Jack Smith

We can't judge anti-aging gurus: they're only halfway through the marathon

Jack Smith argues the longevity influencers (Bryan Johnson, Asprey, Attia, Huberman, Rhonda Patrick) can't actually be proven good at anti-aging because they're all middle-aged. Judging them now is like calling someone a great marathoner at the halfway point.

“I was just thinking of an analogy, and I kind of felt it's like saying that someone's a great marathon runner, but they're only at the halfway point. Like, maybe these guys are good at avoiding injuries, so they're more likely to complete the marathon. But how do we know if they're gonna get a good time in the marathon? We'll only know when they're like 100 or something in comparison.”

A $15K lawn-chair 'energy vortex' that supposedly cured the family's ailments

Jack spent $15,000 on the Energy Enhancement System, a room of laser-aligned monitors and lawn chairs with no plausible science. After a year of daily headaches that ketamine and ozone therapy couldn't fix, one session in the chair is the only thing he says worked, and it also helped his wife's migraines and her sister's sleep.

“So I'd been struggling with that for a year and I tried loads of stuff like ozone therapy, um, ketamine, like I tried everything and I actually think that this EES thing is the only thing that worked. I just went in there and I sat in a lawn chair for an hour, maybe 2 hours, and then just came out.”

Clone Bodyspec: a mobile DEXA-scan van for countries that lack it

Jack pitches copying Bodyspec, a bootstrapped US company that runs DEXA body-fat scans out of vans parked at CrossFit gyms, into markets like Portugal where a scan only exists in one hospital for $200. Bodyspec hit over $2M in revenue with about 14 vans.

“Bodyspec was bootstrapped and they built it to like more than $2 million in revenue even with just like 14 vans, I think. And the rollout strategy is pretty simple. Like you just partner with like CrossFit gyms and you just park in their parking lot. You know, so you're like, all right, on Monday we're going to be at this CrossFit gym, on Tuesday we'll be here, etc.”

Steal thisBuy a used DEXA machine, drop it in a van, and rotate it through CrossFit gym parking lots in a market that has no affordable body-composition scanning.

A used DEXA scanner costs as little as $15K

Jack notes a new DEXA body-composition machine runs about $50,000 and used units can be found for $15,000, versus roughly $1M for a whole-body MRI scanner, making a mobile-scan business cheap to start.

“And then I saw some used for like $15,000 and then you just put it in a van.”

Brand a concierge biohacking medical-tourism center in a cheap country

Jack pitches a concierge anti-aging center that uses an influencer-referral model: a $6,000 week in India bundles an MRI worth $3,000+, hotels, and blood-test interpretation. The operator owns no machines, just connections to local labs, and gives a top Bryan Johnson leaderboard influencer a free stay in exchange for referring 8 paying guests.

“So he just got the guy who's number 1, number 2 on Bryan Johnson's leaderboard. He told that guy, hey, you can come for free, but just refer 8 people. And you also be there to help people interpret their blood test results or whatever. So get all these other people to pay $6K and I'll give it to you for free.”

Steal thisIn a country with strong, cheap medical tech but weak branding, broker access to local labs and seed demand by comping a longevity influencer in exchange for referrals.

Andreessen: the market matters more than team or product

Jack relays Marc Andreessen's view that the biggest determinant of whether a startup becomes a billion-dollar company is not the team or the product but the market, its size and growth rate, because even flawless execution is capped by a small market.

“He thinks the most important factor is the market. Size of the market and growth rate is saying if you just have a crappy market, you can have amazing execution, the best team ever, but they're inhibited by into how big a company they can build by the size of the market.”

Test 6 ideas with landing pages in 2-3 weeks and let the market pick

Jack describes how Vungle found its winner: rather than committing to one idea, they spun up landing pages for six different business ideas inside two to three weeks, identified mobile apps as the great market, and let that market pull the right product out of them.

“But we actually tried out 6 different business ideas. Like, we created landing pages for each in the space of something like 2, 3 weeks. We iterated on 6 different ideas, and the right idea, um, the market pulled it out of us.”

Steal thisStand up landing pages for several ideas in a couple of weeks and let real demand signals, not your gut, pick the winner.

Charge advertisers for installs, not video views

After a week researching ad networks from first principles, Jack realized apps only care about the end action (installs/spend), not how many people watch a video. Vungle bet on charging only per install while the rest of the industry charged per view, which became its wedge.

“why are these ad networks charging based on how many times someone watches a video? We built a video ad network. We were like, apps, they actually just care about the end action. So they actually only care how many people install their app or how much money these users are gonna spend in their app. They don't actually care how many people watch the video. So why is it that the industry charges that way? And so we kind of made a bet and said, we will charge. It doesn't matter how many people watch your video, we'll just only charge you based on how many people install it.”

Steal thisPrice on the outcome your customer actually wants, even if the whole industry prices on a proxy metric.

You don't have to be first to market to be the biggest

AppLovin launched 6-12 months after Vungle yet grew multiple times bigger (peaking near a $10B+ market cap). Jack uses this as proof that, despite everyone racing to be first on the AI trend, the first mover rarely becomes the biggest.

“you don't have to be the first to market to be the biggest. AppLovin was one of the slower movers. And to give context, they at their peak have been multiple times bigger than Fungal. They went public and probably at their peak in the region of $10 billion market cap.”

