Nov 6, 2024 · 3h 18m · tbpn
Trump's Secret Career (ep7)
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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 analyze Donald Trump's multi-billion-dollar tech venture with Truth Social before exploring defense technology, artificial intelligence trends, founder psychology, and modern tech 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 64.2% of the talking time here. How this is scored →
The hosts as informed peer 6.5 Guest teaching 1.4 Guest disagreement 1.0 The hosts pushing back 1.0
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 2:53:24 Hays dismisses rage as Trump's core ambition driver
Hays rejects the viral premise that ambition is merely channeled rage, arguing that Trump is fundamentally motivated by winning and attention rather than deep-seated internal anger.
Hardest push from the hosts ▶ 2:54:03 Coogan challenges the single-motivation framing of foundersCoogan pushes back on simplistic psychological generalities, noting that figures like Zuckerberg and Jobs display serene focus rather than overt rage.
Biggest teaching moment ▶ 1:14:00 Hays explains Slow Ventures' verticalization thesisHays educates Coogan on Slow Ventures' vertical integration investment thesis, illustrating how tech companies acquire physical operators to capture entire margin chains.
The host holds their own ▶ 3:16:30 Coogan breaks down private jet operational tradeoffsCoogan demonstrates deep domain expertise regarding corporate aviation, comparing runway constraints and delegation logistics between the Gulfstream G650ER and Boeing Business Jet.
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 |
|---|---|---|---|---|---|---|
| The Origins of Truth Social and Pitching SPACs | 7 | 1 | 1 | 1 | Coogan leads the comprehensive deep dive into Truth Social's founding timeline, breaking down the Apprentice contestants' pitch at Mar-a-Lago, the 90-10 equity split, and the mechanics of SPAC blank-check vehicles. | |
| Developing Truth Social and Debate Over Monetization Models | 8 | 2 | 1 | 1 | Coogan analyzes monetization strategies for social networks, contrasting Ben Thompson's extreme aggregator models with Dalton Caldwell's app.net experiment and explaining how programmatic ad targeting achieves superior price discrimination. | |
| Assembling the Team and Resolving Trump Org Conflicts | 7 | 1 | 1 | 1 | Coogan recounts interviewing Truth Social engineer Ryan Lackey and details the internal chaos between libertarian coders and Trump Organization executives demanding cap table concessions. | |
| SPAC Announcement, Devin Nunes, and App Store Launch | 7 | 1 | 1 | 1 | Coogan walks through the regulatory scrutiny from Gary Gensler, the hiring of Devin Nunes, the launch-week App Store trajectory, and Nunes' restructuring of the engineering team. | |
| Settlement Payouts, NASDAQ Listing, and Long-Term Outlook | 7 | 1 | 1 | 1 | Coogan outlines the NASDAQ listing under DJT, the eighteen million dollar SEC fine, and the hundred million dollar legal settlement pocketed by original co-founders Moss and Litinsky. | |
| Sponsor Message: Citadel Securities Market Making Services | 5 | 2 | 1 | 1 | Following the Citadel ad read, the hosts analyze Bowery Farming's bankruptcy, discussing high capital expenditures, low lettuce margins, and the flaws of DTC vertical farming models. | |
| Tweet Reactions: Defending Capitalism, Walking, and Time Shifts | 5 | 1 | 1 | 1 | The hosts react to Martin Shkreli's viral defense of capitalism, debate fully automated luxury communism, and discuss the metabolic benefits of incline walking over running. | |
| Tweet Reactions: Quantified Health, Marriage Trends, and Enterprise Teams | 6 | 2 | 1 | 1 | Coogan and Hays discuss quantified self AI analysis, shifting cultural attitudes toward marriage and fatherhood among tech founders, and the enterprise dominance of Microsoft Teams over Slack. | |
| Tweet Reactions: Public Health Satire, AI Manifestation, and Musk | 6 | 1 | 1 | 1 | Coogan explains how consumer AI tools leverage the PT Barnum effect in subjective use cases like manifestation and tarot reading, while evaluating Elon Musk's engineering and showmanship balance. | |
| Tweet Reactions: AI Wrapper Startups and Visionary Founders | 7 | 1 | 1 | 1 | Coogan encourages young developers to build and monetize fast AI wrappers rather than overthinking venture status symbols, and analyzes Steve Jobs' founder-mode execution. | |
