Apple

The 'Beats by Dre' acquisition: you're buying the person, plus some stuff

Reacting to Reese Witherspoon selling Hello Sunshine for $900M, Shaan argues the numbers don't pencil out from the IP alone — it's like Apple buying Beats. You're really paying for Reese (the person/brand) and getting some content assets thrown in, not buying a cleanly analyzable asset.

“So I think this is like, this is like a Beats by Dre acquisition is kind of what I see it as, which is basically somebody being like, cool, we get Reese, we get Reese and then some stuff, great. I think that's basically like when Apple bought Beats and they're like, great, we get, you know, we get Dr. Dre”

The Apple Store art stunt that got the Secret Service to raid a home

Sam recounts artist Kyle McDonald, who in 2011 installed software on 50 Apple Store computers that secretly photographed shoppers' faces, published it as art, and got his home raided by the Secret Service after Apple reported him.

“And so he went to an Apple store in Brooklyn and they had 50 computers and he installed an app on all 50 computers that automatically took a picture every like 30 or 60 seconds. And anytime it detected a face, it would send him the pictures and he published it as like an art exposit— uh, an art thing of like look at what people look like when they're looking at computers at a laptop in Apple. And after publishing that, the Secret Service raided his home, uh, and Apple, Apple contacted the Secret Service.”

After Apple's opt-out, Facebook only catches 60% of ad conversions

Shaan explains Apple's App Tracking Transparency gutted Facebook's targeting: once users tap 'no' to tracking, Facebook only sees about 60% of conversions from its own ads, missing the other 40%.

“Like even when you send a— show a Facebook ad to somebody, they click it and they go buy a product from you, Facebook's only catching like 60% of those conversions. It doesn't know about the other 40% 'cause they've opted out of tracking or it didn't work.”

The next Apple is a health-monitoring device, not a phone

Shaan predicts the next trillion-dollar consumer-device company won't be a phone company but a healthcare monitor, a wearable measuring what's happening inside your body and feeding the data back to you. He frames Apple itself shifting toward health via wearables.

“So I don't think the next Apple is a phone company. I think the next Apple, the next Apple, which is going to be a trillion dollar company that has, uh, that gives you kind of like a consumer device. I think it's going to be a healthcare monitor. I think it's going to be something that is going to be measuring what's going on inside your body. And feeding that data back to you.”

Network capitalism, not industrial capitalism

Maples explains why he invested in Lyft, Tesla, and Apple as software-defined, network-centric companies. Lyft replaced centralized taxi dispatch with an algorithmic 'invisible hand' matching riders and drivers; Tesla is 'a car company animated by networked capitalism.' He predicts these companies keep displacing incumbents that merely use computers to make industrial processes faster.

“And so why did we invest in Lyft? Lyft was a more modern way to think about getting a ride than taxis. Taxis are a centralized, command and control, tops-down, dispatch-driven technology. Lyft says, hey, riders and drivers can advertise their presence in real time on a network, and algorithms will form an ad hoc connection. So it's kind of like this return of the invisible hand.”

The Steve Jobs hire: an hour later the world rearranged to make his wish true

Shaan retells a (possibly apocryphal) Quora story of an MIT recruit who didn't want to work at Apple. Steve Jobs scoffed at the interview questions, asked only 'Who are you?', took him on a walk, and within an hour had him hired, apartment keys in hand, and his belongings being moved cross-country.

“And Steve Jobs is like, give me a month. It'll be the best month of your life. I will, you know, I'll pay you 3 times what your normal rate would be for the month. You know, for one month, I'll make you pay triple. We'll get you a car or an apartment or whatever else. Just say yes and like, say yes and it's done.”

Bitcoin hit $1T in 12 years vs 42 for Apple, 44 for Microsoft

Saylor argues Bitcoin is the most disruptive technology of our lifetime by citing how long it took companies to reach a trillion-dollar valuation: Google 22 years, Amazon 24, Apple 42, Microsoft 44 — and Bitcoin just 12.

“It took Google 22 years to get to a trillion. It took Amazon 24 years to get to a trillion. It took Apple 42 years to get to a trillion. It took Microsoft 44 years to get to a trillion. It took Bitcoin 12. It's a monetary fire.”

Scoop up boxed vintage Macs as appreciating collectibles

Comparing a first-gen iPod selling for $500-600 to a boxed Mac II at the same price, Shaan argues the vintage computers have far more long-term value and says he'd buy 5-10 to hold.

“Dude, if an old iPod is $500-$600 and Apple II in the box, or Mac II in the box, is also $500, yeah, I definitely know which one I think has more, more like long-term value here. Uh, those, those Those things are collectibles. I think you're spot on. I would scoop up 5 to 10 of those right now and just hold them.”

Steal thisBuy boxed vintage Macs on eBay now and hold them as collectibles.

The aha moment: 'we kind of ruined Gmail', so rebuild email from scratch

Rahul Vohra recounts the Superhuman origin: realizing the browser extensions he and competitors built sit on Gmail like a virus that slows and clutters it, he asked what if email were rebuilt from scratch the way Apple builds a laptop.

“What if we just built it from scratch? What if we built an email experience the same way that Apple built a laptop? For me, that was like the aha moment that no one has done that because it's really scary and nobody knows how and it's very expensive. But I might be one of the few people in the world that could actually pull it off in the sense of pulling together the team and the capital to make it happen.”