Hire 10 people in Pakistan to play games and log every ad

To build a lead-gen database of which advertisers ran on which networks, Vungle hired ~10 people in Pakistan, gave them iPhones, and paid them to play mobile games all day and write down every ad they saw and which network served it.

“One of our hacks we did is we actually had a team of people in about 10 people in Pakistan. And Pakistan is so cheap. So we had an entire office, and they had one job to— and this is why it was really easy to recruit there. We said, just play mobile games all day. We just got them all an iPhone, which like play games all day. And whenever you see an ad, write down what the ad was advertising, and what ad network was using it. And so they basically built us our lead gen database by playing all the games.”

Steal thisTurn cheap human labor into a proprietary data set your competitors don't have.

Build a branded reseller layer on top of industries that can't market

Nomad Capitalist is essentially a well-branded reseller for tax lawyers (book, podcast, conference), charging rich clients a $25K retainer to be routed to attorneys they could find themselves for ~$3K. Jack pitches replicating the formula in other verticals where the underlying experts suck at marketing.

“I think a business opportunity is building a reseller layer on top of these industries that just suck at marketing or communicating what they do, you know. So he's doing it for tax, international tax for really rich people. And I was thinking there's probably other industries where just make an amazing brand website, write a book, go on all the podcasts and make a brand about yourself, hit really great name, right, like Nomad Capitalist, to do that for other industries, I thought was one idea.”

Steal thisPick a high-value service whose experts can't market, then build the brand, book, and podcast that becomes the trusted front door and resell their service.

Read the manual, become the 'AI expert', sell it by vertical

Jack argues that because tools like Midjourney and ChatGPT are brand new, anyone who actually reads the manual and puts in the reps can credibly position as an AI thought leader, run paid workshops, and publish vertical-specific books (ChatGPT for lawyers, for accountants, etc.).

“I think if you just, you know, if you just don't sleep and just learn Midjourney, ChatGPT, learn all of these things only came out recently, you can be a thought leader. And write a book, launch it, launch on Amazon, a book, how to use ChatGPT in your business, and launch it for each vertical using ChatGPT for lawyers and accounting and whatever.”

Steal thisMaster a brand-new tool deeply, then package the knowledge as workshops and vertical-specific books before anyone has credentials.

Read the manual, become the 'AI expert', sell it by vertical

Jack argues that because tools like Midjourney and ChatGPT are brand new, anyone who actually reads the manual and puts in the reps can credibly position as an AI thought leader, run paid workshops, and publish vertical-specific books (ChatGPT for lawyers, for accountants, etc.).

“I think if you just, you know, if you just don't sleep and just learn Midjourney, ChatGPT, learn all of these things only came out recently, you can be a thought leader. And write a book, launch it, launch on Amazon, a book, how to use ChatGPT in your business, and launch it for each vertical using ChatGPT for lawyers and accounting and whatever.”

Steal thisMaster a brand-new tool deeply, then package the knowledge as workshops and vertical-specific books before anyone has credentials.

The iPhone screen-recording hack that became Vungle's moat

Around 2010 you couldn't record an iPhone screen. Jack had an intern jailbreak iPhones and rig a camcorder cable to capture the screen, returning the gear within Apple's 14-day window to stay within their ~$1,000 budget. That unique ability later let Vungle make the best app-install videos, which it gave away for free only to advertisers spending $25K+.

“I told him to spend our entire budget at the Apple Store. I want you to buy the latest iPhone and latest iPad. And your first task as the intern is jailbreak this. And we have 48 hours to figure out if we can record the screen from this because my co-founder thinks it's a waste of time. I think it's not. And, and we, and then we're going to return it within 14 days.”

The iPhone screen-recording hack that became Vungle's moat

Around 2010 you couldn't record an iPhone screen. Jack had an intern jailbreak iPhones and rig a camcorder cable to capture the screen, returning the gear within Apple's 14-day window to stay within their ~$1,000 budget. That unique ability later let Vungle make the best app-install videos, which it gave away for free only to advertisers spending $25K+.

“I told him to spend our entire budget at the Apple Store. I want you to buy the latest iPhone and latest iPad. And your first task as the intern is jailbreak this. And we have 48 hours to figure out if we can record the screen from this because my co-founder thinks it's a waste of time. I think it's not. And, and we, and then we're going to return it within 14 days.”

Law of attraction as projected micro-signals

Jack's practical take on the law of attraction: belief works not by magic but because conviction leaks out through countless micro-signals and body language you can't control. Investors sensed his certainty (he told one fundraising was 'going amazing' when he had no investors) and one freaked out and handed over a term sheet.

“I feel that law of attraction works because there is so many micro signals and body language we are projecting to people all around us that we are not in control of and don't even know.. And so I feel for me, I and my co-founder, we were convinced we're going to raise funding, and we're the shit. And I think that investors and stuff can tell, you know, you can tell if someone's bluffing.”

Outsource your baby monitor to a 'digital night nanny'

Borrowing an idea from Thumbtack founder Jonathan Swanson, Jack hired a virtual assistant in India to watch the baby cam all night with strict rules: start a timer when the baby cries, do nothing if it stops within ~3 minutes, but call and wake him only if crying exceeds 7 minutes. He claims he sleeps better than before having a baby.