| Tweet Reactions: Peanut the Squirrel and Defense Procurement Inefficiencies | 8 | 2 | 1 | 1 | Coogan explains Gell-Mann amnesia via Peanut the Squirrel, then breaks down TransDigm's private equity playbook of buying niche aerospace IP to mark up prices to defense buyers. | |
| Palantir's Surging Market Cap and Earnings Report | 7 | 2 | 1 | 1 | Coogan reviews Palantir's earnings report and capital efficiency, recalling a defense tech conference with CFO Shyam Sankar, and explains why outbound AI sales spam will trigger aggressive AI filtering. | |
| EBITDA Cycles and Wartime Versus Peacetime CEOs | 7 | 2 | 1 | 1 | Coogan explores offensive versus defensive wartime CEOs and argues that Tesla's biggest near-term growth opportunity lies in expanding upward into bespoke high-end luxury vehicle tiers. | |
| Midjourney's David Holz on AI Safety and StarCraft | 6 | 1 | 1 | 1 | Coogan discusses David Holz's StarCraft AI safety anecdote, OpenAI's historical gaming bots with rate-limited APIs, and the lucrative business model of faith-based media platforms like Angel Studios. | |
| The Modern Renaissance of High-End Power Tools | 5 | 1 | 1 | 1 | The hosts joke about the newfound tech-bro appreciation for high-end power tools and playfully defend institutional finance giants BlackRock and Citibank against anti-capitalist critique. | |
| SpaceX Launch Economics and the Musk-Bezos Rivalry | 7 | 1 | 1 | 1 | Coogan compares Elon Musk's all-in operational intensity across SpaceX and X against Jeff Bezos' portfolio management style, followed by admiring Saarinen's 1965 GM Tech Center architecture. | |
| The Pro-Natalist Tech Movement and Lifestyle Design | 5 | 1 | 1 | 1 | The hosts discuss the lifestyle design required to raise large families in tech and debate whether spectating marathons is inferior to participatory events like the running of the bulls. | |
| Palantir Company Culture and Strict Brand Standards | 6 | 2 | 1 | 1 | Coogan and Hays review viral rules for wearing Palantir swag, then analyze how prediction markets like Polymarket create synthetic derivatives to short or hedge private startup equity. | |
| Establishing a New American Elite and Generational Monuments | 7 | 1 | 1 | 1 | Coogan discusses how industrial elites historically built public monuments like Hearst Castle and the Huntington, comparing them to contemporary long-horizon projects by Bezos and Sam Altman. | |
| Non-Toxic Consumer Goods and Materials Science Challenges | 6 | 2 | 1 | 1 | The hosts explore the chemical substitutions in non-stick cookware and reflect on the demographic realities of moving into affluent suburban neighborhoods as young founders. | |
| Channeling Rage Versus Natural Competitive Ambition | 6 | 2 | 2 | 2 | Coogan and Hays debate whether extreme ambition stems from channeled rage or sheer competitive drive, and celebrate San Francisco cafe serendipity for founders debugging live software. | |
| Historical Voting Traditions and the Digital Democracy Gap | 6 | 1 | 1 | 1 | Coogan and Hays reflect on why election voting remains tied to historical horseback-travel schedules and analyze the stability and internal diversification of YC founder-to-founder SaaS sales. | |
| Trillion-Dollar West Coast Companies and Saudi Aramco Origins | 6 | 1 | 1 | 1 | Coogan and Hays discuss the San Francisco origin of Saudi Aramco, celebrate small-scale domestic manufacturing innovations, and comment on the New York Times Tech Guild strike timing. | |
| Linus Torvalds, AI Marketing Skepticism, and Perceived Value | 8 | 1 | 1 | 1 | Coogan refutes Linus Torvalds' skepticism by comparing AI marketing to Nike's brand value, discusses GPU credit circularity, and delivers an in-depth breakdown comparing Gulfstream G650ER and Boeing Business Jets. |
Statements from this episode (63)
Truth Social Reached a $10B Valuation Faster Than Recent Tech Startups
“If you actually look at the numbers, I couldn't name another company that got to a ten billion dollar valuation in tech in less than two years in this recent cycle.”
Pitching Vision to Cornered-Asset Billionaires Is an Extremely Valuable Strategy
“If you have the opportunity to go to like a billionaire's mansion who has like an insane amount of some sort of cornered asset in Trump's case, it's like social capital. But even if it's like somebody who's like, oh yeah, they're sitting on like a massive fore…”
Donald Trump Received 90% Equity in Initial Truth Social Deal
“In this case, Trump got 90% of the new company.”
