Tactic
Bleacher Report's supply-demand approach to content
Shaan recounts Bleacher Report founder Dave Nemitz: rather than writing what writers found interesting like everyone else, they reverse-engineered Google searches (e.g. 'what time is the NFL draft') and over-produced content for high-demand, underserved queries.
“And so he would just reverse engineer it. So he, like, they would just study Google searches and they would say, oh, everybody's searching what time is the NFL draft? He's like, so we would immediately, like, have, like, the number one ranking thing on Google for What time is the NFL Draft, where to watch it and how to watch it and what's going to happen in the draft.”
Steal thisReverse-engineer search demand and over-produce content for high-volume queries incumbents are underserving.
Framework
Old-website-top-Google-result = a money printer
Shaan's tell for a great bootstrap business: any company that ranks at the top of a popular Google search but has a website that looks like it was last updated in 1996. He uses BabyQuip, a peer-to-peer baby-gear rental marketplace, as the example.
“It's again, one of our like telltale signs is any business that shows up at the top of a Google, a popular Google search, but the website looks like it was last updated in like 1996. Those are businesses that print money. And so it's like, congratulations, you've identified a money printer.”
Steal thisSearch a popular query, find the ugly-but-top-ranking site, and you've likely found a quietly profitable business to learn from or copy.
Take
You're early even when you're late: megatrends run longer than you think
Shaan's core thesis: even in 2010 when Google/Apple/Facebook looked mature, buying them would have 10x'd your money — Google's revenue went from $5B to $55B. The lesson is that real megatrends (internet, mobile, cloud, crypto) have far more room to run than they appear, so feeling 'late' is usually wrong.
“2010, when I graduated, Google's revenue was $5 billion. Today, its revenue is $55 billion. And you could do the same thing with Amazon, with Facebook. And if you had just bought those companies back then, you would have made 10x your money, right?”
Steal thisWhen something is a genuine megatrend, ignore the feeling that you're late — they compound over 20-30 year arcs.
Take
The strategy too stupid to sell: just buy FANG and hold
Shaan relays Peter Thiel's point that simply buying FANG (Facebook, Amazon, Netflix, Google) in 2013 and holding would have 6x'd your money and beaten almost any money manager — but advisors can't recommend it because it's too simple to justify their 1% fee.
“if you had just put your money into FANG, which were obviously great companies that were technology companies that were growing, and you didn't even need to know how fast they were growing, but if you just said, these are solid companies that, you know, seems like everybody in America is using their products, you would have made 6 times your money in the last 8 years. And he goes, that would beat the performance of almost any money manager or hedge fund or investment banker that you're thinking of working with.”
Steal thisDefault to the embarrassingly simple buy-and-hold strategy; complexity in investing usually underperforms.
Story
He took the lower salary, moved in with his parents, and chose the messier startup
Furqan had a polished job offer with an early Google infra leader, but picked AppLovin's chaos instead. Adam offered higher-salary/low-stock or lower-salary/high-stock; Furqan took the low salary, moved back in with his parents, and bet on equity because it would be more fun and a higher rate of learning.
“And Adam gave me two options. He gave me a higher salary and a low stock. A lower salary and a higher stock option. And I was like, I kind of just made the decision down to like, well, if I go with Adam, I need to take the low salary, move back in with my parents, take the stock because I'm going to be in it for the ride.”
Number
Print media revenue collapsed from $65B to $17B after 2008
Balaji cites the 'Print Media Disruption' chart: after the 2008 financial crisis, print media advertising revenue fell from around $65 billion to roughly $17 billion while Google and Facebook went vertical.
$17000M
Print media revenue after the 2008 crisis (down from $65B) · USD
“After the financial crisis, print media dropped the revenue from like something like $65 billion down to like $17 billion while Google and Facebook were just going vertical like this, right?”
Framework
You can't abolish the FDA, but you can exit it like we exited the Fed
Balaji argues you don't reform an institution from inside; Google didn't fix Microsoft by becoming Bill Gates, it built a parallel system. You can't abolish the FDA or the Fed, but you can exit the Fed with Bitcoin and build an ethical, fully opt-in parallel system.