“having a virtual assistant I have in India. And basically, he just watches my baby cam all night. And he basically has specific instructions, like, okay, if the baby wakes up and starts crying, you start a timer. And if she just cries for like 3 minutes and goes back to sleep, don't do anything. But if she cries for like more than 7 minutes, then call me and wake me up.”

Steal thisGive a remote VA precise escalation rules so you only get interrupted by the events that actually require you.

Book: 'Don't Tell Me I Can't' on unschooling

Jack's recommendation is 'Don't Tell Me I Can't', a short (2-3 hour) book by a teenager raised unschooled who built a real land/animal business and was loaning money to his parents by 13. The author tragically drowned shortly after writing it.

“the book that I talked about unschooling is like, Don't Tell Me That I Can't. And to, I guess like spoiler alert, like the kid, it really sucks because this kid was building something amazing. He actually drowned and died right after he wrote the book. Kind of sucks, but it's a really short book.”

People said they loved the idea but zero actually paid

Jack Smith warns that verbal enthusiasm is worthless validation. When Vungle offered an app-review service at $20 (a supposed $150 value), developers all said they loved it and would sign up later — and produced zero actual sales.

“And people told us like, oh yeah, love this idea, it's great, I'll sign up as soon as I get home. We got like zero sales. Like people were just telling us the idea is great, they didn't actually want to sign up.”

Steal thisTreat 'I love it, I'll sign up later' as a no — only money or a signed commitment counts as validation.

People said they loved the idea but zero actually paid

Jack Smith warns that verbal enthusiasm is worthless validation. When Vungle offered an app-review service at $20 (a supposed $150 value), developers all said they loved it and would sign up later — and produced zero actual sales.

“And people told us like, oh yeah, love this idea, it's great, I'll sign up as soon as I get home. We got like zero sales. Like people were just telling us the idea is great, they didn't actually want to sign up.”

Steal thisTreat 'I love it, I'll sign up later' as a no — only money or a signed commitment counts as validation.

People said they loved the idea but zero actually paid

Jack Smith warns that verbal enthusiasm is worthless validation. When Vungle offered an app-review service at $20 (a supposed $150 value), developers all said they loved it and would sign up later — and produced zero actual sales.

“And people told us like, oh yeah, love this idea, it's great, I'll sign up as soon as I get home. We got like zero sales. Like people were just telling us the idea is great, they didn't actually want to sign up.”

Steal thisTreat 'I love it, I'll sign up later' as a no — only money or a signed commitment counts as validation.

Abstract to what the advertiser actually wants — Vungle's CPI bet

Vungle was one of the first ad networks to charge cost-per-install instead of CPM/CPC. Jack Smith's principle: figure out the advertiser's true goal (installs, sales, revenue) and bill on that — impressions and clicks are 'false metrics' layered on top.

“So I think you need to abstract What does the advertiser actually want? They don't want clicks. They don't want impressions. If they're D2C, they want sales. They want revenue. That, that's all they care about. The other stuff is layered on top.”

Steal thisPrice your product on the customer's true end-goal metric, not the vanity metric the industry defaults to.

Hunt emerging trends, not categories — Vungle rode the App Store wave

Jack Smith never set out to build an ad company; he looked for emerging high-growth industries (mobile apps, spotted in a Gartner report) and solved the biggest problem there. Vungle launched 12–18 months after the iPhone App Store for 'perfect timing.'

“I would be searching for what are the emerging industries and trends and what are the biggest problems in that. It might be that advertising is a big problem in that industry, but I wouldn't, you know, be searching for an advertising solution.”

Steal thisPick the emerging high-growth market first, then attack its single biggest problem — don't fall in love with a category.

If top VCs can't pick consumer winners, retail investors can't either

Jack Smith explains why he avoids investing in consumer apps: Sequoia backed both WhatsApp (the biggest consumer exit ever) and Secret (which imploded in ~12 months). If firms with full data and board seats can't tell them apart, an outsider has no edge.

“If these guys that have massive teams, they're looking at all the data, they're going to the board meetings of WhatsApp, they have all of these data points, if even them can pick a consumer app that like implodes like 12 months later, how am I gonna be able to pick the winner?”

WallStreetBets clubs together to squeeze hedge funds on GameStop

Jack Smith explains the GameStop saga: hedge funds shorted the 'dying' retailer, so Redditors on r/WallStreetBets pumped the stock to screw them. After Chewy founder Ryan Cohen took an activist stake, GameStop's value went from ~$75M to over $1B in six months.

“People on Reddit in this group WallStreetBets, they basically clubbed together and they were like, hey, let's just screw these hedge fund guys and let's just pump this stock. Now GameStop, the guy, this other actor, the founder of Chewy, had become an activist investor like 6 months ago, just saying like, oh, I think I can improve them.”

Robinhood traders move stocks with cheap Friday-expiry options

Jack Smith explains how small retail traders can move a stock as much as hedge funds: they buy heavily leveraged short-dated options (expiring Friday), so even $1 can move the needle massively — a roulette bet they're fine losing entirely.

“It's because they're all buying crazy leveraged options. They're buying options that expire on Friday, which means that you can essentially move the needle of the stock stock just by putting in like $1, you can move it massively because you're basically doing a game of roulette.”

Why Buffett won't short: capped upside, unlimited downside

Jack Smith relays Warren Buffett's reasoning for avoiding shorts: buying a stock gives capped downside and infinite upside, but shorting flips it — your gain is capped at the stock going to zero while your loss is unlimited if it keeps rising, which forces short-sellers to cover at any price.