SPACs Were a Last Resort Suffering From Severe Adverse Selection
“It basically was a last resort for most companies where if you couldn't really go public and you couldn't access private capital, that was the best. Route. And then also like, which had a huge adverse selection problem.”
Truth Social Built Its Initial Platform by Forking the Mastodon Codebase
“And then they bring on this, like, remote software engineer from Macedonia, and they're basically forking Mastodon.”
Donald Trump Could Have Quickly Built a $100M ARR Substack
“Yeah, and Trump could have thrown up a sub stack and gotten to nine figures of ARR very, very quickly. But he wouldn't, it would have taken much longer to become a billionaire that way.”
Higher-Quality Media Products Can Support Significantly More Advertising
“The higher quality of the content, the more ads you can jam in it, and if you have a media product and you can't put a lot of ads in it usually is just not that great of a product.”
Advertising Outperforms Subscriptions for Platforms via Price Discrimination
“Ads are just much better at price discrimination. And so if you have a billionaire in your audience and you also have a college kid in your audience and you're charging 10 dollars a month, they both pay 10 dollars a month. But if you're doing an ad based model…”
Decentralized CGI Rendering Is One of Crypto's Most Successful Use Cases
“There's this there's this rendering network for CGI where every, every CGI artist has a really beefy computer, but they're not always rendering out their projects. So they can share render time between the computers. So the computer's basically always renderin…”
Truth Social Lost Nearly $400M on $1M Revenue at $10B Valuation
“In the last 12 months they did a little over a million dollars in revenue. They EBITDA was negative one hundred million, net income was negative four hundred million, roughly, three 80, and it's almost a ten billion dollar company.”
DWAC Valuation Surged to $17B Within 24 Hours of Trump Announcement
“The press release claimed that Trump's new media offering would be worth 1.7 billion dollars, but within 24 hours the stock market valued the SPAC at 10 times that amount, seventeen billion.”
Truth Social Had 866K First-Week Installs Versus 100K for Instagram
“More than eight, 866,000 people installed it in the first week. Instagram, by comparison, only signed up about a 100,000 users in its launch week.”
DJT Stock Reached $78 on Day One, Valuing Company at $15B
“That first day, the share price touched 78 dollars, making the company worth about fifteen billion, more than doubling the former president's personal wealth.”
Truth Social Co-Founders Pocketed $100M After Settling Litigation
“Moss and Latinsky won their litigation with the company, And cashed in all, nearly all their shares together pocketing around a hundred million dollars.”
Donald Trump Owns 60% of Trump Media and Refuses to Sell
“Trump has insisted he won't sell his shares, which now amount to about 60% of the company which is very uncommon for a tech founder who starts a tech company, IPOs it in two years.”
Bowery Farming Should Have Targeted Exotic Fruits Instead of Commodity Lettuce
“I think that that is, What they absolutely should have done. I think there's a bunch of interesting angles to do like exotic fruits that are almost like desserts.”
Bowery Farming Is Among the Last High-Profile DTC-Era Failures
“I think what's interesting that where I'd end with Bowery is that this was one of the last, maybe is one of the last super high profile failures from the DTC era”
AI Specialists Will Give Average Users Better Longevity Care Than Elite Clinics
“It's going to be really incredible when the average person with their 10 dollar a month or a ring can get
Even better care from this team of digital specialists than some, you know, public company CEO that's using David Sinclair's like, you know, longevity pro…”
Enterprise SaaS Needs Teams Integrations to Justify a Unicorn Valuation
“It's the building for the teams market that's going to justify your uniform unicorn valuation, not purely the slack.”
Slack Active Users Would Still Be Growing Under Stewart Butterfield
“If Stuart was running slack, you have to imagine he would, that chart would still be going.”
AI for Manifestation Could Become a $100M Business
“And this, and if that trend is real, there's a really big business, there's a hundred million dollar business to be built on just being like AI for manifestation.”
ChatGPT-Based Therapy Products Already Generate $50M in ARR
“There's probably already fifty million dollars of ARR worth of these sort of, like, chat GPT therapy products that are just out there printing.”
Kimia Will Spark a Shopify-Like Movement in Government Contracting
“I think predicting out the next couple years, Kimia's gonna start a similar to what Shopify did. A new movement around government contracting.”
Charlie Munger Called Defense Contractor TransDigm Unethical and Refused to Invest
“Charlie Munger was asked about this on an Invest Like the Best episode. Like, what do you think of Transdime? Like, would you ever invest in this company? And he was like, no, I think it's unethical.”
