hack the 10,000-Hour Rule?

James asks how Annie went from graduate school to becoming one of the world’s best poker players.

[18:04] Borrow Someone Else’s 10,000 Hours

Annie explains why learning from people who have already accumulated expertise can dramatically shorten your own learning curve.

[19:57] The Poker Learning Pod

Annie describes the community around her brother, including Erik Seidel and Dan Harrington, and how their thinking accelerated her development.

[20:43] Experience Is Necessary, but Not Sufficient

Annie argues that putting in hours is not enough; you have to know how to interpret feedback.

[23:15] Finding the Right Learning Community

Even if you cannot immediately surround yourself with world-class experts, Annie says you can identify people who are curious, calm, and committed to improvement.

[25:06] Why Teaching Made Annie Better at Poker

Having to explain strategy to beginners forced Annie to discover assumptions she could not actually defend.

[26:05] The Truth Can Atrophy

Annie uses John Stuart Mill to explain why even correct beliefs become weaker if you never have to defend them.

[30:26] Experts, Peers, and Beginners

James and Annie identify three valuable learning communities: people ahead of you, people alongside you, and people you can teach.

[31:10] How Erik Seidel Taught Annie to Think

Annie remembers being told to stop describing a poker hand as “unlucky” and instead provide the details needed to analyze the decision.

[33:16] Don’t Tell Me How the Hand Ended

Annie explains why knowing an outcome can bias the advice someone gives you.

[34:30] Why Headlines Invent Explanations

James compares outcome bias to financial headlines that explain a market move after it has already happened.

[36:27] The Feedback Loop

Annie describes how expert advice, practice, and immediate feedback can dramatically accelerate learning.

[38:50] Virtual Mentors Count Too

Books and other resources can give you access to expert thought processes even when you cannot know the expert personally.

[39:31] Peer Groups vs. Echo Chambers

Annie explains why a group of peers is only useful if everyone is genuinely open to disagreement and new information.

[43:23] Accuracy, Accountability, and Dissent

Annie outlines the three commitments she believes make a strong decision-making group.

[45:02] Bets as Accountability

Putting odds on a belief forces you to clarify how confident you actually are.

[47:17] Make the Decision Before the Market Crashes

Annie explains how predetermined rules and accountability partners can prevent emotional reactions from taking over.

[48:36] Map the Mines Before You Step on Them

Instead of visualizing only a perfect future, Annie recommends identifying the obstacles and disappointments that could derail you.

[50:43] The Backdoor Into an Expert Community

James uses Judd Apatow and podcasting to show how creating something can give you a reason to approach experts.

[52:25] Start With Three People

Annie explains why community does not need to begin with fame or a large audience.

[53:55] Nate Silver and the Meaning of 30 Percent

James and Annie use probabilistic election forecasting to show why people routinely round uncertainty down to zero or up to certainty.

[57:29] What Probabilities Are Actually For

Annie explains how forecasts can help people decide where to spend their time, attention, or resources.

[01:00:55] Mental Time Travel

Annie introduces a technique for escaping the emotional intensity of the present moment by asking how your future self will view the decision.

[01:01:32] The Blackjack Test

Winning $100 after being up $2,000 feels terrible; losing $100 after being down $2,000 feels great. A year later, the preference becomes obvious.

[01:05:05] Have a Conversation With Your Future Self

Annie describes using time travel with her children, while James introduces his own version: “situation traveling.”

[01:06:10] A Community of Different Versions of You

James and Annie expand the idea to future selves, situational selves, and counterfactual versions of yourself.

[01:09:31] Redefining Winning

Instead of defining winning by whether you made money, Annie suggests defining it by whether you learned.

[01:12:00] Drop Down in Stakes to Learn Faster

Annie remembers moving from high-stakes Hold’em to tiny stud games because she cared more about learning the new game than protecting her status.

[01:15:10] Be Open to Dissent

Annie says disagreement is one of the most powerful accelerators of expertise.

[01:15:52] The Power of “I’m Not Sure”

Certainty shuts down curiosity. Annie argues that acknowledging uncertainty keeps you hungry for information.

[01:19:11] Experts Know What They Don’t Know

One mark of expertise, Annie says, is greater awareness of the boundaries of your knowledge.

[01:20:07] Decision-Making for Parents

Annie explains how she redirects her children from blaming a bad test on the teacher toward planning what they can do next time.

[01:22:00] “Yes, And” as a Decision Tool

James connects Annie’s parenting strategy to improv: accept the current reality, then build forward from it.

[01:23:10] David Letterman, Lauren Conrad, and Bad Dissent

Annie explains why challenging someone directly can backfire when you have not agreed to that kind of conversation.

[01:27:45] How Much Can You Really Hack 10,000 Hours?

James asks how much faster deliberate learning can make someone an expert.

[01:32:40] You Don’t Have to Be Great at This

Annie says even modest improvements in recognizing learning opportunities can double how much you learn.

[01:35:17] “Suck Less” and Let It Compound

Small improvements shift the odds over time. Perfection is unnecessary; direction matters.

[01:37:06] Thinking in Bets

James recommends the book and summarizes the conversation around uncertainty, community, self-compassion, and learning.

[01:38:01] Ryan Holiday’s Secret Influence on the Book

Annie explains how the structure of The Obstacle Is the Way and Ego Is the Enemy influenced the way she wrote Thinking in Bets.

Additional Resources:

• Annie Duke — Official Website
• Annie Duke — Books
• Thinking in Bets — Penguin Random House
• How to Decide — Penguin Random House
• Quit: The Power of Knowing When to Walk Away — Penguin Random House
• Annie Duke — Alliance for Decision Education

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Ron Johnson built the Apple Store as Apple's SVP of Retail, and is the author of Shop Different: How Retail Revealed Apple's Genius.

A Note from James:

I love the Apple Store.

I can walk into one without needing anything and still want to stay. I like looking at the products. I like touching everything. I like the space. I like the feeling.

I remember buying one of my first iPods at the Apple Store on Fifth Avenue in New York. I walked out smiling, listening to music from my childhood that I hadn’t heard in years.

And that feeling was designed.

My guest today, Ron Johnson, is the person who created the Apple Store.

Before Apple, Ron was at Target, where he helped prove that design could matter even in mass-market retail. He worked with Michael Graves and helped establish this idea that something affordable could also be beautiful.

Steve Jobs noticed.

Steve had come back to Apple. The Mac was competing in a world dominated by Windows. And he realized there was something advertising could not do: it could not let someone actually experience the product.

You had to touch a Mac. You had to use it. You had to see why it was different.

So Steve hired Ron.

And together they created something that went against almost every trend in retail at the time.

No giant stacks of boxes. No salespeople hiding behind registers. No pressure to buy. Products sitting openly on simple tables. Lots of light. Lots of employees. A Genius Bar. A place where you could come in, play with the computers, ask questions, learn something, leave without buying anything, and then come back again.

Retail experts said it would fail.

And for a moment, they looked right.

When Apple opened its third store in Texas, Ron walked into the Monday morning executive meeting and Steve Jobs looked at him and basically said, “What are you doing here? You haven’t sold a computer in the state of Texas.”

Ron fixed it.

Eventually, Apple Stores became some of the most productive retail spaces in the world.

Ron’s new book is Shop Different: How Retail Revealed Apple’s Genius. And what I loved about the book is that you get to see how someone who has spent decades thinking about stores actually sees one.

