Jan 9, 2025 · 2h 0m · tbpn
Can This Man Save Los Angeles? (Rick Caruso)
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Co-hosts John Coogan and Jordy Hays analyze real estate mogul Rick Caruso's business philosophy and potential to lead Los Angeles, while discussing firsthand wildfire evacuation experiences, disaster resilience, defense technology, and tech startup culture.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 58.6% of the talking time here. How this is scored →
The hosts as informed peer 5.6 Guest teaching 1.9 Guest disagreement 0.3 The hosts pushing back 0.3
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:21:30 Pushing Back on Middleman Value
Hays ironically suggests the predatory hotel booking platform might claim market efficiency, which Coogan rejects outright as an explicit ad arbitrage scam.
Hardest push from the hosts ▶ 1:04:00 Challenging the Hard Paywall ModelCoogan corrects Hays's assumption about Stratechery's paywalls, clarifying that main articles are freely accessible while premium tiers gate audio and analysis.
Biggest teaching moment ▶ 15:25 Teaching Commercial Real Estate LOI LeverageHays clearly breaks down how Rick Caruso utilized his father's Dollar Rent-A-Car LOIs to secure bank financing for property acquisitions.
The host holds their own ▶ 1:48:30 Explaining the Technical Mechanics of Community NotesCoogan demonstrates insider knowledge of X's Community Notes ranking algorithm, early submission visibility, and consensus requirements.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Starlink Unboxing and Satellite Communication During Disasters | 5 | 3 | 1 | 1 | Coogan details satellite differences between LEO and geostationary systems while Hays explains his firsthand experience using iPhone satellite messaging and local utility shutdowns during the Malibu fire. | |
| The Case for Rick Caruso vs. Karen Bass in Los Angeles | 6 | 2 | 1 | 1 | Coogan breaks down the private security and sensor integration at Rick Caruso's properties while Hays contrasts Caruso's civic competence with Mayor Karen Bass's PR missteps. | |
| Rick Caruso's Origins and Dollar Rent-A-Car Arbitrage | 6 | 4 | 1 | 0 | Coogan recounts Caruso's early legal career and law firm collapse, while Hays explains the financial leverage mechanics of using Dollar Rent-A-Car LOIs to secure bank loans. | |
| Creating Destination Retail and the Philosophy of the Grove | 6 | 2 | 0 | 0 | Coogan details Caruso's retail philosophy regarding anchor tenants versus guest experience, and Hays elaborates on how long-term compounding beats flipping commercial properties. | |
| Human-Centered Design, Community Engagement, and Walkable Spaces | 7 | 3 | 0 | 0 | Coogan cites the engineering and licensing details of the Grove's trolley system and Glendale Galleria disputes, while Hays highlights Caruso's grassroots community engagement tactics. | |
| Real Estate Financing, Liquidity Management, and Avoiding Financialization | 7 | 3 | 1 | 1 | Coogan explores Caruso's debt strategy, Wall Street MBS financing, and liquidity management, contrasting simple operational discipline against dangerous derivative financialization. | |
| Rick Caruso's Civic Leadership and Political Vision for Los Angeles | 6 | 2 | 0 | 0 | The hosts discuss Caruso's mayoral platform, high foot traffic statistics surpassing theme parks, and his founder-mode approach to civic leadership. | |
| Dissecting Disaster Media Coverage and Wildfire Reality | 5 | 2 | 1 | 1 | Coogan and Hays analyze media incentives during natural disasters and discuss the backlash against private firefighting services hired during the Palisades wildfire. | |
| Tech Culture Awards and the Legacy of the Crunchies | 6 | 1 | 0 | 0 | Coogan recalls TechCrunch's historical Crunchies awards and Paul Graham's critique, debating the merits of qualitative versus purely market-driven industry awards. | |
| Andrew McCalip's DogeFin Sculpture and Vacuum Chamber Clearance | 4 | 2 | 0 | 0 | Coogan reads Andrew McCalip's tweet giving away a vacuum chamber and Doge sculpture, casually brainstorming storage logistics with Hays. | |
| Promoted Post: High-Performance Rollerblade Wheels for Office Chairs | 5 | 1 | 0 | 0 | The hosts riff on high-performance rollerblade wheels for office chairs, Kill Tony bucket pull formats, and online public perception dynamics during high-profile legal trials. | |
| Satirical Geopolitics: Greenland Tariffs and the 54-Star American Flag | 4 | 1 | 0 | 0 | Coogan discusses his viral 54-star flag graphic and satirical tariffs on Denmark while Hays jokes about Trumpian geopolitical negotiation memes. | |
| Imperialism Memes and Moving to Greenland | 6 | 2 | 0 | 1 | Coogan examines Ben Thompson's Stratechery business model and track record, comparing subscription paywalls against ad-supported wide distribution. | |
| Strategic Trade Routes: Northwest Passage and US Arctic Ambitions | 6 | 2 | 0 | 0 | Coogan breaks down the strategic value of the Northwest Passage for global Arctic shipping routes, followed by banter about private Boeing 737 jets and supercar tuning culture. | |
| The Degradation of Legacy Luxury Hospitality and Pasadena's Langham Hotel | 6 | 3 | 0 | 0 | Hays shares his background working at a Ritz-Carlton and Coogan recounts personal evacuation bookings at the Langham, criticizing institutional luxury hospitality decay. | |