Palantir Ranks Fourth in Defense Market Cap With Just 3,000 Employees
“It was like every company in defense, all the primes, their market cap, and then their employees, and Palantir is like fourth by market cap, and they have 3000 employees, and every other company has like over a 100,000 employees.”
Palantir Is Potentially a Trillion-Dollar Company
“Yeah, I think there's, that's a potentially a trillion dollar company.”
AI Sales Automation Will Make Interpersonal Relationship Selling More Valuable
“It feels like a lot of sales is all going to go back to relationships. And so the truly gifted salesperson that's just good at making people like them and wanting to do business with them is actually going to excel, even in a world where as a small company, yo…”
Meta Direct-Response Ads Remain Highly Effective Despite Rising CPMs
“Direct response Marketing seems to be working better than ever. Like meta is getting so optimized that. I buy products on a weekly basis from companies I've never heard of because they serve me an ad for a highly relevant product. And that still seems to work.…”
AI Inbox Filtering Will Scale as Fast as AI Sales Spam
“There's going to be an arms race and just as fast as the AI spam increases, like, so will the AI filtering.”
The Best Future Marketers Will Write Code Rather Than Manage Ads
“The really talented marketers of today going forward are going to be looking more like engineers where historically the really sophisticated marketing organizations like ramp as an example, they have like a lot of engineering involvement in the marketing activ…”
High EBITDA Multiples Create Sloppy CEOs and Eventual Turnaround Opportunities
“Good CEOs create high EBITDA multiples. High EBITDA multiples create sloppy CEOs. Bad CEOs create low EBITDA multiples, and low EBITDA multiples create opportunities for good CEOs.”
Sam Altman Lapped Sundar Pichai's Google in AI While Google Coasted
“Yeah, he's making so much money, every employee's making a lot of money, the shareholders are doing well, everybody's just kind of coasting, and then you, it's like, boom, Sam Altman comes in and laps you on AI, all your AI products internally suck, Sam Altman…”
Course Buyers Purchase Creator Brand Rather Than the Actual Instructional Content
“People are just buying the attitude and like the brand and it doesn't matter what the product is. You know, they can sell anything.”
Tesla Could Crush Lucid With Slight Upgrades to Its Vehicle Interiors
“And Lucid Air kind of came in as, like, the top upper market, but they could just crush Lucid with, like, a slight tweak to the interior.”
David Holz's StarCraft Parable Makes the Best Case for AI Safety
“It makes the case for these AI doomers that are like, guys, we need to stop fighting among ourselves. And it needs to be more of like the humans versus AI. And like, we need to take this seriously. And that was more convincing than any like essay that I've see…”
Marketers Worry Too Much About Repetitive Messaging
“It's an example of like marketers that think like, oh, like we're being too repetitive with this messaging where now I just associate Steinman with winning and being committed to winning. And it makes me want to back whatever he does and being optimistic.”
Multiple Billionaires Currently Employ Full-Time Bible Instructors
“We know some people with full-time Bible instructors, some billionaires with full-time Bible instructors”
Angel Studios Is One of Media's Most Underrated and Successful Companies
“And then there's that company, Angel Studios, one of the most underrated
media companies that does really well.”
Tech Workers Are Now Discovering Democratized High-End Power Tools
“Tech guys whose only tools has been a phone and a laptop are now discovering that there's the democratization of super high quality power tools that has been happening like in the background and there's like entire religions oriented around the different brand…”
YouTubers Criticizing BlackRock's Ownership Misunderstand How Funds and ETFs Function
“There's like a cottage industry of YouTubers that just put out endless, like, hit pieces on BlackRock being like, did you know that they own everything, and they don't understand how, like, Fund to Funds or ETFs work.”