Ron can walk into a store and notice the floor, the lighting, the width of the aisle, the employees, the products, where people park, how customers move, what they see first, and whether the place has what he calls a heartbeat.

He sees retail almost like an artist sees a canvas.

And the lessons are much bigger than stores.

They’re about design. Leadership. Kindness. Steve Jobs. Knowing what your customer values. Knowing what parts of your identity are sacred. And maybe most importantly, knowing when not to rush.

What You’ll Learn:

• Why Steve Jobs believed Apple needed its own retail stores.
• How Ron Johnson’s work with design at Target attracted Steve’s attention.
• Why Ron sees retail as a fundamentally human and emotional business.
• How kindness influenced Ron’s relationship with Steve Jobs.
• Why Apple designed the store collaboratively instead of handing the project to a traditional retail team.
• Why location was one of the first messages the Apple Store sent customers.
• How George Blankenship brought critical retail real-estate expertise to Apple.
• Why Apple spent heavily on elaborate window displays in its earliest stores.
• How the Apple Store was divided between new customers and existing owners.
• Why Apple removed almost all visible inventory and boxes from the sales floor.
• How the Genius Bar fit into the original philosophy of service and support.
• Why Apple Store employees were deliberately different from traditional electronics-store employees.
• Why Apple recruited people from bookstores.
• How Apple shifted the retail goal from transaction to relationship.
• Why Ron told employees never to hurry a potential customer.
• What Target taught Ron about differentiation and design.
• How Steve Jobs responded when Apple's first Texas store failed to sell a computer during its opening weekend.
• Why Ron says Steve criticized performance rather than attacking the person.
• What Steve Jobs taught Ron about leadership, delegation, standards, and focus.
• Why Steve wanted A players and gave them room to operate.
• Why Ron believes physical retail is not dying.
• What separates “tired retail” from a store with a heartbeat.
• Why brands need to understand which parts of their identity are sacred.
• How institutional memory slowly pulls companies away from what originally made them special.
• Why Ron believes the best business advice is simply: don’t be in a hurry.

Timestamped Chapters:

[04:38] Seeing a Store Like a Chessboard

James tells Ron that reading the book feels like watching a master see patterns invisible to everyone else.

[06:08] The Apple Store Begins

James asks what Ron and Steve Jobs disagreed about while building the first stores.

[07:29] Building the Store With Steve Jobs

Ron explains why Apple’s stores were developed collaboratively rather than designed independently and presented to Steve for approval.

[08:55] How Target Led Ron to Apple

James asks whether Ron’s design work at Target was what originally caught Steve Jobs’ attention.

[09:21] Why Apple Needed Stores

Ron explains that Steve believed Apple had to control the customer experience if it wanted people to understand why the Mac was different.

[10:40] Kindness in the Steve Jobs Interview

James asks why Ron emphasized kindness when describing his first meeting with Steve.

[11:22] Living in Your Heart

Ron describes his upbringing in Minnesota and why retail taught him to think first about the person in front of him.

[13:26] Going Against the Retail Trend

James and Ron discuss why opening expensive physical stores seemed almost irrational during the rise of Dell, e-commerce, and struggling electronics chains.

[14:00] The Mac Had to Be Experienced

Ron explains why advertising could only take Apple so far. Customers needed to touch the product and experience the operating system themselves.

[15:18] The First Message Is the Location

Ron explains Steve Jobs’ belief that the location of the store itself tells customers something about the brand.

[17:09] Getting People Through the Door

Ron describes the importance of real estate, window displays, and creating stores people felt compelled to enter.

[18:18] A Place to Hang Out

The early Apple Store becomes somewhere customers can surf the internet, play with computers, and spend time without pressure.

[19:27] Simple Enough to Understand at a Glance

Ron explains the original store layout: products and discovery in the front, ownership support and services in the back.

[20:25] The Employee Is the Star

Ron explains why Apple staffed its stores so heavily and designed employees’ jobs around helping customers rather than completing other tasks.

[21:44] Why Tech Stores Felt Intimidating

Ron contrasts Apple’s approach with the employees and environment he saw in traditional computer stores.

[22:43] Hiring From Bookstores

Ron explains why bookstore employees provided a model for the hospitality and discovery experience Apple wanted.

[24:24] Transaction vs. Relationship

Ron compares Target, where customers arrived ready to shop, with Apple, where many customers needed multiple visits before they were ready to buy.

[24:56] Never Hurry the Customer

Ron explains why employees were taught to spend time with people, excite them about the product, and invite them to return.

[25:34] Target vs. Walmart

James and Ron discuss the strategic difference between the two discount retailers and how Target used fashion and design to differentiate itself.

[27:15] How Apple Influenced Tesla Retail

James notices similarities between Tesla and Apple stores, and Ron explains George Blankenship’s role in both companies.

[28:31] “You Haven’t Sold a Computer in Texas”

Ron remembers opening the third Apple Store and walking into an executive meeting before the location had sold a single computer.

[29:51] What Steve Jobs Was Really Criticizing

Ron says Steve’s intensity was about performance and standards, not personal criticism.

[30:20] Steve Jobs as a Leader

Ron explains why Steve focused less on conventional management metrics and more on what Apple should build next and how it could better serve customers.

[31:03] Hire the Best People in the World

Ron talks about Tim Cook, Jony Ive, delegation, A players, and how quickly Steve moved when someone did not fit.

[33:26] Are Physical Stores Dying?

James asks the question Ron hears constantly, and Ron argues that retail formats evolve rather than disappear.

[34:55] Why New Brands Still Want Stores

Ron points to newer specialty brands opening physical locations and explains why demand for good retail space remains strong.

[36:05] Experience Beats Convenience

Ron distinguishes online shopping’s transactional convenience from the emotional experience and sense of belonging a physical store can create.

[37:48] Tired Retail

James brings up JCPenney, and Ron explains why outdated, dim, oversized retail experiences gradually lose relevance.

[39:29] Walking Through Stores as an Art Form

Ron describes visiting stores constantly and reading every product, display, floor, and merchandising decision as evidence of someone’s thinking.

[40:40] What Target Lost

Ron compares today’s Target home assortment with the Target he helped shape decades earlier.

[42:00] The Danger of Losing Institutional Memory

Ron explains how companies gradually drift away from the qualities that originally made them successful.

[42:50] Why the Floor Matters

Ron gives a seemingly small example: Target’s move from bright white flooring to darker concrete changed the emotional character of the store.

[43:59] Every Great Brand Has Something Sacred

James and Ron discuss why companies need to know which parts of the customer experience define their identity and should not be casually changed.

[45:16] The Best Business Advice Ron Ever Got

James asks for Ron’s most important business lesson.

[45:40] Don’t Be in a Hurry

Ron explains why patience, focus, high standards, and sequential innovation were central to Apple’s success.

[47:16] Apple, AI, and the Race for the Next Platform

James and Ron connect the lesson about patience to the enormous investment and uncertainty surrounding artificial intelligence.

[49:03] Closing Thoughts

James reflects on what the Apple Store has meant to him personally and recommends Shop Different.

Additional Resources:

• Shop Different: How Retail Revealed Apple’s Genius — Official Book Site
• Ron Johnson — Official LinkedIn Profile
• Apple Retail
• Apple Fifth Avenue

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Description:

Jon Morrow’s story begins with a diagnosis that was supposed to be a death sentence.

Born with spinal muscular atrophy, Jon was diagnosed at six months old. Doctors told his mother he would likely die by age two. Instead, she fought for him. She fought to keep him alive. She fought to get him into public school. She fought through pneumonia, broken ribs, hospital visits, and a world that did not expect much from him.