| Exposing the Google Ads Hotel Booking Middleman Arbitrage | 7 | 2 | 1 | 1 | Coogan uncovers the technical arbitrage behind third-party Google ad booking sites masquerading as official hotel reservation portals. | |
| Disaster Preparedness: Practical Survival Skills and Personal Defense | 4 | 1 | 0 | 0 | Coogan and Hays discuss practical emergency survival skills including lockpicking, vehicle hotwiring, and personal defense readiness during crises. | |
| Autonomous Carriage Concepts and Robotaxi Aesthetic Differentiation | 5 | 1 | 0 | 0 | The hosts discuss aesthetic differentiation in autonomous robotaxis, Tolkien versus Hindu tech company naming tropes, and startup branding trends. | |
| The Stranded Boeing Starliner Astronauts and Regulatory Discrepancies | 5 | 2 | 0 | 0 | Coogan and Hays analyze the stranded Boeing Starliner astronauts on the ISS, pointing out double standards in regulatory scrutiny between startups and legacy contractors. | |
| Reflecting on the Juicero Debacle and Startup Dietary Struggles | 5 | 1 | 0 | 0 | Coogan recounts humorous personal anecdotes from his Y Combinator batch juicing struggles while evaluating the structural economics behind Juicero's hardware model. | |
| Wildfire Prediction Markets and PolyMarket Financialization | 6 | 2 | 0 | 0 | Coogan examines Polymarket liquidity and incentives surrounding wildfire containment prediction markets, alongside a comedic deep-dive into office feng shui mechanics. | |
| Promoted Post: Rainmaker Careers and Cloud Seeding Innovation | 5 | 1 | 0 | 0 | The hosts promote careers at cloud-seeding startup Rainmaker and highlight Bridger Aerospace's market performance during wildfire outbreaks. | |
| Palmer Luckey and the Mainstreaming of Defense Tech Culture | 7 | 1 | 0 | 0 | Coogan breaks down the mainstreaming of defense tech culture via Palmer Luckey and explains the underlying mechanics and moderation of Community Notes. | |
| Anticipating Varda Space's Second Mission Launch and Growth | 5 | 2 | 0 | 0 | Coogan and Hays wrap up previewing Varda Space's second orbital mission, luxury watch buying advice, and parting endorsements for Ramp. |
Statements from this episode (38)
Coogan: Elon Musk Distributes Starlink Units in Disaster Areas
“Elon's giving out a bunch to people that are in affected disaster areas and hopefully keeping people Online and communicating.”
Coogan: Caruso employs open-carrying LAPD officers and facial recognition at The Grove
“They have off duty LAPD officers who actually open carry a sidearm. They used to be discreet kind of undercover, but then they changed this to carry to show the gun. And they also have facial recognition cameras, license plate scanners, a bunch of different te…”
Jordy Hays: Mayor Bass Stayed in Ghana After Wildfire Briefing
“She was briefed on the fires on Monday, decided to stay in Ghana. ... She was fully briefed.”
Hays: Caruso's properties rank in the top 5% of US retail performance
“His properties are some of the best performing from retail standpoint in, in the country, like in the top five percent”
Jordy Hays: Burglars Stole Unsecured Firearms From Mayor Bass's Home
“She quickly had She quickly had her home robbed by criminals. And she had loose guns in her house. So they, the criminals managed to steal guns that were not in safes.”
Hays: People With Nepotism Advantages Have a Duty to Maximize Them
“I believe it is your duty to maximum, to maximally utilize that, that, that, that advantage relationship, whatever.”
Coogan: Top Dealmakers Create Value by Playing Intermediary Arbitrage on Both Sides
“Because I think too many people think about the deal is like one way. Like I just need the tenant or I just need the bank. And really it's like, he is creating almost like an arbitrage. Like the bank wants to lend to a parking lot that has a relationship with …”
Hays: Rick Caruso never sells his real estate properties
“He became, he's very well known for not selling any of his properties. So he's the sole investor in his properties, but then he never sells. He just benefits from the appreciation and the cashflow.”
Coogan: The Grove's one-block trolley required full train regulatory licensing
“And the trolley is a crazy story because that needed, even though it just goes one block, it needed to be licensed as a train. So we had to go through all the train regulations to get it approved.”
Hays: Caruso's mayoral loss was devastating given his urban development record
“It's so, him losing the last election is so devastating because his body of work is truly He's created, what do you want a city to do? You want it to be highly enjoyable, livable, safe, a place where commerce can thrive, and that's what all of his spaces have …”
Coogan: Startups that cut burn immediately after YC warning survived
“The companies that cut their burn, like the same day that YC issued that letter saying, hey, this is going to be rough. They made it through just fine.”
Hays: Commercial real estate struggled from overreliance on variable-rate debt
“That's been the challenge for the last couple of years of commercial real estate market is most people were using this variable rate debt. Thinking that interest rates will stay low forever, and then all of your profit goes away in months.”