A $10M venture portfolio that would've been richer in the S&P 500

Andrew's blunt take on angel investing: despite a couple of nice returns including a sale to Workday, his roughly $10M venture portfolio would have made him richer, safer, and more liquid had he just put the money in the S&P 500 or Apple. Angel investing is not a good way to make money.

“I probably have a $10 million venture portfolio or something. And if I'd just taken that same money and put it in the S&P 500 or Apple stock or anything else, I would be way richer and it would be way safer. I'd have a more liquid net worth. It would be cash in the bank, right? Like, so I don't think that angel investing is a good way to make money.”

Pick the enemy that doesn't look self-serving

Shaan's refinement of enemy marketing: Hey switched its fight from Gmail (self-serving, since they sell email) to Apple, a more novel story that doesn't look like thinly veiled competitor bashing.

“now they picked Apple, and it was a way better fight to pick because it's a more novel story and it doesn't seem as self-serving as when they picked Gmail as the competitor.”

Steal thisWhen choosing an enemy, avoid the direct competitor you'd obviously profit from beating; pick a fight that tells a more novel story and looks less self-serving.

Cryptographic 'legitimacy seal' baked into cameras to fight deepfakes

Shaan argues the only durable defense against deepfakes is a tamper-proof cryptographic seal applied by the device at capture time, so people learn to trust only video carrying that seal. He notes only Apple, Samsung, and camera makers can implement it, not a startup.

“the phone makers themselves, the device makers themselves, will need to put a cryptographic seal on the video when it's taken. And it's like a tamper-proof seal, like we have with medicine or whatever, where it's like, if this seal is broken, that means this video has been edited in some way. And so at some point people will only trust videos or photos that have this cryptographic seal on them”

Steal thisBuild trust infrastructure at the point of capture, not after the fact; con artists always beat post-hoc validation.

Software that flags when employees' equity cliffs (so managers know who'll quit)

Daniel Gross says no internal HR software told him when his Apple reports' stock would cliff; he wants software that surfaces each employee's financial milestones so managers know when to check in before they leave.

“I just wanted to know for everyone in my org, I want to know what are their important financial milestones. This is Apple, 100,000-person company. There's no software that could tell me this, which is I want to know like "Is most of your stock going to cliff?"”

Steal thisBuild HR tooling that maps each employee's equity vesting and refresh milestones so managers get a 'they may leave' alert.

Build a niche AirPods-accessory FBA business riding Apple's growth curve

Shaan pitches owning a small slice of the booming AirPods-accessory market - replacement cases, aesthetic add-ons - via Amazon FBA, since once Apple killed the headphone jack everyone needs Bluetooth earbuds and the category is exploding.

“I think there's just like a lot of random niche things, but because this is a product that pretty much— once Apple removed the headphone jack, everybody needs Bluetooth headphones now. And so I just think being in that space, you could take a tiny piece and do quite well right now.”

Steal thisPick a fast-growing hardware product and own the #1 Amazon FBA listing for one accessory niche around it.

He cloned Apple's iconic white earbuds for 80 cents

When Apple wasn't yet selling replacement earbuds, a 21-year-old Sheel flew to a Hong Kong electronics fair, negotiated by calculator, and sourced look-alike iPod earbuds — color-matched to the iPod Mini — for 80 cents apiece including packaging.

“And so ultimately I got these headphones. I got these Apple headphones for $0.80 apiece, including packaging, everything. And I did like I at this Hong Kong fair, I went, I like negotiated and I went to visit the factory.”

Edison's genius: plan less, do more

Wilson's core takeaway from Edison's tinkering: as a self-taught non-theorist, Edison brute-forced inventions by trying every material rather than reasoning from first principles. The lesson is to spend less time planning and more time running reps and failing.

“He just dove in and started trying stuff, and he was just unbelievably persistent. He tried and he tried until he brute-forced his way into a solution, into an answer.”

Steal thisPlan less, do more: stop debating the optimal approach and start running reps, failing, and adapting on the fly.

Great investors make large concentrated bets, the opposite of business school

Druckenmiller says every great investor he's studied (Buffett, Icahn, Soros) shares one trait that contradicts MBA teaching: they make large, concentrated bets with high conviction rather than diversifying across 35-40 names. Concentration paradoxically lowers risk because a huge position commands your full attention.

“It's they make large concentrated bets where they have a lot of conviction. They're not buying 35 or 40 names and diversifying. I don't know whether you remember, uh, Icahn a few years ago put $5 billion into Apple, and I don't think he was worth more than $10 billion when he did that, right?”

Steal thisConcentrate into a few high-conviction positions and watch them closely instead of diversifying into names you'll stop paying attention to.

Went home and gave up — woke up to $400K in day-one revenue

On launch day, a bad Apple featuring spot made Ali conclude the company was dead. He went home, watched Netflix, and fell asleep — then woke to discover the game had generated $400,000 in revenue the prior day. It was working.

“So I fall asleep, I wake up the next day, I immediately go to look at our stats and I'm like, oh, we just generated $400,000 in revenue yesterday. So this is working. Holy fuck. This is actually working. We're winning.”