“Google didn't reform Microsoft by becoming, you know, Bill Gates. Google reformed it by building a parallel system.”
Steal thisDon't try to reform a captured institution from inside; build a parallel, opt-in system and let people exit to it.
Number
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.
$12
Years for Bitcoin to reach $1 trillion · years
“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.”
Number
An anonymous Google salary spreadsheet hit 20,000+ entries
Shaan describes how a woman at Google created an anonymous spreadsheet for employees to share salary, level, and location; within 2 days it had 10,000 entries and now over 20,000 — showing how viral the demand for pay transparency is.
$20K
Entries in the anonymous Google salary spreadsheet · entries
“So some woman created this, and within 2 days, 10,000 people had put in their information. And now there's over 20,000 people in the open Google database.”
Billy
Reputation.com: the Pulp Fiction 'wolf' who makes Google scandals disappear
Shaan paints Reputation.com as the internet's fixer: charge a NASCAR driver $100k to make an unflattering Google result vanish, with their big moneymaker being manipulation of Google autocomplete suggestions.
“So the promise was, all right, you know, famous NASCAR driver who doesn't like that story that comes up when you Google your name, $100,000 and we'll make it go away. So they're like the fixer of the, you know, of the internet. They're like the, uh, the wolf in Pulp Fiction.”
Framework
Why incumbents leave premium white space: business model and bundling
Rahul Vohra explains why neither Google nor Microsoft built a premium email product: Google's ad model means you are the product so a paid experience doesn't fit, and Microsoft sells through all-you-can-eat bundles where email is just one checkbox in a one-size-fits-all suite.
“For Google, I believe it's the fundamental business model doesn't support creating a premium email experience, and the company is so large now that it doesn't matter. The fundamental Google business model is of course ads and AdWords. It's to know everything they can possibly know about you, secondarily to keep you in the browser, hence Gmail.”
Steal thisFind a premium segment incumbents structurally can't serve because their business model or bundling strategy forbids it.
Idea
Sketchfab: the category-leading marketplace for 3D-model stock
Shaan flags 3D objects as an underbuilt stock category and is trying to invest in Sketchfab, a marketplace where creators upload and sell rotatable 3D models. He claims Google and Amazon tried to compete and lost badly, with Sketchfab returning ~300 results to their near-zero for common searches.
“And like if you search for like common things like Tesla or a car on both of those engines, the Google one shows like zero results and the Sketchfab one shows like 300. Right? Like, they're just like dominating this market right now. And so I think there's, there's some niche things, there's some niche things that are for different types of stock items that are like not just photos and sounds, but I don't know, 3D objects is a good one.”
Story
How Charity:water poaches Google talent at dinner
Shaan recounts Scott Harrison's playbook for recruiting world-class people into a nonprofit at one-tenth their salary: take the candidate AND their spouse to dinner and deliver the Steve Jobs 'stop selling sugar water, change the world' pitch.
“And he's like, how do you convince somebody to leave their, you know, million-dollar job at Google and like, you know, "Come work for 1/10 of that for me and like save the world." And so I used to, he'd always be in San Francisco, we'd catch up and I'd be like, "So what are you in town for?" And it's always that, he was like, "I'm taking, you know, the person I want and their husband or wife out to dinner and I'm gonna tell 'em, you know, the Steve Jobs line of like, you know, stop selling sugar water and let's, you know, come change the world."”
Steal thisTo close a hard recruit, get their spouse to the dinner and sell the mission, not the salary.
Framework
Productivity perks vs. values perks
Shaan splits employee perks into two buckets: productivity perks (laundry, meals, cleaning) that buy back hours of work, and values/recruiting perks that signal what the company stands for. Google's free food was a productivity perk, not a retention one.
“These really weren't like retention perks so much as they were more like what I'll call productivity perks. They knew they could squeeze an extra 2 hours out of each person's day by automating away a bunch of the busy work that they had to do to run their lives.”