“If I buy the stock stock, I kind of have infinite upside, right? Like, it could go to $100,000 or whatever. But if the stock goes bankrupt, I only lose my $10. I have a capped downside. But if I short the stock, I actually have a capped upside. I can only make a certain amount. If it goes to zero, I only can make $10. But then if it keeps going up, I actually have an unlimited upside.”

Even Sequoia has a graveyard: social bets are nearly impossible to call early

Jack Smith's point, via Shaan: even Sequoia, who led every WhatsApp round into a ~$19-20B exit, also funded social flops like Yik Yak and Whisper. If the best investors swing and miss this much on social, predicting a social hit before it plays out is essentially impossible.

“if even the best guys who have had the home runs have a bunch of swings and misses with social, it just shows how hard it is to correctly predict social before it plays out.”

How Vungle was born from an ad accidentally auto-playing in a meeting

Jack Smith recounts pivoting at AngelPad: after a recorder app blasted a Coke video during an investor meeting, the team realized they could show 15-second video ads for apps inside other apps. Prospective customers immediately offered $5K-$10K ad spend.

“Opened this like sound recorder app and it started like auto-playing on full volume like some video for Coke. Like we're trying to close it, like what the fuck? But then we actually just thought like, hey, wait a minute, what if we had videos like this but like advertising other games and other apps instead of like Coke stuff?”

How Vungle was born from an ad accidentally auto-playing in a meeting

Jack Smith recounts pivoting at AngelPad: after a recorder app blasted a Coke video during an investor meeting, the team realized they could show 15-second video ads for apps inside other apps. Prospective customers immediately offered $5K-$10K ad spend.

“Opened this like sound recorder app and it started like auto-playing on full volume like some video for Coke. Like we're trying to close it, like what the fuck? But then we actually just thought like, hey, wait a minute, what if we had videos like this but like advertising other games and other apps instead of like Coke stuff?”

Charge for what the advertiser actually wants: CPI, not CPM

Jack explains Vungle was one of the first ad networks to charge cost-per-install instead of CPM. Advertisers don't want impressions or clicks; D2C advertisers want sales, so pricing should map to the buyer's true core metric.

“And so we were one of the first to charge CPI, cost per install. So we were like, hey, it doesn't matter if like 10 people watch the video or like 100,000, just pay us a dollar every time someone installs something. So I think you need to abstract What does the advertiser actually want? They don't want clicks. They don't want impressions. If they're D2C, they want sales. They want revenue.”

Steal thisPrice your product on the buyer's true outcome metric (installs, sales), not vanity proxies like impressions.

Hunt emerging trends, not a specific solution like 'advertising'

Jack says he never set out to build an ad company; he found mobile apps via a Gartner report 12-18 months after the App Store launched and attacked the biggest problem in that high-growth market, which happened to be advertising.

“I would be searching for what are the emerging industries and trends and what are the biggest problems in that. It might be that advertising is a big problem in that industry, but I wouldn't, you know, be searching for an advertising solution.”

Steal thisPick an emerging high-growth market first, then attack its single biggest problem rather than starting from a solution.

GameStop: Chewy founder's $75M activist stake becomes $1B+ in 6 months

Jack recaps the WallStreetBets short squeeze: Reddit traders pumped GameStop to spite hedge funds shorting it, while Chewy founder Ryan Cohen's ~$75M activist investment six months earlier had ballooned to over $1 billion, with the stock up 100%+ in a single day.

“Now GameStop, the guy, this other actor, the founder of Chewy, had become an activist investor like 6 months ago, just saying, oh, I think I can improve them. He invested $75 million. It's gone to over a billion. In 6 months. The stock was up at one point over like 100% today alone.”

Why $1 of Robinhood options can move a stock massively

Jack explains the GameStop mechanics: retail traders buy cheap weekly options that expire Friday, which lets a tiny amount of capital move the stock's needle far more than the dollar amount, because they don't care about losing it all.

“They're buying options that expire on Friday, which means that you can essentially move the needle of the stock just by putting in like $1. You can move it massively because you're basically doing a game of roulette. You're like, hey, yeah, I know I'll lose all my money, but I have a small chance of winning.”

Why Warren Buffett won't short: capped upside, infinite downside

Jack explains the asymmetry that makes shorting dangerous: a long position has capped downside and unlimited upside, but a short has capped upside and unlimited downside, which is why Buffett says you can't sleep at night shorting.

“But if I short the stock, I actually have a capped upside. I can only make a certain amount. If it goes to zero, I only can make $10. But then if it keeps going up, I actually have an unlimited upside. That's why on Robinhood or any of these platforms, you have to have special permissions to short a stock, because you actually can lose an infinite amount of money beyond the capital that you assigned to that trade.”

Jack Smith sold Vungle to Blackstone for ~$750M in cash

Sam introduces guest Jack Smith, who founded the mobile ad company Vungle and sold it to private-equity giant Blackstone for roughly $750 million in cash, having raised very little.

“But basically he started this company called Vungle, which was sold to Blackstone, the large PE company, for I think $750 million in cash. They had raised a little bit of money, but not a significant amount. It was a wonderful exit.”

