Dec 2, 2024 · 3h 10m · tbpn
How BILLIONAIRES dress for XMAS (ep17)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of Technology Brothers, hosts John Coogan and Jordy Hays satirize Silicon Valley holiday culture, explore high-end luxury fashion and supercars, and conduct deep dives into venture capital, private equity, and modern media dynamics. Through timeline reactions and comedic hyper-capitalist commentary, they evaluate investment playbooks, macro trends, and frameworks for total commercial value capture.
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 59.2% of the talking time here. How this is scored →
The hosts as informed peer 5.8 Guest teaching 1.3 Guest disagreement 1.5 The hosts pushing back 1.4
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 3:05:30 Hays pushing back on Mount Rushmore angel investor exclusions
Hays interrupts Coogan's historical angel roster to aggressively argue for Sam Altman's early two-percent Stripe investment at a ten-thousand dollar valuation.
Hardest push from the hosts ▶ 3:04:55 Coogan rejecting Calacanis's Mount Rushmore claimCoogan directly rejects Hays's concession that Calacanis belongs on the top-four angel investor Mount Rushmore, citing vastly superior power-law multiples from early tech pioneers.
Biggest teaching moment ▶ 2:57:05 Coogan explaining The Economist's editorial structureCoogan explains to Hays how The Economist enforces institutional voice and eliminates individual bylines through pseudonymous recurring columns.
The host holds their own ▶ 3:05:45 Coogan outlining foundational venture capital historyCoogan demonstrates deep historical expertise in early Silicon Valley capital formation by citing Don Valentine at Cisco and Arthur Rock at Intel.
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 |
|---|---|---|---|---|---|---|
| Apology to Gulfstream and the Autopilot Mea Culpa | 6 | 2 | 2 | 2 | Coogan and Hays playfully critique The Information's holiday fashion guide. Coogan demonstrates detailed knowledge of luxury brands, pricing, and social posturing in Silicon Valley culture. | |
| Colossus Review Launch and the Value of Print | 7 | 1 | 1 | 1 | Coogan walks through the launch of Colossus Review and quotes figures like Jim Simons and John Collison before detailing Garnet Station Partners' small business roll-up playbook. | |
| Is Space Investable? Positive Sum Research Breakdown | 6 | 2 | 2 | 1 | Coogan analyzes Positive Sum Research's report on space startup economics, citing seed dilution numbers and satellite launch risks while Hays adds color on Gundo fundraising. | |
| Graham Duncan Profile: The Talent Whisperer | 7 | 2 | 1 | 1 | Coogan details Graham Duncan's allocator-picking playbook at East Rock Capital, referencing Duncan's reference-checking methods and Enneagram profiling. | |
| Red Bull Founder Wisdom, Life's Work Leaders, and Long-Form Media | 6 | 1 | 1 | 1 | Coogan outlines the career of the Red Bull founder from David Senra's podcast and Patrick O'Shaughnessy's list of life's work leaders. | |
| Listener DMs: Malibu Compound Pitches and Host Dynamics | 5 | 2 | 2 | 2 | The hosts field listener questions regarding pitching at a Malibu compound and establish satirically that their show dynamic is strictly transactional business partnership. | |
| Whistleblower Tactics and Lamborghini Temerario Ad | 5 | 2 | 2 | 1 | Coogan and Hays riff on corporate whistleblowers and industrial espionage before transitioning into a promotional segment for the Lamborghini Temerario. | |
| Timeline: Startup Diets, AMG One Hypercar, and Burning Man Bureaucracy | 6 | 1 | 2 | 2 | Coogan covers capital inflows, startup nutrition memes, Faraz Khan's Mercedes-AMG One delivery, and government management of Burning Man. | |
| Timeline: Canadian Annexation, Taylor Lorenz, and xAI Engineering Ad | 5 | 1 | 2 | 2 | Coogan and Hays joke about Canadian annexation, discuss Taylor Lorenz writing for The Information, and highlight an xAI engineering recruiting post. | |