Framework
Startups die of starvation, not murder
Shaan argues founders shouldn't fear being killed by big competitors. Most companies die because they never got enough customers (starvation/suicide), not because rivals beat them (homicide).
“I always used to say it's starvation that you die from and not murder. And like starvation being you didn't get enough customers. And so like, really you should just be focusing on that. And why didn't you get enough customers? It's not 'cause all the customers went to Facebook or Google. It's like, because the customers didn't know about you, didn't care about you, or tried you and you sucked.”
Steal thisStop obsessing over competitors; obsess over why customers don't know you, don't care, or tried you and bounced.
Number
Bebo sold to AOL for $850M, and the founders owned 70%
Shaan tells how Bebo, dominant in markets like Ireland (more trafficked than Google there), sold to AOL in 2008 for $850 million, more than MySpace got, with founders Michael and Sochi owning 70% of the company at exit.
$850M
Bebo acquisition price (AOL, 2008) · USD
“decides to sell, sells the company for $850 million to AOL. Huge exit at the time, sold for more than MySpace did. And, um, and so amazing exit for Michael and Sochi, and they went on to do a whole bunch of great things, both philanthropically as well as in business. And they own 70% of the company at the exit.”
Fact
Google tried to sell itself for $1 million
Shaan notes that Google's founders were happy to sell the company for just $1 million early on and only kept going because no buyer took the offer.
“Yeah, Google, they wanted to sell for $1 million. They were happy, they were happy to take a $1 million offer and they just didn't get it, so they kept going.”
Idea
Stories beat long text: a Wikipedia or recipe site in Stories format
Shaan argues the Stories format (Instagram, Snapchat) is a superior way to deliver information quickly, and that long-form text/video products like recipe sites or even Wikipedia could be rebuilt as Stories.
“And I also just have a theory that in general Stories have been shown to be like the superior communication format. Like, there's a reason that Instagram Stories, Snapchat Stories, these have taken off, and it's because it's a really quick way to get entertainment or information. It's a great way to communicate from one human to another. And I just think more, more things that are in long-form text or long-form video, you could just convert to story-based formats and do really well. So like Wikipedia today is all about an encyclopedia with long-form text. I wonder if you could create a modern-day Wikipedia using stories as your way of explaining what something is”
Steal thisTake a long-form text product (recipes, encyclopedia) and rebuild it in a quick Stories format.
Number
DuckDuckGo averages 62 million queries per day
Sam cites DuckDuckGo's traffic page: the privacy search engine averages around 62 million queries per day, versus an estimated billions for Google.
$62M
Search queries per day · queries/day
“they average 62 million queries per day”
Story
A $1M+ SEO/YouTube business that died when the algorithms changed
Shaan describes a friend who bought a business for over $1M that depended on SEO and YouTube rankings, doing close to $1M in annual revenue. Two years later, after Google and YouTube algorithm tweaks, the business fell off a cliff and was essentially dead, illustrating the danger of platform dependency.
“Now, 2 years later, like I just talked to him and he said, It's fallen off a cliff. YouTube changed their algorithm and Google changed their algorithm slightly, and my business is essentially dead. Um, and now that's a, you know, that's a business he bought for, for over a million dollars.”
Framework
The 'New Zealand business': self-sufficient, no platform risk
Wilkinson's favorite holding, Dribbble, exemplifies his ideal: a 'New Zealand business' that is self-sufficient with no intermediary or gateway. Designers type Dribbble directly into the URL bar, so there's no Google or Facebook risk, and the captive community can be monetized many ways.
“I always say you want a business to be like New Zealand, right? So New Zealand is in the middle of fucking nowhere. Nobody's paying any attention to it. It's quietly successful. It's totally food and energy independent. It could get cut off from the rest of the world and people would eat and be fine. And it's away from nuclear war. Right. And so when I think about a business, I want a business that there's no intermediary, there's no gateway, and you have a fully self-sufficient society.”
Steal thisFavor businesses where customers come directly to you, so no platform (Google, Facebook) sits between you and your audience.