That expectation became one of the central forces in Jon’s life.

In this From the Archive conversation, James talks with Jon about what it means to live in a world where people expect you to survive, but not necessarily to achieve. Jon explains how his mother gave him a radically different definition of disability: everyone has something they cannot do as well as someone else, but everyone also has something they can do better than most.

For Jon, that thing was his mind.

He learned to write, program, think, sell, and communicate. He used assistive technology, including a sip-and-puff wheelchair and a lip-operated mouse, to work on a computer. He graduated from college, received job offers, and then ran into a brutal financial trap: if he earned too much money, he risked losing the Medicaid benefits that paid for his care.

So Jon changed the rules.

He wrote for free. He built relationships. He worked for Copyblogger without immediate pay, knowing that one day he would ask for help. He wrote viral posts. He moved to Mexico to reduce his healthcare costs. He asked for the favors he had earned. And within months, he built a consulting business that turned into Smart Blogger.

James and Jon also talk about his father’s real estate business, raising $50 million for land deals, the crash that wiped everything out, and the pressure Jon felt when both of his parents needed support. The conversation then moves into blogging, guest posting, courses, coaching, and the economics of turning expertise into an online business.

But the deeper subject is not blogging. It is agency.

Jon argues that any limitation can be overcome, though not always easily and not always without cost. His framework begins with belief: surround yourself with stories of people doing extraordinary things until extraordinary starts to feel normal. Then find the price of what you want. Understand the sacrifice before you begin. And finally, create enough urgency that you cannot drift forever.

For Jon, the “gun to his head” was the fear of ending up in a nursing home. That fear gave him the energy to work 16, 18, even 20 hours a day after moving to Mexico.

The episode is about disability, but it is not only about disability. It is about building a life when the default path will not work. It is about finding the counterpunch. It is about choosing contribution over helplessness. And it is about becoming unstoppable by refusing to let the world’s expectations become your own.

Editorial Note:

This is a From the Archive episode. References to Jon’s business, Unstoppable, Smart Blogger, Medicaid, healthcare costs, assistive technology, brain-machine interfaces, and online publishing reflect the original recording period.

This episode discusses disability, depression, severe illness, traumatic injury, healthcare access, financial stress, fear-based motivation, and nursing-home fears. It should be framed as Jon’s personal story and philosophy, not as medical, legal, mental-health, or financial advice.

What You’ll Learn:

• What spinal muscular atrophy is and how it affected Jon’s life from infancy.
• Why Jon’s mother refused to accept the expectations doctors and schools placed on him.
• How Jon learned to define disability as something everyone experiences in different ways.
• Why expectations can become one of the hardest parts of living with a disability.
• How assistive technology helped Jon work, write, and build a business.
• Why online communities can matter when patients live longer than doctors expected.
• How Jon used his wheelchair as an unexpected advantage in sales and fundraising.
• What Jon learned while raising money for his father’s real estate projects.
• How the 2010 real estate crash forced Jon to reinvent his career.
• Why Medicaid’s income limits trapped Jon financially.
• How writing for free helped Jon build skill, reputation, leverage, and relationships.
• Why Jon moved to Mexico and how that changed the economics of his care.
• How a Copyblogger favor turned into his first wave of consulting clients.
• How Jon built Smart Blogger through consulting, courses, coaching, and audience growth.
• Why Jon eventually reorganized the business so he could return to writing.
• What Jon means by “reconstructing reality.”
• Why he recommends filling your mind with stories of people who have done impossible things.
• How to think about the price of any major goal.
• Why sacrifice is unavoidable, but negotiable.
• How negative reinforcement can create urgency.
• Why fear, when handled deliberately, can become fuel.

Timestamped Chapters:

[02:00] The Tribe You Don’t Want to Belong To

Jon talks about a private Facebook group for adults with his disease and what it feels like to be one of the oldest people with his form of spinal muscular atrophy.

[03:41] Expectations, Disability, and Achievement

James introduces Jon’s work as a writer and entrepreneur, and Jon explains how low expectations can become one of the hardest parts of disability.

[04:31] What Spinal Muscular Atrophy Means

Jon explains the motor-neuron disease that gradually took away his ability to move while leaving his ability to feel intact.

[05:14] Diagnosed at Six Months Old

Jon describes how doctors told his mother he probably would not live past age two.

[07:01] “I’ll Fight It for Him”

Jon tells the story of his mother’s response to the diagnosis and how she fought for his survival, schooling, and care.

[09:18] Life From the Neck Down

James describes Jon in the studio, and Jon explains how he drives his wheelchair with a sip-and-puff system.

[11:09] The Lip-Operated Mouse

Jon describes the TetraMouse, the assistive technology that allows him to use a computer with his lips.

[13:30] Unwanted Tribes and Shared Knowledge

Jon talks about connecting with other adults who have his disease and how patients can discover things doctors have never seen before.

[15:42] Inventing Better Accessibility

Jon describes his idea for a portable lift to make airplane transfers safer for wheelchair users.

[18:29] Achievement as Survival Strategy

James identifies Jon’s insistence that limitations do not remove the possibility of action.

[19:24] The Medicaid Income Trap

Jon explains how Medicaid covered his care but limited how much money he could earn.

[20:52] The Cost of Feeling Useless

Jon talks about how systems that remove work and contribution can destroy self-worth and health.

[22:06] Everyone Is Disabled in Some Way

Jon remembers learning the word “disabled” in kindergarten and the way his mother reframed it.

[24:02] Finding What You Can Do Better

Jon explains how his mother and teachers helped him build confidence around writing, computers, and his mind.

[25:30] Twelve Job Offers He Couldn’t Accept

Jon explains why he had real opportunities after college but could not take them without losing medical coverage.

[26:12] Writing for Free

Jon begins writing articles online because paid work would threaten the benefits he needed to survive.

[26:46] Raising Money in Real Estate

Jon explains how he helped his father raise money for land-development deals.

[29:13] The Real Estate Model

James and Jon break down the economics of buying farmland, rezoning it, and selling it to developers.

[32:04] Raising $50 Million, Then Losing Everything

Jon explains how the crash wiped out the deals, cost his father everything, and forced Jon to find another path.

[34:08] Blogging Becomes the Escape Route

Jon starts writing for blogs, becomes a popular contributor, and begins saving favors instead of taking payment.

[35:28] The Viral Posts

Jon talks about “On Dying, Mothers, and Fighting for Your Ideas” and “How to Quit Your Job, Move to Paradise and Get Paid to Change the World.”

[36:08] Moving to Mexico

Jon explains how relocating to Mexico reduced his healthcare costs and became his escape from the Medicaid trap.

[37:40] A Minivan to Mazatlán

Jon and his mother pack everything they can into a minivan and drive from Charlotte to Mexico.

[39:10] Negotiating a Beachfront Condo

Jon explains how he contacted every owner in a resort building and negotiated the rent down.

[40:19] Cashing In the Favors

Jon asks Copyblogger to tell its readers he is accepting consulting clients.

[41:00] The Power of Free Work

James and Jon unpack why working for free can build skills, reputation, trust, and future leverage.

[42:04] The First Consulting Offer

Jon offers $99 blog critiques and gets 300 clients in 24 hours.

[43:15] From Consulting to Courses

Jon raises his rates, builds recurring revenue, and begins creating products that teach people how to write guest posts.

