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Pivot

Epstein Emails, Kennedy for Congress, and Guest Gov. JB Pritzker

with J.B. Pritzker

Published November 14, 2025
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About This Episode

At a live Pivot show in Chicago, Kara Swisher and Scott Galloway interview Illinois Governor J.B. Pritzker about federal immigration enforcement operations in Chicago, Donald Trump's attacks on the city, crime trends, redistricting, the government shutdown fight, quantum computing, and his positions on issues like minimum wage, health care, Ukraine, and social media regulation. After the interview, Kara and Scott analyze newly released Jeffrey Epstein documents and what they could mean for Donald Trump, discuss Jack Schlossberg's run for Congress and the role of looks and sexism in politics, and break down Kim Kardashian's Skims valuation and celebrity entrepreneurship. They close with an extended audience Q&A on topics including the Fed and economic data, dating and life advice, housing and NIMBYism, and whether Scott would run for president.

Topics Covered

Jeffrey Epstein scandal U.S. politics and elections Immigration policy and border security Homelessness and housing insecurity Quantum computing Healthcare system Minimum wage Social media addiction Ukraine Wealth inequality

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Quick Takeaways

  • Governor J.B. Pritzker praises Chicago residents for organizing against federal immigration raids while criticizing the lack of coordination and misinformation from the Trump administration.
  • Pritzker argues that Trump's portrayal of Chicago as crime-ridden is false, noting a large drop in homicides while condemning Trump's rhetoric and behavior as "demented."
  • Illinois is positioning itself as a national hub for quantum computing through the Chicago Quantum Exchange and a planned quantum campus, competing with Colorado and Maryland.
  • In a lightning-round on national policy, Pritzker backs universal health care, universal child care, a higher federal minimum wage, support for Ukraine (without U.S. boots on the ground), and stricter limits on social media's impact on youth.
  • Kara and Scott see the Epstein document fight as uniquely dangerous for Trump, predicting partial, politically shaped disclosures and highlighting how guilty his behavior appears.
  • They use Jack Schlossberg's congressional bid to discuss how height, voice, and attractiveness still heavily (and unfairly) shape perceptions of political leadership.
  • The hosts dissect Skims' $5 billion valuation as an example of modern celebrity-driven, multi-channel brands, and explain why Kim Kardashian may have little reason to take the company public.
  • Audience questions lead to discussions of the Fed and economic data, the need for massive new housing construction and curbing NIMBYism, and Scott's decision to focus on flipping Congress rather than running for president.

Podcast Notes

Live show introduction and setup in Chicago

Opening welcome and framing of the show

Host city and podcast positioning[1:28]
• The MC greets the audience with "Good evening, Chicago. Greatest city in America."
• He describes the show as "the podcast that cuts through all the spin" and names it as Pivot with Kara Swisher and Scott Galloway.
• He praises Chicago as a city of innovation, hard work, and telling it like it is, and says there is no better place for Pivot to be.
Hosts take the stage[2:48]
• Kara jokes about Washington being louder and dismisses any booing of Washington with a Trump-football-game joke.
• Kara introduces the show formally: "Live from the Chicago Theater, this is Pivot from New York Magazine" and Scott adds "and the Vox Media Podcast Network."
• They identify themselves: "I'm Kara Swisher" and "I'm Scott Galloway."

Interview with Governor J.B. Pritzker: immigration enforcement and Chicago

Introduction of Governor J.B. Pritzker and teaser about Epstein

Guest introduction and popularity note[3:17]
• Scott thanks sponsors and asks the audience to give a huge round of applause to "tonight's special guest, Governor J.B. Pritzker."
• Kara notes that Pritzker seems popular because she's not hearing booing.
Epstein news briefly acknowledged, then parked[3:42]
• Kara says they will talk about a couple of things and will ask about Epstein at the end, mentioning "apparently there was some news today."
• On Epstein, Pritzker says "There's nothing quick about it except Trump, Epstein. I think we know what happened there," indicating a negative view but without details.
• He notes it is "really interesting" timing related to a representative being seated and others joining in on something connected to Epstein, and Kara says they will talk more later.