Tactic
Buy blue-chips on sale, keep dry powder
Shaan's takeaway from people who lived through dot-com and 2008: downturns start great startups and put assets on sale (stocks 50% off, real estate 30% off). He eyes Amazon, Facebook, and Google as blue-chips at a discount, while stressing you can't time the bottom—so having dry powder matters.
“But companies like Amazon, Facebook, Google, I think they are on sale. I think they're a discount. It's like, you know, get these blue chip companies 15% off, 20% off. It might get up to 30, 40% off. And those are opportunities for— because I asked a bunch of people, I said, hey, you know, you saw the dot-com boom and bust.”
Steal thisHold dry powder so you can buy blue-chip companies at 20-40% off during a crash, accepting you can't call the exact bottom.
Idea
Corporate universities: company-run talent pipelines (Google U)
Shaan argues companies should build their own universities to fix broken talent pipelines, citing McDonald's Hamburger U, Shopify's Dev Degree, and his old Google U pitch. He predicts companies will increasingly create or rebrand failing universities to grow talent from the grassroots up.
“which is companies either creating their own or partnering with failing universities, rebranding it as their own and, uh, attracting talent there and having sort of a talent pipeline from the grassroots up because it's so hard for them to recruit talent, recruit top talent.”
Steal thisBuild a branded company university to own your talent pipeline instead of fighting to recruit trained workers.
Number
YouTube now does $14-15B/year after a 'horrible' $1B deal
Shaan uses YouTube as the example of why a few extreme winners justify big-company acquisition appetite: everyone called Google's billion-dollar YouTube purchase a horrible deal, and it now generates $14-15 billion a year in revenue.
$14
YouTube annual revenue · USD billion/year
“Yeah, $14, $15 billion a year now in revenue. And so you need a few of these. Instagram, another one where it's like, you need a few extreme winners, and then big companies will continue to have the appetite.”
Idea
Levels.fyi: crowdsourced comp data as a simple, defensible product
Shaan highlights levels.fyi, built by a remote-work champion (LevelsIO), where employees anonymously submit role, level, base, stock and city, creating an increasingly reliable comp dataset that is the best way to know if you're underpaid or what you'd make elsewhere.
“So it's this dataset of people anonymously putting in their compensation, and the dataset gets richer and richer. So it's actually a fairly reliable resource to say, oh, you know, should I go work at Facebook or Google? I think I'm this level. I can see the pay difference between the two.”
Steal thisCrowdsource a proprietary dataset in a domain where companies keep people in the dark; each submission makes it more valuable and harder to copy.
Framework
Win a market by flooding a new, underpriced ad channel before anyone else
Bradford explains that every dating app that got huge hacked a brand-new acquisition channel before it was understood or expensive: Facebook News Feed, Google Mobile Ads. Plenty of Fish's Markus would stuff a country's channels at launch so any dating search returned only his app.
“all the people that got big all hacked an acquisition channel that was new, and they used Facebook News Feed before it got regulated. They used Google Mobile Ads before they got— anyone knew what they were doing. Marcus knew Facebook Ads inside and out, and when they launched countries, he would just— from what I heard, I tried to read all these people's secrets, but what I heard is they would just basically stuff the channels where you spend so much money no one else can compete.”
Steal thisFind a newly opened, underpriced ad channel and dominate it before competitors notice the arbitrage.
Framework
Become a destination, get out of Google: how Amazon and Yelp diverged
Daniel Gross recounts that pre-Prime, 60-80% of Amazon's traffic came from Google, an existential risk; Amazon escaped by becoming a destination, while Yelp got killed when Google promoted Maps over it.
“we forget before Prime, before Prime, Amazon had this giant existential threat, which is I think 60 to 80% of its traffic came from Google. And this is what killed Yelp at the end of the day, because at some point Google was like, "Mm, we're gonna integrate into Maps and just promote Maps over Yelp."”
Steal thisDon't build a business that depends on Google traffic; race to become a destination people open directly.