[44:17] $35,000 in 24 Hours

Jon launches his first course, sells tens of thousands of dollars in a day, and has his PayPal account frozen.

[45:05] From Boost Blog Traffic to Smart Blogger

Jon launches his own site, builds a 13,000-person pre-launch list, and grows the business rapidly.

[46:17] Seven Figures and 23,000 Students

Jon describes Smart Blogger’s growth through courses and coaching, plus the student success stories that keep him going.

[47:46] Returning to Writing

Jon explains how the business pulled him into management and why he reorganized it so he could write every day again.

[50:09] Personal Development Without the Fluff

Jon says he wants to write about struggle, pain, poverty, and contribution in a way most personal development avoids.

[51:05] The Car Accident

Jon tells the story of the crash that shattered his legs and kept him in and out of hospitals for about a year.

[57:03] Bionics, Brain Chips, and the Future

James and Jon talk about exoskeletons, brain-machine interfaces, and the accessibility technology Jon follows closely.

[01:00:38] Any Limitation Can Be Overcome

Jon says the major takeaway is that limitations can be overcome, though not always easily.

[01:01:11] Reconstructing Reality

Jon explains the first step: train yourself to believe extraordinary achievement is not only possible, but normal.

[01:04:00] Marinating the Mind

Jon recommends spending more time with inspirational stories than with negative inputs.

[01:05:15] Find the Price

Jon explains the second step: understand what the goal will cost before deciding whether to pursue it.

[01:07:37] Sacrifice Is Negotiable, Not Optional

Jon explains that if one sacrifice is non-negotiable, you may need to choose a different path or sacrifice something else.

[01:09:40] Put a Gun to Your Head

Jon describes the third step: create stakes serious enough to force action, while making clear he is using the phrase metaphorically.

[01:11:09] The Nursing Home Fear

Jon explains that his fear of ending up in a nursing home gave him the urgency to build his business.

[01:13:08] Six Months Without the Beach

Jon remembers moving to Mexico and working 16 to 20 hours a day without even going down to the beach.

[01:14:00] Helping as Many People as Possible

Jon says his goal now is less about money and more about helping people through Smart Blogger and Unstoppable.

Additional Resources:

• Jon Morrow — Personal Website
• Smart Blogger
• About Smart Blogger
• Jon Morrow — Smart Blogger Author Page
• Unstoppable
• “7 Life Lessons from a Guy Who Can’t Move Anything but His Face” — Unstoppable
• “On Dying, Mothers, and Fighting for Your Ideas” — Copyblogger
• “How to Quit Your Job, Move to Paradise and Get Paid to Change the World” — ProBlogger
• “Here’s How Jon Morrow Writes” — Copyblogger
• TetraMouse
• stickK Commitment Contracts
• Cure SMA: About Spinal Muscular Atrophy

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:

Carlo Rovelli is one of the smartest people I know. He is a theoretical physicist and the author of a lot of great books, including Seven Brief Lessons on Physics, The Order of Time, Helgoland, White Holes, and now On the Equality of All Things: Lessons on Physics and Philosophy.

He has been on the show before, and at the end of this conversation I told him I felt like he was just tolerating my questions. He was nice about it.

But the first question I asked was: Do I actually exist?

Because in Carlo’s new book, nothing really exists on its own. Not a person, not a particle, not you, not me. Everything exists in relation to something else.

So I spent an hour trying to understand what that means.

Does absolute truth exist? Is free will fake? Are we just machines? Is consciousness quantum? Is everything doomed to decay? Is time real? Was there a before the Big Bang? And what does any of this actually do for us in ordinary life?

Carlo’s answer, again and again, is not that nothing is real. It is that we make a mistake when we try to imagine the world from the outside, as if we were standing somewhere beyond the universe looking in. We are not outside the universe. We are inside it. We are part of it. We know the world through relationships, perspectives, interactions, and limits.

And oddly, that is calming.

Because Carlo says the thing that brought him serenity was not finally knowing everything. It was giving up the need to know everything with absolute certainty.

That is where this conversation goes: physics, quantum mechanics, philosophy, Buddhism, Taoism, Wittgenstein, consciousness, black holes, time, the Big Bang, free will, and the strange comfort of not needing the final answer.

Episode Description:

Carlo Rovelli returns to the show for a conversation about reality, uncertainty, quantum mechanics, time, consciousness, free will, and his new book On the Equality of All Things: Lessons on Physics and Philosophy.

James begins with the central idea of the book: everything in the universe can only be understood in relation to something else. Carlo agrees that this is a good short version of the argument, but immediately pushes back against the need for “absolute” truth. Of course James exists. Of course Carlo exists. The question is why we need to add something heavier and more final than that.

From there, the conversation becomes an exploration of relational reality. Carlo explains that motion is not an illusion just because it depends on perspective. When James says he is sitting still, that is true with respect to Earth. When someone says Earth is moving, that is true with respect to the sun or the galaxy. The mistake is asking which motion is the “real” one outside all relations.

The same frame applies to quantum mechanics. Carlo argues that particles are not little objects with fixed properties sitting there independently of the rest of the world. A particle is what it manifests in interaction. It is a set of relations. This is why quantum mechanics has forced such a profound change in the way physicists think about reality.

James keeps pressing the practical question: What do we gain from knowing this?

Carlo’s answer is partly scientific and partly philosophical. We gain better questions. We stop asking impossible questions like “Who is really not moving?” or “What is the final foundation of everything?” We become more aware of our own perspective. And we may become more capable of understanding people whose moral, political, or philosophical perspectives differ from ours.

The conversation moves through the Big Bang and the possibility of a Big Bounce, with Carlo stressing that science is powerful precisely because it knows its own ignorance. Science is not the final story. It is an ongoing process of learning, correcting, testing, and replacing older models with better ones.

James and Carlo then talk about time. Carlo explains that Earth is so small, compared with the universe, that we experience conversation as almost instantaneous. That gives us the illusion that time is the same for everyone. But physics has shown that time is not universal. Every star and galaxy has its own time, and the idea of “now” across the whole universe does not really work.

The second half of the conversation turns toward philosophy and human life. Carlo connects his thinking to Eastern philosophy, Zhuangzi, Buddhism, Taoism, and Wittgenstein. For him, accepting the partial, perspectival, incomplete nature of knowledge is not depressing. It is serene.

James also asks about consciousness, free will, and whether quantum mechanics can explain the mind. Carlo respects Roger Penrose but says he does not think consciousness is specifically quantum. The brain is physical. Choices are physical. But that does not make choice unreal. The mistake, Carlo says, is imagining a separate ghost or soul outside the physical brain that is supposed to make the decision.

The episode closes with James trying to find one absolute: everything decays. Carlo says no. The universe also creates order. Galaxies form. Stars light up. Life emerges. Water and oil separate into structure. Civilization produces books. Nature is not simple decay. It is more complicated, more beautiful, and still not fully understood.

What You’ll Learn:

• Why Carlo Rovelli thinks there is no useful “view from outside” the universe.
• Why existence does not need to be “absolute” to be real.
• How motion only makes sense relative to something else.
• Why relative does not mean arbitrary.
• How quantum mechanics challenges the idea that the world is made of independent objects.
• Why Carlo sees particles as manifestations of interactions.
• Why science is powerful partly because it knows what it does not know.
• What the Big Bounce idea suggests about the Big Bang.
• Why time is not the same everywhere in the universe.
• Why there may be no single universal “now.”
• Why physics does not explain everything, even if nothing escapes physics.
• How Eastern philosophy, Taoism, Buddhism, and Wittgenstein shaped Carlo’s thinking.
• Why giving up certainty can create serenity.
• Why Carlo does not think consciousness is specifically quantum.
• How Carlo thinks about free will without invoking a separate soul or ghost.
• Why quantum mechanics should not be turned into vague New Age thinking.
• Why nature is not only decay, but also structure, order, evolution, and growth.