Federal immigration operations in Chicago and statewide

Overview of Operation Midway Blitz and federal presence[4:32]
• Kara shifts to Chicago and "controversial immigration operations" that have taken place for nearly 60 days.
• She mentions Border Patrol official Gregory Bovino and jokes about his looks, calling him someone trying to get cast as the guy whose face melted in Raiders of the Lost Ark and saying he is too short for that.
• She notes many agents are reportedly planning to leave with the Trump administration's downshift in an operation named "Operation Midway Blitz."
• Reports indicate that federal agents could return "fourfold" in the spring, prompting further concern.
Community response in Chicago: whistles, protests, and video documentation[5:01]
• Pritzker emphasizes that "it's the people of Chicago" who have reacted and protected neighbors and friends.
• He describes widespread purchase and use of whistles when residents see "unmarked vehicles and guys wearing masks" to warn neighbors that "ICE is here" so they can protect themselves and know their rights.
• He says for two months residents have been "under siege" by Customs and Border Patrol (CBP), ICE, and Gregory Bovino, and that the city "stepped up, activated, peacefully protested, and has pushed back."
Breakdown in communication between federal and state governments[6:02]
• Kara asks how he deals with these operations and notes that "they don't call you" and "they don't communicate at all."
• Pritzker says it's the first time in his lifetime that the federal government isn't talking to the state government about operations it wants to do within the state, calling it "very frustrating."
• He says they learn of things from the news based on statements from "this lying spokesperson at the Department of Homeland Security, Tricia McLaughlin," and then must sort out what's true and respond.
Use of citizen video to challenge federal actions[6:54]
• Pritzker says they've asked people to pull out their phones and video everything they see involving enforcement actions.
• He states that this has led to federal court cases "that we have won," attributing success in part to the video evidence captured by residents.

Legal limits and state strategy against federal immigration enforcement

Supremacy clause constraints and limited immunity for federal officers[9:02]
• Asked what he can do if agents return in the spring with four times the force, Pritzker cites the supremacy clause of the Constitution giving federal law enforcement authority as long as they follow federal law.
• He notes federal officers have "limited immunity" even if they're not following the law, and says no one at the federal level is holding them accountable.
• He concludes it's "very hard to push back on them," so the strategy has focused on informing people of their rights and documenting abuses.
Who is being targeted by ICE and CBP, according to Pritzker[9:36]
• Pritzker says Donald Trump claimed he was going after the "worst of the worst" but instead they are going after people who have been in the state a long time, paying taxes, following the law, and raising families.
• He says ICE and CBP are stopping people with brown or black skin and asking for U.S. citizenship papers, and he stresses that he and others do not carry citizenship papers and "we shouldn't have to in this country."

Example from Staunton, Illinois and statewide reach of operations

Story of an undocumented business owner detained[8:15]
• Pritzker emphasizes that ICE and CBP have been "all over the state" including suburbs and downstate, not just Chicago.
• He tells a story from Staunton, Illinois (central Illinois) about an undocumented man who has raised a family there, owns a restaurant, and has been in the U.S. for over 20 years.
• He says federal agents arrived, grabbed this man, and "disappeared him" for a whole day, leaving his family without knowing his whereabouts.
• In a town of 4,000, about 500 people showed up to protest his detention, which Pritzker uses as an example of community pushback.

Pritzker on Trump, Chicago crime narrative, and redistricting politics

Pitching Illinois and Chicago as a "product"

Scott's anecdote about visiting Chicago with his son[13:19]
• Scott describes his annual "bucket list" weekend with his sons and says his youngest, living in London, chose Chicago over Paris as his destination.
• They visited a steakhouse, a batting cage, and the tallest building in Chicago, and Scott says they had a fantastic weekend.
Pritzker's sales pitch for Illinois and Chicago[13:36]
• Scott frames states and cities as a "product" with taxes and services and asks Pritzker to pitch Illinois to a recent graduate or highly skilled immigrant.
• Pritzker says Illinois is already a destination for most kids at universities in the Midwest, noting an "enormous influx" from states like Michigan, Indiana, and Missouri.
• He touts Chicago as an exciting, vibrant city with great jobs at tech companies and cites an "interesting fact" from Google that Chicago is the most requested U.S. office transfer location within the company.
• Pritzker notes Google bought a building from the state of Illinois in the center of Chicago to establish a major presence, calling it "absolutely gorgeous" once complete.
• He also highlights Chicago as a great sports town and a great place to raise a family, and says he has lived in multiple other regions but has found no more decent people in a big city than in Chicago.