Coogan: The Grove drew 20M pre-pandemic visitors, topping Disneyland
“The Grove became one of the region's top attractions with about twenty million visitors in the immediate pre-pandemic years, edging out Disneyland.”
Hays: Insurance companies regularly hire private firefighting brigades
“Insurance companies leverage private firefighting brigades all the time.”
Coogan: Locking social media accounts halts viral cancellations by killing quote tweets
“I just lock the account, and then it shuts down all the quote tweets, and then everyone just moves on, because like, they're not getting that, like, they don't have anything to go off of.”
Coogan: Tech awards should judge qualitative and artistic merit, not revenue
“Award shows should be more, if you're doing an award show for tech, you should lean towards something that's a little bit more qualitative, a little bit more artistic, but you won't be doing an award show for tech because we already got that locked down, so do…”
Hays: Angel investing is primarily about low entry prices and clout
“Usually you want to be investing pre-incorporation. You want to be given that handshake before the company's even been formed. So you're going to get the best price and the most clout, which is what angel investing is all about. Low entry prices and clout.”
Coogan: Online Virality Will Not Influence Criminal Trial Jurors
“I think the jurors are going to get in there. They're not going to care. They're not going to be extremely online. The lawyers will filter for that and voir dire.”
Coogan: A senior Trump official praised his 54-star flag mockup
“Someone pretty high up in the Trump administration texted me and was like, this looks great.”
Hays: Ad-supported media outperforms subscriptions by maximizing audience reach
“So the reason that ads are the best business model for media is cause you get the widest possible reach, right?”
Hays: Joe Rogan's influence dropped dramatically during Spotify exclusivity
“You remember Joe Rogan's influence fell off a cliff for a few years when he was off YouTube and you basically didn't hear about him.”
John Coogan: Evan Spiegel and Snap Own a Private Boeing 737
“It turns out that N three E an airliner seven 37 configured as a private jet is owned by Snapchat and Evan Spiegel. The operator is listed as S E logistics. Short for Spiegel Evan. Snapchat owns the largest private hangar at Van Nuys airport.”
Hays: Snapchat will never make money and acts as employee enrichment scheme
“Spiegel's actually somebody I would like to see step away from Snapchat. It's never going to make any money. There's a sort of an enrichment scheme for employees.”
Hays: Legacy luxury hotel interiors and food have degraded despite service
“The thing you can count on legacy hotel brands for is service. Like if you're having an issue on the property, they will Typically go above and beyond to try to resolve it. The challenge is the actual interiors are for the most part falling apart. So they're n…”
Hays: Ritz-Carlton, Four Seasons, and St. Regis offer a mediocre guest experience
“You have the Ritz Carlton, you have the Four Seasons, you have what St. Regis, you have all these hotels, which are beautiful properties, very expensive properties, but actually mid experience.”
Hays: Design hotels like 1 Hotel lack legacy hospitality service culture
“You have like one hotel, the proper hotel, these hotels where the interiors, like they paid for cool contemporary interior designers, but then they're just not actually, they don't have like the service culture typically that you get at these legacy hotels.”
Coogan: Middleman booking sites re-book rooms through Expedia at wholesale rates
“Literally all they're doing is they just have someone there who books Through Expedia at an even lower rate on your behalf. And so when you show up to the Four Seasons, they're like, yeah, we have you, but we don't have your information for some reason.”
Coogan: Booking middleman sites arbitrage Google search ads against hidden fees
“And they're just arbitraging the Google ad cost of winning that auction and the fees that they can add. So they think, okay, it cost us 20 dollars to acquire this customer. We'll add a hundred dollars of fees at the last second.”
Coogan: 'Invest Early' Social Formats Succeed Because People Want Early Access
“Also just that, that meme template of, like, buy now, invest now, we're still small, like, people want to get in on things early, and so I think that works generally.”
Hays: Rebooting Juicero IP could get 10,000 pre-orders
“You could easily get, I think, 10,000 pre-orders for that thing if you just rebooted the Juicero IP.”
Coogan: Polymarket gives Palisades fire containment a 1% chance by Friday
“The poly market on will the Palisades fire be contained by Friday. It's down at like one percent.”
Coogan: Wildfire prediction markets provide valuable public information
“I think it's actually still valuable to know, okay, I shouldn't expect the fire to be put out”
Coogan: Paul Graham's office layout is a feng shui disaster
“The problem, of course, is that he's not in the power position. This is a feng shui disaster.”
Coogan: Bridger Aerospace owns six Super Scoopers and jumped 11.6% today
“Bridger Aerospace owns six super scoopers, including the one you saw on your timeline today. These are the planes that put out the fires. It's a public company. The ticker is BAER, Bridger Aerospace Group Holdings, and just today, they're up 10%. 11.6 to be ex…”
Hays: Anduril raised its seed round at around $97M post-money
“The Andrew Seed Round was done at like, 97 post or something like that.”
Coogan: Varda's second mission launches from Vandenberg and lands in Australia
“And this time they're launching from Vandenberg, but they're landing down under in Australia.”