Timestamped Chapters:

[05:04] Does Anything Exist Absolutely?

James asks whether he, Carlo, or the chair exists, and Carlo explains why ordinary existence is enough without adding the word “absolute.”

[06:47] We Exist Through Relations

Carlo explains that identity, friendship, love, social position, and knowledge all happen through relationships.

[08:41] Motion Is Relative, Not Fake

James uses the example of sitting still while Earth moves, and Carlo explains why “really moving” is the wrong question.

[09:31] Morality Without Absolutes

Carlo argues that morality can be meaningful and powerful without being independent of human beings.

[10:44] Relative Does Not Mean Arbitrary

Carlo clarifies that relational truth is not the same as saying anything goes.

[12:05] Quantum Mechanics and the Relational World

Carlo explains how quantum mechanics led him toward the idea that things do not have fixed properties independent of interaction.

[14:35] What Happens When We Are Not Looking?

James asks why quantum mechanics feels strange, and Carlo explains that the confusion begins when we try to describe what happens without interaction.

[16:29] Everything Is a Process

Carlo connects quantum reality to everyday reality: apples rot, stones become sand, and nothing is perfectly fixed forever.

[17:21] Before the Big Bang?

James asks what the first particle could have interacted with, and Carlo explains why the Big Bang may not have been an absolute beginning.

[20:22] The Big Bounce

Carlo discusses the possibility that the universe went through a phase of maximum compression before expanding.

[21:40] Science Knows Its Ignorance

Carlo explains why science is not about having final answers, but about knowing what we know and what we still do not know.

[22:58] Science Is Not the Final Story

James asks about string theory and scientific certainty, and Carlo says science is an ongoing process of learning more.

[24:29] Physics Does Not Explain Everything

Carlo explains why fundamental physics underlies everything but does not replace chemistry, biology, mechanics, or other forms of knowledge.

[25:13] Time Is Not the Same for Everyone

James asks about time, distance, and the Big Bang, and Carlo explains why the idea of one universal “now” is an illusion.

[27:44] How Do We Know Anything?

Carlo defends the power of science, pointing to Maxwell, Einstein, black holes, gravitational waves, and GPS.

[30:11] Will Science Ever Be Complete?

James asks whether even an advanced alien civilization would still face unknowns, and Carlo says he doubts science will ever reach a final story.

[31:20] Gödel, Ignorance, and No Theory of Everything

Carlo treats Gödel’s theorem as an analogy for the impossibility of closing knowledge, while stressing how far we still are from complete understanding.

[32:49] Zhuangzi, Taoism, and Serenity

James connects Carlo’s thinking to Eastern philosophy, and Carlo explains why giving up the need for certainty made his life more serene.

[37:00] Consciousness and Quantum Mechanics

James asks about Roger Penrose and consciousness; Carlo says he does not think the brain is specifically quantum in the relevant sense.

[38:08] Consciousness as Perspective

Carlo explains consciousness as part of a relational world: a piece of nature with information about the rest of nature.

[41:06] Avoiding New Age Quantum Thinking

James asks about law-of-attraction-style interpretations, and Carlo distinguishes serious quantum theory from vague extrapolation.

[42:53] Objects Are Not as Solid as They Seem

Carlo says quantum mechanics challenges the idea that the world is made of fixed, independent objects with properties of their own.

[44:22] Arguing With the Metaphysicians

Carlo describes the Princeton philosophy conversations that helped become the basis of the book.

[46:29] Copernicus, Darwin, and Quantum Reality

Carlo compares quantum mechanics to earlier scientific revolutions that forced humans to rethink their place in the world.

[48:18] What Will Future Science Change?

James asks what discoveries might blow our minds 100 or 200 years from now, and Carlo points to quantum gravity, black holes, and the mind.

[51:10] Free Will Without the Ghost

James asks about determinism and choice; Carlo says freedom is not an illusion, but the idea of a separate nonphysical chooser is.

[54:11] Does Everything Decay?

James tries to find one absolute truth, and Carlo says nature also produces structure, complexity, life, and order.

Additional Resources:

• On the Equality of All Things — Simon & Schuster
• Carlo Rovelli — Simon & Schuster Author Page
• Carlo Rovelli — Penguin Random House Author Page
• Science Friday: “Why physics and philosophy need each other”
• Helgoland — Penguin Random House
• White Holes — Penguin Random House
• Seven Brief Lessons on Physics — Penguin Random House
• The Order of Time — Penguin Random House
• Reality Is Not What It Seems — Penguin Random House
• Anaximander — Penguin Random House

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Description:

Kareem Abdul-Jabbar joins James for a From the Archive conversation about basketball, identity, mentorship, faith, writing, civil rights, and his book Becoming Kareem: Growing Up On and Off the Court.

The episode begins with basketball. James asks Kareem how the game has changed since his playing days, and Kareem explains the shift toward the three-point shot, the rule changes around physical defense, and the way modern spacing has altered how teams score.

But the conversation quickly becomes deeper than basketball.

James sees Becoming Kareem as a book about the search for identity. Kareem agrees, explaining that Black Americans have often had identities imposed on them—first through slavery, then through Jim Crow, then through the lingering assumptions and limitations of American racism. His own journey required rejecting those imposed definitions and building an identity he could be proud of.

Kareem emphasizes the importance of mentors. Some were direct mentors, like John Wooden and Bruce Lee. Others were cultural or intellectual mentors, like Malcolm X. Together, they helped him understand not only how to succeed, but how to think about who he wanted to become.

The central advice Kareem gives young people is simple: knowledge is power. Learn what your future could be. Seek out what motivates you. Do not let someone else define your path. Every person has a unique spark, and the work is to discover where that spark leads.

James and Kareem also talk about fundamentals. Kareem remembers John Wooden expecting him to graduate and teaching his players the smallest details of preparation, including how to put on their socks. The lesson is that success depends on doing the basic things correctly before the glamorous work begins.

The conversation then turns to Kareem’s life as a writer. James asks about the challenge of moving from basketball into Sherlock Holmes fiction. Kareem explains that writing Mycroft Holmes required serious preparation: understanding Victorian England, Arthur Conan Doyle’s canon, and the possibilities hidden inside Mycroft’s brief appearances.

Kareem also reflects on Islam, his conversion, and the way faith gave him a moral anchor. He talks about being raised Catholic, studying Islam, reading The Autobiography of Malcolm X, and finding a belief system that helped him understand right and wrong.

Near the end, James asks about Kareem’s seriousness in photos and the HBO documentary Kareem: Minority of One. Kareem explains that his height made him visible everywhere he went, and that constant scrutiny made him more guarded than someone who could disappear into a crowd.

The episode closes with the idea that everyone is, in some way, a minority of one. Every person has to figure out their own path, and often that path is not the one their parents followed. Kareem’s story is about basketball, but it is also about becoming a whole person.

Editorial Note:

This is a From the Archive episode. References to Kareem’s career scoring record, the state of the NBA, Becoming Kareem, and his then-current writing projects reflect the original recording period.