Trump's attacks on Chicago, crime, and Pritzker's "demented" comment

Trump's comments on the "Miracle Mile" and crime[13:34]
• Kara recounts that Trump called the "Miracle Miles Shopping Center" (misnaming it) once the nation's best but now with more than a 28% vacancy, and urged to "call in the troops fast" to address murder and crime.
• She corrects that it's actually the "Magnificent Mile" and says she assumes the city can handle real estate vacancies without federal troops.
Pritzker's response and description of Trump as "demented"[14:06]
• Kara notes that Pritzker previously said of Trump, "The man is demented. He really has no idea what he's doing," and asks about that choice of words.
• Pritzker says Trump "loves to dump on the city of Chicago" but insists the state and city are "on the rise" with many good things going for them.
• He says Trump's negative portrayal "doesn't help" and notes Trump has such a bad reputation in Chicago that many people would like to tear his name off his building.
• Kara jokes that the problem with Trump's building is the badly sized font of the "Trump" name.
• Pritzker says Trump doesn't read or try to understand anything, pointing out Trump also previously claimed credit for a "precipitous" four-year crime drop in Chicago, including homicide rates being cut in half.
• Pritzker notes that ICE and CBP have been in Chicago for two months and "not getting the worst of the worst off the streets" yet Trump claims their crime reduction success is because of him.
• He reiterates his frustration that Trump has "the biggest bully pulpit in the world" and uses it to talk negatively about Chicago, and says he will "stick with demented" as a description.

Redistricting battles and Illinois' congressional map

National redistricting dynamics and state pairings[17:04]
• Kara notes the country is in the middle of a "massive redistricting war" that could determine control of Congress, and that Republicans might actually lose seats due to their efforts.
• Pritzker says Trump is pushing Republican governors and legislatures to redistrict, citing neighboring Indiana as "on again, off again" on redistricting.
• He mentions state pairings like Missouri and Maryland, and California acting to cancel out Texas through redistricting moves.
Potential impact on Illinois[18:02]
• Pritzker says if Indiana proceeds with redistricting when they meet in December, it might push Illinois toward redistricting as well.
• He notes Illinois currently has 14 Democrats out of 17 congressional seats and says Democrats are "doing okay" in the state.

Government shutdown vote and criticism of Democratic senators

Pritzker's view on the eight Democrats who voted to end the shutdown[18:22]
• Asked if seven Democratic senators should have voted to end the shutdown, Pritzker corrects that there were eight and calls it "probably the biggest mistake" he has seen in his political career.
• He says Democrats had just won elections "everywhere in the country" eight days prior, which should have stiffened their spines instead of loosening them.
• He expresses particular disappointment in Illinois' senior senator, saying he has done many good things but made a bad decision in this vote.
• He praises the state's other senator, Tammy Duckworth, for criticizing the senior senator and voting against ending the shutdown.
Why Pritzker thinks the vote was wrong and Trump's role[19:34]
• Pritzker believes many senators thought the shutdown had gone on too long and was hurting people, and that they could "rescue the country" by ending it.
• He argues the real problem was created by Donald Trump, who refused to sit down with Democrats and wanted to shut down the government.
• He characterizes Trump's stance as wanting to "deny people food" to force the country to accept less health care, while Democrats wanted restoration of affordable health care.
• He says it's Democrats who fight for people to be fed and get health care, and Republicans and Trump who stand against it, calling it a powerful campaign contrast.
• He laments that people rely on Democrats to "do the responsible thing" while Republicans and Trump "get away with murder" politically.

Pritzker on technology, quantum ambitions, and national policy lightning round

Illinois' quantum computing strategy

Building the Chicago Quantum Exchange and quantum campus[22:43]
• Kara notes Massachusetts is trying to become an AI hub, and says Illinois is leaning into quantum computing.
• Pritzker lists Illinois' major institutions for quantum and AI: Argonne National Laboratory, Fermilab, University of Chicago, University of Illinois, Northwestern, and nearby Purdue and University of Wisconsin-Madison.
• He recounts University of Chicago approaching him in 2019 about building the Chicago Quantum Exchange and making Illinois a quantum hub.
• At that time he had just passed or was about to pass a major infrastructure bill and agreed to invest, insisting that the University of Illinois be a partner.
• He says they are now building a quantum campus and that three states-Colorado, Maryland, and Illinois-are competing to be the national quantum hub, with Illinois "in the lead."