Bold, Unoptimized Workplace Architecture Pays Off Long-Term for Companies
“Making like bold design decisions like that, that are, they go against the obvious optimization of like square footage. Like it is going to cost you more to do this, but it's going to make a statement and it's going to be more important to the business long-te…”
The Pro-Natalism Movement Is Becoming the New Cultural Norm in Tech
“10 years ago, he would have been ostracized for saying something like this. It would have just been so Random, but the pro natalist movement is like now becoming like the norm, like the new norm. At least within the tech community”
Raising a Large Family Requires Designing Lifestyle and Location Around It
“I mean, the trick is just, like, breaking free of the memetics around, like, what it takes to have a dozen kids. Like, yeah, you probably need to live on a ranch outside of a major city. Probably not raising a dozen kids in Manhattan unless you're a trillionai…”
Palantir Maintains Unmatched Talent Density for a 20-Year-Old Company
“Palantir, fantastic team. I, from some random content thing, I got a DM from a kid who just, like, graduated from some school and went to Palantir, and it was, like, still a cut above. It's a twenty-year-old company. Like, you just don't see that anywhere else…”
Bowery Farming Was Worth $2 Billion and Is Now Worth Zero
“What's interesting about this is that, you know, having the news around Bowery today is like, okay, this is a two billion dollar company that's was, that's now as of whatever, this last week, worth zero.”
Private Venture Markets Effectively Function as Legalized Insider Trading
“The interesting thing though is that the private markets effectively have legalized insider trading already, right? All the private markets are, is like using inside knowledge on companies, teams, founders, and placing bets accordingly.”
Startup Prediction Markets Will Severely Lack Liquidity for Series A Companies
“And so I could imagine this, but for a lot of startups, like the liquidity is just not going to be there because there just aren't going to be that many people that care about some series A company that like is got some VC platform teams have entire”
Elon Musk Practices Targeted Impact Investing Over Diffuse Non-Profit Philanthropy
“He's doing impact investing, even though, like, some people might not like the impact that he's having. Like, his, he's putting his wealth to work in, like, very specific targeted ways. Essentially, much more than, like, You know, oh, diffusing a billion dolla…”
Funding Cultural Monuments Is Rationally Profitable for Tech Investors Seeking Deal Flow
“These are dividends that get paid to society and pay back in probably better ways than most of the other things because they build the brand and founders want to work with them and so they get better deal flow. So it actually is rational.”
Jeff Bezos's 10,000-Year Clock Project Will Probably Succeed Within 20 Years
“It'll probably work, but in the next 20 years, you know, it just takes time, and then it'll just be this thing that people go visit.”
Buying a Company With Sub-$500k Cash Flow Is Just Buying a Job
“Buying a company with less than half a million of cash flow is buying a job.”
Being the Youngest Operator in Wealthy Neighborhoods Yields Massive Networking Alpha
“And so, yeah, but I think, I don't know, there's a lot of alpha and just going and being in a place where you're The younger person with energy that's still in, in the trenches, basically, because all those other people just want to back what you do, basically…”
True Moats in Hard Tech Come From Compounding Hardware Operational Learnings
“And the real hard tech is going after like a five to 10 year old hard tech company that's competing in the same exact category of, as you, that has more resources, that has more learnings, that has more customer relationships.”
Early YC Batch Loyalty Gives Member Companies an Unfair B2B Distribution Moat
“One of YCs like moats is that if you could be in YC and you don't go in YC and then somebody that's competing for your, in your same category does there, the loyalty is like very real. Like they are going to use your competitor out of At least in the early day…”
Hiring Platforms Suffer Catastrophic Revenue Collapses During Tech Industry Downturns
“This happens with hiring companies a lot. They're like doing great in a bull market. And then as soon as the riffs start and all the companies are laying off, their revenue just goes to zero because no one's hiring. So no one's paying for hiring platforms beca…”
The 3D Printing Promise Will Materialize as Localized Small-Scale Agile Manufacturing
“I think the original promise of Three D printing where people were like, oh, you're going to just be able to buy something online and three D printed in your office or whatever. And like, I think that will basically come true, but it won't necessarily look lik…”
Perplexity CEO Offered to Replace Striking NYT Workers With AI
“The real, I guess the perplexity CEO did a PR push today saying that he would happily replace all of their writers with AI. Like he did a piece today.”
Dismissing Marketing Is an Engineering Mistake Because It Creates Real Value
“It's like the classic, like you know, programmer mistake of like marketing doesn't matter. In my opinion. So it's like, 90% is marketing. Let's talk about Nike. Is that a valuable company? Does that bring people joy? Is it valuable? It's 90% marketing, of cour…”
Huge Amounts of Financial Credit Are Currently Being Collateralized by GPUs
“There's huge amounts of credit being extended that is backed By GPUs.”
Overbuilt AI Infrastructure Will Eventually Enable Future Winners Post-Bubble
“This could lead to a bubble that pops, but it still could be amazing that all this stuff gets built out and there's all this infrastructure. And that's exactly what happened in the dot-com boom. There was a lot of dark fiber and that's what enabled Google to g…”