Since this conversation was recorded, LeBron James has surpassed Kareem Abdul-Jabbar as the NBA’s all-time leading scorer. The conversation remains historically valuable because it captures Kareem reflecting on his record, his era, and his evolution before that milestone changed.

What You’ll Learn:

• How Kareem thinks basketball changed after his era.
• Why the three-point shot transformed modern NBA strategy.
• Why Becoming Kareem is ultimately a book about identity.
• How imposed identity shaped Kareem’s experience as a Black American.
• Why knowledge is power in the search for a future.
• How mentors helped Kareem understand who he was and who he wanted to become.
• What John Wooden taught him about education, discipline, and preparation.
• Why fundamentals matter before talent can fully express itself.
• How the lesson of “putting on your socks” applies far beyond basketball.
• Why Bruce Lee’s “one kick 10,000 times” idea connects to the skyhook.
• How Kareem approached writing Sherlock Holmes fiction through Mycroft.
• Why religion became part of Kareem’s search for identity.
• How Islam gave him a moral anchor.
• Why constant public scrutiny made him more guarded.
• Why competitive fire separates great athletes from talented ones who do not fully develop.
• Why every generation has to find its own path.

Timestamped Chapters:

[02:38] How Basketball Changed

Kareem explains how the three-point shot, rule changes, and less physical defense changed the modern NBA.

[04:14] Beyond Basketball

James introduces Becoming Kareem and frames Kareem’s life as a continuing search for identity.

[05:44] Rejecting an Imposed Identity

Kareem explains how Black Americans have had identities imposed on them and why his journey required building one he could be proud of.

[07:03] Mentors and the Making of a Self

James points to Coach Wooden, Bruce Lee, Muhammad Ali, Wilt Chamberlain, Malcolm X, and other influences who shaped Kareem’s identity.

[08:17] Knowledge Is Power

Kareem says young people should seek knowledge, understand what motivates them, and choose a path instead of accepting one imposed by others.

[09:57] Education, UCLA, and Community

Kareem explains why earning a college degree mattered to him personally and to his community.

[11:12] Finding Your Path in America

Kareem talks about the many ways to become successful and the need to figure out what you want to pursue.

[12:12] Fundamental Preparation

Kareem explains why every field requires fundamentals, whether basketball, chemistry, law, or any other discipline.

[13:05] John Wooden and the Socks Lesson

James and Kareem discuss Wooden teaching players how to put on socks and why small details determine whether bigger work can happen.

[14:26] The Skyhook and 10,000 Kicks

James connects Bruce Lee’s practice philosophy to Kareem’s skyhook and the discipline of repeating one skill until it becomes mastery.

[15:46] Becoming a Sherlock Holmes Writer

Kareem explains the challenge of entering a new creative field and writing about Mycroft Holmes.

[17:02] Finding the Blank Space in Mycroft

James notes that Kareem built a story from Arthur Conan Doyle’s brief suggestion that Mycroft was, at times, the British government.

[17:39] Religion and Identity

Kareem explains how his Catholic upbringing, interest in monotheism, African history, and The Autobiography of Malcolm X led him toward Islam.

[18:49] A Moral Anchor

Kareem says Islam helped him clarify his belief system and understand right and wrong.

[20:06] A Minority of One

James asks why Kareem often appeared so serious in photos, and Kareem explains the effect of lifelong scrutiny.

[21:31] What Coach Wooden Still Teaches Him

Kareem reflects on Wooden’s example, expectations, and belief that effort in academics and athletics was worthwhile.

[22:47] Talent, Skill, and Competitive Fire

Kareem says competitive fire often separates championship athletes from talented players who never fully make it.

[24:35] Civil Rights and Speaking Up Young

James asks about the Cleveland Summit, Muhammad Ali, and Kareem’s early role in civil-rights conversations.

[25:54] Everyone Is a Minority of One

James and Kareem return to the question of identity and the need for each generation to define its own path.

Additional Resources:

• Kareem Abdul-Jabbar Official Website
• Becoming Kareem — Hachette Book Group
• Mycroft Holmes Series — Penguin Random House
• Kareem Abdul-Jabbar — Simon & Schuster Author Page
• We All Want to Change the World — Penguin Random House
• Game of Death — Janus Films

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Note from James:

In 1790, one of the easiest ways to get rich in America was the old-fashioned way: marry someone rich.

George Washington did pretty well that way. Benjamin Franklin, meanwhile, was so deep in debt that he offered to marry a woman if her parents would mortgage their house to pay off his printing press debt. When they said no, he married someone else who had money.

And back then, debt was not just annoying. It could land you in debtor’s prison. Actual prison. And not just you—your wife and kids could go too.

Fast-forward to the 1900s, and most Americans still were not buying stocks. Only a tiny percentage owned shares. Everyday people were gambling, playing the numbers, using dream-interpretation books to decide what lottery number to play, and trying to find some edge that would move them a little closer to security.

My guest today, Joseph Moore, literally wrote the book on this: How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t).

The book is full of strange, funny, surprising stories about money in America: Franklin, Washington, debtor’s prison, the Great Depression, bucket shops, real estate booms, FIRE, crypto, debt, index funds, and all the scams people keep falling for.

But the bigger lesson is that the basic patterns have not changed as much as we think.

People want security. People want freedom. People want hope. People want a way out. And whenever there is hope, there is usually someone selling a formula.

Joseph has very little patience for the usual personal finance myths. Debt does not make you rich. Opportunity makes you rich. Real estate is not always a magic wealth machine. The stock market was not designed to be everyone’s retirement plan. FIRE can work, but it can also become the CrossFit of personal finance. And optimism, marriage, mobility, risk, and solving other people’s problems may matter more than almost anything else.

If you think the rules for getting rich have changed completely, this conversation may convince you how little human nature has changed.

Episode Description:

Joseph Moore joins James to talk about the long, strange history of getting rich in America.

His book, How to Get Rich in American History, looks at 300 years of financial advice—what worked, what failed, what people kept repeating, and what today’s money culture keeps forgetting.

The conversation starts in 1790, with George Washington, Martha Washington, Benjamin Franklin, Stephen Girard, debt, leverage, and debtor’s prison. Joseph explains that many early American fortunes were built through risk, borrowed money, marriage, luck, and then—critically—de-leveraging over time.

That becomes one of the core lessons of the episode: debt does not make people rich. Opportunity does. Debt is only a tool that allows someone to grab more of an opportunity than they otherwise could. But if the opportunity is not real, or the person cannot handle the risk, debt destroys them.

James and Joseph then move into real estate. Joseph argues that real estate is a good way to build a modest middle-class fortune, but not usually the path to the biggest fortunes. In modern America, he says, real estate often functions as a short on the dollar, an income annuity in a low-dividend world, a tax shelter, and a way for ordinary people to use leverage they could not access anywhere else. But that does not make buying a house automatically smart. Renting versus buying depends on age, mobility, location, family needs, inflation, taxes, maintenance, transaction costs, and opportunity cost.

The conversation then turns to the stock market. Joseph challenges the usual historical charts that claim anyone could have invested a fixed sum in 1929 and held forever. Most Americans could not invest that way. There were no index funds, mutual funds had high fees, and buying an index directly required enormous capital. Instead, everyday people went to bucket shops, bet on price moves, played the numbers, and treated gambling as a kind of financial hope.

James and Joseph also discuss passive investing, shadow indexing, the rise of ETFs and 401(k)s, and the way the stock market has become a mass retirement promise. Joseph points out that this is historically new. For most of American history, no ordinary person would have expected to retire on the stock market.