Lightning-round policy questions framed around a hypothetical presidential run

Mandatory national service[23:43]
• Scott asks for Pritzker's gut response to "mandatory national service."
• Pritzker favors some kind of service where people can, for example, attend trade school or help build infrastructure, emphasizing service to the country beyond just military duty.
Lowering Medicare age and universal health care[24:22]
• Scott suggests lowering Medicare eligibility by three years each year a president is in office, effectively moving toward socialized medicine.
• Pritzker responds that he is "for universal health care" and believes everybody deserves to have a doctor.
Universal child care[24:31]
• Asked about universal child care, Pritzker enthusiastically supports it, saying he came into office with 25 years of experience in child care and early childhood care.
Raising the federal minimum wage[24:37]
• Scott floats raising the federal minimum wage from $7.25 to $20 or $25 an hour.
• Pritzker calls this "my topic" and notes that $7.25 an hour is about $14,000 a year, on which no one can live.
• He says someone working two full-time minimum-wage jobs would make about $28,000 a year and would be unable to properly raise a family while doing it.
• He advocates raising the national minimum wage to at least $15, citing Illinois' move to $15 and saying hundreds of thousands of people no longer live in poverty in Illinois because of that increase.
Support for Ukraine and opposition to U.S. boots on the ground[25:37]
• Scott asks about a massive increase in support and armaments, including long-range missiles and potentially boots on the ground in Ukraine.
• Pritzker says he does not want to send U.S. boots on the ground but believes Ukrainians should fight their own war with U.S. support.
• He argues Russia is not America's friend and wants a piece of the rest of Europe, and that Ukraine stands in the way, so the U.S. "ought to be supporting" Ukraine.
• He contrasts Joe Biden, whom he says was doing the right thing, with Trump, who "walked away" and let Vladimir Putin kill hundreds of thousands in Ukraine while falsely styling himself as a peacemaker.
Section 230 and social media's impact on youth[26:33]
• Scott proposes removing Section 230 protections for algorithmically elevated social media content.
• Pritzker calls social media "probably the biggest danger to young people" in the country and says limits are needed.
• He describes his attempt to pass a law banning cell phones in classrooms across Illinois and says they will try again, while arguing the federal government should do much more.

Pritzker's 2028 bench talk and coyness about a presidential run

Deflection on presidential ambitions[26:55]
• Kara presses Pritzker on how close he is to a presidential run, asking for a timeframe.
• Pritzker replies that he loves being governor of Illinois and is running for re-election.
• He says Democrats have "probably the greatest bench" they have had for quite some time for 2028 but does not directly commit to or rule out his own run.
• Kara jokes that she thinks he's running for president, teasing him about slimming down and looking good as he exits the stage.

Post-interview news discussion: Epstein documents and Trump

New documents from the Epstein estate and House actions

Scope of document releases and Epstein's emails about Trump[30:53]
• Kara reports that House Republicans released over 20,000 pages of documents from the Epstein estate.
• House Democrats released emails where Epstein claimed President Trump "spent hours at my house with a trafficking victim" and that Trump "knew about the girls at Mar-a-Lago."
• The emails, sent to Ghislaine Maxwell and author Michael Wolff between 2011 and 2019, suggest Epstein believed he had leverage over Trump.
• She says the Trump administration held a Situation Room meeting over the House effort to force release of all DOJ Epstein files.
• Kara notes the House passed the ability to vote on releasing the files and mentions that even Lauren Boebert refused to change her vote.
Legislative path and likelihood of full file release[31:31]
• Kara explains that after passing the House, the measure must pass the Senate and then go to Trump, who she predicts will veto it, meaning a veto-proof majority would be necessary.
• She concludes it is unlikely that all files will come out at once, predicting instead a "drip, drip, drip" release over time.
• She cites another Epstein email claiming Trump did not get a massage but "knew about the girls," calling that "the lowest fucking bar" for exculpation.