| Timeline: Friend.com Shrek Hack, Dodge Viper ACR, and GM's F1 Entry | 6 | 1 | 1 | 1 | Coogan breaks down the UX and prompt injection vulnerabilities of friend.com, followed by automotive discussions on the Dodge Viper ACR and GM entering Formula One. | |
| Timeline: Conversion Hacks, Silicon Valley Replicability, and Carry Ad | 6 | 1 | 2 | 2 | Coogan discusses e-commerce checkout conversion friction and pushes back on the claim that Silicon Valley can be effortlessly replicated elsewhere. | |
| Timeline: Biotech Shorting, Real-Time News on X, and Palantir Culture | 5 | 1 | 1 | 1 | Coogan examines Martin Shkreli's short thesis on Cassava Sciences, real-time news velocity on X versus legacy outlets, and Palantir's retail investor culture. | |
| Timeline: Holiday Hustle, Logistics Ransomware, and Mullet Capitalism | 6 | 1 | 1 | 1 | Coogan discusses holiday work productivity, supply chain ransomware negotiations, and Packy McCormick's framing of 'mullet capitalism.' | |
| Timeline: Strip Mall Private Equity, X Verification, and Wrapper Startups | 5 | 1 | 1 | 1 | Coogan and Hays discuss strip mall private equity strategies, X verification incentives, and Every's incubation of AI wrapper products. | |
| Timeline: Bridgit Mendler's Aero Startup and the Huracan Sterrato | 5 | 1 | 1 | 1 | Coogan discusses Bridgit Mendler's Northwood Space satellite communications startup and the cultural impact of techno-optimism. | |
| Timeline: Male Fitness Psychology, Cold War Honeypots, and Debanking | 6 | 1 | 2 | 2 | Coogan playfully counters Chris Power's take on counterintelligence honeypots, then analyzes Marc Andreessen's Rogan interview regarding Operation Choke Point 2.0 debanking. | |
| Private Equity vs. Venture Capital in Government Efficiency | 7 | 1 | 1 | 1 | Coogan explains why private equity operating playbooks are far better suited to government cost-cutting at DOGE than venture capital growth models. | |
| Tech News as Sports Culture and Barbell Investment Strategies | 6 | 1 | 1 | 1 | Coogan and Hays examine tech media treated like sports entertainment and the dynamics of barbell portfolio allocation. | |
| Rewarding Kids with Financial Derivatives Over Candy | 5 | 1 | 1 | 1 | Coogan and Hays riff on financial literacy for kids, NFT price floors, and Chris Black's minimalist holiday gift advice. | |
| Promoted Post: David Perel's Writing Craft Resource | 4 | 1 | 1 | 1 | The hosts give a sponsored shoutout to David Perel's writing platform, Steve Cohen's 24-hour stock exchange, and Palmer Luckey refuting TechCrunch. | |
| Joshua Steinman's Marketing Playbook and 'In the Trenches' Gambling | 6 | 2 | 2 | 2 | Coogan and Hays discuss Joshua Steinman's messaging strategy, Slack profile aesthetics, and the long-term holding power of Flock Safety equity. | |
| Promoted Post: American Alchemy's Search for Documentary Editors | 5 | 1 | 1 | 1 | Coogan highlights American Alchemy's editor search, Anduril's brand aesthetics, and ChatGPT's two-year anniversary. | |
| DOGE Prestige and Peter Thiel's 'The Diversity Myth' Retrospective | 7 | 1 | 2 | 2 | Coogan provides context on Peter Thiel and David Sacks's 1995 book 'The Diversity Myth' and analyzes The Economist's anonymous byline model. | |
| German Notary Series A Inefficiencies vs. US Capital Velocity | 8 | 2 | 3 | 3 | Coogan challenges the notion of Jason Calacanis on the angel investing Mount Rushmore by systematically naming superior historical investors including Don Valentine, Peter Thiel, Arthur Rock, and Eugene Kleiner. |
Statements from this episode (68)
Coogan: Jim Simons made more money from math and data than anyone in history
“Jim Simons, who made more money using math and data than anyone in history, said, be guided by beauty.”
Hays: The New York Times takes a very negative view on business and tech
“The issue is the New York Times has gone down this very dark path of taking a very negative view on the world, business, technology.”