From there, the episode moves to FIRE: financial independence, retire early. Joseph has lived part of that story himself. He built enough wealth through rental real estate after 2008 to stop working for a period, only to discover that early retirement was not automatically fulfilling. He compares FIRE to CrossFit: extreme, demanding, sometimes powerful, sometimes injurious, and not a lifestyle most people actually want.

The final section asks the big question: What has consistently worked?

Joseph boils the lessons down to five pillars: solve other people’s problems, take risks, move toward opportunity, marry well, and believe you can. James adds that optimism matters because it keeps people in the game long enough to get more shots on goal.

The result is a conversation about money, but also about history, risk, luck, marriage, mobility, discipline, scams, and the difference between getting rich and staying rich.

What You’ll Learn:

• Why early American wealth often involved marriage, leverage, luck, and risk.
• How George Washington’s marriage to Martha helped fund the Washington we remember.
• Why Benjamin Franklin’s public advice about debt did not match his own early financial behavior.
• What debtor’s prison meant in early America, including the risk to families.
• Why debt is a tool, not a wealth strategy by itself.
• Why opportunity—not debt—is what actually makes people rich.
• Why real estate can build middle-class wealth but rarely creates the biggest fortunes.
• How buying a home can reduce mobility and opportunity, especially for younger people.
• Why renting versus buying is situational, not a universal rule.
• Why most Americans historically could not invest in the stock market the way modern charts imply.
• What bucket shops and “the numbers” reveal about everyday financial hope.
• How passive investing changed the purpose of the stock market.
• Why stock-market concentration is not new, but mass participation is.
• Why FIRE can work mathematically and still fail psychologically.
• How older financial-independence stories often hid trust funds, inheritances, or outside support.
• Why inflation is one of the biggest risks to early retirement.
• Why getting rich and staying rich require different behavior.
• Why successful people often take risk early and reduce risk later.
• Why optimism is financially useful when it keeps people in the game.
• The five recurring pillars Joseph sees across American wealth-building history.

Timestamped Chapters:

[05:00] How to Get Rich in 1790

James asks Joseph how someone got rich in early America, starting with George Washington, Martha Washington, and marriage as a financial strategy.

[07:24] Stephen Girard and Benjamin Franklin’s Debt

Joseph compares Stephen Girard’s leveraged rise with Franklin’s messy early business debts.

[10:29] Debt Does Not Make You Rich

Joseph explains that opportunity creates wealth, while debt simply lets someone reach for more of that opportunity.

[11:23] Debtor’s Prison Was Real

Joseph explains why failing in the 1790s could mean prison not only for the debtor, but for the debtor’s family.

[12:25] The Real Estate Myth

Joseph argues that real estate can build modest wealth, but rarely creates the biggest fortunes.

[13:43] Real Estate as a Short on the Dollar

Joseph explains modern real estate as an inflation bet, income annuity, tax shelter, and leverage tool.

[15:22] You Need an Edge

James argues that every bet has someone on the other side, which means investors need to know what their advantage actually is.

[16:18] Beating the Market, Missing the Moment

Joseph tells the story of shorting Jim Cramer stock pops, beating the market net of theory, losing to fees, and missing his daughter’s first steps.

[19:56] Shadow Passive Investing

James and Joseph discuss hedge funds, index tracking, fees, and the way much of Wall Street quietly follows the same big benchmarks.

[20:31] The Index Revolution

Joseph explains why Vanguard’s 1976 index fund changed investing for ordinary Americans—and why passive investing may create new structural risks.

[24:24] The Four Percent of Stocks That Matter

James and Joseph discuss stock-market returns, T-bills, concentration, and why a small number of companies drive most gains.

[25:16] The Second Bank Crash

Joseph compares modern market concentration to the 1830s, when the Second Bank of the United States made up a huge share of the stock market before collapsing.

[26:21] The Stock Market as a Retirement Promise

Joseph explains why turning the stock market into a mass retirement strategy is historically new.

[29:58] The Problem With “The Chart”

Joseph criticizes the classic financial-advisor chart that assumes someone in 1929 invested a large sum, held forever, and never touched it.

[31:17] Bucket Shops and Playing the Numbers

Joseph explains how everyday people used gambling, bucket shops, and lottery-like games as financial hope when stock ownership was out of reach.

[34:04] The Mean Moves Through Time

Joseph explains why history is not physics and why the “average” keeps changing as the economy changes.

[35:49] Renting vs. Buying

James and Joseph debate the homeownership myth, maintenance, taxes, transaction costs, mobility, family stability, and when buying can make sense.

[41:02] FIRE and the Question of Enough

James asks how much is enough in 2026, and Joseph explains why the answer depends on location, expectations, security, and lifestyle.

[44:24] FIRE as the CrossFit of Personal Finance

Joseph compares FIRE to an extreme discipline that can work for some people but injure others if they push too hard.

[45:38] Geoarbitrage and Selling the Dream

James and Joseph discuss moving somewhere cheaper, Instagram FIRE influencers, and the difference between living the dream and monetizing the dream.

[46:00] The Long History of Financial Independence

Joseph traces earlier versions of FIRE through Sylvester Judd, Thoreau, Emerson, and Helen and Scott Nearing.

[49:17] Inflation and the FIRE Risk

Joseph explains how Your Money or Your Life and bond-heavy financial independence strategies ran into changing interest-rate realities.

[50:23] Five Pillars of Getting Rich

Joseph lays out the durable lessons: solve problems, take risks, move more, marry well, and believe you can.

[53:43] Marriage, Optimism, and Staying in the Game

James and Joseph talk about supportive partnership, optimism, savings discipline, and why staying in the game increases opportunity.

[56:11] The Line Between Optimism and Recklessness

Joseph distinguishes productive optimism from gambling and explains why control over outcomes matters.

[58:28] Getting Rich vs. Staying Rich

Joseph explains why many wealthy people take risk early, then de-lever over time to keep what they built.

[01:00:00] Leverage, Trading, and the Guy Who Never Stops

James and Joseph discuss extreme leverage, Bitcoin futures, Jesse Livermore, gamblers, and why some people cannot walk away.

Additional Resources:

Joseph Moore - History Helps

How to Get Rich in American History - Book Page

How to Get Rich in American History - Google Books

Next Big Idea Club: “The Changing Rules for Getting Rich in America”

Fast Company: “How the rules of getting rich in the U.S. change with every era”

The Motley Fool Interview with Joseph Moore

Meb Faber Show Interview

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Description:

This is a From the Archive episode with Seth Godin.

Seth Godin returns to the show for a conversation about making work that matters in a world obsessed with hits, rankings, followers, algorithms, and approval.

James opens by talking about Seth’s long body of work: Purple Cow, Linchpin, Graceful, thousands of blog posts, and Seth’s then-new podcast Akimbo. Seth explains why he had thought about podcasting for years but resisted it because audio creates a different kind of intimacy. In print, the voice in the reader’s head is the reader’s own voice. In audio, the voice belongs to the person speaking.

That intimacy made podcasting powerful, but also something Seth wanted to handle carefully.

From there, James asks about the structure of Akimbo. Seth says the key to a strong solo format is assertion. What are you saying that is not obvious? What are you asking people to see differently? If you cannot make the point in 15 minutes, maybe you cannot make it at all.

The conversation then moves into hits. Seth explains that platforms benefit from the long tail, but creators can suffer inside it. Amazon, iTunes, Facebook, Twitter, and other platforms need endless creators to show up with work, but they also train people to believe that if they do not hit number one, they failed.