Scott's view: Epstein as a powerful posthumous figure and Trump's apparent guilt

Epstein's influence on U.S. politics[32:39]
• Scott says he thought earlier scandals were red lines for Trump but they were not, and now sees Epstein as uniquely powerful.
• He claims the third most powerful person in the world is a "dead pedophile," because Epstein's scandal is driving decisions like closing Congress.
• Scott speculates there are people in a room querying AI models like ChatGPT and Anthropic to generate headline-grabbing stunts whenever Epstein resurfaces in the news cycle.
• He argues Speaker Johnson is effectively a "block" preventing Epstein from returning to the news and says Congress would not have been closed down except for fear over information about Trump's relationship with Epstein.
Kara on QAnon, Bannon, and how Trump's allies frame Epstein[34:51]
• Kara believes the issue is "no good" for Trump and that his numbers are dropping, calling Epstein the "third rail" for QAnon-aligned communities.
• She notes this topic is a foundational pillar for that set, which is why figures like Boebert, Nancy Mace, and Marjorie Taylor Greene lean into it heavily.
• She mentions Steve Bannon calling Trump imperfect but "divine" and guided by divine providence, interpreting that as effectively saying "he might be a pedophile, but he's God's pedophile," which she considers a problematic argument.

Speculation on partial releases, pardons, and the clemency system

Predictions about how Epstein files might be managed[35:18]
• Scott predicts a "soft release" of heavily redacted and massaged files that expose Democrats while hiding "really crazy stuff," with officials pretending it is a full release.
• He believes there are videos and photographs beyond what has surfaced and compares potential evidence to the Prince Andrew photo.
• Kara notes that Trump is again calling the whole matter a hoax.
Scott's criticism of how pardons are monetized[39:08]
• Scott argues the clemency and pardon system is a "wonderful" mechanism to correct injustices, but says it has been perverted and monetized.
• He imagines that if one of his kids were in prison, he would start donating millions to the GOP, attend a dinner, and offer $10 million to get his kid a pardon, estimating a one-in-three chance of success.
• He laments that this monetization diverts resources from clemency lawyers working to free people who are actually innocent or oversentenced.
Visual evidence and public reaction[40:28]
• Kara thinks the public is "a visual species" and anticipates that a picture or video will be pivotal in shaping perceptions of Trump's connection to Epstein.

Jack Schlossberg candidacy, appearance, and sexism in politics

Jack Schlossberg's run and the role of looks

Schlossberg's background and campaign[42:05]
• Kara reports that Jack Schlossberg, 32-year-old grandson of President John F. Kennedy, is running for Congress in retiring Representative Jerry Nadler's Manhattan district.
• She notes Schlossberg first gained attention during the 2024 election via viral social media videos mixing shirtless content and political commentary.
• In his campaign video he says the country is facing a crisis at every level, according to Kara.
• Kara asks whether being handsome, connected, and shirtless qualifies someone for Congress today.
Scott's argument about sexism, height, and leadership perceptions[43:36]
• Scott notes the primary absolute criterion for elected representatives is having a college degree, and that for 40 years more women than men have been graduating.
• He says women now comprise about 60% of college students and this is heading towards two-to-one, yet only 26% of elected representatives are women, which he calls "wildly sexist."
• He argues people conflate a deep voice and height with leadership skills, giving examples of a short, high-IQ person with a high-pitched voice versus a tall person with a lower IQ.
• He cites Secretary Hillary Clinton and Vice President Kamala Harris as evidence of sexism in electoral outcomes, asking "How the fuck did they lose?"
• Scott admits he himself wants a good-looking person to run for president and describes wanting someone "tall and dreamy" to lead Democrats.
• He says he would vote for Schlossberg and even jokes about personally applying sunscreen lotion, calling him a "tall drink of lemonade."

Business segment: Kim Kardashian's Skims and celebrity entrepreneurship

Skims' valuation, growth, and expansion plans

Funding round details and scale[46:57]
• Kara says Kim Kardashian's shapewear brand Skims raised $225 million in new funding led by Goldman Sachs, bringing its valuation to $5 billion.
• She notes this is up from a $4 billion valuation two years ago and that the six-year-old company is expected to surpass $1 billion in net sales this year.
• Kara reports that Skims plans to expand internationally with stores in London and Dubai by mid-2026, after opening 18 U.S. locations and partnering with Nike.
Scott's analysis of celebrity brands and going (or not going) public[46:46]
• Scott compares Skims to other celebrity brands: Kim Kardashian's sister's beauty brand, Rihanna's brand, and Jessica Simpson's company, noting many top out at a few hundred million to $1 billion valuations.
• He says what is unique about Skims is its $5 billion private valuation and states he does not think Kim will take it public.
• He explains that the number of public companies has been cut in half over 40 years due to regulatory burdens and quarterly reporting pressures, while abundant private capital now provides liquidity without going public.
• Scott notes that to scale, brands typically must be multi-channel, and Skims is doing that by opening stores; he calls Kim Kardashian a "remarkable entrepreneur."
• He describes the wealth-creation "sweet spot" for celebrities as securing equity stakes in promising brands early (citing Roger Federer's stake in On) rather than building their own companies from scratch.