Get in early when a platform is still nascent

Jack's edge across Product Hunt and collectibles platforms is the same: join when there are only a few hundred users, because small and new means less competition and more arbitrage opportunity.

“So I think Product Hunt is similar with the collectibles thing in terms of just like, I joined when it only had a couple of hundred users. And so it's like identifying something nascent and then seeing if there's, obviously when things are small, there's more opportunities around because there's less competition.”

Steal thisFind platforms with only a few hundred users and become the power user before the crowd arrives.

The $3/hour Philippines team bidding on collectibles 24/7

Jack ran a team in the Philippines at $3/hour placing bids on fractional-collectibles platforms so heavily that Masterworks' CEO emailed to ask what he was doing, confused by the logs showing one user placing constant orders.

“I just told them like, "Hey, I have these guys in the Philippines, like $3 an hour just placing bids." Because they were like, yeah, because we were pretty confused, like, this guy who sold his company, is he just bored in Hawaii that he's just logged onto our platform 24/7, like bidding on stuff?”

Earn ~9% lending into a pooled, never-defaulted collectibles loan book

As a lender Jack puts capital into PWCC's pooled loan program, spread across many borrowers, earning ~9% a year; PWCC has run it for 10 years with zero defaults because it can seize and sell the collateral it already holds.

“I put in let's say $250,000 that I'm lending, and PWCC will then spread that across all the loans that they have. And there I get paid like 9% a year interest. That is taxed at ordinary income, so it's the highest tax, so you know, up to 50% interest.”

Scarcity is only credible from an independent grader

Jack's bear case on NBA Top Shot: the producer itself declares the assets scarce and runs the trading, whereas in physical cards an independent grader like PSA certifies scarcity, separate from whoever makes the cards. Self-declared scarcity is no more meaningful than valuing every YouTube clip.

“The reason that I wouldn't be bullish on this is because they are the ones claiming that the assets are valuable and facilitating the trading. Like, in the basketball or the collectible world, it kind of works because the grading authority saying how scarce something is is independent of the producers that are making the basketball stuff.”

A phone-camera app that instantly IDs and prices a trading card

Jack pitches a Shazam-for-cards: hold your iPhone up to a card and it identifies it and shows a value range by grade, the same computer-vision approach already used for plant, bird, and math-problem identification, to demystify live pack breaks.

“have people done the thing where they kind of like use like an iPhone app, kind of like that plant scanner app that basically just lets you just hold up your phone to a card you own and it tells you like, this is this card, it's worth between this and this depending on how it got graded.”

Steal thisBuild an image-recognition app that scans a collectible and returns its identity plus a value range by grade.

Aggregate everyone's attic card collections like Better World Books

Jack sees latent demand in the millions of childhood card binders no one will bother grading or listing; copy his friend Xavier's Better World Books model, get people to mail in their old cards for free, then scan and resell at scale.

“So I think somebody could do that if you could get everybody to go into their garage or their attic and go get their card collection and just mail you all their shit. And if you had an efficient way to like scan those, I think that could be a somewhat interesting opportunity”

Steal thisGet owners to mail in their dormant collections for free, then use cheap scanning to identify and resell the winners.

eBay sold 45 million cards in 2020, roughly $900M in GMV

eBay disclosed it sold 45 million trading cards in 2020; at a ~$20 average that is about $900 million of GMV in cards alone, with the broader fractional market estimated around $1.5 billion.

“did 45 million cards sold in 2020. If you just take an average of $20, that's $900 million of GMV just on trading cards, let alone any other type of collectible that's sold on eBay, right?”

Turn each athlete into an ETF of their own cards

Dibbs makes collecting approachable by letting people 'buy into a player' rather than a specific card: each player becomes a little ETF, a basket of cards collateralizing the position, so buyers bet on Luka or Giannis without learning card-grading science.

“They're turning players into their own little ETF of a collection of cards that are associated with that player. You don't have to know that this is a 19— or sorry, like a 2010 rookie card of this mint grade from this base set collection that's never going to get reproduced or whatever. You don't have to know all that. You just have to buy into the player at a certain price point, and you know that it's collateralized by the underlying card assets.”

Steal thisBundle a category's confusing individual assets into a single recognizable name buyers already believe in.

ISAs for creators: MrBeast funds and promotes you for a revenue cut

MrBeast floated doing income-share agreements with up-and-coming channels, taking 10-15% of their revenue in exchange for promotion and help, since the exposure (like Lambda School pairing training with job placement) matters more than the capital.

“I would love to do like an ISA, like I'll promote you and you keep doing your thing, I'll help you, but I'll take, you know, 10, 15% of your channel's revenue. This is like a pretty compelling idea 'cause I think I think more than the— you have to do it like an income share agreement where you're not just giving them capital, you have to help them get the exposure”

Steal thisPair capital with distribution: take a revenue cut of creators and use your own audience to kingmake them.

Put $300 of skin in the game to learn an emerging market

Shaan's on-ramp for any nascent space: download the apps and risk ~$300 (90 days of coffee money) just to start checking and learning, the same way his smart friends' weekend dabbling was the early signal for crypto.

“And I would take like $300, right? Like go take like, I don't know, 90 days of coffee money, like skip your daily coffee and like be like, okay, that's $300, and go like get a little bit of skin in the game just to learn how these platforms work. And look at— and then you'll, once you've skin in the game, you'll start checking on it.”