Coogan: Garnet Station Partners has compounded at 33% since 2014
“Since their founding in 2014, Garnet Station Partners has compounded at 33%.”
Hays: Efficient operations double small-business growth, not CRMs
“A lot of people on X right now are like, oh, I'm going to buy this boring business and add like a great CRM, and they think they're going to add like double revenue off of that, and it's like, no, you actually double growth or revenue, whatever metric your Nor…”
Coogan: The cost of reaching LEO has decreased 200x since 1960
“How the cost of reaching LEO has decreased.
Yeah.
200 X since 1960.”
Coogan: Under 25% of space startups reach orbit
“Fewer than one in four space companies have made it to orbit.
More than half of these needed more than five years to do so.
The capital to reach first launch means seed investors can expect equity dilution of up to 90%.”
Coogan: Relativity Space seed investors endured 88% cumulative dilution
“The cumulative dilution from their seed to series F has been 88%, but their seed round was 1.1 million on a 3.6 million dollar valuation.”
Hays: Founders should focus on share price over percentage ownership
“Dilution does not mean you're having to give back your shares.
You know, it's not like you're getting less shares over time.
And so as long as the per, yeah, as long as the per share price is going up, like you need to be less fixated on how much of the pie yo…”
Hays: Prolonged reference calls force people off rehearsed scripts
“A lot of, one of Graham's strategies that's interesting when he's doing reference calls is just to keep The reference on the phone longer, because the longer you spend, the harder it is to stay on script.”
Coogan: Graham Duncan was an early seed investor in Paradigm
“And a lot of listeners might know Paradigm, the crypto firm founded by Fred Ersam and Matt Wang who left Sequoia to join that, and Graham Duncan was one of the first seed investors in in Paradigm.”
Coogan: Graham Duncan manages $2 billion across just five families
“Today he manages two billion dollars for five families.”
Coogan: Red Bull was profitable by year three and paid no dividends for 13 years
“The company reached profitability in its third year and has been profitable every year since. He took no dividends for the first 13 years, reinvested everything, never IPO'd.”
Hays: Consumer brand founders can stay private, but their brand cannot
“If you're running a consumer brand and you want to be private, great. Your consumer brand should be getting the most amount of attention that you basically possibly can get.”
Coogan: Uncut full-day livestreams of major figures will outgrow Bloomberg
“Whoever figures out how to do that, the livestream, full day, interview with someone big, they're gonna be bigger than Bloomberg, for sure.”
Hays: Podcast infighting occurs when co-hosts are friends, not business partners
“There are some popular podcasts out there that have quite a lot of infighting. And the reason is almost always because they're friends and not business partners.”
Hays: S&P 500 up ~30% since Michael Burry tweeted 'Sell'
“I think the S&P is up like 30% since Michael Burry tweeted at the beginning of the year. Sell.”
Coogan: Meta exec apologies to Palmer Luckey reflect genuine regret, not expediency
“I think it's, it is impressive, mostly because they didn't need to do this. Like, Palmer is not in charge of Meta. Meta is bigger than Anderl, and sure, they might want to align a little bit more with the new administration, but I do think that there's a genui…”
Hays: Never delete an underperforming post, just publish the next thing
“If a post is not hitting, do not delete it. Just post the next thing.”
Coogan: Flopped content has no downside because nobody saw it
“If your major post or your big moment like flops, by definition, no one saw it. So you can just take another swing.”
Hays: Friend.com's $1.8M Domain Was Paid in Multi-Year Installments
“Avi, to, I think it's common knowledge now, he didn't pay for it all up front. It was like a multi-year contract.”
Coogan: Push-Based Interactions Are Essential UI Patterns for AI Products
“Push, not pull. I've said this is always, always a really important UI pattern because it's so hard to think about.”
Hays: The US Will Take More Formula 1 Races From Overseas
“Soon we'll, we'll have, we'll take more and more of the races from overseas.”
Hays: Garry Tan is why investors should be long SF real estate
“Gary's the reason that you should be extremely long SF real estate right now.”
Coogan: Martin Shkreli successfully predicted Cassava Sciences' 83% stock collapse
“Sava collapsed at -83% today. The GOAT, Martin Screlly called it. Screlly says, if you have dollars on Robinhood or Interactive Brokers, short Sava now. And he called it.”