Audience Q&A and closing reflections

Andrew Yang's question about Scott running for president

Yang's prompt and Scott's answer[55:57]
• Andrew Yang introduces himself as a former presidential candidate and asks Scott if he would run for president and what his platform would be.
• Scott jokingly says his platform would be "a chicken in every pot and a Cialis in every cupboard."
• More seriously, Scott says he has the primary qualifications to run (narcissism and some money) but has decided instead to move back from London, be in the fight, and focus on flipping Congress and putting a Democrat back in the White House.
• He says he will devote his time, treasure, and talent to those goals and highlights that he and Kara want to shine a light on what they consider an outstanding Democratic bench.

Student question on economic data, the Fed, and Trump's influence

White House withholding data and Fed policy[58:31]
• A University of Chicago student named Rohil asks about the White House saying October inflation and jobs data will probably never be released and what the Fed will do in December.
• Kara responds that they "have to release those numbers" and says they will be bad, mentioning other reports show a 50,000 jobs decline.
• She speculates that Trump might simply not release the numbers even if it is illegal, since he often does not follow legal norms, but that if he doesn't, other indicators like those from Goldman Sachs and consumer sentiment will fill the void.
• On the Fed, she thinks economic conditions are starting to decline and says they will probably lower interest rates, then jokes that she "could give a shit."
Scott's offer and critique of elite universities[1:00:10]
• Scott offers the student a summer internship at his company, Prop G Media, praising his presence and credentials.
• He describes touring Northwestern and University of Chicago with his son and notes UChicago's 4% admissions rate.
• Scott argues that any university with an endowment over $1 billion that is not growing its freshman class faster than population growth should lose tax-free status, calling them hedge funds offering classes.
• He says UChicago is better than most: while its endowment rose sevenfold, its freshman class grew 40%, which he sees as less exclusionary than peers.
• He recounts telling his son to "break up with this bitch before she breaks up with us" upon hearing the 4% admit rate, and personifies UChicago as a barefoot Nobel laureate feeding pigeons in a park.

Listener gratitude and dating-life update

How prior advice led to a long-term relationship[1:04:00]
• A woman named Pat thanks Kara and Scott, saying Kara is "terrific" and Scott is "pretty great."
• She recounts calling Kara's other podcast in 2022 about a dating quandary and says Kara advised her to think more widely, live her life, and see what happens, while jokingly inviting her to be a lesbian.
• Pat reports that she found an amazing partner and has been with him for three years, thanking them for widening her life.
• Kara jokes about "trying to do things for the heterosexuals" and Scott adds a quip about widows being happier after their husbands die and lesbian couples divorcing more because "they're both listening."

Question on leveraging existing private real estate to solve housing

Kara's view: innovation, NIMBYism, and a housing-first agenda[1:06:24]
• A woman named Paula asks how to use existing, privately owned real estate to increase housing stock and solve the housing crisis, emphasizing that "without consistent sleeping places" society will keep going in circles.
• Kara says she has recently reported on housing and describes "astonishing innovation" in materials and construction that can produce safe, quick-to-build housing.
• She criticizes "nimby fucking governments" for preventing this housing from being built, especially near subways and transit where people can access cities.
• Kara argues homelessness is directly tied to not having homes, with stress from insecurity contributing to mental illness and instability.
• She says if she were running for president, two priorities would be: getting everyone to a working wage (she mentions $25) and getting people homes.
• She notes hedge funds are buying a large share of homes, stating that 38% of sales are now from hedge funds, and asks how to address that while also building, repurposing, and reusing housing.
Scott's call to "build, baby, build" and critique of exclusionary culture[1:08:29]
• Scott says the slogan should be "build, baby, build" instead of "drill, baby, drill," advocating massive housing construction and tax subsidies to weaponize the private sector.
• He opposes rent control, arguing it reduces housing stock, and says Americans have embraced a "rejectionist, exclusionary culture" that inflates asset prices.
• He compares elite college admissions to a homeless shelter bragging that it turned away 90% of people who showed up, arguing universities should behave as public servants, not "Hermes bags."
• Scott points out homeowners often fight new housing permits to protect their own home values, which contributes to the crisis.
• He praises programs that match seniors who have large homes and need help with young men who need housing, saying he loves that model.
• Kara calls that an astonishing program that helps with crises affecting both the elderly and young people.
Closing message: action and optimism[1:10:18]
• Kara says it is easy to doomscroll but stresses there is a lot of innovation and that people should "get the fuck up" and start walking and acting to change things.
• She says they saw change in the last election and that if there were great Republicans, they would support them too, but right now things are "really ugly."
• They express great hope for the country and explain that part of the reason for the tour is their love of talking with people, thanking Chicago for being a great crowd.