Steal thisRisk a trivial amount of money in any new market just to force yourself to start paying attention and learning.

The taxi-driver top signal: get out when amateurs pile in

Jack timed the crypto crash by noticing a stranger at a wedding had taken a second mortgage to buy crypto, the same way classic wisdom says to exit a market once your taxi driver gives you stock tips.

“I'm like, what are you doing? That's what I said, when your taxi driver is giving you stock tips, that's the time to get out of that market. For me now, I'm buying for the long term, but I only have Bitcoin and Ethereum.”

A stranger billionaire paid $25K for Sam's private Lyme doctor

Sick and undiagnosed, Sam was connected through Jack Smith to a woman who'd shut down a $10B hedge fund after getting Lyme. She spent days helping him diagnose it, then quietly paid $25,000 for a private specialist before he could object.

“she's a billionaire who— her and she had a hedge fund and a multibillion-dollar, $10 billion hedge fund, and they shut it down because they got sick and it was from Lyme. And Jack knew her from some event. And he puts me in touch with this woman and she doesn't even ask my name. For 3 days she talks to me for like 2 hours a day, helping me diagnose what's wrong.”

Vungle's $750M Blackstone exit

Jack Smith's mobile video ad network Vungle was acquired by private equity firm Blackstone, in a deal rumored to be worth $750 million in cash.

“Private equity firm Blackstone is set to acquire Vungle for an undisclosed sum that is hotly rumored to be $750 million US dollars in cash.”

8-year-old Jack sold 'itchy bombs' in the playground

Jack's first business at age 8: he picked itchy seed pods from a tree, branded them 'itchy bombs', and sold them in the playground for 25 cents each to put down kids' backs.

“And so basically I just picked loads of them with my brother and I sold them in the playground as like itchy bombs. And so I told people like, put this down someone's back and they're going to get really itchy. And then I think I sold each one for $0.25 and yeah, I got quite a lot of like people from people's older siblings and stuff were coming to buy them for me in the playground and stuff.”

At 12, Jack underbid Indian freelancers to learn on the job

At 12, Jack ditched his allowance to avoid chores and bid on Upwork/Guru projects below even Indian freelancers' rates — taking jobs he didn't know how to do and learning them on the client's dime.

“Basically, I just went on those sites and so as a worker, I bid on projects and I bid on them even lower than like the guys in India and stuff because I'm like 12 years old, so any money is a lot for me. Basically, I bid on projects that I didn't even know how to do them and then basically I just learned how to do them. Basically, people were paying me to learn.”

Steal thisBid on freelance work slightly above your skill level and learn the skill while getting paid to deliver it.

Procrastination as a deal-flow engine

Jack argues most of his wins came from 'productive procrastination' — browsing tech news and the internet — not productivity hacks. Being busy on the wrong thing is worse than looking up to spot new opportunities.

“I think actually most of the successes that I've had have actually come from when I've maybe been like procrastinating. Because I think you can have all the productivity tips in the world, but then if you're being productive working on the wrong thing, then you're kind of being a busy bee but with your head down, you know, not looking up to see what's around you.”

Steal thisSchedule deliberate browsing of tech news and new platforms as deal flow, not as wasted time.

Dropbox's launch post on Hacker News was trashed as a bad idea

Jack points out Drew Houston announced Dropbox in the Hacker News Show section as a solo founder, and the still-visible comments are full of people calling it a terrible idea they don't need because they have a USB stick.

“Drew Houston, I think when he was a solo founder, announced his Dropbox idea in the Hacker News show section. You can actually still see the post online. This is another bit to bear in mind is if you look on that post now, all of the comments are about how his idea is so terrible and it's definitely going to fail. People are like, "Why do I need this? I've got a USB stick. This is a shit idea."”

Don't say 'how can I help' — name the specific help you offer

Jack's cold-outreach rule: never ask 'how can I help?' because it forces the other party to figure out your skills. Instead state exactly what you can do (e.g. 'help with your pitch deck') so the offer is easy to accept.

“Well, not 'How can I help?' because then, you know, that puts the onus on the other party to have to think for you, and then they don't know your skill sets and stuff, right? So for me, I was like, 'Hey, if you need help with your pitch deck,' because I knew that they were kind of trying to raise funding and stuff.”

Steal thisIn cold outreach, replace 'how can I help' with one concrete, named offer the recipient can accept instantly.

The LinkedIn ad targeting hack: minimum audience of 7 people

Jack reverse-engineered a new LinkedIn ad system by repeatedly shrinking the audience until it accepted an ad targeting just 7 people, then padded it with 6 irrelevant strangers so the one person he wanted would see it.

“And so I kept on doing that one after another and then basically found found out that it would let me submit an ad when I had an advertisement targeting only 7 people. I don't know why 7 was the number. Again, probably someone pushed the wrong— perhaps they meant it's 7,000 people and they only pressed 7 by mistake.”

Steal thisHunt for exploits on newly launched ad platforms before they harden — the rules aren't enforced yet.

The bait-and-switch ad: approve a clean ad, then swap the creative

Because new LinkedIn ads were manually reviewed but editable after approval, Jack submitted an innocent ad, then swapped it for one showing the AngelPad founder's face urging connections to pass along an 'urgent message' linking to his pitch video.