Hays: X provides a more accurate read on breaking news than legacy media
“Here's why X ends up being a better way to process real-time news events, is when a journalist is writing about something, they can only talk and do so many things at once, right? Like, news is breaking, they're trying to get, yep, The, you know, the story and…”
Coogan: Global logistics relies heavily on outdated Windows XP software
“Of course the global logistics industry runs with a lot of outdated software. There's a lot of windows XP, a lot of, you know, a lot of older computers, not a lot of like, you know, up-to-date latest hardware across everything on chips and all sorts of differe…”
Hays: Private market investing is effectively legalized insider trading
“The thing with the private markets is it's basically just like nonstop, like insider trading, but it's legalized. So if you know more about a specific company, you are allowed to invest as much as you want into that business. And you have a real edge there.”
Hays: Starbucks lease agreements block competing coffee shops
“When Starbucks does a lease deal, they block other coffee shops from coming into that, that Whatever property”
Coogan: Bridgit Mendler's Northwood Space Is Funded by Founders Fund
“Building a Northwood space communications hard tech company funded by Delian at Founders Fund”
Coogan: Bridgit Mendler Is an Underrated Voice for Techno-Optimism
“She's just, like, doing probably more positive techno-optimism, like, proselytization... She is, she's a very, very important voice, very underrated, whereas, like, a lot of the a lot of the techno-optimist people, like, we exist in this, like, echo chamber.”
Coogan: Founders must build deep personal ties with critical partners to avoid abrupt debanking
“If you have a critical partner like your bank or like your fulfillment center or some supplier, like you should be going out to dinner with them. You should be attending their, you know, kids wedding and going and really getting to know them because At the ver…”
Hays: Debanking wave drove Andreessen Horowitz and top VCs to Washington
“When this was all happening was when Andreessen and other firms realized they needed to spend way more time in Washington because they were They were like, there's actually bigger games being played here that are not just in our world.”
Hays: SMB buyers face adverse selection against private equity competitors
“This whole X movement around you should buy a small business because there are thousands of private equity bros that are highly trained, highly efficient, ruthless, that are all hunting for these same deals. And one, given their experience, they can probably p…”
Coogan: DOGE requires private equity restructuring skills, not venture capital
“The goal of Doge is retooling the balance sheet, right-sizing the income statement, getting, like, the, getting out of the red and just shrinking bloat, and that's what private equity does best, not venture capital.”
Hays: Deferring Deals to New Year Signals Lack of Urgency or Apathy
“It's either there's no urgency or you haven't shown them that there's real urgency or urgency necessary, or they don't care.”
Hays: Cold plunge company Plunge reached nine-figure run rate in two years
“And this company plunge bootstrap to literally nine figure run rate in like two years. Just selling cold plunges.”
Coogan: Jane Street captures all generated value without leaking alpha
“The exact opposite of this is like Jane street. There's not a single dollar of value creation that is not captured by that firm. Right. Because there's no alpha that's leaked whatsoever”
Coogan: Hustlers University demotes non-paying members to wins-only channel
“If you don't pay your bill, they don't kick you out entirely. They just demote you to a status where you can only see the wins channel. So you're only seeing other dudes being like, made my first million, made my first 100,000.”
Hays: The best way to monetize business advice is education
“But at the end of the day, if you sell business advice, the best way to monetize it is through education.”
Hays: The best investors are generalists who bet big on talent and opportunity
“My favorite investors are generalists. They look For opportunity and talent. Yep. And they bet big when they find those two things in the same place.”
Hays: Ozempic is derived from Gila monster venom
“Well, as we all know, Ozempic, Ozempic is, is the Gila monster. Gila monster venom.”
Hays: The winners on LinkedIn will all eventually move to X
“The winners on LinkedIn will all eventually end up on X,”
Coogan: Narrative and controversy drive value in art and NFTs
“Story is what drives value in art, and so the fact that Bored Ape has this controversial, there's all these conspiracy theories about it, it's very fascinating.”