Seth’s alternative is the smallest viable audience. Find the specific group you seek to serve. If it is 500 people, make something so good for those 500 people that they cannot help but tell someone else. That is more useful than chasing a vague mass audience or gaming a category so you can call yourself a bestseller.

James and Seth connect this to Purple Cow. The book spread because Seth gave people a phrase they could use in a meeting. A “purple cow” became a way to describe something remarkable before people necessarily knew where the phrase came from.

That is a key idea in the episode: every hit changes the people it touches. It does not simply entertain. It gives people a new belief, a new language, or a new way to see.

Seth also explains the deeper forces under a lot of culture: fear and status. Fear keeps people from doing work that might not work. Status makes people compare themselves to the wrong people and measure the wrong things. The creator’s job is to notice both, then act generously anyway.

The episode closes with the craft itself. Seth says he does not check blog stats, does not read Amazon reviews, and does not shape his work around critics. The question is simpler: Did you change someone for the better in a way you are proud of?

If yes, do it again.

Editorial Note:

This is a From the Archive episode. References to Akimbo as a newer podcast, This Is Marketing as an upcoming book, the altMBA, platform dynamics, bestseller lists, podcasting, and Seth’s then-current projects reflect the original recording period.

What You’ll Learn:

• Why Seth Godin resisted podcasting for years.
• How audio creates a different kind of intimacy than writing.
• Why a solo podcast needs a clear assertion.
• Why Seth focuses on overlooked, underthought, ignored, or uncomfortable ideas.
• Why platforms benefit from the long tail more than most creators do.
• Why chasing hits can distort the work.
• What Seth means by the “smallest viable audience.”
• Why a hit has to change people, not just entertain them.
• How Purple Cow spread by giving people useful language.
• Why trying to avoid criticism often makes work invisible.
• How fear and status shape culture, creativity, marketing, and self-worth.
• Why random events should not be taken personally.
• Why generosity requires emotional labor.
• What it means to choose your customers and choose your future.
• Why second-order teaching matters more to Seth than personal credit.
• Why being “amazing” starts long before the hustle.
• Why the best work lives in the territory of “this might not work.”
• Why Seth does not read reviews or track stats.
• How to protect the craft from outside measurement.

Timestamped Chapters:

[03:19] Seth Godin Returns

James welcomes Seth back and introduces his books, blog, and new podcast Akimbo.

[05:15] Why Seth Started a Podcast

Seth explains that he had thought about podcasting for years, but worried about the intimacy of audio.

[07:05] Choosing the Right Medium

Seth explains why a podcast reaches people differently than writing and why he avoids formats, like Twitter, that do not fit the work he wants to do.

[08:17] The Solo Podcast Format

James asks about Seth being the only guest on Akimbo, and Seth says a solo show needs a strong assertion.

[09:24] Overlooked, Underthought, and Hard to Confront

Seth distinguishes his style from pure contrarianism and says he is drawn to things people have missed or avoided.

[10:47] Hitsville and the Long Tail

James brings up Seth’s Akimbo episode on hits, platforms, Amazon, podcasts, and the explosion of available work.

[12:21] The Trap of Platform Thinking

Seth explains how platforms train creators to feel defective if they do not become number one.

[13:25] Editors Cannot Pick the Hits

Seth argues that people cannot reliably predict hits and that creators should not try to game their way to the top.

[15:00] The Smallest Viable Audience

Seth explains why serving a specific small group can be more powerful than chasing the masses.

[16:21] This Might Not Work

James brings up Seth’s large limited-edition book and how it was built for a specific audience instead of the broad market.

[17:26] Why You Cannot Reverse-Engineer Gangnam Style

Seth explains why many talented people try hard and still do not hit, because hits also involve randomness.

[19:14] Don’t Bet Your Work on Oprah or Bieber

Seth explains why waiting for a powerful person to anoint your work is a bad strategy.

[20:13] Finding the People Who Must Share It

Seth uses the idea of R naught to explain why a small group of people who must tell others can create spread.

[20:35] Why Purple Cow Spread

Seth explains how the milk carton, the title, and the phrase itself helped people talk about the idea.

[22:26] Every Hit Makes a Change Happen

Seth says the real question is: What change are you trying to make in the people who engage with your work?

[23:35] What Akimbo Is Trying to Change

Seth explains that Akimbo is for people who want to think more deeply about culture and change it for the better.

[25:14] Randomness, Fear, and Status

James connects Seth’s episodes, and Seth explains that much of his work is about fear and status.

[27:13] Don’t Take Randomness Personally

Seth says creators should expect that many launches will not become hits and organize their work accordingly.

[28:33] The Craft vs. the Outside World

James and Seth discuss how publishers, reviewers, bestseller lists, rankings, and critics can distract from the actual work.

[29:21] It’s Not for You

Seth explains why broadening a project for everyone can make it average, and why creators should be willing to say who the work is for.

[32:29] What Will You Do With the Microphone?

Seth says he wakes up thinking about the people he seeks to serve, not how to increase traffic or revenue.

[33:30] Why Seth Ignores Stats and Reviews

Seth explains that he does not check blog traffic, book sales, or Amazon reviews because that helps him keep doing the work.

[34:43] Choose Your Customers, Choose Your Future

Seth gives the six-word version of audience selection and explains why customers shape the work.

[35:04] Thirsty, Dissatisfied, and Generous

Seth describes his ideal audience and explains generosity as emotional labor in service of other people.

[37:22] Second-Order Teaching

Seth says he wants to be judged not by his work, but by what people who learned from him teach others.

[38:18] Be the Person They Want to Find

Seth explains why the real work happens before SEO, LinkedIn tactics, or hustle.

[40:02] How Do You Become Amazing?

James asks the direct question, and Seth says the essence is confronting fear and doing emotional labor.

[41:00] Where Art and Innovation Live

Seth says the work that might not work is where generosity, art, innovation, and magic happen.

[42:05] Warby Parker and the Risk of Something New

Seth uses Warby Parker as an example of doing something advisors said would not work.

[42:49] How Seth Builds an Episode

Seth explains how a coincidence becomes a podcast: collect stories, find the non-obvious insight, and connect the dots.

[45:07] Seth the Collector

Seth describes himself as someone who collects moments, stories, and observations that may become blog posts or lessons.

[46:34] Self-Awareness and the Craft

James connects Seth’s work to the ability to keep distance between your belief in the craft and society’s measurements.

[47:04] Jiro, Awards, and the Wrong Reward

Seth talks about Jiro Dreams of Sushi and the danger of external validation taking over the craft.

[48:40] Marriage, Space, and Stories

James asks Seth about marriage, and Seth talks about listening, keeping promises, creating space, and the stories people tell themselves.

[52:18] Advice for James’s Podcast

James asks how to change the show, and Seth suggests making one out of every four episodes a solo episode.

[53:08] This Is Marketing and Closing Thoughts

Seth says his next book is This Is Marketing, James recommends Akimbo, and Seth signs off by telling him to keep making a ruckus.

Additional Resources:

• Seth Godin Official Website
• Seth’s Blog
• Akimbo
• Akimbo on Apple Podcasts
• This Is Marketing — Penguin Random House
• Purple Cow — Seth’s Store
• Purple Cow — Penguin Random House
• Linchpin — Penguin Random House
• The Dip — Penguin Random House
• The Practice — Penguin Random House
• By the Way Bakery

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