“So basically I would create like an innocent looking ad, um, just targeting whatever, and then I'd change it after they approved it, um, because otherwise they wouldn't have approved it. So basically the and it said, it had a picture of the founder of AngelPad's face and it said, "Do you know Tomasz? We've got an urgent message we need to get to him. Click here."”

Pitch yourself as the 'wild card' when you don't fit

Surrounded by AngelPad teams of ex-Google engineers and PhDs, Jack and his co-founder turned their lack of technical pedigree into the pitch: take all safe bets plus one wild card that could be an epic failure or a massive success.

“And we were like, "Why don't you just choose us as just like a wild card. Like, it could be an epic failure or it could be a massive success. Uh, so that was our pitch, is like, we know we don't fit in, but at least we can be a wild card.”

Steal thisWhen you can't out-credential the field, pitch yourself as the high-variance wild card a portfolio needs.

Vungle was born from an annoying Coke ad interrupting a meeting recording

Vungle's video-ad idea came when a loud Verizon/Coke video ad blared while Jack tried to record a meeting. The insight: replace the brand ad with a 15-second trailer for another mobile game — and app developers immediately offered $5K-$10K to be first in line.

“We opened the app and then this crazy Verizon or Coke video ad started playing really loudly and we couldn't mute. And it was really annoying. But then we thought like, oh, wait a minute. Wait a minute, instead of advertising like Coke or something, why don't we have the video advertising a different game?”

Cure the cancer, not the itch

At AngelPad, Jack tested 6 landing pages in 6 days; ideas got praise but zero sales. An investor's framing crystallized why: don't build something that cures a customer's itch (nice-to-have) — build what cures their cancer (must-have).

“He said, Don't create a business where you're curing your customer's itch. Like, if you don't exist, they're like, oh, well, it's just an itch, it doesn't matter. Like, your antidote for my itch is nice, but, you know, whatever. He's like, create something where it cures your customer's cancer.”

Steal thisValidate by trying to actually sell each idea in a day — praise is worthless, only a sale or a pre-payment counts.

Naivety as an edge: charge per-user, not CPM

Knowing nothing about advertising let Vungle see it through the customer's eyes: app developers wanted users, not impressions. So instead of the industry-standard CPM, Vungle charged ~$2 per actual user acquired — a massive differentiator born of ignorance.

“So just pay us like $2 for every user we get you. It doesn't matter if we get you a user after they see your video once or like 100,000 times. We're just going to charge you based on how many users we get you. And then that again was a massive differentiator for us. And it became because we were naive.”

Steal thisReprice against the customer's true desired outcome instead of inheriting the industry's default billing unit.

Nearly every early unicorn broke a 'Silicon Valley rule'

Jack regretted following VC norms (no family/husband-wife teams, no co-CEO/president split). After leaving, he found that of the ~20 unicorns then existing, almost all broke one: Eventbrite (husband-wife), Stripe (brothers), Lyft (CEO + president).

“When I looked at them, pretty much every single one broke one of those rules. Rules. Um, Eventbrite is a husband and wife team. Um, Stripe, they are brothers. Um, Lyft, one of the co-founders is CEO, the other one is president. So kind of there is no rules in Silicon Valley”

Become the #1 user of every new platform

Jack's repeatable playbook: when a new platform launches, post daily to top its leaderboard. He automated a midnight Product Hunt post to stay the #1 user uncatchable — which drew inbound from a Sequoia partner and a stream of startup deal flow.

“And so, I just posted each day and then I made it a bit more scalable. Again, I'm a crappy software engineer. If I was doing this again, I would just hire someone off Upwork, could probably get it done for like $10 or something. I basically did this myself, but I could have hired someone for $10. I created just a script to automatically schedule a post to Product Hunt each day at exactly midnight. That's when the leaderboard resets.”

Steal thisPick a brand-new platform with a leaderboard and post daily to lock in the top spot before anyone else shows up.

Blackstone buys Vungle for a rumored $750M in cash

Jack Smith co-founded mobile ad network Vungle, which private equity firm Blackstone acquired for a price rumored to be $750 million in cash.

“Private equity firm Blackstone is set to acquire Vungle for an undisclosed sum that is hotly rumored to be $750 million US in cash.”

Itchy Bombs: an 8-year-old's first hustle

Jack Smith's first business memory was picking itchy seed pods with his brother at age 8 and selling them in the playground for 25 cents each, branded as 'Itchy Bombs.'

“And so basically I just picked loads of them with my brother and I sold them in the playground as like itchy bombs. And so I told people like, put this down someone's back and they're going to get really itchy. And then I think I sold each one for 25 cents.”

Bid below Indian freelancers, then learn the job after winning it

At 12, Jack gave up his allowance rather than do chores, then bid on Upwork/guru.com projects below even Indian freelancers on tasks he didn't know how to do, learning each skill after winning the bid.

“I bid on projects, and I bid on them even lower than like the guys in India and stuff, right? Because I'm like 12 years old, so any money is a lot for me. And so basically I bid on projects that I didn't even know how to do them, And then basically I just learned how to do them. So basically people were paying me to learn.”

Steal thisWin freelance bids on work above your skill level, then learn the skill on the client's dime.

Procrastination as a discovery engine, not a vice

Jack argues most of his breakthroughs came not from productivity hacks but from 'productive procrastination'—reading tech news and exploring online—then actioning on what he found by reaching out to companies.