Hays: Bored Ape profile pictures will soon become contrarian and cool
“Now, right now, it's cringe, but it will soon be contrarian and cool to Rockin' Ape.”
Hays: The New York Times sent 'How Long Gone' a cease-and-desist over cover art
“Chris Black has a podcast called how, how long gone. And when they released the podcast, they used art like cover art that looked Very similar to a New York Times podcast and the New York Times sent them a cease and desist and they turned it into a they turned…”
Coogan: Packy McCormick is one of the greatest tech writers in history
“Paki McCormick, he's been on the show before. One of the greatest writers in tech history.”
Hays: Physical print editions for Substack writers is a viable business
“I honestly, hilariously think that there's a business to be built of going to all the sub stack writers and saying, I will make a high quality printed version of your sub stack.”
Coogan: Flying cars already exist in the form of helicopters
“My hot take on flying cars has always been that we have them. They're called helicopters and you can just go buy one as long as you're wealthy enough.”
Coogan: SEC approves first 24/7 stock exchange backed by Point72
“The first around-the-clock U.S. Stock Exchange wins SEC approval, and who backed it? None other than Steve Cohen's .72 Ventures.”
Hays: Social media posters have replaced traditional media as domain experts
“The posters are the experts now.”
Hays: Marketers should repeat their core messages fifty times more
“And it's a lesson of any, you know, even you can apply to any single, whatever marketing messages you have, say it 50 times more than you already are. And it'll be a lot more effective.”
Coogan: Sequoia Partner Who Backed Nvidia Still Holds Distributed Shares
“You know that the partner at Sequoia who did the NVIDIA deal still owns the stock? Cause after they went public, it was distributed, just held.”
Coogan: Flock Safety Is Insulated From Big Tech Disruption
“Life's work entrepreneur and a fantastic company that's building something that can just go forever because there's no one that's gonna, resistant to disruption, And no large incumbent. You're not going to be like Slack getting clipped by teams.”
Coogan: 'China's final warning' is a Russian proverb for toothless warnings
“China's final warning is a Russian proverb, meaning a warning that carries no real consequences.”
Coogan: Anduril's Brand Design Signals Elite Overall Company Execution
“Even their brand design, even their merch is unique and powerful, and has great aesthetics, and it's just a sign that everything in that company is running really, really smoothly, really, really well.”
Coogan: OpenAI First-Mover Advantage Beat Fast Competitor Parity
“Gemini came out and was comparable, and Claude came out and was comparable very, very quickly, but being first was so powerful.”
Hays: OpenAI Built Consumer Scale After Wrappers Reached Tens of Millions ARR
“Before chat GPT, there were products like copy.ai that were leveraging the API well, and like had gotten to decent, not scale, but tens of millions of ARR, and then OpenAI was like, oh, actually we're a consumer product company now, and then now they have hund…”
Coogan: OpenAI's UI Design Is Underrated Compared to Its Models
“The simple UI and the UI stuff at OpenAI is really underrated. I think everyone focuses on the research and the innovation and the actual models, but the UI and the user experience is just fantastic.”
Coogan: Haptic Feedback While Typing Will Become Standard in AI Products
“Like the little thing where when it's typing, you feel the haptic feedback. That's a really nice touch. Very innovative. I've never seen anyone do that before. Now it's going to be a standard across all the AI product.”
Hays: A major capital allocator is joining DOGE
“The man will go unnamed, but there is a major major capital allocator.”
Hays: An anonymous collective of Substack writers could crush right now
“I think a sub, a really, really well executed sub stack that was entirely anonymous, a collective of anonymous writers could crush right now.”
Coogan: Dev/Agents raised $56M seed round at a $500M valuation
“TechCrunch announcing an AI agent startup slash dev slash agents raised a massive fifty six million dollar seed round at five hundred million dollar valuation.”
Hays: Calacanis deserves a spot on angel investing's Mount Rushmore
“If there was a Mount Rushmore of angel investors, he certainly would be on it with the Uber.”
Coogan: Calacanis misses Mount Rushmore of Kleiner, Thiel, Valentine, and Rock
“My Mount Rushmore is, is are those four guys and sorry, Jason you don't make the cut.”