Number
$1 in Domino's IPO beat Google's IPO by 5x
Sam cites that a dollar invested in Domino's IPO would have returned five times more than the same dollar invested in Google's IPO, partly because the tech names were priced high from the start.
$5
Domino's IPO return vs Google IPO · x
“If you invested $1 in Domino's IPO vs. Google's IPO, you would have made 5 times more.”
Story
Lost a quarter million in 42 days buying a content site killed by Penguin
After selling his own business, Valley bought a content site that thrived for 42 days, then collapsed when Google's Penguin update crushed its keywords because the previous owner had cheated. He lost about $250K.
“I actually, I bought a content site and had 42 amazing days, and then the floor fell out from beneath it. It was the Penguin update, so it got crushed. All the keywords that are on page one got crushed because the guy that built it cheated like crazy. And, uh, it was a very valuable lesson, lost about a quarter of a million dollars.”
Take
Bitcoin is the internet; competing with it is AOL fighting the open web
Svetski argues Bitcoin is a basic, unstoppable network that routes value the way the internet routes data — and the winners will be the value-added services built on top of it. A bank's send/store/receive service needing hundreds of millions in infrastructure can be replicated with a small app for a couple hundred grand.
“And the analogy that I give to people is trying to compete with Bitcoin is like AOL trying to compete with the internet. The companies that succeeded were the ones like Google, Netscape, etc., who built on the internet, which was this really dumb basic packet routing network.”
Framework
No money, no plan, no technology — the 3 things that kill a company in excess
Alibaba's internal motto warned that an excess of money, plans, or technology will kill any company. Each becomes a crutch that erodes creativity, adaptability and customer focus.
“there are 3 things that will kill any company if in excess. So if you have an excess of any of these 3 things, it'll kill your company. Money, plans, and technology. That's not what I was expecting. So then he continued to explain that at Alibaba they had this internal motto. No money, no plan, no technology.”
Steal thisTreat abundant cash, rigid plans, and tech-for-tech's-sake as risks, not assets.
Take
Treat angel checks as paid education
Belsky rationalized his first risky Pinterest check (a big chunk of his salary) as buying an education from Ben Silbermann, who had the West Coast network he lacked. His takeaway: when you deeply respect someone you can learn from, find a way to work with them.
“And, you know, the one or the other thing I did though to rationalize it for myself, I remember is Ben had worked at Google. He had a network on the West Coast. I was just like, you know, new entrepreneur in New York. Didn't have any of that network. I actually felt like I would learn a lot from this. And so in some ways I was like, you know, I'm sort of paying for an education.”
Steal thisJustify an early angel check by the education and relationship, not the return — then the worst case is you learned something.
Take
Don't put all your traffic eggs in one basket
After Facebook crushed publisher reach, Ramon made traffic diversification a core principle. He never wants to be 100% dependent on Google, email, or push; email is the most reliable channel but everything can change overnight.
“Don't put all your eggs in one basket. And, and, and Yeah, still to today, like when I buy or sell or buy, start a site, it's like I want a diverse traffic. Traffic, yeah. I don't want to be 100% depending on Google, 100% even email, or 100%, you know, a push notification. From all these, the email is still the best bet”
Steal thisDiversify traffic across Facebook, Google, email, and push so one algorithm change can't kill your business.
Story
How Druckenmiller flipped from Bitcoin skeptic to buyer: the 86% diamond hands
Druckenmiller long called crypto 'a solution in search of a problem,' but Fed money-printing during the CARES Act gave it a problem to solve. The clincher came from Paul Tudor Jones: when Bitcoin fell from $17,000 to $3,000, 86% of holders never sold, proving a base of religious-zealot holders behind a finite-supply asset.
“Then the second thing that happened is I got a call from Paul Jones, and he says to me, uh, do you know that when Bitcoin went from $17,000 to $3,000 86% of the people that owned it at $17,000 never sold it. Well, this was huge in my mind. Here's something with a finite supply, 86% of the owners are religious zealots. I mean, who the hell holds something through $17,000 to $3,000?”