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Grassroots civic action-like communities organizing, documenting abuses, and asserting their rights-can effectively constrain powerful institutions even when formal channels are blocked or unresponsive.

Reflection Questions:

  • • When have you seen a local community successfully push back against a larger institution, and what specific tactics made a difference?
  • • In the issues you care about, how could you and a few peers start gathering evidence, sharing information, or organizing neighbors in a similar way?
  • • What is one concrete situation right now where you could shift from private frustration to some small, coordinated public action this month?
2

Raising basic living standards through policies like higher minimum wages, universal health care, and child care can move large numbers of people out of poverty and stabilize families far more reliably than piecemeal fixes.

Reflection Questions:

  • • Which basic needs in your own life (income, health care, child care, housing) feel most precarious, and how would they look under more universal, reliable support?
  • • How might your views on economic policy change if you focused less on abstract ideology and more on whether a proposal clearly reduces or entrenches poverty?
  • • What local or national policy campaign aligned with these principles could you support with your time, money, or voice over the next year?
3

Exclusionary scarcity mindsets-in housing, education, or opportunity-often protect incumbents' asset values at the expense of broader social health, whereas deliberate expansion ("build, baby, build") creates resilience and shared prosperity.

Reflection Questions:

  • • Where in your own life do you instinctively resist expansion or inclusion (in your neighborhood, workplace, or networks) to protect your perceived status or comfort?
  • • How would your decisions change if you prioritized long-term community health and opportunity over short-term property values or prestige?
  • • What is one concrete way you could support more housing, educational access, or opportunity in your city, even if it feels slightly uncomfortable personally?
4

Transparency and accountability around uncomfortable information-whether economic data or politically damaging files-are essential for trust; attempts to hide or spin such information usually signal deeper problems and erode legitimacy further.

Reflection Questions:

  • • In your organization or community, where are you tempted to withhold or soften bad news, and what signal does that send to others about trust?
  • • How might your decisions improve if you assumed that critical information will eventually surface and planned from the outset to handle it openly?
  • • What is one situation right now where you could choose radical transparency instead of damage control, and how would you prepare yourself for the short-term discomfort?
5

We systematically overvalue superficial traits like height, voice, and physical attractiveness in leaders, which can blind us to deeper competence and reinforce sexism and other biases unless we consciously correct for it.

Reflection Questions:

  • • When you picture an ideal leader or expert, what physical or stylistic traits come to mind first, and how might those be shaped by bias rather than merit?
  • • How could you deliberately slow down and interrogate your first impressions of candidates, colleagues, or public figures before equating charisma with competence?
  • • What is one decision-hiring, voting, promoting-where you can explicitly list and weigh substantive criteria to counteract your own appearance-based bias?
6

Unchecked social media dynamics, especially algorithm-driven amplification targeting young people, can become a public health issue, so setting structural boundaries (like phone-free classrooms) is often more effective than relying on individual willpower.

Reflection Questions:

  • • How much of your current media environment is shaped by algorithms rather than by your deliberate choices, and what effect do you notice on your attention and mood?
  • • In what contexts-work, family, school-could you or your community experiment with stronger collective boundaries around phones or social apps?
  • • What is one concrete, time-bound rule you could adopt this week (e.g., phone-free meetings, app limits, screen-free evenings) to test how structural constraints change your behavior?

Episode Summary - Notes by Casey

Epstein Emails, Kennedy for Congress, and Guest Gov. JB Pritzker
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