“I think actually most of the successes that I've had have actually come from when I've maybe been like procrastinating, because I think you can have all the productivity tips in the world, but then if you're being productive working on the wrong thing, then you're kind of being a busy bee but with your head down, you know, not looking up to see what's around you.”

Steal thisSchedule unstructured browsing of tech news and demos as deliberate deal flow, then act fast on what catches your eye.

Don't ask 'how can I help'—offer a specific skill

Jack's outreach rule: never ask 'how can I help,' which forces the other party to think for you. Instead name a concrete skill you'll contribute, like helping with their pitch deck.

“Well, not how can I help, because then, you know, that puts the onus on the other party to have to think for you and then they don't know your skill sets and stuff. So for me, I was like, hey, if you need help with your pitch deck, because I knew that they were kind of trying to raise funding and stuff.”

Steal thisWhen cold-reaching founders, offer one specific skill ('help with your pitch deck'), never the vague 'how can I help?'

The LinkedIn ad targeted at a single person

Unable to get into AngelPad among 2,000 applicants for one spot, Jack discovered a loophole in LinkedIn's new ad system letting him target an ad down to essentially one specific person to reach the accelerator's founder.

“I'd found this kind of loophole hack on LinkedIn where I was able to create an advertisement and target it down to a specific person. So LinkedIn has its kind of own ad system like Google AdWords, but they— I think it was a software engineer, like, I think some software engineer had done this as a bug that I found I could set the targeting so specifically, say, like, job title AngelPad, job title CEO, that there's kind of only one person who that ad would show it to, you know.”

Nascent platforms hold the undiscovered hacks

Jack's thesis: the best exploitable opportunities live on brand-new platforms. Mature systems like Google AdWords have 15-20 years of optimization and armies of engineers, leaving no easy hacks, while a just-launched ad system is wide open.

“I think this is where the most opportunities are, is when it's like a nascent platform. Um, if you're trying to find hacks on Google AdWords, there's probably none left because, you know, people have like 15, 20 years experience with Google words, you know, and they've got loads of engineers working on it. LinkedIn, this ad system was new. They just launched it. And so I was just testing it out.”

Steal thisHunt for exploits on newly launched platforms, not mature ones where every edge is already taken.

Pitch yourself as the wild card

Knowing they were the only non-engineer team against 11 software-heavy companies, Jack pitched AngelPad's founder to take them as the deliberate wild card—an epic failure or massive success—turning their obvious weakness into the reason to bet on them.

“But what we told Tomas is we said, "Hey, look, you've got 11 other companies, all heavy software engineering backgrounds, and you've got one last spot." And we were like, "Why don't you just choose us as just a wild card? It could be an epic failure, or it could be a massive success." So, that was our pitch. We know we don't fit in, but at least we can be a wild card.”

Steal thisWhen you don't fit the standard profile, pitch yourself as the deliberate high-variance wild card bet.

How Vungle's real idea was found by selling 6 landing pages in a week

Two weeks before demo day with a doomed app-store idea, Jack and his co-founder built crappy landing pages for 6 different ideas and tried to sell each in a day; only when they pitched 15-second video 'movie trailers' for apps did developers throw $5K-$10K at a nonexistent product.

“And so roughly 2 weeks before the demo day, what we did is we just came up with like 6 different business ideas related to this idea of how can app developers get users. And we spent like half an hour each, like creating a super crappy landing page for each one. And basically we just spent a day trying to actually sell each idea.”

Steal thisValidate ideas by trying to actually sell each one with a throwaway landing page in a single day—real money beats compliments.

Nearly every early unicorn broke a Silicon Valley 'rule'

After leaving Vungle, Jack found that of the ~20 unicorns at the time, almost all violated conventional VC rules: Eventbrite is a husband-and-wife team, Stripe is brothers, and Lyft has one co-founder as CEO and one as president.

“When I looked at them, pretty much every single one broke one of those rules. Rules. Eventbrite is a husband and wife team. Stripe, they are brothers. Lyft, one of the co-founders is CEO, the other one is president. So kind of there is no rules in Silicon Valley, but at the time I kind of went along with different investors telling me.”

Jack Smith sold for $800M and got off every treadmill

Sam's pick for 'having the most fun' is his friend Jack Smith, who sold his company for ~$800M (walking away with nearly $100M after tax) by 26. Now in his early 30s, he lives in a Hawaii rental, has ~150 Twitter followers, does no angel investing, and pen-pals with prison inmates - content with what he has and off the content/money/status treadmills.

“Jack Smith sold his company for $800 million, something like that. He probably walked away with before tax, nearly 9 figures. So nearly $100 million. He started the company when he was 23. He quit working there when he was 26.”

Become the #1 user of a brand-new platform

Jack's playbook if starting over at 20: spot a just-launched platform like Product Hunt early (under 200 users), post daily until you're the #1 user, automate it with a cheap script, then leverage the leaderboard visibility—Sequoia partners and startups came to him because he was prominent there.

“I saw Product Hunt. It launched, had, I think, under 200 views or something. I was like, oh, this just seems pretty interesting. And then I just started using it every single day. I just would post new products to it every single day. So, you know, a few minutes of work each day. And then quickly, I just became the number one user on the site, and they had like a ranking board.”

Steal thisFind a new platform with a leaderboard, become its #1 user through daily consistency (automate it), and convert the visibility into connections and deal flow.